2024/02/17 更新

写真a

イワサキ アリヒロ
岩﨑 有紘
IWASAKI Arihiro
所属
理工学部 准教授
連絡先
メールによる問い合わせは《こちら》から
外部リンク

学位

  • 博士(理学) ( 慶應義塾大学 )

  • 修士(理学) ( 慶應義塾大学 )

学歴

  • 2016年3月
     

    慶應義塾大学   理工学研究科   基礎理工学専攻   博士後期   修了

  • 2009年3月
     

    慶應義塾大学   理工学研究科   基礎理工学専攻   博士前期   修了

  • 2007年3月
     

    慶應義塾大学   理工学部   化学科   卒業

経歴

  • 2023年4月 - 現在

    中央大学   理工学部 応用化学科   准教授

  • 2022年4月 - 2023年3月

    慶應義塾大学   理工学部 化学科   専任講師

  • 2017年4月 - 2022年3月

    慶應義塾大学   理工学部 化学科   助教

  • 2015年4月 - 2017年3月

    慶應義塾大学   理工学部化学科   助教(有期)

  • 2014年4月 - 2015年3月

    慶應義塾大学大学院   理工学研究科   助教(有期・研究奨励)

  • 2009年 - 2013年3月

    リアル化学株式会社   開発部開発課   研究員

▼全件表示

所属学協会

  • 2022年7月 - 現在

    日本菌学会

  • 2016年4月 - 現在

    有機合成化学協会

  • 2016年4月 - 現在

    毒素シンポジウム

  • 2016年4月 - 現在

    日本ケミカルバイオロジー学会

  • 2009年4月 - 現在

    日本化学会

研究キーワード

  • 海洋天然物化学

研究分野

  • ナノテク・材料 / 生物分子化学

論文

  • Isolation and Identification of Plant-Growth Inhibitory Constituents from Polygonum chinense Linn and Evaluation of Their Bioherbicidal Potential

    Thang Lam Lun, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Plants   12 ( 7 )   2023年4月

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    掲載種別:研究論文(学術雑誌)  

    Polygonum chinense Linn. is a medicinal and invasive plant that belongs to the family Polygonaceae. The pharmacological activities and phytochemical constituents of Polygonum chinense are well reported, but the allelopathic effects and potent allelopathic substances of P. chinense remain to be investigated. Hence, this experiment was conducted to separate and characterize potentially allelopathic substances from an extract of the Polygonum chinense plant. The Polygonum chinense plant extracts highly suppressed the growth of cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), barnyard grass (Echinochloa crusgalli (L.) P. Beauv.), and timothy grass (Phleum pratense L.) seedlings in a species- and concentration-dependent way. Two active substances were separated using a series of purification procedures and determined through spectral analysis as (−)-3-hydroxy-β-ionone and (−)-3-hydroxy-7,8-dihydro-β-ionone. These two compounds significantly suppressed the seedling growth of Lepidium sativum (cress) at concentrations of 0.01 and 1 mM, respectively. The extract concentrations necessary for 50% growth inhibition (I50 values) of the cress hypocotyls and roots were 0.05 and 0.07 mM for (−)-3-hydroxy-β-ionone, respectively, and 0.42 and 1.29 mM for (−)-3-hydroxy-7,8-β-ionone, respectively. These findings suggest that these two compounds are in charge of the inhibitory effects of the Polygonum chinense extract and may serve as weed control agents.

    DOI: 10.3390/plants12071577

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  • Unique Initiation and Termination Mechanisms Involved in the Biosynthesis of a Hybrid Polyketide-Nonribosomal Peptide Lyngbyapeptin B Produced by the Marine Cyanobacterium Moorena bouillonii. 査読 国際誌

    Fumitaka Kudo, Takuji Chikuma, Mizuki Nambu, Taichi Chisuga, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Akimasa Miyanaga, Tadashi Eguchi

    ACS chemical biology   18 ( 4 )   875 - 883   2023年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Lyngbyapeptin B is a hybrid polyketide-nonribosomal peptide isolated from particular marine cyanobacteria. In this report, we carried out genome sequence analysis of a producer cyanobacterium Moorena bouillonii to understand the biosynthetic mechanisms that generate the unique structural features of lyngbyapeptin B, including the (E)-3-methoxy-2-butenoyl starter unit and the C-terminal thiazole moiety. We identified a putative lyngbyapeptin B biosynthetic (lynB) gene cluster comprising nine open reading frames that include two polyketide synthases (PKSs: LynB1 and LynB2), four nonribosomal peptide synthetases (NRPSs: LynB3, LynB4, LynB5, and LynB6), a putative nonheme diiron oxygenase (LynB7), a type II thioesterase (LynB8), and a hypothetical protein (LynB9). In vitro enzymatic analysis of LynB2 with methyltransferase (MT) and acyl carrier protein (ACP) domains revealed that the LynB2 MT domain (LynB2-MT) catalyzes O-methylation of the acetoacetyl-LynB2 ACP domain (LynB2-ACP) to yield (E)-3-methoxy-2-butenoyl-LynB2-ACP. In addition, in vitro enzymatic analysis of LynB7 revealed that LynB7 catalyzes the oxidative decarboxylation of (4R)-2-methyl-2-thiazoline-4-carboxylic acid to yield 2-methylthiazole in the presence of Fe2+ and molecular oxygen. This result indicates that LynB7 is responsible for the last post-NRPS modification to give the C-terminal thiazole moiety in lyngbyapeptin B biosynthesis. Overall, we identified and characterized a new marine cyanobacterial hybrid PKS-NRPS biosynthetic gene cluster for lyngbyapeptin B production, revealing two unique enzymatic logics.

    DOI: 10.1021/acschembio.3c00011

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  • Total Synthesis of Caldorazole, a Potent Mitochondrial Respiratory Chain Inhibitor without Chiral Centers. 国際誌

    Yuta Miyamoto, Arihiro Iwasaki, Haruka Fujimura, Chihiro Kudo, Naoaki Kurisawa, Osamu Ohno, Kiyotake Suenaga

    The Journal of organic chemistry   88 ( 5 )   3208 - 3216   2023年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Caldorazole (1) is a novel polyketide that was isolated from a marine cyanobacterium in 2022. It is a unique natural product that exhibits potent inhibitory activity against mitochondrial respiratory chain complex I despite having no chiral centers. To establish a method for obtaining caldorazole without relying on biological resources and for constructing a useful synthetic route for studies of its structure-activity relationship, we achieved the first total synthesis of caldorazole using a convergent synthetic route.

    DOI: 10.1021/acs.joc.2c03007

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  • Allelopathic Substances of Osmanthus spp. for Developing Sustainable Agriculture

    Hisashi Kato-Noguchi, Yuri Hamada, Misuzu Kojima, Sanae Kumagai, Arihiro Iwasaki, Kiyotake Suenaga

    Plants   12 ( 2 )   2023年1月

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    掲載種別:研究論文(学術雑誌)  

    Osmanthus fragrans Lour. has been cultivated for more than 2500 years because of the fragrance and color of the flowers. The flowers and roots have been used in tea, liquors, foods, and traditional Chinese medicine. The species contains more than 180 compounds including terpenoids, phenylpropanoids, polyphenols, flavonoids, and sterols. However, there has been limited information available on the allelopathic properties and allelopathic substances of O. fragrans. We investigated the allelopathy and allelopathic substances of O. fragrans and Osmanthus heterophyllus (G.Don) P.S. Green, as well as Osmanthus × fortunei Carrière, which is the hybrid species between O. fragrans and O. heterophyllus. The leaf extracts of O. fragrans, O. heterophyllus, and O. × fortunei suppressed the growth of cress (Lepidium sativum L.), alfalfa (Medicago sativa L.), Lolium multiflorum Lam., and Vulpia myuros (L.) C.C.Gmel with the extract concentration dependently. The extract of the hybrid species O. × fortune was the most active among the extracts. The main allelopathic substances of O. × fortunei and O. fragrans were isolated and identified as (+)-pinoresinol and 10-acetoxyligustroside, respectively. (+)-Pinoresinol was also found in the fallen leaves of O. × fortunei. Both compounds showed an allelopathic activity on the growth of cress and L. multiflorum. On the other hand, several allelopathic substances including (+)-pinoresinol may be involved in the allelopathy of O. heterophyllus. O. fragrans, O. heterophyllus, and O. × fortunei are evergreen trees. but their senescent leaves fall and cover the soil under the trees. It is possible that those allelopathic substances are liberated through the decomposition process of the leaves into their rhizosphere soil, and that they accumulate in the soil and provide a competitive advantage to the species through the inhibition of the growth of the neighboring competing plants. Therefore, the leaves of these Osmanthus species are allelopathic and potentially useful for weed management options in some agriculture settings to reduce commercial herbicide dependency for the developing sustainable agriculture systems.

    DOI: 10.3390/plants12020376

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  • Assessment of the Phytotoxic Potential of Dregea volubilis (L.f.) Benth. ex Hook.f. and Identification of its Phytotoxic Substances for Weed Control

    Ei Han Kyaw, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Agriculture (Switzerland)   12 ( 11 )   2022年11月

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    掲載種別:研究論文(学術雑誌)  

    The phytotoxic potential of plants and the effect of their active components on another plant species is being explored as a potential alternative to synthetic herbicides for weed control. In the current study, we investigated the phytotoxic potential of the leaves of Dregea volubilis (L.f.) Benth. ex Hook.f. against four test plants [timothy (Phleum pratense L.), barnyard grass (Echinochloa crus-galli (L.) P. Beauv), lettuce (Lactuca sativa L.), and alfalfa (Medicago sativa L.)] and observed significant growth inhibition on those plants at concentrations >3 mg D.W. equivalent extract mL−1. A bioassay-governed purification of the D. volubilis extracts using different chromatography phases produced two growth inhibitory compounds, 3-hydroxy-α-ionone (compound 1) and 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one (compound 2). The compounds retarded the growth of barnyard grass and cress (Lepidium sativum L.) with I50 (concentration required for 50% growth suppression) values ranging from 0.098 to 0.450 mM for 3-hydroxy-α-ionone and 0.029 to 0.420 mM for 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one. Thus, the extracts and identified compounds may have the possibility to be utilized as bioagents for weed control.

    DOI: 10.3390/agriculture12111826

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  • Two Allelopathic Substances from Plumbago rosea Stem Extracts and Their Allelopathic Effects

    Thang Lam Lun, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Agronomy   12 ( 9 )   2022年9月

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    掲載種別:研究論文(学術雑誌)  

    The plant Plumbago rosea Linn., belonging to the Plumbaginaceae family, is an important medicinal herb distributed in part of Southeast Asia, and there are many reports of its pharmacological properties. However, the allelopathic activities of P. rosea have not been examined. Thus, the present study was conducted to assess the allelopathic activity of P. rosea and to identify its allelopathic substances. The aqueous methanol stem extract of P. rosea significantly suppressed the seedling growth of barnyard grass (Echinochloa crus-galli L. P. Beauv.), Italian ryegrass (Lolium multiflorum Lam.), timothy (Phleum pretense L.), cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), and alfalfa (Medicago sativa L.). The extract of P. rosea was then purified through chromatographic steps, and two active substances were isolated and determined as 7,4′,5′-tri-O-methyl dihydroquercetin and 7,4′,5′-tri-O-methylampelopsin. The two compounds significantly inhibited the seedling growth of cress, with 7,4′,5′-tri-O-methylampelopsin showing a greater inhibitory effect than 7,4′,5′-tri-O-methyl dihydroquercetin. This result may be due to the 3′-OH group in 7,4′,5′-tri-O-methylampelopsin. The effective concentrations of both compounds required for 50% growth inhibition (EC50 values) of cress seedlings were 0.24 mM and 0.59 mM for root and shoot, and 0.07 mM and 0.21 mM, respectively. These findings suggest that the two compounds may contribute to the allelopathic effect of P. rosea and could be used as a natural source of allelopathic substances.

    DOI: 10.3390/agronomy12092020

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  • Phytotoxic Effects of Senna garrettiana and Identification of Phytotoxic Substances for the Development of Bioherbicides

    Ramida Krumsri, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Agriculture (Switzerland)   12 ( 9 )   2022年9月

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    掲載種別:研究論文(学術雑誌)  

    Phytotoxic substances in plants that may serve as alternative natural herbicides for controlling weeds are required for sustainable agriculture. We explored the phytotoxic activities of aqueous methanol extracts of Senna garrettiana (Craib) Irwin & Barneby leaves and the active substances they contain. The results revealed that the S. garrettiana leaf extracts had significant phytotoxic effects on three dicotyledons (Lepidium sativum L., Lactuca sativa L., and Medicago sativa L.) and two monocotyledons (Phleum pratense L. and Lolium multiflorum Lam.). An bioassay-guided isolation process yielded three active substances; caffeic acid, methyl caffeate, and (S)-6-hydroxymellein inhibited the seed germination, seedling growth, and biomass accumulation of L. sativum in a concentration-dependent manner. Based on the concentration required for 50% growth inhibition (IC50), (S)-6-hydroxymellein had the highest inhibitory effects on L. sativum in all test parameters, followed by methyl caffeate and caffeic acid. The L. sativum roots were the most susceptible to (S)-6-hydroxymellein (IC50 = 383 µM) and caffeic acid (IC50 = 2627 µM), whereas methyl caffeate (IC50 = 1361 µM) had the greatest effect on the L. sativum shoots. Thus, three isolated compounds may explain the phytotoxic effects of the S. garrettiana extracts. Consequently, caffeic acid, methyl caffeate, and (S)-6-hydroxymellein could be potential candidates for the future production of bioherbicides.

    DOI: 10.3390/agriculture12091338

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  • Allelopathic Activity of a Novel Compound, 5,6-Dihydrogen-11 alpha-O-acetyl-12 beta-O-tigloyl-17 beta-marsdenin, and a Known Steroidal Glycoside from the Leaves of Marsdenia tenacissima (Roxb.) Moon 査読

    Seinn Moh Moh, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    AGRONOMY-BASEL   12 ( 7 )   2022年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Medicinal plants are rich sources of bioactive substances that can be used to develop environmentally friendly weed control alternatives. Marsdenia tenacissima (Roxb.) Moon is a traditional medicinal plant well known for its pharmacological activities and several bioactive compounds. However, its allelopathy and related substances have not been reported. Hence, the present study was conducted to explore the allelopathic potential and substances from M. tenacissima leaves. Aqueous methanol extracts of M. tenacissima showed significant inhibitory activities against the growth of cress (Lepidium sativum L.) and Italian ryegrass (Lolium multiflorum Lam.). The extracts were purified through various chromatography steps, and two allelopathic substances were isolated and determined by spectral data to be steroidal glycoside 1 (5,6-dihydrogen-11 alpha-O-acetyl-12 beta-O-tigloyl-17 beta-marsdenin), a novel compound, and steroidal glycoside 2 (5,6-dihydrogen-11 alpha,12 beta-di-O-tigloyl-17 beta-marsdenin). Both compounds significantly inhibited the growth of cress seedlings. Steroidal glycoside 1 showed 1.6- and 4-times greater growth inhibitory potential against the cress shoots and roots than steroidal glycoside 2. The concentrations needed for 50% growth inhibition of the cress seedling shoots and roots were 0.46 and 0.03 mM for steroidal glycoside 1, respectively, and 0.74 and 0.12 mM for steroidal glycoside 2, respectively. Therefore, these results suggest that steroidal glycosides 1 and 2 may be responsible for the allelopathy of the M. tenacissima leaves.

    DOI: 10.3390/agronomy12071536

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  • Isolation and Total Synthesis of Beru'amide, an Antitrypanosomal Polyketide from a Marine Cyanobacterium Okeania sp. 国際誌

    Raimu Taguchi, Arihiro Iwasaki, Akira Ebihara, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

    ORGANIC LETTERS   24 ( 25 )   4710 - 4714   2022年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A 68 mu g amount of an acyclic polyketide, named beru'amide, was isolated from a marine cyanobacterium Okeania sp. Beru'amide contains six unique moieties in its relatively small skeleton. By applying several cutting-edge techniques, including DFT-based chemical shift calculations, we achieved the structure determination and the total synthesis of this highly functionalized scarce natural product. Furthermore, beru'amide was shown to have strong antitrypanosomal activity.

    DOI: 10.1021/acs.orglett.2c02013

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  • Isolation of Caldorazole, a Thiazole-Containing Polyketide with Selective Cytotoxicity under Glucose-Restricted Conditions 国際誌

    Osamu Ohno, Arihiro Iwasaki, Kyouhei Same, Chihiro Kudo, Erika Aida, Kazuya Sugiura, Shimpei Sumimoto, Toshiaki Teruya, Etsu Tashiro, Siro Simizu, Kenji Matsuno, Masaya Imoto, Kiyotake Suenaga

    ORGANIC LETTERS   24 ( 25 )   4547 - 4551   2022年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Caldorazole (1) was isolated from the marine cyanobacterium Caldora sp. collected on Ishigaki Island, Okinawa, Japan. Its structure was determined to be a new polyketide that contained two thiazole rings and an O-methylenolpyruvamide moiety. Caldorazole (1) showed strong cytotoxicity toward tumor cells that had been seeded at a high density. Cell death induced by 1 in HeLa and A431 cells was also observed only in the presence of the glycolysis blocker 2-deoxy-D-glucose (2DG). Co-treatment with 1 and 2DG remarkably decreased ATP levels in these cells. Furthermore, 1 selectively inhibited complex I in the mitochondrial respiratory chain. Thus, 1 was demonstrated to exert cytotoxicity toward human tumor cells by blocking mitochondrial respiration.

    DOI: 10.1021/acs.orglett.2c01566

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  • Structural Determination, Total Synthesis, and Biological Activity of Iezoside, a Highly Potent Ca2+-ATPase Inhibitor from the Marine Cyanobacterium Leptochromothrix valpauliae 査読 国際誌

    Naoaki Kurisawa, Arihiro Iwasaki, Kazuya Teranuma, Shingo Dan, Chikashi Toyoshima, Masaru Hashimoto, Kiyotake Suenaga

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   144 ( 24 )   11019 - 11032   2022年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Sarco/endoplasmic reticulum Ca2+-ATPase (SERCA) is a membrane protein on the endoplasmic reticulum (ER) that transports Ca2+ from the cytosol into the ER. As its function is associated with various biological phenomena, SERCA has been recognized as a promising druggable target. Here, we report the second-strongest SERCA-inhibitory compound known to date, which we isolated from the marine cyanobacterium Leptochromothrix valpauliae and named iezoside (1). The structure of iezoside (1) is fundamentally different from that of any other SERCA inhibitor, and its potency is the strongest among marine natural products (K-i 7.1 nM). In this article, we report our comprehensive analysis of iezoside (1), which covers its isolation, structural characterization supported by density functional theory (DFT) calculations and statistical analysis, total synthesis, and clarification of the mode of action of its potent antiproliferative activity (IC50 6.7 +/- 0.4 nM against HeLa cells).

    DOI: 10.1021/jacs.2c04459

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  • Targeted Discovery of Amantamide B, an Ion Channel Modulating Nonapeptide from a South China Sea Oscillatoria Cyanobacterium 国際誌

    Te Li, Chuchu Xi, Yiyi Yu, Ning Wang, Xiao Wang, Arihiro Iwasaki, Fang Fang, Lijian Ding, Shuang Li, Weiyan Zhang, Ye Yuan, Tingting Wang, Xiaojun Yan, Shan He, Zhengyu Cao, C. Benjamin Naman

    JOURNAL OF NATURAL PRODUCTS   85 ( 3 )   493 - 500   2022年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Amantamide B (1) is a new linear nonapeptide analogue of the cyanobacterial natural product amantamide A (2), and both have methyl ester and butanamide termini. These compounds were discovered in this study from the organic extract of a tropical marine filamentous cyanobacterium, Oscillatoria sp., collected around the Paracel Islands in the South China Sea. The use of LC-MS/MS molecular networking for sample prioritization and as an analytical dereplication tool facilitated the targeted isolation of 1 and 2. These molecules were characterized by spectroscopy and spectrometry, and configurational assignments were determined using chemical degradation and chiral-phase HPLC analysis. Compounds 1 and 2 modulated spontaneous calcium oscillations without notable cytotoxicity at 10 mu M in short duration in vitro testing on primary cultured neocortical neurons, a model system that evaluates neuronal excitability and/or the potential activity on Ca2+ signaling. Both molecules were also found to be moderately cytotoxic in longer duration bioassays, with in vitro IC50 values of 1-10 mu M against CCRF-CEM human T lymphoblastoid cells and U937 human histiocytic lymphoma cells. These formerly undiscovered bioactivities of known compound 2 expand upon its previously reported function as a selective CXCR7 agonist among 168 GPCR targets.

    DOI: 10.1021/acs.jnatprod.1c00983

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  • Allelopathy of the Medicinal Plant Dregea volubilis (L.f.) Benth. ex Hook.f. and Its Phytotoxic Substances with Allelopathic Activity

    Ei Han Kyaw, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    AGRONOMY-BASEL   12 ( 2 )   2022年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Allelopathic plants and their related phytotoxic chemicals have been explored as alternatives for environmentally friendly weed management. Dregea volubilis (L.f.) Benth. ex Hook.f., a woody vine, is well-known for its uses in various therapeutic treatments, and several bioactive compounds have been isolated from this species. However, to date, no phytotoxic substances from D. volubilis have been reported. Hence, in this research, we aimed to investigate the allelopathic effect of D. volubilis and characterize its phytotoxic substances. Extracts of D. volubilis exhibited significant inhibitory activity against the seedling growth of Italian ryegrass (Lolium multiflorum Lam.) and cress (Lepidium sativum L.). The extracts were purified through several chromatography steps, yielding two phytotoxic substances, and using spectroscopy, their structures were determined as dehydrovomifoliol and loliolide. The compounds inhibited the Italian ryegrass and cress seedlings with the I-50 (concentrations needed for 50% inhibition) values ranging from 0.022 to 0.102 mM, for loliolide and 3.24-4.60 mM, for dehydrovomifoliol. These results suggest that both phytotoxic compounds might be responsible for the allelopathy of D. volubilis, and they may be released into the soil through the decomposition of the D. volubilis leaf and probably act as allelopathic active substances. Therefore, the extracts of D. volubilis and its related phytotoxic compounds may be applied as biological agents for controlling weeds.

    DOI: 10.3390/agronomy12020303

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  • Assessment of Allelopathic Potential of Senna garrettiana Leaves and Identification of Potent Phytotoxic Substances

    Ramida Krumsri, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    AGRONOMY-BASEL   12 ( 1 )   2022年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Senna garrettiana (Craib) Irwin & Barneby (Fabaceae) is a medicinal plant known to be rich in biologically active compounds that could be exploited to produce bioherbicides. The present study was conducted to explore the allelopathic potential and phytotoxic substances of S. garrettiana. Extracts of S. garrettiana leaves were found to significantly inhibit the growth of Lepidium sativum L. and Echinochloa crus-galli (L.) P. Beauv. (p <= 0.05). The phytotoxic substances were isolated and identified as vanillic acid and ferulic acid by bioassay-directed fractionation and spectral data analysis. The two compounds were shown to significantly inhibit the seed germination, seedling growth, and dry biomass of L. sativum. Based on the concentration required for 50% growth inhibition (defined as IC50), the roots of L. sativum were the most sensitive to the compounds, and the inhibitory effect of ferulic acid (IC50 = 0.62 mM) was >1.3 times more potent than that of vanillic acid (IC50 = 0.82 mM). In addition, a mixture of the two compounds (0.3 mM) resulted in synergistic inhibitory activity against the L. sativum roots compared with the individual compounds. These results suggest that the extracts of S. garrettiana leaves and their phytotoxic compounds have potential as candidate natural herbicides.

    DOI: 10.3390/agronomy12010139

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  • Odookeanynes A and B, Acetylene-Containing Lipopeptides from an Okeania sp. Marine Cyanobacterium 国際誌

    Aki Yamano, Yuka Asato, Noriyuki Natsume, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    JOURNAL OF NATURAL PRODUCTS   85 ( 1 )   169 - 175   2022年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Odookeanynes A (1) and B (2), two acetylene-containing lipopeptides, were isolated from an Okeania sp. marine cyanobacterium collected in Okinawa, Japan. Their structures were elucidated by spectroscopic analysis and Marfey's analysis of acid hydrolysates. Odookeanynes A (1) and B (2) dose-dependently promoted the differentiation of mouse 3T3-L1 preadipocytes in the presence of insulin.

    DOI: 10.1021/acs.jnatprod.1c00915

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  • Allelopathy and Allelopathic Substances of Fossil Tree Species Metasequoia glyptostroboides

    Yuki Matuda, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    AGRONOMY-BASEL   12 ( 1 )   2022年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Metasequoia glyptostroboides Hu et W.C. Cheng is one of the oldest living conifer species, and it has remained unchanged for millions of years compared to its fossils from the Cretaceous period. The species are cultivated in the parks, gardens, and roadsides in many countries. We investigated the allelopathy and allelopathic substances in fallen leaves of M. glyptostroboides. An aqueous methanol extract of the fallen leaves inhibited the growth of cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), alfalfa (Medicago sativa L.), Lolium multiflorum Lam., Phleum pretense L., and Vulpia myuros (L.) C.C.Gmel. The extract was then purified by several chromatographic steps, and two allelopathic substances were isolated and determined by spectral data to be (+)-rhododendrol and 9-epi-blumenol C. The compound inhibited the growth of cress and L. multiflorum. M. glyptostroboides is a deciduous perennial tree, and accumulation of its fallen leaves occur on the soil under the trees. Therefore, those allelopathic substances in the fallen leaves may be liberated into the rhizosphere soil during the decomposition process of fallen leaves and provide a competitive advantage for M. glyptostrob through the growth inhibition of competing plant species nearby. Therefore, M. glyptostroboides is allelopathic, and (+)-rhododendrol and 9-epi-blumenol C may be contribute to the allelopathy.

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  • Phytotoxic activity of Clerodendrum indicum (L.) Kuntze and its potential phytotoxic substance

    Ei Han Kyaw, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    EMIRATES JOURNAL OF FOOD AND AGRICULTURE   33 ( 10 )   884 - 892   2021年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:UNITED ARAB EMIRATES UNIV  

    Clerodendrum indicum (L.) Kuntze (Lamiaceae), an annual shrub, is renowned for being used in folk medicine in South Asian countries. Several pharmacological properties and many bioactive secondary metabolites from C. indicum have been well documented. However, the phytotoxic activities and the related phytotoxic substances with the allelopathic activity of C. indicum have not yet been reported. Thus, we explored the phytotoxic activity of C. indicum and identified its phytotoxic substance. In the experiment, the dry C. indicum leaves were extracted with aqueous methanol, and then the filtrate of the extracts was concentrated using a rotary evaporator to obtain crude extracts. The C. indicum crude extracts significantly inhibited the shoots and roots of six target species: alfalfa, cress, lettuce, barnyard grass, Italian ryegrass, and timothy. The inhibition increased when the extract concentration was increased. The crude extracts of C. indicum were separated in several chromatography steps, and a phytotoxic substance was isolated and characterized using spectroscopy as p-coumaric acid. p-Coumaric acid significantly suppressed the growth of lettuce and timothy seedlings at concentrations greater than 0.3 and 1 mM, respectively. The concentrations of p-coumaric acid required for 50% inhibition (I-50) of the shoots and roots of lettuce and timothy were 0.65 and 0.17 mM, and 0.81 and 0.67 mM, respectively. This study is the first report on isolating p-coumaric acid in C. indicum. The results, therefore, suggest that p-coumaric acid may partly contribute to the phytotoxic properties of C. indicum.

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  • First Total Synthesis and Structure-Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapis sp. Marine Cyanobacterium. 国際誌

    Arihiro Iwasaki, Kazuya Teranuma, Naoaki Kurisawa, Yulia Rahmawati, Ghulam Jeelani, Tomoyoshi Nozaki, William H Gerwick, Kiyotake Suenaga

    Journal of natural products   84 ( 9 )   2587 - 2593   2021年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Iheyamide A (1) is an antitrypanosomal linear peptide isolated from a Dapis sp. marine cyanobacterium by our group in 2020, and based on structure-activity relationships of its natural analogues, the C-terminal pyrrolinone moiety has been identified as the phamacophore for its antiparasitic activity. Further, we isolated this pyrrolinone moiety by itself as a new natural product from the marine cyanobacterium and named it iheyanone (2). As expected, iheyanone (2) showed antitrypanosomal activity, but its potency was weaker than iheyamide A (1). To clarify more detailed structure-activity relationships, we completed a total synthesis of iheyamide A (1) along with iheyanone (2) and evaluated the antitrypanosomal activities of several synthetic intermediates. As a result, we found that the longer the peptide chain, the stronger the antitrypanosomal activity. As iheyamide A (1) showed selective toxicity against Trypanosoma brucei rhodesiense, these findings can provide design guidelines for antitrypanosomal drugs.

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  • Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium. 国際誌

    Naoaki Kurisawa, Keisuke Otomo, Arihiro Iwasaki, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

    The Journal of organic chemistry   86 ( 18 )   12528 - 12536   2021年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC50 4.5 μM), compared to normal human cells (WI-38, IC50 > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.

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  • Isolation and Total Synthesis of Bromoiesol sulfates, Antitrypanosomal arylethers from a Salileptolyngbya sp. Marine Cyanobacterium. 国際誌

    Akira Ebihara, Arihiro Iwasaki, Youhei Miura, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

    The Journal of organic chemistry   86 ( 17 )   11763 - 11770   2021年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Bromoiesol sulfates A (1) and B (2), new polyhalogenated aryl sulfates, were isolated from a Salileptolyngbya sp. marine cyanobacterium along with their hydrolyzed compounds, bromoiesols A (3) and B (4). To pick up the candidates of their structures, we used Small Molecule Accurate Recognition Technology (SMART), an artificial intelligence-based structure-prediction tool, and their structures were elucidated on the basis of single-crystal X-ray diffraction analysis of bromoiesols (3 and 4). In addition, to verify the structures, the total synthesis of bromoiesol A sulfate (1) and bromoiesol A (3) was achieved. The bromoiesol family, especially bromoiesols (3 and 4), selectively inhibited the growth of the bloodstream form of Trypanosoma brucei rhodesiense, the causative agent of human African sleeping sickness.

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  • Phytotoxicity of the novel compound 3-hydroxy-4-oxo-β-dehydroionol and compound 3-oxo-α-ionone from Albizia richardiana (Voigt.) King &amp; Prain

    Kawsar Hossen, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Environmental Technology and Innovation   23   2021年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER  

    To protect our environment from the toxic effect of herbicides, it is necessary to reduce the application of synthetic herbicides for controlling weeds in crop fields as well as to increase the use of natural herbicides produced from plant sources. Phytotoxic compounds obtained from plant species have gained attention as an alternate biological method for managing weeds. Albizia richardiana was previously reported to contain a number of phytotoxic substances. Therefore, we carried out this study to investigate more allelopathic substances in Albizia richardiana leaves. Aqueous methanol extracts of Albizia richardiana leaves were significantly inhabited the seedling growth of the two test species (alfalfa and timothy) in a concentration-dependent manner. The two most active substances were separated through different chromatographic steps and characterized as a novel compound 3-hydroxy-4-oxo-β-dehydroionol [(E)-6-hydroxy-3-(3-hydroxybut-1-en-1-yl)-2,4,4-trimethylcyclohexa-2,5-dien-1-one], and compound 3-oxo-α-ionone [3,5,5-trimethyl-4-(3-oxo-1-butenyl)-2-cyclohexen-1-one]. The novel compound 3-hydroxy-4-oxo-β-dehydroionol showed relatively stronger growth inhibitory potential compare to the compound 3-oxo-α-ionone and significantly restricted the seedling growth of crees and timothy. The required concentration for 50% reduction in the growth (I50 values) of the cress and timothy seedlings varied from 63.78 to 141.61 μM for 3-hydroxy-4-oxo-β-dehydroionol and 1059.60 to 1616.10 μM for 3-oxo-α-ionone. The results indicate that these two allelopathic compounds may be responsible for the phytotoxicity of Albizia richardiana leaves.

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  • Metabolomic Characterization of a cf. Neolyngbya Cyanobacterium from the South China Sea Reveals Wenchangamide A, a Lipopeptide with In Vitro Apoptotic Potential in Colon Cancer Cells. 国際誌

    Lijian Ding, Rinat Bar-Shalom, Dikla Aharonovich, Naoaki Kurisawa, Gaurav Patial, Shuang Li, Shan He, Xiaojun Yan, Arihiro Iwasaki, Kiyotake Suenaga, Chengcong Zhu, Haixi Luo, Fuli Tian, Fuad Fares, C Benjamin Naman, Tal Luzzatto-Knaan

    Marine drugs   19 ( 7 )   2021年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Metabolomics can be used to study complex mixtures of natural products, or secondary metabolites, for many different purposes. One productive application of metabolomics that has emerged in recent years is the guiding direction for isolating molecules with structural novelty through analysis of untargeted LC-MS/MS data. The metabolomics-driven investigation and bioassay-guided fractionation of a biomass assemblage from the South China Sea dominated by a marine filamentous cyanobacteria, cf. Neolyngbya sp., has led to the discovery of a natural product in this study, wenchangamide A (1). Wenchangamide A was found to concentration-dependently cause fast-onset apoptosis in HCT116 human colon cancer cells in vitro (24 h IC50 = 38 μM). Untargeted metabolomics, by way of MS/MS molecular networking, was used further to generate a structural proposal for a new natural product analogue of 1, here coined wenchangamide B, which was present in the organic extract and bioactive sub-fractions of the biomass examined. The wenchangamides are of interest for anticancer drug discovery, and the characterization of these molecules will facilitate the future discovery of related natural products and development of synthetic analogues.

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  • Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.

    Arihiro Iwasaki, Naoaki Kurisawa, Tingting Wang, Xiaohui Li, Haixi Luo, Chengcong Zhu, Gaurav Patial, Xiaojun Yan, Shan He, Tal Luzzatto-Knaan, Fuli Tian, C. Benjamin Naman, Kiyotake Suenaga

    TETRAHEDRON LETTERS   75   2021年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Lingaoamide (1), a new cyclic heptapeptide natural product, was isolated from a freshwater Oscillatoria cyanobacterium. The producing organism was collected in Chinese water spinach paddy farm fields in Lingao County, Hainan, China. The structure of 1 was determined by conventional mass spectrometry, NMR spectroscopy, and chemical degradation studies. Lingaoamide concentration-dependently up-regulates the biogenesis of pro-pathogenic melanin pigments (melanogenesis) in the rice blast fungus, Magnaporthe grisea, when tested in vitro. This molecule also exhibits weak in vitro inhibition (MIC 32 mu g/mL) of Gram-negative Pseudomonas aeruginosa and Gram-positive Bacillus pumilus, and does not appear to impact plant growth or immune response in vivo using the model organism, Arabidopsis thaliana. (C) 2021 Elsevier Ltd. All rights reserved.

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  • Motobamide, an Antitrypanosomal Cyclic Peptide from a Leptolyngbya sp. Marine Cyanobacterium. 国際誌

    Hiroki Takahashi, Arihiro Iwasaki, Naoaki Kurisawa, Ryota Suzuki, Ghulam Jeelani, Teruhiko Matsubara, Toshinori Sato, Tomoyoshi Nozaki, Kiyotake Suenaga

    Journal of natural products   84 ( 5 )   1649 - 1655   2021年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Motobamide (1), a new cyclic peptide containing a C-prenylated cyclotryptophan residue, was isolated from a marine Leptolyngbya sp. cyanobacterium. Its planar structure was established by spectroscopic and MS/MS analyses. The absolute configuration was elucidated based on a combination of chemical degradations, chiral-phase HPLC analyses, spectroscopic analyses, and computational chemistry. Motobamide (1) moderately inhibited the growth of bloodstream forms of Trypanosoma brucei rhodesiense (IC50 2.3 μM). However, it exhibited a weaker cytotoxicity against normal human cells (IC50 55 μM).

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  • Correction to Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium. 国際誌

    Naoaki Kurisawa, Arihiro Iwasaki, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

    Journal of natural products   84 ( 4 )   1423 - 1423   2021年4月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/acs.jnatprod.1c00282

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  • Komesuamide and odopenicillatamide, two linear lipopeptides from the marine cyanobacterium Caldora penicillata

    Kaori Ozaki, Atsuhide Jinno, Noriyuki Natsume, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    TETRAHEDRON   85   2021年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The linear lipopeptides komesuamide (1) and odopenicillatamide (2) were isolated from Caldora penicillata a marine cyanobacterium collected in Okinawa. The structures of these compounds were established by spectroscopic analyses, and the absolute configurations were determined by HPLC analyses of the acid hydrolysates. Both compounds showed glucose uptake activity at 40 mM in cultured L6 myotubes. (C) 2021 Elsevier Ltd. All rights reserved.

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  • Isolation and identification of three potential phytotoxic compounds from Chrysopogon aciculatus (Retz.) Trin

    Md Shafiqul Islam, Farhana Zaman, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Acta Physiologiae Plantarum   43 ( 4 )   2021年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER HEIDELBERG  

    We conducted an investigation to search for the possibility of phytotoxic compounds and then identify them in C. aciculatus. The aqueous methanol extracts of C. aciculatus imposed a strong suppressive effect on the shoots and roots growth of Medicago sativa and Echinochloa crus-galli. The C. aciculatus extracts were subsequently purified through chromatography and three growth-inhibitory compounds were identified by spectral data as methyl cis-p-coumarate, methyl trans-p-coumarate, and trans-ferulaldehyde. The seedlings growth of Lepidium sativum was suppressed by methyl cis-p-coumarate, methyl trans-p-coumarate, and trans-ferulaldehyde. The I50 values (concentration required for 50% growth inhibition) for the seedling growth of L. sativum ranged from 1.25 to 1.73 mM for methyl cis-p-coumarate, 0.74 to 1.23 mM for methyl trans-p-coumarate, and 1.05 to 1.84 mM for trans-ferulaldehyde. Our finding indicates that methyl cis-p-coumarate, methyl trans-p-coumarate, and trans-ferulaldehyde may contribute to the phytotoxic effects of C. aciculatus.

    DOI: 10.1007/s11738-021-03221-5

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  • Identification and Application of Bioactive Compounds from Garcinia xanthochymus Hook. for Weed Management

    Md Mahfuzur Rob, Kawsar Hossen, Mst. Rokeya Khatun, Keitaro Iwasaki, Arihiro Iwasaki, Kiyotake Suenaga, HISASHI KATO-NOGICHI

    Applied Sciences   11 ( 5 )   2021年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    The allelopathic potential of plant species and their related compounds has been increasingly reported to be biological tools for weed control. The allelopathic potential of Garcinia xanthochymus was assessed against several test plant species: lettuce, rapeseed, Italian ryegrass, and timothy. The extracts of G. xanthochymus leaves significantly inhibited all the test plants in a concentration- and species-specific manner. Therefore, to identify the specific compounds involved in the allelopathic activity of the G. xanthochymus extracts, assay-guided purification was carried out and two allelopathic compounds were isolated and identified as methyl phloretate {3-(4-hydroxyphenyl) propionic acid methyl ester} and vanillic acid (4-hydroxy-3-methoxybenzoic acid). Both of the substances significantly arrested the cress and timothy seedlings growth. I-50 values (concentrations required for 50% inhibition) for shoots and roots growth of the cress and timothy were 113.6-104.6 and 53.3-40.5 mu M, respectively, for methyl phloretate, and 331.6-314.7 and 118.8-107.4 mu M, respectively, for vanillic acid, which implied that methyl phloretate was close to 3- and 2-fold more effective than vanillic acid against cress and timothy, respectively. This report is the first on the presence of methyl phloretate in a plant and its phytotoxic property. These observations suggest that methyl phloretate and vanillic acid might participate in the phytotoxicity of G. xanthochymus extract.

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  • Bioorganic Study of New Natural Products Isolated from Marine Cyanobacteria

    Arihiro Iwasaki, Kiyotake Suenaga

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   79 ( 2 )   133 - 144   2021年2月

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    記述言語:日本語   出版者・発行元:SOC SYNTHETIC ORGANIC CHEM JPN  

    Natural products, well known for unique chemical diversity and bioactivity, are the compounds that organisms have acquired in evolutionary history. They have attracted attentions from not only organic chemists but also scientists in related fields and have provided breakthroughs for science. Against this background, we have investigated the secondary metabolites of marine organisms, especially cyanobacteria, and have discovered various novel bioactive compounds. In this account, our recent research activities regarding the isolation, structure determination, total syntheses and biological activities of our novel natural products are described.

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  • Phytotoxic Activity and Growth Inhibitory Substances from Albizia richardiana (Voigt.) King &amp; Prain

    Kawsar Hossen, Arihiro Iwasaki, Kiyotake Suenaga, HISASHI KATO-NOGICHI

    Applied Sciences   11 ( 4 )   2021年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Albizia richardiana, a fast-growing, large deciduous tree belonging to the Fabaceae family, grows well in hot and humid areas but mainly grows in the tropics of the Old World. The medicinal and other uses of Albizia richardiana are well documented, but the phytotoxic effects of this tree have not yet been investigated. We conducted this study to investigate the phytotoxic activity of Albizia richardiana leaves and to identify growth inhibitory substances for controlling weeds in a sustainable way. Aqueous methanol extracts of Albizia richardiana leaves greatly suppressed the growth of cress and barnyard grass seedlings in a concentration- and species-dependent manner. Two phytotoxic substances were separated using several purification steps and characterized through spectral analysis as dehydrovomifoliol and loliolide. Dehydrovomifoliol and loliolide significantly arrested the seedling growth of cress in the concentrations of 0.1 and 0.01 mM, respectively. The extract concentrations needed for 50% growth inhibition (I-50 values) of cress seedlings were 3.16-3.01 mM for dehydrovomifoliol and 0.03-0.02 mM for loliolide. The results suggest that these two allelopathic substances might play a vital role in the phytotoxicity of Albizia richardiana leaves.

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  • Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium Caldora penicillata. 国際誌

    Arihiro Iwasaki, Keisuke Ohtomo, Naoaki Kurisawa, Ikuma Shiota, Yulia Rahmawati, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

    Journal of natural products   84 ( 1 )   126 - 135   2021年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Hoshinoamide C (1), an antiparasitic lipopeptide, was isolated from the marine cyanobacterium Caldora penicillata. Its planar structure was elucidated by spectral analyses, mainly 2D NMR, and the absolute configurations of the α-amino acid moieties were determined by degradation reactions followed by chiral-phase HPLC analyses. To clarify the absolute configuration of an unusual amino acid moiety, we synthesized two possible diastereomers of hoshinoamide C and determined its absolute configuration based on a comparison of their spectroscopic data with those of the natural compound. Hoshinoamide C (1) did not exhibit any cytotoxicity against HeLa or HL60 cells at 10 μM, but inhibited the growth of the parasites responsible for malaria (IC50 0.96 μM) and African sleeping sickness (IC50 2.9 μM).

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  • Allelopathic Potential and Active Substances from Wedelia Chinensis (Osbeck). 国際誌

    Kawsar Hossen, Krishna Rany Das, Shun Okada, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Foods (Basel, Switzerland)   9 ( 11 )   2020年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Wedelia chinensis (Asteraceae) is a wetland herb native to India, China, and Japan. It is a valuable medicinal plant recorded to have pharmaceutical properties. However, the phytotoxic potential of Wedelia chinensis has not yet been examined. Thus, we carried out this study to establish the allelopathic effects of Wedelia chinensis and to identify its phytotoxic substances. Extracts of Wedelia chinensis exhibited high inhibitory activity against the root and shoot growth of cress, alfalfa, rapeseed, lettuce, foxtail fescue, Italian ryegrass, timothy, and barnyard grass. The inhibition was varied with species and was dependent on concentrations. The extracts were separated through several purification steps, and the two effective substances were isolated and characterized as vanillic acid and gallic acid using spectral analysis. Vanillic acid and gallic acid significantly arrested the growth of cress and Italian ryegrass seedlings. The concentrations of vanillic acid and gallic acid needed for 50% inhibition (I50 values) of the seedling growth of the cress and Italian ryegrass were 0.04-15.4 and 0.45-6.6 mM, respectively. The findings suggest that vanillic acid and gallic acid may be required for the growth inhibitory activities of Wedelia chinensis.

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  • Dactylospenes A-E, Sesterterpenes from the Marine Sponge Dactylospongia elegans. 査読 国際誌

    Hao-Bing Yu, Bin-Bin Gu, Arihiro Iwasaki, Wen-Li Jiang, Andrew Ecker, Shu-Ping Wang, Fan Yang, Hou-Wen Lin

    Marine drugs   18 ( 10 )   2020年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Chemical investigation on a marine sponge, Dactylospongia elegans, yielded five new γ-oxygenated butenolide sesterterpene derivatives, dactylospenes A-E (1-5), as well as two known biosynthetically related compounds, luffariellolide (6) and furospinosulin B (7). The structures of these compounds were elucidated on the basis of their spectroscopic data, experimental and calculated electronic circular dichroism (ECD) analysis, as well as comparison of the NMR data with those of known analogs. These metabolites are the first γ-oxygenated butenolide sesterterpenes to be reported from this genus. These compounds were evaluated in antimicrobial, anti-inflammatory, and cytotoxic assays. Only compounds 1, 3, and 6 exhibited moderate cytotoxicity against DU145, SW1990, Huh7, and PANC-1 cancer cell lines with IC50 values in the range of 2.11-13.35 μM. Furthermore, compound 2, without cytotoxicity, exhibited significant inhibitory effects (inhibitory rate 77.5%) on nitric oxide production induced by lipopolysaccharide at 10 μM.

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  • Potential use of Schumannianthus dichotomus waste: the phytotoxic activity of the waste and its identified compounds. 査読 国際誌

    Md Mahfuzur Rob, Arihiro Iwasaki, Kiyotake Suenaga, Kaori Ozaki, Toshiaki Teruya, Hisashi Kato-Noguchi

    Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes   55 ( 12 )   1 - 7   2020年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS INC  

    The phytotoxic potential of the leaves and twigs of Schumannianthus dichotomus, discarded in the mat-making industry against four test plants (lettuce (Lactuca sativa L.), rapeseed (Brassica napus L.), foxtail fescue (Vulpia myuros (L.) C.C. Gmel.) and timothy (Phleum pratense L.)) was investigated and found strong phytotoxic activity. An assay-guided fractionation of S. dichotomus extarcts against cress (Lepidium sativum L.) through a series of column chromatography steps yielded two compounds, 8-(5-oxo-2,5-dihydrofuran-2-yl) octanoic acid (ODFO) and (E)-6-hydroxy-2,6-dimethylocta-2,7-dienoic acid (8-carboxylinalool). ODFO and 8-carboxylinalool showed strong phytotoxic activity against cress and timothy. The concentrations required for 50% growth inhibition (I50 value) of the seedlings of cress and timothy were 111.94-128.01 and 36.30-91.75 µM, respectively, for ODFO, but the values were much higher at 315.98-379.13 and 107.92-148.41 µM, respectively, for 8-carboxylinalool, indicating the stronger phytotoxic activity of ODFO. This study is the first to isolate ODFO and 8-carboxylinalool from S. dichotomus and their phytotoxic potential while ODFO is firstly encountered from any natural source. The growth inhibitory activity of the identified compounds may explain their role in the phytotoxic activity of S. dichotomus, which suggests the possible use of its leaves and twigs or its active constituents as natural bioherbicides.

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  • Assessment of allelopathic potential of Dalbergia cochinchinensis Pierre and its growth inhibitory substance

    Ramida Krumsri, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    EMIRATES JOURNAL OF FOOD AND AGRICULTURE   32 ( 7 )   513 - 521   2020年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:UNITED ARAB EMIRATES UNIV  

    In forestry systems, many types of forest trees possess allelopathic properties and release a wide variety of allelochemicals that influence the growth and development of surrounding species. Dalbergia cochinchinensis, a forest tree distributed in Southeast Asia, is reputed to possess several biological properties and contain several secondary compounds. However, there have been no studies on the allelopathy of D. cochinchinensis. Therefore, D. cochinchinensis leaf extracts were examined for allelopathic potential. The present study showed that D. cochinchinensis extracts significantly inhibited the seedling growth of six test plant species: timothy, Italian ryegrass, barnyard grass, cress, alfalfa, and lettuce. Concentrations of the D. cochinchinensis extracts negatively correlated with the shoot length (r =-0.50 to -0.89) and root length (r =-0.65 to -0.89) of all the test plant species. The extracts were then purified using several chromatographic steps and the growth inhibitory substance was isolated. The chemical structure of the substance was identified through spectroscopic analysis as 3,4-dihydroxybenzoic acid (protocatechuic acid). Protocatechuic acid at a concentration higher than 3 mM significantly inhibited the growth of cress seedlings, whereas barnyard grass seedlings were inhibited at concentrations higher than 0.3 mM. As the protocatechuic acid concentration increased, the seedling growth of cress and barnyard grass was significantly reduced. I-50 values showed the effectiveness of protocatechuic acid against both test plant species was apparently greater on root growth than shoot growth. Results of this study suggest that protocatechuic acid isolated from D. cochinchinensis might be responsible for its inhibitory effects.

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  • Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Aki Yamano, Noriyuki Natsume, Miki Yamada, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    Journal of natural products   83 ( 5 )   1585 - 1591   2020年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Irijimasides A-E (1-5), a series of new 14-membered macrolide glycosides, were isolated from a marine cyanobacterium collected in Okinawa. The gross structures of 1-5 were established by spectroscopic analysis, including 2D NMR, while absolute stereostructures were determined based on NOESY spectra, chemical derivatization, and ECD data. All five macrolides suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced tartrate-resistant acid phosphatase (TRAP) activity in mouse RAW264 macrophage cells, indicating that these compounds inhibit osteoclast formation.

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  • Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium. 査読 国際誌

    Naoaki Kurisawa, Arihiro Iwasaki, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

    Journal of natural products   83 ( 5 )   1684 - 1690   2020年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Iheyamides A (1), B (2), and C (3), new linear peptides, were isolated from a marine Dapis sp. cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Iheyamide A (1) showed moderate antitrypanosomal activities against Trypanosoma brucei rhodesiense and Trypanosoma brucei brucei (IC50 = 1.5 μM), but the other two analogues, iheyamides B (2) and C (3), did not (IC50 > 20 μM, respectively). The structure-activity relationship clarified that an isopropyl-O-Me-pyrrolinone moiety was necessary for the antitrypanosomal activity. Furthermore, the cytotoxicity of 1 against normal human cells, WI-38, was 10 times weaker than its antitrypanosomal activity (IC50 = 18 μM).

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  • A kaurene-type novel phytotoxic substance in Wedelia chinensis

    Krishna Rany Das, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Tetrahedron Letters   61 ( 11 )   2020年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    © 2020 Elsevier Ltd Wedelia chinensis has been widely used as a traditional medicine and several bioactive compounds have been isolated. We investigated phytotoxic property and phytotoxic substances in the species. An aqueous methanol extract of W. chinensis inhibited the growth of roots and shoots of cress. The extracts were then purified by several chromatographic runs with monitoring the inhibitory activity and a phytotoxic substance was isolated. The substance was determined by spectral data to be a novel kaurene-type compound, wedelienone. Wedelienone inhibited the growth of cress and timothy (Phleum pratense L) at concentrations greater than 10–30 μM. These results suggest that wedelienone may contribute to the phytotoxic effects caused by the extracts.

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  • Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Keitaro Iwasaki, Arihiro Iwasaki, Shimpei Sumimoto, Teruhiko Matsubara, Toshinori Sato, Tomoyoshi Nozaki, Yumiko Saito-Nakano, Kiyotake Suenaga

    Journal of natural products   83 ( 2 )   481 - 488   2020年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    An antimalarial lipopeptide, ikoamide, was isolated from an Okeania sp. marine cyanobacterium. Its gross structure was established by spectroscopic analyses, and the absolute configuration was clarified based on a combination of chiral-phase HPLC analyses, spectroscopic analyses, and derivatization reactions. Ikoamide showed strong antimalarial activity with an IC50 value of 0.14 μM without cytotoxicity against human cancer cell lines at 10 μM.

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  • Phytotoxic Activity and Identification of Phytotoxic Substances from Schumannianthus dichotomus. 査読 国際誌

    Md Mahfuzur Rob, Kawsar Hossen, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Plants (Basel, Switzerland)   9 ( 1 )   2020年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    The phytotoxic potential of plants and their constituents against other plants is being increasingly investigated as a possible alternative to synthetic herbicides to control weeds in crop fields. In this study, we explored the phytotoxicity and phytotoxic substances of Schumannianthus dichotomus, a perennial wetland shrub native to Bangladesh, India, and Myanmar. Leaf extracts of S. dichotomus exerted strong phytotoxicity against two dicot species, alfalfa and cress, and two monocot species, barnyard grass and Italian ryegrass. A bioassay-driven purification process yielded two phenolic derivatives, syringic acid and methyl syringate. Both constituents significantly inhibited the growth of cress and Italian ryegrass in a concentration-dependent manner. The concentrations required for 50% growth inhibition (I50 value) of the shoot and root growth of cress were 75.8 and 61.3 μM, respectively, for syringic acid, compared with 43.2 and 31.5 μM, respectively, for methyl syringate. Similarly, to suppress the shoot and root growth of Italian rye grass, a greater amount of syringic acid (I50 = 213.7 and 175.9 μM) was needed than methyl syringate (I50 = 140.4 to 130.8 μM). Methyl syringate showed higher phytotoxic potential than syringic acid, and cress showed higher sensitivity to both substances. This study is the first to report on the phytotoxic potential of S. dichotomus and to identify phytotoxic substances from this plant material.

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  • Allelopathic potential and identification of two allelopathic substances in Eleocharis atropurpurea

    Zaman, F., Iwasaki, A., Suenaga, K., Kato-Noguchi, H.

    Plant Biosystems   155 ( 3 )   510 - 516   2020年

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    掲載種別:研究論文(学術雑誌)  

    Eleocharis atropurpurea is an annual weed and distributed widely in pantropical and subtropical regions. Yet, there have been no studies on the allelopathy of E. atropurpurea. Therefore, we investigated the allelopathic potential of E. atropurpurea to identify allelopathic substances from it. The aqueous methanolic extracts of E. atropurpurea showed an inhibitory effect on the seedling growth of lettuce, rapeseed, barnyard grass and foxtail fescue. Inhibition was species- and concentration-dependent. Two substances, syringaldehyde and acetosyringone, were isolated by using chromatography and using spectroscopy their structures were determined. Syringaldehyde and acetosyringone inhibited the shoot and root growth of cress and barnyard grass at concentrations greater than 3.0 mM except shoot growth of barnyard grass by acetosyringone. Concentration and seedling growth of cress and barnyard grass displayed a negative correlation. The I 50 values of syringaldehyde and acetosyringone for the shoot and root growth of cress were 1.67 and 1.61 mM, and 1.49, and 1.29 mM, respectively, whereas for the shoot and root growth of barnyard grass the values were 4.09 and 2.41 mM, and 4.54 and 1.92 mM, respectively. Therefore, it is suggested that these compounds may contribute to the inhibitory effects of E. atropurpurea.

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  • Tree Fern Cyathea lepifera May Survive by Its Phytotoxic Property. 査読 国際誌

    Noriyuki Ida, Arihiro Iwasaki, Toshiaki Teruya, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Plants (Basel, Switzerland)   9 ( 1 )   2019年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Cyatheaceae (tree ferns) appeared during the Jurassic period and some of the species still remain. Those species may have some morphological and/or physiological characteristics for survival. A tree fern was observed to suppress the growth of other ligneous plants in a tropical forest. It was assumed that the fern may release toxic substances into the forest floor, but those toxic substances have not yet been identified. Therefore, we investigated the phytotoxicity and phytotoxic substances of Cyathea lepifera (J. Sm. ex Hook.) Copel. An aqueous methanol extract of C. lepifera fronds inhibited the growth of roots and shoots of dicotyledonous garden cress (Lepidum sativum L.), lettuce (Lactuca sativa L.), and alfalfa (Medicago sativa L.), and monocotyledonous ryegrass (Lolium multiflorum Lam.), timothy (Phleum pratense L.), and barnyardgrass (Echinochloa crus-galli (L.) P. Beauv.). The results suggest that C. lepifera fronds may have phytotoxicity and contain some phytotoxic substances. The extract was purified through several chromatographic steps during which inhibitory activity was monitored, and p-coumaric acid and (-)-3-hydroxy-β-ionone were isolated. Those compounds showed phytotoxic activity and may contribute to the phytotoxic effects caused by the C. lepifera fronds. The fronds fall and accumulate on the forest floor through defoliation, and the compounds may be released into the forest soils through the decomposition process of the fronds. The phytotoxic activities of the compounds may be partly responsible for the fern's survival.

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  • Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Kaori Ozaki, Arihiro Iwasaki, Dai Sezawa, Haruka Fujimura, Tomoyoshi Nozaki, Yumiko Saito-Nakano, Kiyotake Suenaga, Toshiaki Teruya

    Journal of natural products   82 ( 10 )   2907 - 2915   2019年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The bioassay-guided fractionation of an Okeania sp. marine cyanobacterium collected in Okinawa led to the isolation of the lipopeptide mabuniamide (1). The gross structure of 1 was determined by spectroscopic analyses, and its absolute configuration was determined using Marfey's analysis of the acid hydrolysate of 1. The absolute configuration of 1 was confirmed by total synthesis. Mabuniamide (1) stimulated glucose uptake in cultured rat L6 myotubes. In addition, mabuniamide (1) and its stereoisomer (2) exhibited moderate antimalarial activity.

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  • Cytotoxic Microcolin Lipopeptides from the Marine Cyanobacterium Moorea producens. 査読 国際誌

    Hao-Bing Yu, Evgenia Glukhov, Yueying Li, Arihiro Iwasaki, Lena Gerwick, Pieter C Dorrestein, Bing-Hua Jiao, William H Gerwick

    Journal of natural products   82 ( 9 )   2608 - 2619   2019年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Nine new linear lipopeptides, microcolins E-M (1-9), together with four known related compounds, microcolins A-D (10-13), were isolated from the marine cyanobacterium Moorea producens using bioassay-guided and LC-MS/MS molecular networking approaches. Catalytic hydrogenation of microcolins A-D (10-13) yielded two known compounds, 3,4-dihydromicrocolins A and B (14, 15), and two new derivatives, 3,4-dihydromicrocolins C and D (16, 17), respectively. The structures of these new compounds were determined by a combination of spectroscopic and advanced Marfey's analysis. Structurally unusual amino acid units, 4-methyl-2-(methylamino)pent-3-enoic (Mpe) acid and 2-amino-4-methylhexanoic acid (N-Me-homoisoleucine), in compounds 1-3 and 8, respectively, are rare residues in naturally occurring peptides. These metabolites showed significant cytotoxic activity against H-460 human lung cancer cells with IC50 values ranging from 6 nM to 5.0 μM. The variations in structure and attendant biological activities provided fresh insights concerning structure-activity relationships for the microcolin class of lipopeptides.

    DOI: 10.1021/acs.jnatprod.9b00549

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  • Garcienone, a Novel Compound Involved in Allelopathic Activity of Garcinia Xanthochymus Hook. 査読 国際誌

    Md Mahfuzur Rob, Arihiro Iwasaki, Ryota Suzuki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Plants (Basel, Switzerland)   8 ( 9 )   2019年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Plants are sources of diversified allelopathic substances that can be investigated for use in eco-friendly and efficient herbicides. An aqueous methanol extract from the leaves of Garcinia xanthochymus exhibited strong inhibitory activity against barnyard grass (Echinochloa crus-galli (L.) P. Beauv.), foxtail fescue (Vulpia myuros (L.) C.C.), alfalfa (Medicago sativa L.), and cress (Lepidium sativum L.), and appears to be a promising source of allelopathic substances. Hence, bio-activity guided purification of the extract through a series of column chromatography steps yielded a novel compound assigned as garcienone ((R, E)-5-hydroxy-5-((6S, 9S)-6-methyl-9-(prop-13-en-10-yl) tetrahydrofuran-6-yl) pent-3-en-2-one). Garcienone significantly inhibited the growth of cress at a concentration of 10 μM. The concentrations resulting in 50% growth inhibition (I50) of cress roots and shoots were 120.5 and 156.3 μM, respectively. This report is the first to isolate and identify garcienone and to determine its allelopathic potential.

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  • Marine Natural Products: A Source of Novel Anticancer Drugs. 査読 国際誌

    Shaden A M Khalifa, Nizar Elias, Mohamed A Farag, Lei Chen, Aamer Saeed, Mohamed-Elamir F Hegazy, Moustafa S Moustafa, Aida Abd El-Wahed, Saleh M Al-Mousawi, Syed G Musharraf, Fang-Rong Chang, Arihiro Iwasaki, Kiyotake Suenaga, Muaaz Alajlani, Ulf Göransson, Hesham R El-Seedi

    Marine drugs   17 ( 9 )   2019年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI  

    Cancer remains one of the most lethal diseases worldwide. There is an urgent need for new drugs with novel modes of action and thus considerable research has been conducted for new anticancer drugs from natural sources, especially plants, microbes and marine organisms. Marine populations represent reservoirs of novel bioactive metabolites with diverse groups of chemical structures. This review highlights the impact of marine organisms, with particular emphasis on marine plants, algae, bacteria, actinomycetes, fungi, sponges and soft corals. Anti-cancer effects of marine natural products in in vitro and in vivo studies were first introduced; their activity in the prevention of tumor formation and the related compound-induced apoptosis and cytotoxicities were tackled. The possible molecular mechanisms behind the biological effects are also presented. The review highlights the diversity of marine organisms, novel chemical structures, and chemical property space. Finally, therapeutic strategies and the present use of marine-derived components, its future direction and limitations are discussed.

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  • Total Synthesis, Stereochemical Revision, and Biological Assessment of Iriomoteolide-2a. 査読 国際誌

    Keita Sakamoto, Akihiro Hakamata, Arihiro Iwasaki, Kiyotake Suenaga, Masashi Tsuda, Haruhiko Fuwa

    Chemistry (Weinheim an der Bergstrasse, Germany)   25 ( 36 )   8528 - 8542   2019年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Iriomoteolide-2a is a marine macrolide metabolite isolated from a cultured broth of the benthic dinoflagellate Amphidinium sp. HYA024 strain. This naturally occurring substance was reported to show remarkable cytotoxic activity against human cancer cell lines HeLa and DG-75 and in vivo antitumor activity against murine leukemia P388 cell line. Herein, the total synthesis, stereochemical revision, and biological assessment of iriomoteolide-2a are reported in detail. Total synthesis of the proposed structure 1 of iriomoteolide-2a featured a late-stage convergent assembly of three components by a Suzuki-Miyaura coupling, an esterification, and a ring-closing metathesis. However, the NMR data of synthetic 1 were not identical to those of the natural product. Careful analysis of the NMR data of the authentic material and synthesis/NMR analysis of appropriately designed model compounds led to consideration of four possible stereoisomers 2-5 as candidates for the correct structure. Accordingly, total syntheses of 2-5 were achieved by taking advantage of the convergent strategy, and comparison of the NMR spectra of synthetic 2-5 with those of the natural product led to the conclusion that 5 shows the correct relative configuration of iriomoteolide-2a. The absolute configuration of this natural product was finally established through chiral HPLC analysis of synthetic 5/ent-5 with the authentic sample. The antiproliferative activity of the synthetic compounds was assessed against HeLa and A549 cells to show that, in contrast to expectation, synthetic 5 and ent-5 were only marginally active in these cell lines. This work clearly underscores the vital role of total synthesis in the establishment of the structure and biological activity of natural products.

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  • Phytotoxic potential of Chrysopogon aciculatus (Retz.) Trin. (Poaceae)

    Md Shafiqul Islam, Farhana Zaman, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Weed Biology and Management   19 ( 2 )   51 - 58   2019年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2019 Weed Science Society of Japan The creeping weed, Chrysopogon aciculatus (Retz.) Trin., is widely known for its use as folk medicine, while its phytotoxic potential has not been examined. Therefore, we carried out an investigation into the phytotoxic potential of C. aciculatus to identify phytotoxic substances. C. aciculatus extracts showed inhibitory effects on shoot and root growth of cress, lettuce, rapeseed, and Italian ryegrass. Inhibition was both species-dependent and concentration-dependent. Two substances, (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (9-HO-ODDEA) and rhizopycnin A, were isolated using chromatographies and characterized by spectral analysis. 9-HO-ODDEA retarded shoot and root growth of cress at concentrations higher than 1.0 and 0.3 mM, respectively, while on cress seedling by rhizopycnin A, the inhibition began from 1.0 mM. The concentrations needed for 50% inhibition of the shoot and root growth of test plants ranged from 1.71–2.31, and 0.71–0.72 mM for 9-HO-ODDEA and rhizopycnin A, respectively. These results indicate that these substances may contribute, to a certain extent, to the phytotoxic activity of C. aciculatus.

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  • Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata

    Kaori Ozaki, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    TETRAHEDRON   75 ( 25 )   3382 - 3386   2019年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC50 values of 0.13 nM and 1.1 mu M. (C) 2019 Elsevier Ltd. All rights reserved.

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  • Allelopathic Potency and an Active Substance from Anredera cordifolia (Tenore) Steenis. 査読 国際誌

    Ichsan Nurul Bari, Hisashi Kato-Noguchi, Arihiro Iwasaki, Kiyotake Suenaga

    Plants (Basel, Switzerland)   8 ( 5 )   2019年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Plants  

    Anredera cordifolia (Tenore) Steenis is widely planted as an ornamental and medicinal plant in Indonesia. On the other hand, in some other countries this plant is classified as a noxious weed. As a harmful weed, A. cordifolia is reported to have the ability to smother all native vegetation, collapse canopies of tall trees, cultivate as a ground cover and disrupt native seedling development. There is no available information about the involvement of any allelochemicals from A. cordifolia related to these issues. The present study evaluated the allelopathic effect by isolating and identifying the allelopathic substance from A. cordifolia leaf extract. The allelopathic potency of A. cordifolia was determined by a series of bioassays of shoot and root growth on some selected test plants. Separation and purification of the active substances was achieved through several chromatography processes. Finally, the substances with allelopathic activity were identified through high-resolution electrospray ionization mass spectrometry (HRESIMS) analysis and determined by the specific rotation of compound, proton and carbon NMR spectroscopies. The results show that A. cordifolia possesses allelopathic properties which affect other plant species. The isolated compound from the plant material, 3-hydroxy-alpha-ionone, may contribute to the allelopathic effects of A. cordifolia.

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  • (+)-Isoamericanol A: A Plant Growth Inhibitor from Heliotropium indicum

    Sirinapa Chaipon, Sutjaritpan Boonmee, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Natural Product Communications   14 ( 5 )   2019年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © The Author(s) 2019 Article reuse guidelines: sagepub.com/journals-permissions A plant growth inhibitory substance was isolated from Heliotropium indicum by bioassay-guided purification and characterized to be (+)-isoamericanol A. (+)-Isoamericanol A significantly inhibited seedling growth of cress at a concentration greater than 0.1 mM. The concentrations of (+)-isoamericanol A required for 50% growth inhibition of cress roots and hypocotyls were 0.5 and 0.4 mM, respectively. This inhibition indicates that (+)-isoamericanol A had a growth inhibitory activity and may contribute to the allelopathic effect of H. indicum. This report is the first on the plant growth inhibitory activity of (+)-isoamericanol A as an allelopathic substance.

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  • Phytotoxic activity of Chinese violet (Asystasia gangetica (L.) T. Anderson) and two phytotoxic substances

    Masahiko Suzuki, M. A. Chozin, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Weed Biology and Management   19 ( 1 )   3 - 8   2019年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2019 Weed Science Society of Japan Chinese violet (Asystasia gangetica (L.) T. Anderson) is a perennial invasive weed belonging to Acanthaceae. Leaves of this weed have been suggested to possess phytotoxic activity. However, phytotoxic substances in this weed have not yet been reported. Therefore, the present study investigated phytotoxic activity of Chinese violet extracts and phytotoxic substances. The extracts of Chinese violet leaves inhibited the root and shoot growth of cress, lettuce, alfalfa, barnyard grass, ryegrass, and timothy, where the level of inhibition increased with increasing extract concentrations. Bioassay-guided separations of the extracts led to isolation of two phytotoxic substances, indole-3-carboxaldehyde and (6R,9S)-3-oxo-α-ionol. Indole-3-carboxaldehyde significantly inhibited the root and shoot growth of cress at concentrations ≥100 and 30 μmol L −1 , respectively, and concentrations of the substance required for 50% growth inhibition were 210 and 127 μmol L −1 for cress roots and shoots, respectively. The other substance, (6R,9S)-3-oxo-α-ionol, was reported to have strongly inhibited cress roots and shoots. The present results suggest that Chinese violet contains two phytotoxic substances indole-3-carboxaldehyde and (6R,9S)-3-oxo-α-ionol, and those substances may play an important role in the phytotoxic activity of Chinese violet.

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  • Phytotoxic activity of kiwifruit leaves and isolation of a phytotoxic substance 査読

    Okada, S., Iwasaki, A., Kataoka, I., Suenaga, K., Kato-Noguchi, H.

    Scientia Horticulturae   250   243 - 248   2019年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.scienta.2019.02.029

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  • Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta. 査読 国際誌

    Shimpei Sumimoto, Masayuki Kobayashi, Rio Sato, Seiichi Shinomiya, Arihiro Iwasaki, Shoichiro Suda, Toshiaki Teruya, Toshiyasu Inuzuka, Osamu Ohno, Kiyotake Suenaga

    Organic letters   21 ( 4 )   1187 - 1190   2019年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Organic Letters  

    Minnamide A is a lipopeptide with a unique repeating structure consisting of hydroxy and proposed β-branched methyl groups. The absolute configuration of minnamide A was determined by a combination of chemical degradation, chiral HPLC analyses, and synthetic methods. Minnamide A showed growth-inhibitory activity toward HeLa cells with an IC50 value of 0.17 μM and rapidly induced cell death at a concentration of 2 μM. Minnamide A induced the copper-mediated accumulation of reactive oxygen species.

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  • Evaluation of allelopathic competency of Lamium amplexicaule and identification of its allelopathic active substance

    Chisato Sakamoto, Masahiko Suzuki, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Emirates Journal of Food and Agriculture   31 ( 2 )   76 - 80   2019年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2017 United Arab Emirates University. The weedy annual grass Lamium amplexicaule (L.) originated from the Mediterranean region, spreads quickly, and becomes naturalized in areas it invades. It was assumed that volatile phytotoxic substances are one of the invasive characteristics of L. amplexicaule. However, no volatile compound has been found. Therefore, we re-evaluated the allelopathic potential of L. amplexicaule and investigated the phytotoxic substances with allelopathic activity. An extract of L. amplexicaule inhibited the root and shoot growth of Lepidium sativum, Lactuca sativa, Arctium lappa, Lolium multiflorum Lam., Echinochloa crus-galli, and Vulpia myuros, which indicates that the extract has an allelopathic effect. The extract was purified using bioassay-guided chromatographic separations, and a phytotoxic substance with allelopathic activity was isolated and characterized as methyl caffeate. The compound significantly inhibited the root and shoot growth of L. sativum and L. multiflorum. The present results suggest that methyl caffeate may contribute to the allelopathic effect of the L. amplexicaule extracts and consequently, may be partly responsible for the invasive characteristics of the species.

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  • Evaluation of phytotoxic potential and identification of phytotoxic substances in Cassia alata Linn. leaves

    Krishna Rany Das, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Acta Agriculturae Scandinavica Section B: Soil and Plant Science   69 ( 6 )   479 - 488   2019年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2019, © 2019 Informa UK Limited, trading as Taylor &amp; Francis Group. Cassia alata (Caesalpiniaceae) is a large perennial shrub native to tropical America. It is an important medicinal and ornamental plant and has been reported to possess several pharmacological properties. However, phytotoxic substances from C. alata have not yet been documented in the literature. Therefore, this study seeks to evaluate the phytotoxic potential of C. alata leaves and to identify inhibitory substances for the purpose of eco-friendly weed management. The effect of aqueous methanol extracts of C. alata on the seedling growth of alfalfa, cress, lettuce, rapeseed, barnyard grass, foxtail fescue, Italian ryegrass, and timothy was examined. The level of inhibition of the extracts corresponded to concentration. Several chromatographic steps were performed to separate the extracts, and through spectroscopic analysis, two active substances were isolated and characterised as rutin and syringone. These two active substances significantly inhibited the seedling growth of cress and foxtail fescue. The range of I 50 values (required concentration for 50% growth inhibition) of rutin and syringone for the seedling growth of cress and foxtail fescue were 129.5–417.8 and 160.1–466.5 µM, respectively. These results indicate that the two identified active phytotoxic substances from C. alata may be responsible for its growth inhibitory properties.

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  • Plant growth inhibitory activity of the extracts of acmella oleracea and its growth inhibitory substances

    Hisashi Kato-Noguchi, Prapaipit Suwitchayanon, Sutjaritpan Boonmee, Arihiro Iwasaki, Kiyotake Suenaga

    Natural Product Communications   14 ( 6 )   2019年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © The Author(s) 2019 Aqueous methanol extracts of Acmella oleracea inhibited the growth of roots and shoots of cress (Lepidum sativum), lettuce (Lactuca sativa), Italian ryegrass (Lolium multiflorum), and barnyard grass (Echinochloa crus-galli) with the extract concentration-dependent manner. The extracts were then purified and 2 growth inhibitory substances were isolated and identified by spectral data as (E,E)-2,4-undecadien-8,10-diynoic acid isobutylamide (compound 1) and nona-(2Z)-en-6,8-diynoic acid 2-phenylethylamide (compound 2). Compound 1 inhibited the growth of cress roots and shoots at concentrations greater than 0.3 mM and that of barnyard grass root at concentrations greater than 0.03 mM. Compound 2 inhibited the growth of cress shoots and barnyard grass roots at concentrations greater than 1 mM. The inhibition on the seedling growth indicates that both compounds had growth inhibitory activity and may contribute to the inhibitory effect of A. oleracea extracts. This is the first report of having growth inhibitory activity of compounds 1 and 2 on plants.

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  • Phytotoxic activity of crop residues from Burdock and an active substance. 査読 国際誌

    Masahiko Suzuki, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes   54 ( 11 )   877 - 882   2019年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS INC  

    Problems related to weed management such as outbreaks of herbicide-resistant weeds have recently increased. An interesting approach to such problems is to use plant materials with phytotoxic activity. Burdock (Arctium lappa L.) is a biennial herb belonging to Asteraceae and is cultivated in several countries. The present study investigated the phytotoxic activity of burdock and its active substances. Extracts of both burdock leaves and roots inhibited the shoot and root growth of cress and barnyard grass, where the level of inhibition increased with increasing extract concentration. The leaf extracts had 2.0-2.5 times higher activity than the root extracts. Bioassay-guided separations of the leaf extracts led to isolation of a phytotoxic substance, onopordopicrin. Onopordopicrin significantly inhibited the shoot and root growth of cress and barnyard grass. The concentrations of the substance required for 50% growth inhibition were 0.27 and 0.26 mM for cress shoots and roots, respectively, and 1.86 and 0.35 mM for barnyard grass shoots and roots, respectively. The present results suggest that burdock leaves have high phytotoxic activity and onopordopicrin may play a major role in the activity. Burdock leaves may be a good resource for weed management.

    DOI: 10.1080/03601234.2019.1636600

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  • Allelopathic property and an allelopathic substance in Eleocharis atropurpurea (Retz.)

    Farhana Zaman, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Theoretical and Experimental Plant Physiology   30 ( 4 )   347 - 355   2018年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2018, Brazilian Society of Plant Physiology. Plants, which include crops, weeds, and trees, are able to release effective allelochemicals that inhibit the growth and development of other plants. Eleocharis atropurpurea, a small, annual tufted weed, is renowned for being widely found in crop fields, yet there have been no studies on the allelopathy of E. atropurpurea (Cyperaceae). Thus, we explored the allelopathic potential and allelochemicals in E. atropurpurea and found that aqueous methanol extracts of E. atropurpurea inhibited the seedling growth of Lepidium sativum, Medicago sativa, Lolium multiflorum, and Phleum pratense. There was a significant negative correlation between the seedling growth of the test plants and extract concentration. Extracts were purified using several chromatographic steps and one growth inhibitory substance was isolated and identified by spectroscopic analysis as trans-ferulaldehyde. The active substance trans-ferulaldehyde significantly inhibited the shoot and root length of Lepidium sativum at concentrations higher than 1.0 and 3.0 mM, respectively, whereas the seedling length of Echinochloa crus-galli was inhibited by trans-ferulaldehyde at concentrations higher than 3.0 mM. The trans-ferulaldehyde I50 values for the growth of Lepidium sativum and Echinochloa crus-galli were in the range of 0.73–3.68 mM. The growth inhibitory results of this study suggest that trans-ferulaldehyde may be responsible for the inhibitory effects of E. atropurpurea and may contribute to weed allelopathy.

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  • Hoshinoamides A and B, Acyclic Lipopeptides from the Marine Cyanobacterium Caldora penicillata. 査読 国際誌

    Arihiro Iwasaki, Takato Tadenuma, Shimpe Sumimoto, Ikuma Shiota, Teruhiko Matsubara, Yumiko Saito-Nakano, Tomoyoshi Nozaki, Toshinori Sato, Kiyotake Suenaga

    Journal of natural products   81 ( 11 )   2545 - 2552   2018年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Journal of Natural Products  

    Hoshinoamides A (1) and B (2), new acyclic lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata. Their structures were elucidated by spectroscopic analyses and degradation reactions. Hoshinoamides A (1) and B (2) did not exhibit any cytotoxicity against HeLa cells at 10 μM, but inhibited the in vitro growth of the malarial parasite Plasmodium falciparum (IC50 = 0.52 and 1.0 μM, respectively).

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  • Croissamide, a proline-rich cyclic peptide with an N-prenylated tryptophan from a marine cyanobacterium Symploca sp. 査読

    Iwasaki K, Iwasaki A, Sumimoto S, Sano T, Hitomi Y, Ohno O, Suenaga K

    Tetrahedron Letters   59 ( 42 )   3806 - 3809   2018年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Tetrahedron Letters  

    © 2018 Elsevier Ltd Croissamide, a proline-rich cyclic peptide that contains an N-prenylated tryptophan, was isolated from a marine cyanobacterium Symploca sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on chiral HPLC analyses of acid hydrolysates.

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  • Isolation and identification of a phytotoxic substance in kiwifruit leaves 査読

    Okada, S., Iwasaki, A., Kataoka, I., Suenaga, K., Kato-Noguchi, H.

    Acta Horticulturae   1218   207 - 212   2018年10月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:Acta Horticulturae  

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  • Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family. 査読 国際誌

    Arihiro Iwasaki, Haruka Fujimura, Shinichiro Okamoto, Takafumi Kudo, Shizuka Hoshina, Shimpei Sumimoto, Toshiaki Teruya, Kiyotake Suenaga

    The Journal of organic chemistry   83 ( 17 )   9592 - 9603   2018年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Two new jahanyne analogues, jahanene and jahanane, highly N-methylated lipopeptides, were isolated from a marine cyanobacterium Okeania sp., and their structures were determined by NMR and MS. In addition, we achieved total syntheses of the jahanyne family and assessed their activities. The resulting growth-inhibitory activity of jahanyne was nearly one-tenth of the previously reported activity. Furthermore, we found that the degree of unsaturation at the terminus of the fatty acid moiety affected the growth-inhibitory activity against human cancer cells.

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  • Isolation and identification of a growth inhibitory substance from Heliotropium indicum L. 査読 国際誌

    Sirinapa Chaipon, Prapaipit Suwitchayanon, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Acta biologica Hungarica   69 ( 3 )   259 - 269   2018年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AKADEMIAI KIADO ZRT  

    Heliotropium indicum L. belongs to the family Boraginaceae. The plant has been used as a folk medicine because it contains substances of various biological activities. It is also identified as a common weed which grows wildly in crop fields in tropical and subtropical regions of the world. However, there is little information on the allelopathic effect in this plant. Therefore, this study was undertaken to investigate the growth inhibitory effect and to identify the growth inhibitory substances in H. indicum. An aqueous methanol extract of H. indicum inhibited shoot and root growth of barnyard grass, foxtail fescue, timothy, cress, lettuce and rapeseed at concentrations higher than 10 mg dry weight equivalent extract/mL. The concentrations required for 50% growth inhibition (I50) of those test plants ranged from 3-282 mg dry weight equivalent extract/mL. The extract was then separated using a sequence of chromatographic fractionations and a growth inhibitory substance was isolated and identified by spectral analysis as methyl caffeate. Methyl caffeate inhibited the growth of lettuce and foxtail fescue at concentrations higher than 1.0 mM. The results suggest that methyl caffeate may contribute to the growth inhibitory effect of H. indicum and may play an important role in the allelopathic effect of H. indicum.

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  • Izenamides A and B, Statine-Containing Depsipeptides, and an Analogue from a Marine Cyanobacterium. 査読 国際誌

    Yuki Kanamori, Arihiro Iwasaki, Shimpei Sumimoto, Teruhiko Matsubara, Toshinori Sato, Kiyotake Suenaga

    Journal of natural products   81 ( 7 )   1673 - 1681   2018年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Journal of Natural Products  

    Izenamides A, B, and C (1-3), new linear depsipeptides, were isolated from a taxonomically distinct marine cyanobacterium. Izenamides A and B contain a statine moiety [(3 S,4 S)-4-amino-3-hydroxy-6-methylheptanoic acid] and inhibited the activity of cathepsin D, an aspartic peptidase. Meanwhile, izenamides did not show growth-inhibitory activity against HeLa, HL60, or MCF-7 cells at up to 10 μM.

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  • Plant growth inhibitory activity and active substances with allelopathic potential of cogongrass (Imperata cylindrica) rhizome 査読

    Suzuki Masahiko, Tominaga Tohru, Ohno Osamu, Iwasaki Arihiro, Suenaga Kiyotake, Kato-Noguchi Hisashi

    Weed Biology and Management   8 ( 2 )   92 - 98   2018年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;Cogongrass (Imperata cylindrica [L.] Raeusch.) is a perennial rhizomatous grass that belongs to the Poaceae and is widely distributed in tropical, subtropical and temperate regions over the world. The grass is strongly invasive and is suggested to have allelopathic potential. However, limited information is available on allelopathic substances in cogongrass rhizomes. Therefore, the allelopathic potential and substances in cogongrass rhizomes were investigated. The extracts of cogongrass rhizomes inhibited the root and shoot growth of barnyard grass, ryegrass, timothy, cress, lettuce and alfalfa. After bioassay-guided separations of the extracts, four growth inhibitory substances, 5-methoxyflavone, 5,2&#039;-dimethoxyflavone, methyl caffeate and abscisic acid, were isolated. 5-Methoxyflavone, 5,2&#039;-dimethoxyflavone and methyl caffeate significantly inhibited the root and shoot growth of cress at concentrations of ≥0.03-0.3m mol L&lt;sup&gt;-1&lt;/sup&gt; and their concentrations required for 50% growth inhibition were 0.079-0.24, 0.23-1.1 and 0.59-0.88m mol L&lt;sup&gt;-1&lt;/sup&gt;, respectively. The other isolated substance, abscisic acid, has been reported to have strong growth inhibitory activity. Its

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  • Evaluation of phytotoxic activity of leaf and stem extracts and identification of a phytotoxic substance from Caesalpinia mimosoides Lamk. 査読

    Boonmee Sutjaritpan, Iwasaki Arihiro, Suenaga Kiyotake, Kato-Noguchi Hisashi

    Theoretical and Experimental Plant Physiology   30 ( 2 )   129 - 139   2018年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;Caesalpinia mimosoides (Fabaceae) has been used as a folk medicine and reported to have pharmacological properties. However, the phytotoxicity of C. mimosoides has not yet been studied. Therefore, the phytotoxic activity of C. mimosoides leaf and stem extracts was evaluated against the growth of dicotyledonous and monocotyledonous plants. Aqueous methanol extracts of C. mimosoides leaves and stems exhibited inhibitory effects on the growth of all the test plants. The growth of the test plants decreased with the increase of concentrations of the extracts. Comparison of the concentrations required for 50% growth inhibition (I&lt;sub&gt;50&lt;/sub&gt; values) indicates that the leaf extracts had more inhibitory effects than the stem extracts. Thus, the active substances in the leaf extracts were purified using column chromatographic separations and a growth inhibitory substance was isolated and identified as methyl gallate by using spectral analysis. This study reports the first isolation of methyl gallate in C. mimosoides leaves. Methyl gallate at 10 mM completely inhibited the growth of cress shoots and inhibited its roots by 4.7% of control growth. At the same concentration, the shoots and

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  • Ypaoamides B and C, Linear Lipopeptides from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Kosuke Sueyoshi, Miki Yamada, Aki Yamano, Kaori Ozaki, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    Journal of natural products   81 ( 4 )   1103 - 1107   2018年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Two new pyrrolinone-containing lipopeptides, ypaoamides B (1) and C (2), were isolated from an Okeania sp. marine cyanobacterium collected in Okinawa. Their structures were determined by spectroscopic analysis and Marfey's analysis of acid hydrolysates. Ypaoamides B (1) and C (2) stimulated glucose uptake in cultured rat L6 myotubes. In particular, ypaoamide B (1) showed potent activity and activated AMP-activated protein kinase.

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  • Total synthesis of janadolide 査読

    Ojima Daisuke, Mine Hitomi, Iwasaki Arihiro, Suenaga Kiyotake

    Tetrahedron Letters   59 ( 14 )   1360 - 1362   2018年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;The first total synthesis of janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, is described. The synthesis of an unsaturated hydroxycarboxylic acid was effected via the lithiation of vinyl iodide followed by addition to a Weinreb amide with a tert-butyl group and stereoselective 1,2-reduction. The cyclic structure was constructed by macrolactamization at the amide bond between the proline moiety and fatty acid moiety.&lt;/p&gt;

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  • Caldorin, a new polyketide from the marine cyanobacterium Caldora penicillata 査読

    Shiota Ikuma, Iwasaki Arihiro, Sumimoto Shimpei, Tomoda Hiroshi, Suenaga Kiyotake

    Tetrahedron Letters   59 ( 13 )   1261 - 1263   2018年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;A new polyketide with a cis-fused decalin ring scaffold, caldorin, was isolated from the marine cyanobacterium Caldora penicillata. The gross structure and relative configuration were elucidated by spectroscopic analyses. We also clarified that caldorin is a weak SOAT inhibitor and moderate osteoblast differentiation inhibitor. On the other hand, caldorin did not exhibit cytotoxicity against either HeLa or HL60 cells.&lt;/p&gt;

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  • Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria. 査読 国際誌

    Eisuke Sato, Maho Morita, Haruo Ogawa, Masato Iwatsuki, Rei Hokari, Aki Ishiyama, Satoshi Ōmura, Arihiro Iwasaki, Kiyotake Suenaga

    Bioorganic & medicinal chemistry letters   28 ( 3 )   298 - 301   2018年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Biselyngbyaside, an 18-membered macrolide glycoside from marine cyanobacteria, and its derivatives are known to be sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitors. Recently, a SERCA orthologue of the malaria parasite, PfATP6, has attracted attention as a malarial drug target. To provide a novel drug lead, we designed new synthetic analogs of biselyngbyolide B, the aglycone of biselyngbyaside, based on the co-crystal structure of SERCA with biselyngbyolide B, and synthesized them using the established synthetic route for biselyngbyolide B. Their biological activities against malarial parasites were evaluated.

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  • Identification of 6,7-dimethoxychromone as a potent allelochemical from jatropha podagrica

    Sutjaritpan Boonmee, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Natural Product Communications   13 ( 11 )   1515 - 1518   2018年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2018 Natural Product Incorporation. Jatropha podagrica Hook. is cultivated as an ornamental plant and is also used in traditional medicine. The species has various pharmacological properties, but it has not yet been investigated for any potential allelopathic activity and allelopathic substances. In this study, an allelopathic active substance was isolated from an aqueous methanol extract of J. podagrica leaves through chromatography and reverse-phase HPLC. The substance was characterized as 6,7- dimethoxychromone by spectral analysis. 6,7-Dimethoxychromone significantly inhibited the shoots and roots of cress at concentrations greater than 0.3 mM. The concentrations required of 6,7-dimethoxychromone for 50% growth inhibition of cress shoots and roots were 0.95 and 0.83 mM, respectively. The inhibitory activity against the seedling growth of cress indicates that 6,7-dimethoxychromone may contribute to the allelopathic effects and may be responsible for the allelopathic activity in J. podagrica. This report is the first on the allelopathic activity of 6,7-dimethoxychromone as an allelopathic substance from J. podagrica.

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  • Evaluation of phytotoxic potential and identification of phytotoxic compounds in Rumex maritimus

    Islam, M.S., Iwasaki, A., Suenaga, K., Kato-Noguchi, H.

    Plant Biosystems   152 ( 4 )   2018年

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    掲載種別:研究論文(学術雑誌)  

    DOI: 10.1080/11263504.2017.1338630

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  • Total Synthesis of Kanamienamide and Clarification of Biological Activity. 査読 国際誌

    Daisuke Ojima, Arihiro Iwasaki, Kiyotake Suenaga

    The Journal of organic chemistry   82 ( 23 )   12503 - 12510   2017年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The total synthesis of kanamienamide, an enamide with an enol ether and an 11-membered macrolactone of marine origin, was achieved. The synthesis features the construction of an enamide adjacent to an enol ether by Buchwald amidation and an 11-membered ring by Mitsunobu lactonization. In addition, on the basis of the biological assay of synthetic 1, we clarified that kanamienamide (1) was not an apoptosis-like cell death inducer, as reported in the isolation paper, and revealed its real biological activity as a necrosis-like cell death inducer.

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  • 2-Methoxystypandrone, a potent phytotoxic substance in Rumex maritimus L 査読

    Islam Md Shafiqul, Iwasaki Arihiro, Suenaga Kiyotake, Kato-Noguchi Hisashi

    Theoretical and Experimental Plant Physiology   29 ( 4 )   195 - 202   2017年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;Herbicide use has raised concerns which results in the need to find an alternative approach, using natural methods, of controlling weeds. Phytotoxic substances released from plants have been used to manage weeds biologically. Rumex maritimus, belonging to the Polygonaceae family, is well known to have a wide range of biological properties. However, the phytotoxic properties of R. maritimus is not well documented. Thus, we conducted an investigation into the phytotoxic potential of R. maritimus and attempted to find out its phytotoxic substances. Leaf, stem and root extracts of R. maritimus exhibited a strong inhibitory effects on root and shoot length of Lactuca sativa L., Medicago sativa L., Lolium multiflorum Lam., Phleum pratense L. With increasing extract concentration, inhibition increased. One substance, 2-methoxystypandrone, was purified after a series of chromatography and characterized by spectral data. 2-Methoxystypandrone reduced the seedling length of Lepidium sativum at concentration ≥ 3 μM. The required 50% growth inhibition concentration of Lepidium sativum seedling for 2-methoxystypandrone was ranged 5.8–11.8 μM. Therefore, it is suggested that the phyt

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  • Three New Malyngamides from the Marine Cyanobacterium Moorea producens. 査読 国際誌

    Kosuke Sueyoshi, Aki Yamano, Kaori Ozaki, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    Marine drugs   15 ( 12 )   2017年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI AG  

    Three new compounds of the malyngamide series, 6,8-di-O-acetylmalyngamide 2 (1), 6-O-acetylmalyngamide 2 (2), and N-demethyl-isomalyngamide I (3), were isolated from the marine cyanobacterium Moorea producens. Their structures were determined by spectroscopic analysis and chemical derivatization and degradation. These compounds stimulated glucose uptake in cultured L6 myotubes. In particular, 6,8-di-O-acetylmalyngamide 2 (1) showed potent activity and activated adenosine monophosphate-activated protein kinase (AMPK).

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  • Two allelopathic substances from Paspalum commersonii Lam. 査読

    Zaman Farhana, Iwasaki Arihiro, Suenaga Kiyotake, Kato-Noguchi Hisashi

    Acta Agriculturae Scandinavica Section B: Soil and Plant Science   68 ( 4 )   342 - 348   2017年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;Paspalum commersonii (Poaceae) is a herbaceous perennial weed distributed in the tropics and subtropics regions and grows mainly in the moist, or even flooded soil. It often appears in the rice field as a competitive weed and difficult to manage. Its strong competitive nature indicates possible allelopathic potential of P. commersonii. However, no studies have been found yet on the allelopathic activity of P. commersonii. Thus, we investigated the allelopathic potential of this weed and determined its allelopathic substances. Aqueous methanol extracts of P. commersonii showed concentration-dependent inhibitory activity on the seedling growth of cress, alfalfa, rapeseed, lettuce, barnyard grass, foxtail fescue, Italian ryegrass, and timothy. Two substances were isolated through bioassay-guided fractionation and their structures were determined through spectral data as dehydrovomifoliol and loliolide. Dehydrovomifoliol and loliolide started inhibiting the shoot and root growth of cress at concentrations greater than 3 and 0.03 mM, respectively. The concentrations required for 50% inhibition (I&lt;sub&gt;50&lt;/sub&gt;) of cress shoot and root growth were 3.34 and &gt;3.50 mM for dehydrovo

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  • Kohamamides A, B, and C, Cyclic Depsipeptides from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Arihiro Iwasaki, Ikuma Shiota, Shimpei Sumimoto, Teruhiko Matsubara, Toshinori Sato, Kiyotake Suenaga

    Journal of natural products   80 ( 6 )   1948 - 1952   2017年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Kohamamides A, B, and C (1-3), new cyclic depsipeptides that belong to the kulolide superfamily, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Kohamamide B (2) exhibited moderate cytotoxicity against HL60 cells. Although many natural products in the kulolide superfamily have been isolated from cyanobacteria collected in various parts of the world, kohamamides 1-3 are the first members to be isolated from the East Asian marine environment. In addition, unlike other members of this superfamily, kohamamides 1-3 contain a Leu residue adjacent to the Pro residue, rather than another lipophilic amino acid.

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  • Phytotoxic property of the invasive plant Tithonia diversifolia and a phytotoxic substance. 査読 国際誌

    Masahiko Suzuki, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    Acta biologica Hungarica   68 ( 2 )   187 - 195   2017年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AKADEMIAI KIADO RT  

    Tithonia diversifolia (Hermsl.) A. Gray is a perennial invasive plant and spreads quickly in the invasive areas. The extracts of T. diversifolia were found to be toxic to several crop plant species such as rice, maize, sorghum, lettuce and cowpea, and several putative allelopathic substances were identified. However, there is limited information available for the effects of T. diversifolia on wild plants including weed plant species. We investigated the allelopathic potential of T. diversifolia extracts on weed plants, and searched for phytotoxic substances with allelopathic activity. An aqueous methanol extract of T. diversifolia leaves inhibited the growth of weed plants, Lolium multiflorum Lam., Phleum pretense L., Echinochloa crus-galli (L.) Beauv. The extract was then purified by several chromatographic runs and a phytotoxic substance with allelopathic activity was isolated and identified by spectral analysis as tagitinin C. The substance inhibited the growth of Lolium multiflorum, Phleum pratense and Echinochloa crus-galli at concentrations greater than 0.1 - 0.3 mM. The present results suggest that T. diversifolia may possess allelopathic potential on weed plants and tagitinin C may be responsible for the allelopathic effects of T. diversifolia. The allelopathic potential of T. diversifolia may contribute to its invasive characteristics.

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  • Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Arihiro Iwasaki, Takato Tadenuma, Shimpei Sumimoto, Taichi Ohshiro, Kaori Ozaki, Keisuke Kobayashi, Toshiaki Teruya, Hiroshi Tomoda, Kiyotake Suenaga

    Journal of natural products   80 ( 4 )   1161 - 1166   2017年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.

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  • Odobromoamide, a Terminal Alkynyl Bromide-Containing Cyclodepsipeptide from the Marine Cyanobacterium Okeania sp. 査読

    Kosuke Sueyoshi, Takafumi Kudo, Aki Yamano, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   90 ( 4 )   436 - 440   2017年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the novel cyclodepsipeptide odobromoamide (1). The gross structure of 1 was determined by spectroscopic analyses, and its absolute stereochemistry was determined using a variety of different methods, including chemical derivatization and degradation followed by HPLC analysis. In addition, odobromoamide (1) exhibited broad-spectrum cytotoxicity against a human cancer cell line panel.

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  • Isolation and Total Synthesis of Hoshinolactam, an Antitrypanosomal Lactam from a Marine Cyanobacterium. 査読 国際誌

    Hidetoshi Ogawa, Arihiro Iwasaki, Shimpei Sumimoto, Masato Iwatsuki, Aki Ishiyama, Rei Hokari, Kazuhiko Otoguro, Satoshi O Mura, Kiyotake Suenaga

    Organic letters   19 ( 4 )   890 - 893   2017年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    In the search for new antiprotozoal substances, hoshinolactam, an antitrypanosomal lactam, was isolated from a marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configuration was determined by the first total synthesis. Hoshinolactam showed potent antitrypanosomal activity with an IC50 value of 3.9 nM without cytotoxicity against human fetal lung fibroblast MRC-5 cells (IC50 > 25 μM).

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  • Isolation and identification of two potential phytotoxic substances from the aquatic fern Marsilea crenata

    Md Shafiqul Islam, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    JOURNAL OF PLANT BIOLOGY   60 ( 1 )   75 - 81   2017年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER HEIDELBERG  

    Organic agriculture emphasized using of biologically originated herbicides and phytotoxic substances are being considered as a replacement to chemical herbicides. Marsilea crenata is an aquatic perennial fern distributed in the South-East Asian countries and is well known for various biological properties. However, to date, there has been no report that addresses the phytotoxicity of Marsilea crenata. Therefore, we explored phytotoxic properties and phytotoxic substances from Marsilea crenata. An aqueous methanol extracts of Marsilea crenata showed inhibition on the seedling growth of cress, lettuce, alfalfa, barnyard grass, Italian ryegrass, and foxtail fescue. Inhibition increased with increasing extract concentration. The extract was purified by several chromatographic steps and two phytotoxic substances were isolated and identified by spectroscopic analysis as loliolide and isololiolide. At the concentration of 30 mu M, loliolide and isololiolide inhibited seedling growth of cress and barnyard grass by 41.3 to 51.1%, and 58.15 to 87.5% of control seedlings, respectively. The concentrations required for 50% inhibition of cress and barnyard grass seedlings ranged from 32.1 to 128.5 mu M for loliolide, 37.0 to 176.2 mu M for isololiolide. These results suggest these compounds may be responsible for phytotoxic effects of Marsilea crenata extract and could be an important part of organic agriculture.

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  • Myrislignan, a growth inhibitor from the roots of citronella grass

    Prapaipit Suwitchayanon, Prapaipit Suwitchayanon, Kiyotake Suenaga, Arihiro Iwasaki, Hisashi Kato-Noguchi

    Natural Product Communications   12 ( 7 )   1077 - 1078   2017年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    A phytotoxic compound was isolated from the root extracts of Cymbopogon nardus by bioassay-guided purification and characterized to be myrislignan. Myrislignan significantly inhibited seedling growth of cress at a concentration greater than 100 μM (p &lt; 0.05). The concentrations required for 50% growth inhibition of myrislignan on hypocotyl and root growth of cress were 429 μM and 517 μM, respectively. The inhibition on seedling growth indicated that myrislignan had a phytotoxic activity and may contribute to the phytotoxic effect of C. nardus.

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  • Allelopathic potential and an allelopathic substance in mango leaves

    Masahiko Suzuki, Md Sirajul Islam Khan, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi

    ACTA AGRICULTURAE SCANDINAVICA SECTION B-SOIL AND PLANT SCIENCE   67 ( 1 )   37 - 42   2017年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS AS  

    The present study was aimed to determine the allelopathic potential of mango (Mangifera indica L.) leaves and to identify allelopathic substances in the leaves. The aqueous methanol extracts of mango leaves inhibited seedling growth of garden cress, radish, rapeseed, foxtail fescue and crabgrass, and the inhibitory effects increased with the increasing extract concentration, suggesting that mango leaves may contain allelopathic substances. The extract was then purified by several chromatographic runs through a bioassay-directed fractionation, and an growth inhibitory substance was isolated and identified by spectral data as methyl-3,4,5-trihydroxybenzoate (methyl gallate). Methyl gallate at the concentration of 10 mM inhibited 98.6% and 99.8% of root and shoot growth of garden cress relative to the control, respectively, and 94.4% and 49.3% of those of foxtail fescue, respectively. The concentrations of methyl gallate required for 50% growth inhibition (I-50) on garden cress roots and shoots were 3.9 and 3.3 mM, and those on foxtail fescue roots and shoots were 1.5 and 9.5 mM, respectively. It is the first report of an allelopathic substance in mango leaves and allelopathic activity of methyl gallate. Therefore, the mango leaves may have potential as a soil additive material for the weed management options.

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  • Total synthesis and stereochemical determination of yoshinone A. 査読 国際誌

    Seiichi Shinomiya, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga

    Phytochemistry   132   109 - 114   2016年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50 value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.

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  • Total Synthesis of Miuraenamides A and D. 査読 国際誌

    Daisuke Ojima, Ayano Yasui, Koh Tohyama, Keita Tokuzumi, Eisuke Toriihara, Kayoko Ito, Arihiro Iwasaki, Tomohiko Tomura, Makoto Ojika, Kiyotake Suenaga

    The Journal of organic chemistry   81 ( 20 )   9886 - 9894   2016年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Miuraenamides A and D, cyclodepsipeptides with antimicrobial and antitumor activity, were synthesized. The synthesis of an unsaturated hydroxycarboxylic acid moiety, starting from a chiral epoxide, was achieved by Suzuki-Miyaura coupling as a key step. As a result, the overall yield for miuraenamide A over the longest linear sequence is 3.2%, while the yield of the previously reported procedure is 1.9%. In addition, the cell growth-inhibitory activity and anti-Phytophthora activity of the synthesized compounds were evaluated.

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  • Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii. 査読 国際誌

    Shimpei Sumimoto, Arihiro Iwasaki, Osamu Ohno, Kosuke Sueyoshi, Toshiaki Teruya, Kiyotake Suenaga

    Organic letters   18 ( 19 )   4884 - 4887   2016年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 μM and induced apoptosis-like cell death.

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  • Urumamide, a novel chymotrypsin inhibitor with a β-amino acid from a marine cyanobacterium Okeania sp.

    Kanamori Yuki, Iwasaki Arihiro, Sumimoto Shinpei, Suenaga Kiyotake

    Tetrahedron Letters   57 ( 37 )   4213 - 4216   2016年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    &lt;p&gt;Urumamide, a novel cyclic depsipeptide that contains a β-amino acid, was isolated from a marine cyanobacterium Okeania sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on Marfey&#039;s analyses and chiral HPLC analyses of hydrolysis products. Biologically, urumamide inhibited the growth of human cancer cells. In addition, urumamide inhibited chymotrypsin.&lt;/p&gt;

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  • Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium. 査読 国際誌

    Hidetoshi Ogawa, Arihiro Iwasaki, Shinpei Sumimoto, Yuki Kanamori, Osamu Ohno, Masato Iwatsuki, Aki Ishiyama, Rei Hokari, Kazuhiko Otoguro, Satoshi O̅mura, Kiyotake Suenaga

    Journal of natural products   79 ( 7 )   1862 - 6   2016年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

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  • Total synthesis and absolute configuration of koshikalide

    Kazuki Kunifuda, Arihiro Iwasaki, Masashi Nagamoto, Kiyotake Suenaga

    TETRAHEDRON LETTERS   57 ( 29 )   3121 - 3123   2016年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The first total synthesis of koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide. (C) 2016 Elsevier Ltd. All rights reserved.

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  • Anti-obesity activities of the yoshinone A and the related marine γ-pyrone compounds 査読

    Koyama Tomoyuki, Kawazoe Yoshinori, Iwasaki Arihiro, Ohno Osamu, Suenaga Kiyotake, Uemura Daisuke

    Journal of Antibiotics   69 ( 4 )   348 - 51   2016年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Isolation and Structure of Kurahyne B and Total Synthesis of the Kurahynes. 査読 国際誌

    Shinichiro Okamoto, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga

    Journal of natural products   78 ( 11 )   2719 - 25   2015年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Kurahyne B (2), a new analogue of kurahyne (1), was isolated from the marine cyanobacterium Okeania sp. Its gross structure was elucidated based on spectroscopic analyses, and the absolute configuration was established by total synthesis. Kurahyne B (2) inhibited the growth of both HeLa and HL60 cells, with IC50 values of 8.1 and 9.0 μM, respectively. The growth-inhibitory activity of kurahyne B was the same as kurahyne (1). In parallel, the first total synthesis of kurahyne (1) was also achieved.

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  • Identification of a molecular target of kurahyne, an apoptosis-inducing lipopeptide from marine cyanobacterial assemblages. 査読 国際誌

    Arihiro Iwasaki, Osamu Ohno, Shun Katsuyama, Maho Morita, Yukiko Sasazawa, Shingo Dan, Siro Simizu, Takao Yamori, Kiyotake Suenaga

    Bioorganic & medicinal chemistry letters   25 ( 22 )   5295 - 8   2015年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    In 2014, we isolated kurahyne, an acetylene-containing lipopeptide, from a marine cyanobacterial assemblage of Lyngbya sp. Kurahyne exhibited growth-inhibitory activity against human cancer cells, and induced apoptosis in HeLa cells. However, its mode of action is not yet clear. To elucidate its mode of action, we carried out several cell-based assays, and identified the intracellular target molecule of kurahyne as sarco/endoplasmic reticulum Ca(2+) ATPase (SERCA). In addition, we found that kurahyne inhibited the differentiation of macrophages into osteoclasts.

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  • Total synthesis and stereochemical reassignment of maedamide

    Ayano Takayanagi, Arihiro Iwasaki, Kiyotake Suenaga

    TETRAHEDRON LETTERS   56 ( 34 )   4947 - 4949   2015年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The first total synthesis of maedamide, an acyclic peptide isolated from a marine cyanobacterial assemblage of Lyngbya sp., was achieved. This synthesis led to reassignment of the allo-D-Ile of maedamide to be which was supported by H-1 and C-13 NMR data. (C) 2015 Elsevier Ltd. All rights reserved.

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  • Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina. 査読 国際誌

    Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Teruhiko Matsubara, Satoshi Shimada, Toshinori Sato, Kiyotake Suenaga

    Journal of natural products   78 ( 4 )   901 - 8   2015年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Mebamamides A and B, new lipopeptides with four d-amino acid residues and a 3,8-dihydroxy-9-methyldecanoic acid residue, were isolated from the green alga Derbesia marina. Their gross structures were elucidated by spectroscopic and ESI-ITMS analyses. The absolute configurations except for the two leucines were revealed based on chiral-phase HPLC analyses of the acid hydrolysate and a modified Mosher's method. A distinction between D-Leu and L-Leu in the sequence was established by the application of a dansyl-Edman method to the partial acid hydrolysate. Mebamamide A did not exhibit any growth inhibitory activity against HeLa and HL60 cells at 10 μM, and mebamamide B did not exhibit any growth inhibitory activity against those cells at 100 μM. Additionally, it was suggested that mebamamide B induced the differentiation of HL60 cells into macrophage-like cells at 100 μM.

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  • Jahanyne, an apoptosis-inducing lipopeptide from the marine cyanobacterium Lyngbya sp. 査読 国際誌

    Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Hidetoshi Ogawa, Kim Anh Nguyen, Kiyotake Suenaga

    Organic letters   17 ( 3 )   652 - 5   2015年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    An acetylene-containing lipopeptide, jahanyne, was isolated from the marine cyanobacterium Lyngbya sp. Its gross structure was established by spectroscopic analyses, and the absolute configuration was clarified based on a combination of chiral HPLC analyses, spectroscopic analyses, and derivatization reactions. Jahanyne significantly inhibited the growth of human cancer cells and induced apoptosis in HeLa cells.

    DOI: 10.1021/ol5036722

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  • An inhibitor of the adipogenic differentiation of 3T3-L1 cells, yoshinone A, and its analogs, isolated from the marine cyanobacterium Leptolyngbya sp.

    Toshiyasu Inuzuka, Keita Yamamoto, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga, Yoshinori Kawazoe, Daisuke Uemura

    TETRAHEDRON LETTERS   55 ( 49 )   6711 - 6714   2014年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Three novel compounds, yoshinones A, B1, and B2, were isolated from the marine cyanobacterium Leptolyngbya sp., and their structures were elucidated by NMR spectral analysis. Yoshinone A, but not yoshinone B1 or B2, inhibited the differentiation of 3T3-L1 cells into adipocytes. In addition, yoshinone A did not exhibit cytotoxicity, suggesting that yoshinone A may be useful in studies on the treatment of obesity. (C) 2014 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2014.10.032

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  • Maedamide, a novel chymotrypsin inhibitor from a marine cyanobacterial assemblage of Lyngbya sp.

    Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Shoichiro Suda, Kiyotake Suenaga

    TETRAHEDRON LETTERS   55 ( 30 )   4126 - 4128   2014年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Maedamide, a novel chymotrypsin-inhibiting depsipeptide, was isolated from a cyanobacterial assemblage that mostly consisted of Lyngbya sp. Its structure was elucidated by spectroscopic analyses and chiral HPLC analyses of hydrolysis products. Maedamide selectively inhibited chymotrypsin but not elastase and trypsin. In addition, Maedamide strongly inhibited the growth of HeLa cells and HL60 cells. (C) 2014 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2014.05.099

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  • Kurahamide, a Cyclic Depsipeptide Analog of Dolastatin 13 from a Marine Cyanobacterial Assemblage of Lyngbya sp.

    Arihiro Iwasaki, Shinpei Sumimoto, Osamu Ohno, Shoichiro Suda, Kiyotake Suenaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   87 ( 5 )   609 - 613   2014年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Kurahamide, a new dolastatin 13 analog, was isolated from a marine cyanobacterial assemblage, consisting mostly of Lyngbya sp. Its gross structure was elucidated by spectroscopic analysis, and the stereochemistries were assigned based on a chiral HPLC analysis of hydrolysis products. Kurahamide strongly inhibited elastase and chymotypsin in vitro. In addition, kurahamide moderately inhibited the growth of human cancer cells, including HeLa and HL60 cells.

    DOI: 10.1246/bcsj.20140008

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  • Kurahyne, an acetylene-containing lipopeptide from a marine cyanobacterial assemblage of Lyngbya sp.

    Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Shoichiro Suda, Kiyotake Suenaga

    RSC ADVANCES   4 ( 25 )   12840 - 12843   2014年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Kurahyne, a new acetylene-containing lipopeptide, was isolated from a cyanobacterial assemblage that mostly consisted of Lyngbya sp. Its structure was elucidated by spectroscopic analyses and chiral HPLC analyses of hydrolysis products. Kurahyne inhibited the growth of human cancer cells and induced apoptosis in HeLa cells, and it seemed to localize in mitochondria.

    DOI: 10.1039/c4ra00132j

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  • Isolation and structure of koshikalide, a 14-membered macrolide from the marine cyanobacterium Lyngbya sp.

    Arihiro Iwasaki, Toshiaki Teruya, Kiyotake Suenaga

    TETRAHEDRON LETTERS   51 ( 6 )   959 - 960   2010年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A 14-membered macrolide, koshikalide (1), was isolated from the marine cyanobacterium Lyngbya sp., and its planar structure was elucidated by spectroscopic analysis. The relative stereochemistry of C-I I and C-13 was elucidated by NOESY experiments and by an analysis of (1)H-(1)H coupling constants. Koshikalide (1) exhibited weak cytotoxicity against HeLa S(3) cells. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.12.041

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  • 20-N-methylpurpuramine E: New bromotyrosine-derived metabolite from Okinawan marine sponge Pseudoceratina purpurea

    Toshiaki Teruya, Arihiro Iwasaki, Kiyotake Suenaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   81 ( 8 )   1026 - 1027   2008年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    A new bromotyrosine-derived metabolite. 20-N-methylpurpuramine E (1), was isolated from the marine sponge Pseudoceratina purpurea. The structure was elucidated by spectroscopic analysis. 20-N-Methylpurpuramine E (1) showed weak cytotoxicity against HeLa S-3 Cells.

    DOI: 10.1246/bcsj.81.1026

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▼全件表示

書籍等出版物

  • Marine Natural Products, Topics in Heterocyclic Chemistry Vol. 58

    Kiyotake Suenaga, Arihiro Iwasaki, Reda A. Abdelhamid, Nicole E. Avalon, Bill J. Baker, Erick M. Carreira, Sarah Dietrick, Darren J. Dixon, Ahmed H, H. El-Desoky, Masaru Enomoto, James R. Frost, Haruhiko Fuwa, Kristin Herrera, Yasuhiro Igarashi, Jun Ishihara, Hayate Ishizuka, Pavol Jakubec, Carlos Jiménez, Hiromasa Kiyota, Sofia Kokkaliari, Hiroyuki Konno, Masaki Kuse, Shigefumi Kuwahara, Steven V. Ley, Kazuo Nagasawa, Kentaro Okano, Ryuichi Sakai, Philipp Sondermann, Tomoya Sugai, Sachiko Tsukamoto, Robert A. Uria, Toshiyuki Wakimoto, Joshua Welsch, Bingjie Yang, Ryan M. Young( 範囲: Bioactive Substances from Marine Cyanobacteria)

    Springer  2021年  ( ISBN:9789811646362

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    総ページ数:viii, 517 p.   記述言語:英語  

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講演・口頭発表等

  • 海洋シアノバクテリア由来新規鎖状ペプチド hedoamide の構造と生物活性

    栗澤 尚瑛, 岩﨑 有紘, Ghulam Jeelani, Yulia Rahmawati, 野崎 智義, 末永 聖武

    日本化学会 第103春季年会  2023年3月 

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    会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来新規天然物の発見とその価値の探索

    岩崎有紘

    日本化学会 第103春季年会 若い世代の特別講演会  2023年3月 

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    会議種別:口頭発表(招待・特別)  

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  • 海洋産シアノバクテリア由来新規Madangolide類縁体の単離と構造決定

    萩原 大尋, 末永 聖武, 岩崎 有紘

    日本化学会 第103春季年会  2023年3月 

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    会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来の新規配糖体マクロリドakunolide類の単離及び構造決定

    梅田 海里, 岩崎 有紘, 末永 聖武

    日本化学会 第103春季年会  2023年3月 

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    会議種別:口頭発表(一般)  

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  • Biselyngbyaside 人工類縁体の合成研究

    先山 佳寿, 岩崎 有紘, 末永 聖武

    日本化学会 第103春季年会  2023年3月 

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    会議種別:口頭発表(一般)  

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  • 微量ポリケチドberu'amideの単離,構造決定,全合成および生物活性

    田口 黎武, 岩崎 有紘, 海老原 玲, Ghulam Jeelani, 野崎 智義, 末永 聖武

    第 12 回 CSJ 化学フェスタ 2022  2022年10月 

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    会議種別:ポスター発表  

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  • 微量ポリケチドberu'amideの単離,構造決定,全合成および生物活性

    田口黎武, 岩崎有紘, 海老原玲, Ghulam Jeelani, 野崎智義, 末永聖武

    第64回天然有機化合物討論会  2022年9月 

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    会議種別:口頭発表(一般)  

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  • 沖縄県産海洋シアノバクテリア由来新規多ハロゲン化アリールエーテル類の単離,構造決定,生物 活性および全合成

    海老原玲, 岩崎有紘, 三浦洋平, Ghulam Jeelani, 野崎智義, 末永聖武

    第68回トキシンシンポジウム  2022年9月 

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    会議種別:口頭発表(一般)  

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  • 初心者のための海洋シアノバクテリア採集入門

    岩﨑有紘

    第55回天然物化学談話会  2022年6月 

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    会議種別:口頭発表(一般)  

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  • リングビアペプチンB推定生合成遺伝子クラスター中の二鉄含有酸化酵素の機能解析

    楠部瑞樹, 竹間琢自, 岩﨑有紘, 末永聖武, 宮永顕正, 工藤史貴, 江口正

    日本化学会第102春季年会  2022年3月 

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  • 海洋シアノバクテリア由来新規ポリケチドTomurulineの全合成

    宮本裕太, 藤村遥, 岩崎有紘, 末永聖武

    日本化学会第102春季年会  2022年3月 

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  • 海洋シアノバクテリア由来ペプチド・ポリケチドハイブリッド配糖体iezosideの合成研究

    寺沼和哉, 栗澤尚瑛, 岩﨑有紘, 末永聖武

    日本化学会第102春季年会  2022年3月 

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  • 海洋シアノバクテリア由来新規テルペノイドの単離,構造決定

    海老原玲, 岩﨑有紘, 末永聖武

    日本化学会第102春季年会  2022年3月 

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  • 沖縄県産海洋シアノバクテリア由来の新規不飽和δ-ラクトン含有ポリケチド類の単離と構造決定

    高橋寛樹, 岩崎有紘, 金井航, 末永聖武

    日本化学会第102春季年会  2022年3月 

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  • 海洋産リポペプチド Minnamide A 脂肪酸部分の合成研究

    岸本勇志, 小林正幸, 岩崎有紘, 末永聖武

    日本化学会第102春季年会  2022年3月 

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  • 鹿児島県産海洋シアノバクテリア由来新規ポリケチド化合物Beru’amideの単離と構造決定、及び全合成研究

    田口黎武, 岩崎有紘, 末永聖武

    日本化学会第102春季年会  2022年3月 

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  • Natural Products from Marine Cyanobacteria: Fascinating Structures and Biological Activities 招待

    Arihiro Iwasaki

    German-Japanese Meeting 2022 Green Aquatic Biology: Ecology meets Synthetic Biology  2022年3月 

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    記述言語:英語  

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  • 海洋シアノバクテリア Leptolyngbya sp. 由来新規環状ペプチド類の単離、構造決定、生物活性

    高橋寛樹, 岩崎有紘, 栗澤尚瑛, 鈴木良太, JEELANI Ghulam, 野崎智義, 末永聖武

    第11回CSJ化学フェスタ  2021年10月 

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    海老原玲, 岩崎有紘, 末永聖武, 三浦洋平, GHULAM Jeelani, 野崎智義

    第11回CSJ化学フェスタ  2021年10月 

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  • 新規ペプチド-ポリケチドハイブリッド配糖体 iezoside の構造と生物活性

    栗澤尚瑛, 岩﨑有紘, 寺沼和哉, 旦慎吾, 豊島近, 橋本勝, 末永 聖武

    第63回天然有機化合物討論会  2021年9月 

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  • 海洋シアノバクテリア由来新規ペプチド-ポリケチドハイブリッド化合物 iezoside の 構造と生物活性

    栗澤尚瑛, 岩﨑有紘, 末永聖武

    第67回トキシンシンポジウム  2021年9月 

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  • 新規 SERCA 阻害剤 iezoside の構造と生物活性

    栗澤尚瑛, 岩﨑有紘, 寺沼和哉, 旦慎吾, 豊島近, 末永聖武

    日本ケミカルバイオロジー学会第15回年会  2021年6月 

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  • 海洋シアノバクテリア Leptolyngbya sp. 由来新規環状ペプチド類の単離と構造決定

    高橋 寛樹, 岩﨑有紘, 鈴木良太, 末永聖武

    日本化学会第101春季年会  2021年3月 

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  • 沖縄県産海洋シアノバクテリア由来の鎖状ペプチド komesuamide の単離、構造決定と生物活性

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    日本化学会第101春季年会  2021年3月 

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  • 海洋シアノバクテリア由来新規ペプチド-ポリケチドハイブリッド化合物 iezoside の構造と生物活性

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    日本化学会第101春季年会  2021年3月 

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  • 海洋産リポペプチドMinnamide Aペプチド部の合成研究

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    日本化学会第101春季年会  2021年3月 

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  • 海洋シアノバクテリア由来新規鎖状デプシペプチドkinenzolineの単離及び全合成

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    日本化学会第101春季年会  2021年3月 

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  • 海洋産抗トリパノソーマ鎖状ペプチドIheyanide Aの全合成

    寺沼和哉, 栗澤尚瑛, 岩﨑有紘, 末永 聖武

    日本化学会第101春季年会  2021年3月 

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  • 新規チアゾール含有ポリケチドtomurulineの合成研究

    宮本裕太, 岩崎有紘, 末永 聖武

    日本化学会第101春季年会  2021年3月 

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  • 海洋産リポペプチド Minnamide A 脂肪酸部分の合成研究

    岸本 勇志, 佐藤理央, 岩崎有紘, 末永 聖武

    日本化学会第101春季年会  2021年3月 

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  • Biselyngbyaside 人工類縁体の合成研究

    廣瀬太朗, 佐藤英祐, 岩﨑有紘, 末永 聖武

    日本化学会第101春季年会  2021年3月 

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  • 沖縄県産海洋シアノバクテリア由来新規多ハロゲン化アリールエーテル類の単離と構造決定,及び全合成研究

    海老原玲, 岩﨑有紘, 末永聖武

    日本化学会第101春季年会  2021年3月 

     詳細を見る

  • 海洋シアノバクテリア由来の新規鎖状ペプチドiheyamide類の構造と生物活性

    栗澤尚瑛, 岩﨑有紘, Ghulam Jeelani, 野崎智義, 末永聖武

    第62回天然有機化合物討論会  ( オンライン開催 )   2020年9月 

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋シアノバクテリア由来の生物活性物質 招待

    末永聖武, 岩﨑有紘, 森田真布, 佐藤英祐, 照屋俊明, 大野修

    農芸化学会2020年度大会、シンポジウム「シアノバクテリアと未来を描く」  ( 誌上開催 )   2020年3月 

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    記述言語:日本語   会議種別:口頭発表(招待・特別)  

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  • 細胞老化に関わるLncRNA(LINC00942)の発現を制御する成分の探索

    礒田隆宏, 岩﨑有紘, 岡部伊織, 宍戸まゆみ, 斉藤優子, 末永聖武, 楊 一幸

    日本薬学会第140年会  ( 誌上開催 )   2020年3月 

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  • Synthetic Studies on Ikoamide

    末永聖武, 駱永翰, 岩﨑有紘

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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    記述言語:英語   会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来リポペプチド Jahanyne 類のアポトーシス誘導活性の作用機序解明研究

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    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 直接的アルキン濃縮精製法を駆使した海洋シアノバクテリア由来新規リポペプチド類の単離と構造決定

    髙橋寛樹, 岩﨑有紘, 大金賢司, 中尾周平, 闐闐孝介, 袖岡幹子, 末永聖武

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • リングビアぺプチンB推定生合成遺伝子クラスター中にコードされる酵素の機能解析

    竹間琢自, 澄本慎平, 岩﨑有紘, 末永聖武, 宮永顕正, 工藤史貴, 江口 正

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 海洋鎖状リポペプチド hoshinoamide C の全合成と絶対立体配置の決定

    大友啓介, 末永聖武, 岩﨑有紘

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来新規鎖状ペプチド Iheyamide 類の単離と構造決定

    栗澤尚瑛, 岩﨑有紘, 末永聖武

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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  • 沖縄産海洋シアノバクテリア由来新規鎖状ペプチドの単離、構造決定および糖取り込み活性の評価

    尾崎香織, 澄本慎平, 岩﨑有紘, 末永聖武, 照屋俊明

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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  • 海洋産リポペプチドMinnamide A脂肪酸部分の合成研究1

    岸本勇志, 小林正幸, 佐藤理央, 岩﨑有紘, 末永聖武

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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  • 海洋産リポペプチドMinnamide A脂肪酸部分の合成研究2

    小林正幸, 佐藤理央, 岸本勇志, 岩﨑有紘, 末永聖武

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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  • 海洋産リポペプチドMinnamide Aペプチド部分の合成研究

    佐藤理央, 小林正幸, 岸本勇志, 岩﨑有紘, 末永聖武

    日本化学会第100春季年会  ( 誌上開催 )   2020年3月 

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  • Discovery and Biological Activities of Novel Lipopeptides Isolated from Marine Cyanobacteria 招待

    慶應義塾大学 複雑分子の革新的合成 国際シンポジウム  2019年12月 

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    記述言語:英語  

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  • 海洋性シアノバクテリア由来鎖状リポペプチド Jahanyne 類の構造,全合成および生物活性

    保科静香, 岩﨑有紘, 藤村 遥, 岡本慎一朗, 工藤隆文, 澄本慎平, NGUYEN Kim Anh, 小川英俊, 大野 修, 照屋俊明, 末永聖武

    第9回CSJ化学フェスタ  ( タワーホール船堀 )   2019年10月  日本化学会

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  • Discovery, total synthesis and mode of action of kurahyne, a novel ER stress–inducer from a marine cyanobacterium 招待

    Arihiro Iwasaki

    One Belt, One Road’ Young Scientist Forum  2019年9月 

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  • 強力な抗トリパノソーマ活性を示す海洋天然物hoshinolactam類の単離、構造決定、 全合成と生物活性

    岩崎有紘, 小川英俊, 澄本慎平, 鄭丞宰, 岩月正人, 石山亜紀, 穂刈玲, 乙黒一彦, 大村智, 中野由美子, 野崎智義, 末永聖武

    第61回天然有機化合物討論会  ( 広島国際会議場 )   2019年9月 

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  • 医薬品候補物質の探索源としての海洋シアノバクテリア 招待

    岩﨑有紘

    2019年ラン藻ゲノム交流会  2019年6月 

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  • 海洋天然物 jahanyne 類の全合成および結合タンパク質の同定

    保科静香, 岩﨑有紘, 藤村遥, 岡本慎一朗, 工藤隆文, 照屋俊明, 末永聖武

    日本ケミカルバイオロジー学会第14回年会  ( ウインクあいち(名古屋市) )   2019年6月 

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  • 海洋シアノバクテリア由来鎖状リポペプチドMinnamide Aの単離、構造決定および生物活性

    澄本慎平, 小林正幸, 佐藤理央, 四宮誠一, 岩﨑有紘, 須田彰一郎, 照屋俊明, 犬塚俊康, 大野修, 末永聖武

    日本ケミカルバイオロジー学会第14回年会  ( ウインクあいち(名古屋市) )   2019年6月 

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  • Discovery, total synthesis and mode of action of kurahyne, a novel ER stress–inducer from a marine cyanobacterium 招待

    Hainan Institute of Science and Technology  2019年5月 

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  • 海洋リポペプチドJahanyne類の結合タンパク質の探索及び同定

    保科静香, 岩﨑有紘, 工藤隆文, 照屋俊明, 末永聖武

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • チアゾール含有ポリケチドtomurulineの合成研究2

    藤村 遥, 工藤千尋, 大野 修, 岩﨑有紘, 末永聖武

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • 海洋シアノバクテリア由来の新規ペプチド hoshinoamides C-E の単離と構造

    塩田育万, 岩﨑有紘, 澄本慎平, 末永聖武

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • 沖縄県産海洋シアノバクテリア由来新規鎖状リポペプチドの単離と構造決定

    岩﨑慶太郎, 岩﨑有紘, 澄本慎平, 末永聖武

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • 海洋産リポペプチドMinnamide AにおけるC-9位メチル基の合成的手法による絶対立体配置の決定

    小林正幸, 佐藤理央, 澄本慎平, 四宮誠一, 照屋俊明, 岩﨑有紘, 末永聖武

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • Janadolideの標的たんぱく質同定のためのプローブ合成を志向した人工類縁体の合成研究

    大友啓介, 小島大輔, 小川英俊, 岩﨑有紘, 末永聖武

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • 沖縄県産海洋シアノバクテリアにおける新規生理活性物質の探索

    尾崎香織, 瀬澤 大, 藤村 遥, 岩﨑有紘, 末永聖武, 照屋俊明

    日本化学会第99春季年会  ( 甲南大学岡本キャンパス )   2019年3月  日本化学会

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  • Discovery, Total Synthesis and Mode of Action of Kurahyne, a Novel ER Stress–Inducer from a Marine Cyanobacterium 招待

    Arihiro Iwasaki

    Skaggs School of Pharmacy and Pharmaceutical Sciences Seminar Series, University of California San Diego  2019年1月 

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    記述言語:英語  

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  • Cytotoxicity Structure-activity Relationship and Synthesis of Biotin Probes of Marine Lipopeptide Jahanyne and Related Compounds. 国際会議

    Shizuka Hoshina, Arihiro Iwasaki, Takafumi Kudo, Toshiaki Teruya, Kiyotake Suenaga

    30th IUPAC Symposium on the Chemistry of Natural Products,  ( Athens, Greece )   2018年11月 

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  • A marine lipopeptide, minnamide A: Synthetic studies for assignment of the C-9 methyl stereochemistry. 国際会議

    Masayuki Kobayashi, Shimpei Sumimoto, Seiichi Shinomiya, Toshiaki Teruya, Arihiro Iwasaki, Kiyotake Suenaga

    30th IUPAC Symposium on the Chemistry of Natural Products,  ( Athens, Greece )   2018年11月 

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  • Isolation and structure determination of two new peptides from marine cyanobacteria. 国際会議

    Keitaro Iwasaki, Arihiro Iwasaki, Simpei Sumimoto, Kiyotake Suenaga

    30th IUPAC Symposium on the Chemistry of Natural Products,  ( Athens, Greece )   2018年11月 

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  • Isolation and Structure Determination of Four New Compounds from Marine Cyanobacteria. 国際会議

    Ikuma Shiota, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga

    30th IUPAC Symposium on the Chemistry of Natural Products,  ( Athens, Greece )   2018年11月 

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  • Structure, Total Synthesis and Biological Activities of Marine Lipopeptide Jahanyne and its Analogs 招待

    Arihiro Iwasaki, Shinichiro Okamoto, Haruka Fujimura, Takafumi Kudo, Shizuka Hoshina, Shimpei Sumimoto, Toshiaki Teruya, Kiyotake Suenaga

    International Congress on Pure and Applied Chemistry Langkawi 2018  2018年11月 

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  • 海洋性鎖状リポペプチド、Jahanyne類の構造と合成、生物活性

    岩﨑有紘, 岡本慎一朗, 藤村 遥, 工藤隆文, 保科静香, 澄本慎平, 中野由美子, 野崎智義, 照屋俊明, 末永聖武

    第60回天然有機化合物討論会  ( 久留米シティプラザ )   2018年9月 

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  • Structure, Total Synthesis and Biological Activities of Marine Lipopeptide Jahanyne and its Analogs 招待

    Arihiro Iwasaki

    Inner Mongolia University  2018年6月 

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  • 抗寄生虫活性を示す海洋天然物の作用機序解明を指向した合成研究

    岩﨑有紘, 小島大輔, 小川英俊, 保科静香, 鄭 丞宰, 岩月正人, 中野由美子, 石山亜紀, 穂刈 玲, 乙黒一彦, 大村智, 野崎智義, 末永聖武

    日本ケミカルバイオロジー学会第13回年会  ( 東京医科歯科大学 )   2018年6月  日本ケミカルバイオロジー学会

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  • 海洋生物由来リポポリサッカライド(LPS)機能調節物質の探索

    人見 悠毅, 寺崎 拓郎, 岩﨑 有紘, 末永 聖武, 松野 研司, 大野 修

    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • 沖縄県産海洋シアノバクテリア由来新規環状ペプチドcroissamideの単離と構造決定

    岩﨑 慶太郎, 岩﨑 有紘, 澄本 慎平, 末永 聖武

    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • 抗寄生虫活性を示す新規海洋天然物の単離、構造決定、全合成と生物活性

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    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • 海洋性シアノバクテリア由来鎖状リポペプチドJahanyne類の構造、全合成および生物活性

    保科 静香, 岩﨑 有紘, 藤村 遥, 岡本 慎一朗, 工藤 隆文, 澄本 慎平, NGUYEN Kim Anh, 小川 英俊, 大野 修, 照屋 俊明, 末永 聖武

    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • チアゾール含有ポリケチドtomurulineの合成研究

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    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • 海洋シアノバクテリア由来の新規ポリケチドcaldorinの単離と構造2

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    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • 海洋産リポペプチドMinnamideAの合成研究と立体化学の決定2

    小林 正幸, 澄本 慎平, 四宮 誠一, 照屋 俊明, 岩﨑 有紘, 末永 聖武

    新規素材探索研究会第17回セミナー  ( 新横浜フジビューホテル )   2018年6月  新規素材探索研究会

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  • 海洋シアノバクテリア由来の新規天然物に関する生物有機化学的研究 招待

    岩﨑有紘

    第6回慶應有機化学若手シンポジウム  2018年5月 

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  • Structure and synthetic study of lipopeptides, isolated from marine cyanobacteria. 招待 国際会議

    Shimpei Sumimoto, Daisuke Ojima, Masayuki Kobayashi, Seiichi Shinomiya, Arihiro Iwasaki, Toshiaki Teruya, Kiyotake Suenaga

    2018 International Conferenece on Frontier Chemistry and Life Sciences  ( Kaohsiung Medical University, Kaohsiung )   2018年5月 

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  • 海洋シアノバクテリア由来の新規ポリケチド caldorin の単離と構造

    塩田育万, 岩﨑有紘, 澄本慎平, 関 怜子, 小林啓介, 供田 洋, 末永聖武

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 海洋産リポペプチドMinnamide Aの合成研究と立体化学の決定

    小林正幸, 澄本慎平, 四宮誠一, 照屋俊明, 岩﨑有紘, 末永聖武

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 新規チアゾール含有ポリケチドtomurulineの合成研究

    藤村 遥, 工藤千尋, 大野 修, 岩﨑有紘, 末永聖武

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 海洋リポペプチドJahanyne類の構造活性相関とビオチンプローブの合成

    保科静香, 岩﨑有紘, 工藤隆文, 照屋俊明, 末永聖武

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 海洋生物由来のリポポリサッカライド(LPS)の機能を阻害する化合物の探索

    寺崎拓郎, 岩﨑有紘, 末永聖武, 松野研司, 大野 修

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 沖縄県産海洋シアノバクテリア由来新規環状ペプチドの単離と構造決定

    岩崎慶太郎, 岩﨑有紘, 末永聖武

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 石垣島産海洋シアノバクテリア由来、新規鎖状ペプチドホシノアミド類の単離と構造

    岩﨑有紘, 蓼沼隆人, 澄本慎平, 松原輝彦, 佐藤智典, 末永聖武

    日本化学会第98春季年会  ( 日本大学船橋キャンパス )   2018年3月  日本化学会

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  • 沖縄県産海洋生物における糖取り込み物質の探索

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    日本化学会第96春季年会  ( 同志社大学京田辺キャンパス )   2016年3月  日本化学会

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    Pacifichem 2015  ( Honolulu )   2015年12月 

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    記述言語:英語   会議種別:ポスター発表  

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  • Yoshinone A: A novel natural product that shows an anti-obesity activity. 国際会議

    Yoshinori Kawazoe, Tomoyuki Koyama, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga, Daisuke Uemura

    Pacifichem 2015  ( Honolulu )   2015年12月 

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    記述言語:英語   会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来新規小胞体ストレス誘導剤クラハインの構造,合成および作用機序解明

    岩﨑有紘, 大野修, 澄本慎平, 岡本慎一朗, 森田真布, 旦慎吾, 矢守隆夫, 末永聖武

    第57回天然有機化合物討論会  ( 神奈川県民ホール )   2015年9月 

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋生物由来新規生物活性物質の構造と生物活性

    岩﨑有紘, 大野 修, 澄本真平, 末永聖武

    日本ケミカルバイオロジー学会第10回年会  2015年6月  日本ケミカルバイオロジー学会

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋酸微細藻類由来新規リポペプチド類の構造と生物活性

    岩﨑有紘, 大野 修, 澄本慎平, 末永聖武

    新規素材探索研究会第14回セミナー  ( 新横浜フジビューホテル )   2015年6月  新規素材探索研究会

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋産ポリケチドyoshinone Aの合成研究

    四宮誠一, 岩﨑有紘, 大野 修, 末永聖武

    新規素材探索研究会第14回セミナー  ( 新横浜フジビューホテル )   2015年6月  新規素材探索研究会

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    記述言語:日本語   会議種別:ポスター発表  

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  • t-Bu基を有する海洋シアノバクテリア由来新規環状リポペプチドの単離と構造決定

    小川英俊, 岩﨑有紘, 澄本慎平, 大野 修, 末永聖武

    新規素材探索研究会第14回セミナー  ( 新横浜フジビューホテル )   2015年6月  新規素材探索研究会

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    記述言語:日本語   会議種別:ポスター発表  

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  • 新規鎖状リポペプチドkurahyne類の全合成

    岡本慎一朗, 岩﨑有紘, 大野 修, 末永聖武

    新規素材探索研究会第14回セミナー  ( 新横浜フジビューホテル )   2015年6月  新規素材探索研究会

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  • 海洋シアノバクテリア由来新規エナミドの単離と構造決定

    澄本慎平, 岩﨑有紘, 大野 修, 末永聖武

    新規素材探索研究会第14回セミナー  ( 新横浜フジビューホテル )   2015年6月  新規素材探索研究会

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋微細藻類由来新規リポペプチドの構造および生物活性

    岩崎有紘, 大野 修, 澄本慎平, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 新規海洋産ポリケチドyoshinone Aの合成研究

    四宮誠一, 岩崎有紘, 大野 修, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:ポスター発表  

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  • t-Bu基を有する海洋シアノバクテリア由来新規環状リポペプチドの単離と構造決定

    小川英俊, 岩崎有紘, 澄本慎平, 大野 修, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 特異な脂肪酸鎖をもつ海産シアノバクテリア由来新規鎖状リポペプチドの単離と構造決定

    澄本慎平, 岩崎有紘, 大野 修, 犬塚俊康, 照屋俊明, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 鎖状デプシペプチドMaedamideの単離、構造決定および合成研究

    高柳綾乃, 岩崎有紘, 大野 修, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 新規ペプチド化合物kurahyne類の全合成

    岡本慎一朗, 岩崎有紘, 大野 修, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 海洋産マクロリドkoshikalideの合成研究と絶対立体配置の決定

    国府田一樹, 長本雅司, 岩崎有紘, 末永聖武

    日本化学会第95春季年会  ( 日本大学船橋キャンパス )   2015年3月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来新規小胞体ストレス誘導剤kurahyneの単離と機能解析

    大野 修, 岩崎有紘, 旦 慎吾, 矢守隆夫, 末永聖武

    第18回日本がん分子標的治療学会学術集会  ( 仙台 )   2014年6月 

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  • 海洋シアノバクテリア由来新規小胞体ストレス誘導剤kurahyneの単離と機能解析

    岩﨑有紘, 大野 修, 旦 慎吾, 矢守隆夫, 末永聖武

    日本ケミカルバイオロジー学会第9回年会  ( 大阪大学 )   2014年6月 

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリア由来新規小胞体ストレス誘導剤 kurahyne の単離と機能解析

    岩崎 有紘, 大野 修, 旦 慎吾, 矢守 隆夫, 末永 聖武

    新規素材探索研究会第13回セミナー  ( 新横浜 )   2014年6月 

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋シアノバクテリア由来新規小胞体ストレス誘導剤 kurahyne の単離と機能解析

    岩崎 有紘, 大野 修, 旦 慎吾, 矢守 隆夫, 末永 聖武

    化学療法基盤支援活動第3回シンポジウム  ( 名護 )   2014年5月 

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    記述言語:日本語   会議種別:ポスター発表  

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  • 海洋シアノバクテリアが形成するバイオマット由来の新規生物活性物質の単離と構造

    岩崎有紘, 大野 修, 澄本慎平, 須田彰一郎, 末永聖武

    日本化学会第94春季年会  ( 名古屋大学 )   2014年3月  日本化学会

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    記述言語:日本語   会議種別:口頭発表(一般)  

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  • 海洋シアノバクテリアが形成するバイオマット由来の新規リポペプチドの単離と構造

    岩﨑有紘, 澄本慎平, 大野修, 須田彰一郎, 末永聖武

    日本農芸化学会関東支部大会  ( 慶應義塾大学 )   2013年11月  日本農芸化学会関東支部

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▼全件表示

受賞

  • 第37回 若い世代の特別講演会 講演証

    2023年3月   日本化学会   海洋シアノバクテリア由来新規天然物の発見とその価値の探索

    岩崎有紘

  • 第20回 天然物化学談話会奨励賞

    2021年7月   天然物化学談話会・同奨励賞選考委員会   海洋シアノバクテリア由来新規天然物の発見と、その価値の探索

  • 第33回井上研究奨励賞

    2017年2月   公益財団法人井上科学振興財団  

  • 藤原賞(藤原奨学金基金)

    2016年3月   藤原奨学金基金  

  • 第57回天然有機化合物討論会 奨励賞

    2015年9月   第57回天然有機化合物討論会実行委員会  

  • 毒素シンポジウム 第62回奨励賞

    2015年7月   毒素シンポジウム運営委員会   海洋シアノバクテリア由来、新規小胞体ストレス誘導剤クラハインの単離、構造決定、作用機序解明

  • 日本ケミカルバイオロジー学会 第10回年会 ポスター賞

    2015年6月   日本ケミカルバイオロジー学会   海洋生物由来新規生物活性物質の構造と生物活性

  • 新学術領域研究「天然物ケミカルバイオロジー」第7回若手研究者ワークショップ 優秀講演賞

    2015年6月   新学術領域研究「天然物ケミカルバイオロジー」   藍藻由来新規アポトーシス誘導剤、クラハインの構造と作用機序解明

  • 日本化学会第95春季年会 学生講演賞

    2015年3月   日本化学会   海洋微細藻類由来新規リポペプチドの構造および生物活性

    岩崎有紘

  • 新規素材探索研究会 第13回セミナー 最優秀ポスター賞

    2014年6月   新規素材探索研究会   海洋シアノバクテリア由来新規小胞体ストレス誘導剤kurahyneの単離と機能解析

    岩崎有紘

  • 化学療法基盤支援活動第3回シンポジウム 優秀ポスター賞

    2014年5月   文部科学省 科研費・がん支援 化学療法基盤支援活動班   海洋シアノバクテリア由来新規小胞体ストレス誘導剤kurahyneの単離と機能解析

    岩崎有紘

▼全件表示

共同研究・競争的資金等の研究課題

  • 難培養性シアノバクテリア由来新規天然有機化合物の探索・合成展開による創薬基盤構築

    研究課題/領域番号:21KK0099  2021年10月 - 2025年3月

    日本学術振興会  科学研究費助成事業 国際共同研究加速基金(国際共同研究強化(B))  国際共同研究加速基金(国際共同研究強化(B))  筑波大学、慶應義塾大学

    吉田 将人, 岩﨑有紘, 植草義徳

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    担当区分:研究分担者 

    配分額:18980000円 ( 直接経費:14600000円 、 間接経費:4380000円 )

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  • 海洋生物がもつ末端アルキン天然物のケミカルスペースの開拓

    研究課題/領域番号:21K14747  2021年4月 - 2024年3月

    日本学術振興会  科学研究費助成事業 若手研究  若手研究  慶應義塾大学

    岩崎 有紘

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    配分額:4550000円 ( 直接経費:3500000円 、 間接経費:1050000円 )

    末端アルキンをもつ海洋天然物に注目し、構造と生物活性の多様性の解明を目的とする本研究において、今年は以下に述べる実績をあげた。
    (1)構造の多様性について:真栄田岬で採集した海洋シアノバクテリアより、末端アルキンをもつ環状リポペプチドを単離した。本化合物は、ペプチド鎖と末端アルキン含有脂肪酸部からなる構造であり、脂肪酸部にはアシル化された水酸基とgemジメチル構造をもつ。ヒト子宮頸がん細胞を用いた細胞増殖阻害活性の結果、本化合物は細胞毒性を示さないことを明らかにした。現在、熱帯病原虫に対する増殖阻害活性(トリパノソーマおよびマラリア)とウイルス感染阻害活性(エボラウイルスおよびCOVID-19)の評価を実施している。また、大度海岸で採集したOkeania属海洋シアノバクテリアより、新規末端アルキン含有鎖状リポペプチドを2種単離し、オオドオケアニンAおよびBと名付けた。本化合物が脂肪細胞分化促進活性をもつこと見出した。
    (2)生物活性の多様性について:当研究室で過去に発見した末端アルキン含有リポペプチド(クラハインおよびジャハナイン)のウイルス感染阻害活性(エボラウイルスおよびCOVID-19)の評価を実施している
    (3)探索対象生物の拡張に向けた取り組みについて:探索対象生物を拡張するために実験環境を整備した。従来は海洋シアノバクテリアやカイメン、ホヤといった採集が容易で比較的大型の集合体を形成する生物をソースとしてきたが、あらたに海洋放線菌や海洋糸状菌を対象とした探索を実施するために、菌類の培養環境を構築した。現在、特定の菌類を分離するための選択培地について検討を進めており、一部の海洋放線菌についてはその分離と大量培養に成功した。現在、成分探索を実施している。
    (4)その他:末端アルキン天然物を探索する過程で7種の新規天然物を単離し、その構造と生物活性を明らかにした。

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  • ビッグデータと人工知能を活用した熱帯病治療薬候補物質の探索

    2022年4月 - 2023年3月

    慶應義塾大学  学事振興資金 部門横断型  慶應義塾大学

    岩﨑有紘, 植草義徳

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    担当区分:研究代表者 

    配分額:1600000円 ( 直接経費:1600000円 )

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  • 温泉藻のもつ有用天然物の網羅的探索

    2021年10月 - 2022年9月

    戸部眞紀財団  研究助成  慶應義塾大学

    岩﨑有紘、植草義徳

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    担当区分:研究代表者 

    配分額:1000000円 ( 直接経費:850000円 、 間接経費:150000円 )

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  • 海洋天然物由来の抗寄生虫薬リードの創出

    研究課題/領域番号:18K14346  2018年4月 - 2021年3月

    日本学術振興会  科学研究費助成事業 若手研究  若手研究  慶應義塾大学

    岩崎 有紘

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    配分額:4160000円 ( 直接経費:3200000円 、 間接経費:960000円 )

    海洋天然物由来の抗寄生虫薬リード化合物の創出を目指す本研究に関し、本年度は以下の実績を上げた。
    (1) nM オーダーで抗寄生虫活性を示す環状リポペプチド、ジャナドライドについて、その全合成を達成した。確立した合成ルートを元に、各アミノ酸残基に改変を加えた11種類の類縁体群を合成した。現在、これらの分子の抗寄生虫活性の評価を行っている。
    (2) nM オーダーで抗寄生虫活性を示すラクタム、ホシノラクタムについて、脂肪酸部末端に改変を加えた2種の類縁体群を合成した。さらに天然より、新規類縁体2種を新たに単離、構造決定し、それらの全合成を達成した。現在、これらの分子の抗寄生虫活性の評価を行っている。
    (3) 沖縄、奄美地方に生息する海洋シアノバクテリアより、抗寄生虫活性を示す以下の新規化合物群を新たに単離し、その構造を決定した。ホシノアミドAおよびB:特徴的な長鎖アミノ酸部を持つ鎖状ペプチド化合物であり、10 μM の濃度でもヒト細胞に毒性を示さない一方で、マラリア原虫に対して 0.5~1 μM の濃度で増殖を阻害する。イコアミド:2個のメトキシ基を含む脂肪酸鎖を持つ鎖状リポペプチドであり、ヒト由来細胞に毒性を示すよりも 10 倍薄い濃度で、マラリア原虫の増殖を阻害する (IC50: 0.14 μM)。マブニアミド:N末端にブタン酸部を持つ鎖状リポペプチドであり、40 μM の濃度でもヒト細胞に毒性を示さない一方で、マラリア原虫に対して 1.4 μM の濃度で増殖を阻害する。本化合物の全合成も達成した。
    (4) 所属研究室でこれまでに単離してきた天然物およびその合成類縁体およそ70種について、マラリア原虫、赤痢アメーバ、ジアルジアに対する増殖阻害活性を評価した。その結果、いくつかの有望な活性を示す化合物が見つかった。

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  • ディープラーニングと革新的NMR手法を組み合わせた次世代型天然物探索法の開発

    2019年4月 - 2020年3月

    慶應義塾大学  若手研究者育成ものづくり特別事業「若手研究者の海外共同研究の推進」  慶應義塾大学

    岩﨑有紘

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    担当区分:研究代表者 

    配分額:1000000円 ( 直接経費:1000000円 )

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  • 難培養性海洋シアノバクテリアのもつ、医薬品候補物質の生合成遺伝子クラスターの特定

    2018年4月 - 2019年3月

    慶應義塾大学  若手研究者育成ものづくり特別事業「若手研究者の海外共同研究の推進」  慶應義塾大学

    岩﨑有紘

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    担当区分:研究代表者 

    配分額:1000000円 ( 直接経費:1000000円 )

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  • 海洋天然物由来、抗寄生虫活性を有する医薬品シードの探索

    2017年4月 - 2018年3月

    慶應義塾大学  指定研究プロジェクト 次世代先端分野探索研究  慶應義塾大学

    岩﨑有紘

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    担当区分:研究代表者 

    配分額:300000円 ( 直接経費:300000円 )

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  • 有用海洋シアノバクテリアの生合成遺伝子の解析

    2016年4月 - 2017年3月

    慶応工学会  研究費援助  慶應義塾大学

    岩﨑有紘

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    担当区分:研究代表者 

    配分額:300000円 ( 直接経費:300000円 )

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  • 小胞体ストレス誘導剤クラハインの活性発現メカニズムの解明

    研究課題/領域番号:15H06584  2015年8月 - 2017年3月

    日本学術振興会  科学研究費助成事業 研究活動スタート支援  研究活動スタート支援  慶應義塾大学

    岩崎 有紘

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    配分額:2730000円 ( 直接経費:2100000円 、 間接経費:630000円 )

    海洋天然物クラハインは、破骨細胞分化阻害活性と小胞体膜上のカルシウムイオンポンプ(SERCA)阻害活性を有する鎖状リポペプチドである。本化合物の示す生物活性の作用機序解明を目的として研究を行った。
    結果として、以下のことが明らかとなった。
    ①クラハインによる破骨細胞分化阻害活性に、プロヒビチン-1および-2が関与している可能性が示唆された。②クラハインのSERCA結合部位として、全アミノ酸配列(およそ1000残基)中、特定の14残基のいずれかが関与する可能性が示唆された。③クラハイン類似海洋天然物2種を発見し、それらの構造を解明し、全合成を達成した。また、構造活性相関に関する知見を得た。

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▼全件表示

現在の担当授業科目

  • 2023年度   化学2   学部

  • 2023年度   卒業研究Ⅰ   学部

  • 2023年度   卒業研究Ⅱ   学部

  • 2023年度   基礎有機化学   学部

  • 2023年度   応用化学実験2   学部

委員歴

  • 2017年9月 - 現在

    天然物化学談話会世話人会   天然物化学談話会世話人  

  • 2022年12月 - 2023年5月

    第10回慶應有機化学若手シンポジウム実行委員会   実行委員  

  • 2020年1月 - 2023年3月

    毒素シンポジウム 運営事務局   運営委員  

  • 2021年12月 - 2022年5月

    第9回慶應有機化学若手シンポジウム実行委員会   実行委員  

  • 2017年9月 - 2021年8月

    慶應義塾大学理工学部化学科   広報委員  

  • 2020年5月 - 2021年5月

    第8回慶應有機化学若手シンポジウム実行委員会   実行委員  

  • 2019年7月 - 2019年12月

    日本化学会 第100春季年会 プログラム編成委員  

  • 2019年8月 -  

    中堅・若手リーダーのための YUGOKAFe(有機合成化学協会) サポーター  

  • 2018年12月 - 2019年5月

    第7回慶應有機化学若手シンポジウム実行委員会   委員長  

  • 2017年12月 - 2018年5月

    第6回慶應有機化学若手シンポジウム実行委員会   実行委員  

  • 2016年7月 - 2017年7月

    第52回天然物化学談話会実行委員会   実行委員  

  • 2016年12月 - 2017年5月

    第5回慶應有機化学若手シンポジウム実行委員会   実行委員  

  • 2016年5月 - 2017年3月

    日本化学会・第97春季年会   会場・総務小委員会委員  

  • 2015年12月 - 2016年5月

    第4回慶應有機化学若手シンポジウム実行委員会   実行委員  

  • 2015年4月 - 2015年9月

    第57回天然有機化合物討論会 実行委員会   実行委員  

▼全件表示

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