2021/11/07 更新

写真a

クボタ タカアキ
久保田 高明
KUBOTA Takaaki
所属
医歯薬学域 教授
職名
教授

学位

  • 博士(薬学) ( 2002年3月   北海道大学 )

研究キーワード

  • 立体化学

  • アルカロイド

  • 海洋由来真菌

  • アクチン

  • チューブリン

  • 分子標的

  • リード化合物

  • Natural Products Chemistry

  • Natural Products Chemistry

  • 天然物有機化学

  • 天然物有機化学

  • がん分子標的

  • がん治療

  • バイオプローブ

  • 殺細胞活性

  • 医薬リード

  • 海洋天然物

  • イエジマリド

  • 天然薬物

  • 天然物ライブラリー

  • 機能性天然分子

  • 海洋生物

  • ポリケチド合成酵素

  • 生物・生体工学

  • 天然資源

研究分野

  • ライフサイエンス / 生物有機化学

  • ナノテク・材料 / 構造有機化学、物理有機化学

  • ナノテク・材料 / 生物分子化学

  • ライフサイエンス / 薬系化学、創薬科学

学歴

  • 北海道大学    

    1999年4月 - 2002年3月

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    国名: 日本国

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  • 北海道大学    

    1997年4月 - 1999年3月

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    国名: 日本国

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  • 東京理科大学   薬学部   製薬学科

    1992年4月 - 1996年3月

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    国名: 日本国

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経歴

  • 岡山大学   学術研究院医歯薬学域(薬学系)   教授

    2021年4月 - 現在

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  • 岡山大学   大学院医歯薬学総合研究科(薬学系)   教授

    2020年11月 - 2021年3月

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  • 昭和薬科大学   薬学部   教授

    2015年4月 - 2020年10月

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  • 北海道大学   大学院薬学研究院   准教授

    2010年4月 - 2015年3月

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  • 北海道大学   大学院先端生命科学研究院   准教授

    2009年2月 - 2010年3月

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  • 北海道大学   大学院薬学研究院   准教授

    2008年9月 - 2009年1月

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  • 北海道大学   大学院薬学研究院   講師

    2006年4月 - 2008年8月

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  • 北海道大学   大学院薬学研究科   講師

    2005年4月 - 2006年3月

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  • 北海道大学   大学院薬学研究科   契約職員(研究員)

    2005年2月 - 2005年3月

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  • ワシントン大学   化学科   博士研究員

    2003年4月 - 2005年1月

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  • 日本学術振興会   日本学術振興会特別研究員(PD)

    2002年4月 - 2003年3月

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  • 日本学術振興会   日本学術振興会特別研究員(DC)

    2001年4月 - 2002年3月

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所属学協会

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委員歴

  • 日本薬学会   生薬天然物部会常任世話人  

    2021年4月 - 現在   

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  • 日本生薬学会   関西支部委員  

    2021年4月 - 現在   

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  • 日本薬学会   関東支部執行部  

    2020年3月 - 2021年2月   

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  • 日本生薬学会   財務理事  

    2018年 - 現在   

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    団体区分:学協会

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  • 日本生薬学会   学会誌編集委員会編集副委員長  

    2018年 - 現在   

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    団体区分:学協会

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  • 日本生薬学会   財務理事補佐  

    2017年   

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    団体区分:学協会

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  • 日本生薬学会   学会誌編集委員会委員  

    2016年 - 2017年   

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    団体区分:学協会

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  • 日本生薬学会   代議員  

    2016年 - 2017年   

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    団体区分:学協会

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  • 日本生薬学会   北海道支部庶務  

    2014年   

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    団体区分:学協会

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  • 日本生薬学会   北海道支部監事  

    2012年 - 2013年   

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    団体区分:学協会

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  • 日本生薬学会   北海道支部委員  

    2010年 - 2011年   

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    団体区分:学協会

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  • 日本生薬学会   北海道支部監事  

    2008年 - 2009年   

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    団体区分:学協会

    日本生薬学会

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  • 日本薬学会   代議員  

    2008年 - 2009年   

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    団体区分:学協会

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  • 日本薬学会   北海道支部庶務幹事  

    2008年   

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    団体区分:学協会

    日本薬学会

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  • 日本薬学会   トピックス専門小委員  

    2007年 - 2008年   

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    団体区分:学協会

    日本薬学会

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  • 日本薬学会   北海道支部幹事  

    2007年   

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    団体区分:学協会

    日本薬学会

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  • 日本生薬学会   北海道支部庶務  

    2006年 - 2007年   

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    団体区分:学協会

    日本生薬学会

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論文

  • Macrocarquinoids A–C, new meroterpenoids from Sargassum macrocarpum 査読

    Hiromi Niwa, Shin ichiro Kurimoto, Takaaki Kubota, Mitsuhiro Sekiguchi

    Journal of Natural Medicines   75 ( 1 )   194 - 200   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:SPRINGER JAPAN KK  

    The production and accumulation of advanced glycation end products (AGEs) have been implicated in diabetes and diabetic complication. This study was conducted as a search for an AGE inhibitor from brown alga,Sargassum macrocarpum.Separation and purification were performed using AGEs inhibitory activity as an index, yielding isolation of 11 meroterpenoids, of which 3 were new compounds: macrocarquinoids A (1), B (6), and C (9). Their structures were elucidated using NMR spectral analysis with 2D techniques. All tested compounds showed AGEs inhibitory activity. Particularly, macrocarquinoid C (9) possessed the strongest activity (IC50: 1.0 mM) of isolated compounds. This activity was stronger than that of aminoguanidine (positive control).[GRAPHICS].

    DOI: 10.1007/s11418-020-01449-y

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  • Kamiohnoyneosides A and B, two new polyacetylene glycosides from flowers of edible Chrysanthemum "Kamiohno" 査読

    Shin ichiro Kurimoto, Hiroki Fujita, Satomi Kawaguchi, Yu F. Sasaki, Takanori Nakamura, Takaaki Kubota

    Journal of Natural Medicines   75 ( 1 )   167 - 172   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)  

    Two new polyacetylene glycosides, kamiohnoyneosides A and B, were isolated from the flowers of edible Chrysanthemum "Kamiohno", along with a known polyacetylene glycoside and two known monoterpene glycosides. The structures of new compounds were elucidated on the basis of spectroscopic data. Kamiohnoyneoside A and three known compounds moderately inhibited formation of Nε-(carboxymethyl)lysine, one of the representative advanced glycation endproducts.

    DOI: 10.1007/s11418-020-01443-4

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  • Integrated omics unveil the secondary metabolic landscape of a basal dinoflagellate 査読

    Girish Beedessee, Takaaki Kubota, Asuka Arimoto, Koki Nishitsuji, Ross F. Waller, Kanako Hisata, Shinichi Yamasaki, Noriyuki Satoh, Jun’ichi Kobayashi, Eiichi Shoguchi

    BMC Biology   18 ( 1 )   2020年12月

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    掲載種別:研究論文(学術雑誌)  

    Background: Some dinoflagellates cause harmful algal blooms, releasing toxic secondary metabolites, to the detriment of marine ecosystems and human health. Our understanding of dinoflagellate toxin biosynthesis has been hampered by their unusually large genomes. To overcome this challenge, for the first time, we sequenced the genome, microRNAs, and mRNA isoforms of a basal dinoflagellate, Amphidinium gibbosum, and employed an integrated omics approach to understand its secondary metabolite biosynthesis. Results: We assembled the ~ 6.4-Gb A. gibbosum genome, and by probing decoded dinoflagellate genomes and transcriptomes, we identified the non-ribosomal peptide synthetase adenylation domain as essential for generation of specialized metabolites. Upon starving the cells of phosphate and nitrogen, we observed pronounced shifts in metabolite biosynthesis, suggestive of post-transcriptional regulation by microRNAs. Using Iso-Seq and RNA-seq data, we found that alternative splicing and polycistronic expression generate different transcripts for secondary metabolism. Conclusions: Our genomic findings suggest intricate integration of various metabolic enzymes that function iteratively to synthesize metabolites, providing mechanistic insights into how dinoflagellates synthesize secondary metabolites, depending upon nutrient availability. This study provides insights into toxin production associated with dinoflagellate blooms. The genome of this basal dinoflagellate provides important clues about dinoflagellate evolution and overcomes the large genome size, which has been a challenge previously.

    DOI: 10.1186/s12915-020-00873-6

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  • The manzamine alkaloids 査読 国際誌

    Takaaki Kubota, Shin ichiro Kurimoto, Jun'ichi Kobayashi

    Alkaloids: Chemistry and Biology   84   1 - 124   2020年

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    記述言語:英語   掲載種別:論文集(書籍)内論文  

    The manzamine alkaloids are absolutely one of the most fascinating marine natural products. The representative manzamine alkaloids, manzamines A-C, were isolated from a marine sponge Haliclona sp. collected off Cape Manzamo, Okinawa, Japan. The manzamine alkaloids are a unique class of alkaloids possessing a characteristic heterocyclic system, and exhibit a diverse range of bioactivities including cytotoxicity, antimicrobial activity, antimalarial activity, antiviral and antiinflammatory activities, antiinsecticidal activity, and proteasome inhibitory activity. About 100 manzamine alkaloids have been isolated from more than 16 species of marine sponges belonging to 5 families. The unusual ring systems, an intriguing suggested biogenetic pathway, and promising biological activities of manzamine alkaloids have attracted great interest as challenging targets for the total synthesis. This review is the continuation of the previous review published in volume 60 of The Alkaloids and covers isolation, structure elucidation, biosynthesis and biogenesis, chemical synthesis, and biological activity of manzamine alkaloids reported from 2003 to 2018.

    DOI: 10.1016/bs.alkal.2020.03.001

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  • Ma’edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp. 査読

    Shin-ichiro Kurimoto, Satsuki Seino, Jane Fromont, Jun'ichi Kobayashi, Takaaki Kubota

    Organic Letters   21 ( 21 )   8824 - 8826   2019年11月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    DOI: 10.1021/acs.orglett.9b03457

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  • Symbiodinolactone A, a new 12-membered macrolide from symbiotic marine dinoflagellate Symbiodinium sp. 査読

    Shin ichiro Kurimoto, Yurika Iinuma, Jun'ichi Kobayashi, Takaaki Kubota

    Tetrahedron Letters   59 ( 51 )   4496 - 4499   2018年12月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:Elsevier {BV}  

    A new 12-membered macrolide, symbiodinolactone A, was isolated from the culture broth of symbiotic marine dinoflagellate Symbiodinium sp. The gross structure of symbiodinolactone A was elucidated by spectroscopic analyses, and the relative configuration was elucidated by the J-based configuration analysis and density-functional theory calculations. Symbiodinolactone A is the new 12-membered macrolide possessing an E double bond between C-4 and C-5, a branched methyl group at C-7, and a 1,2,3-trihydroxybutyl group at C-11. Symbiodinolactone A is the first usual size macrolide and the first non-nitrogen-containing macrolide from dinoflagellate Symbiodinium sp. Symbiodinolactone A might be generated by the unexplained dinoflagellate polyketide biosynthetic machinery.

    DOI: 10.1016/j.tetlet.2018.11.018

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  • Ishigadine A, a new canthin-6-one alkaloid from an Okinawan marine sponge Hyrtios sp. 査読

    Hideaki Takahashi, Shin ichiro Kurimoto, Jun'ichi Kobayashi, Takaaki Kubota

    Tetrahedron Letters   59 ( 51 )   4500 - 4502   2018年12月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:Elsevier {BV}  

    A new indole alkaloid with the canthin-6-one skeleton, ishigadine A, has been isolated from an Okinawan marine sponge Hyrtios sp. The structure of ishigadine A was elucidated on the basis of spectroscopic analyses. Ishigadine A is a new canthin-6-one alkaloid possessing a hydroxy group, a 1,3-dimethyl-4-methylthioimidazolium, and a 1-propylguanidine. Ishigadine A is the third canthin-6-one alkaloid from sponges. Ishigadine A might be generated from L-arginine, L-histidine, and L-tryptophan. Ishigadine A exhibited moderate cytotoxicity against L1210 murine leukemia cells.

    DOI: 10.1016/j.tetlet.2018.11.019

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  • Ceratinadins E and F, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp. 査読 国際誌

    Shin Ichiro Kurimoto, Taito Ohno, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Satoshi Ōmura, Jun’ichi Kobayashi, Takaaki Kubota

    Marine Drugs   16 ( 12 )   463   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:MDPI} {AG  

    Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka'iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).

    DOI: 10.3390/md16120463

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  • New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities 査読

    Hien Minh Nguyen, Takuya Ito, Shin ichiro Kurimoto, Mika Ogawa, Nwet Nwet Win, Vo Quoc Hung, Hoai Thi Nguyen, Takaaki Kubota, Jun'ichi Kobayashi, Hiroyuki Morita

    Bioorganic and Medicinal Chemistry Letters   27 ( 14 )   3043 - 3047   2017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 investigation of the Vietnamese marine sponge Spongia sp. led to the isolation of three new sesquiterpene phenols, langconols A-C (1-3), and one new sesquiterpene hydroxyquinone, langcoquinone C (4), together with two known meroterpenoids (5 and 6). Their structures were determined on the basis of spectroscopic analyses and comparisons with published data. Furthermore, the antibacterial assays of the isolates 1-6 suggested that 4 and 6 had significant antibacterial activities against Bacillus subtilis and Staphylococcus aureus, with MICs ranging from 6.25 to 25.0 mu M, while 1 and 3 possessed significant antibacterial activities against B. subtilis with MICs of 12.5 and 25.0 mu M, respectively. In contrast, cyto-toxic assays of the isolated compounds 1-6, as well as compounds 7-15 previously isolated from this sponge, indicated that 1 and the previously reported anti-B. subtilis and anti-S. aureus sesquiterpene phenol 9 lacked cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervix cancer) and a human normal cell line (WI-38 fibroblast). (C) 2017 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2017.05.060

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  • Zamamidine D, a Manzamine Alkaloid from an Okinawan Amphimedon sp. Marine Sponge 査読

    Takaaki Kubota, Kenta Nakamura, Shin ichiro Kurimoto, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun’ichi Kobayashi

    Journal of Natural Products   80 ( 4 )   1196 - 1199   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  

    A new manzamine alkaloid, zamamidine D (1), was isolated from an Okinawan Amphimedon sp. marine sponge. The structure of zamamidine D (1) including the relative configuration was elucidated on the basis of spectroscopic data. Zamamidine D (1) is the first manzamine alkaloid possessing a 2,2'-methylenebistryptamine unit as the aromatic moiety instead of a beta-carboline unit. Zamamidine D (1) showed antimicrobial activity against several bacteria and fungi.

    DOI: 10.1021/acs.jnatprod.6b01110

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  • Stylissamide I, a new cyclic heptapeptide from an okinawan marine sponge Stylissa sp. 査読

    Takaaki Kubota, Kenta Nakamura, Shin Ichiro Kurimoto, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi

    Heterocycles   95 ( 2 )   799 - 806   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)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A new cyclic heptapeptide, stylissamide I (1), was isolated from an Okinawan marine sponge Stylissa sp. The structure of stylissamide I (1) was elucidated to be cydo-(L-Tyr(1)-L-Tyr(2)-L-Tyr(3)-L-Pro(1)-L-Pro(2)-L-Val-L-Pro(3)) by extensive spectral analyses and Marfey's method. Stylissamide I (1) showed antifungal activity against Aspergillus niger.

    DOI: 10.3987/COM-16-S(S)45

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  • Hyrtinadines C and D, new azepinoindole-type alkaloids from a marine sponge Hyrtios sp. 査読

    Takaaki Kubota, Kenta Nakamura, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   64 ( 7 )   975 - 978   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:PHARMACEUTICAL SOC JAPAN  

    New bisindole alkaloids, hyrtinadines C (1) and D (2), have been isolated from an Okinawan marine sponge Hyrtios sp. The structures of hyrtinadines C (1) and D (2) were elucidated based on analyses of the spectral data. Hyrtinadines C (1) and D (2) were the relatively rare alkaloids possessing a 3,4-fused azepinoindole skeleton. Hyrtinadines C (1) and D (2) showed antimicrobial activity.

    DOI: 10.1248/cpb.c16-00201

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  • Biosynthetic study of amphidinin A and Amphidinolide P 査読

    Takaaki Kubota, Hayato Sato, Takahiro Iwai, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   64 ( 7 )   979 - 981   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:PHARMACEUTICAL SOC JAPAN  

    The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with C-13-labeled acetates. C-13-NMR data of C-13-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C-1 units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C-1 units derived from C-2 of cleaved acetates. The all branched C-1 units of 1 and 2 were derived from C-2 of cleaved acetates.

    DOI: 10.1248/cpb.c16-00202

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  • Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part I: Synthesis of the C1-C13 Subunit 査読

    Koji Ochiai, Sankar Kuppusamy, Yusuke Yasui, Tsubasa Okano, Yasunobu Matsumoto, Nishant R. Gupta, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi, Yujiro Hayashi

    Chemistry - A European Journal   22 ( 10 )   3282 - 3286   2016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:WILEY-V C H VERLAG GMBH  

    Amphidinolide N, the structure of which has been recently revised, is a 26-membered macrolide featuring allyl epoxide and tetrahydropyran moieties with 13 chiral centers. Due to its challenging structure and extraordinary potent cytotoxicity, amphidinolide N is a highly attractive target of total synthesis. During our total synthesis studies of the 7,10-epimer of the proposed structure of amphidinolide N, we have synthesized the C1-C13 subunit enantio- and diastereoselectively. Key reactions include an l-proline catalyzed enantioselective intramolecular aldol reaction, Evans aldol reaction, Sharpless asymmetric epoxidation and Tamao-Fleming oxidation. To aid late-stage manipulations, we also developed the 4-(N-benzyloxycarbonyl-N-methylamino)butyryl group as a novel ester protective group for the C9 alcohol.

    DOI: 10.1002/chem.201504674

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  • Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis 査読

    Koji Ochiai, Sankar Kuppusamy, Yusuke Yasui, Kenji Harada, Nishant R. Gupta, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi, Yujiro Hayashi

    Chemistry - A European Journal   22 ( 10 )   3287 - 3291   2016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:WILEY-V C H VERLAG GMBH  

    The total synthesis of 7,10-epimer of the proposed structure of amphidinolideN was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP linchpin as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.

    DOI: 10.1002/chem.201504675

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  • Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis 査読

    Masafumi Tokuoka, Tomoki Kikuchi, Yasutomo Shinohara, Akifumi Koyama, Shin Ichiro Iio, Takaaki Kubota, Jun'ichi Kobayashi, Yasuji Koyama, Akira Totsuka, Hitoshi Shindo, Kazuo Sato

    Bioscience, Biotechnology and Biochemistry   79 ( 12 )   2081 - 2085   2015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:TAYLOR & FRANCIS LTD  

    Speradine A is a derivative of cyclopiazonic acid (CPA) found in culture of an Aspergillus tamarii isolate. Heterologous expression of a predicted methyltransferase gene, cpaM, in the cpa biosynthesis gene cluster of A. tamarii resulted in the speradine A production in a 2-oxoCPA producing A. oryzae strain, indicating cpaM is involved in the speradine A biosynthesis.

    DOI: 10.1080/09168451.2015.1065167

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  • Tyrokeradines G and H, new bromotyrosine alkaloids from an Okinawan Verongid sponge 査読

    Takaaki Kubota, Shinya Watase, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'Ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   25 ( 22 )   5221 - 5223   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  

    Two new bromotyrosine alkaloids, tyrokeradines G (1) and H (2), have been isolated from an Okinawan marine sponge of the order Verongida. The structures of 1 and 2 were elucidated on the basis of spectroscopic data. Tyrokeradine G (1) is the first bromotyrosine alkaloid possessing a beta-alanine unit, while tyrokeradine H (2) is a rare bromotyrosine alkaloid possessing a N-substituted pyridinium ring. Tyrokeradines G (1) and H (2) showed antifungal activity. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2015.09.061

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  • Amphidinin G, a putative biosynthetic precursor of amphidinin A from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Takahiro Iwai, Haruaki Ishiyama, Kanae Sakai, Tohru Gonoi, Jun'Ichi Kobayashi

    Tetrahedron Letters   56 ( 8 )   990 - 993   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:PERGAMON-ELSEVIER SCIENCE LTD  

    A new linear polyketide, amphidinin G (1), has been isolated from a symbiotic marine dinoflagellate Amphidinium sp. The planar structure of 1 was established mainly based on the 2D NMR data and the stereochemistry was elucidated by the combination off-value analysis, modified Mosher's method, and NMR chemical shift comparison with synthetic analogues. Amphidinin G (1) was expected to be a biosynthetic precursor of amphidinin A (2), a known linear dinoflagellate polyketide. Amphidinin G (1) showed antifungal activity against Trichophyton mentagrophytes. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2015.01.058

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  • Iejimalide C is a potent V-ATPase inhibitor, and induces actin disorganization 査読

    Sayaka Kazami, Masak Takaine, Hiroyasu Itoh, Takaaki Kubota, Jun'ichi Kobayashi, Takeo Usui

    Biological and Pharmaceutical Bulletin   37 ( 12 )   1944 - 1947   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:PHARMACEUTICAL SOC JAPAN  

    Iejimalides (IEJLs) A-D are 24-membered macrolides isolated from a tunicate Eudistoma cf. rigida, and exhibit potent cytotoxicity in vitro and antitumor activity in vivo. We previously reported that the molecular target of IEJL-A and -B was the vacuolar-type H+-ATPases (V-ATPases). However IEJL-C and -D, which are sulfonylated IEJL-A and -B, respectively, show more potent antitumor activity, and their molecular targets remain to be discovered. Here, we report that IEJL-C is also a potent V-ATPase inhibitor by binding in a site similar to the bafilomycin-binding site. Two-hour treatment with IEJL-C resulted in the complete disappearance of acidic organelles in HeLa cells. Interestingly, after 24-h treatment, small actin aggregates were observed instead of actin fibers. The same actin reorganization was also observed in cells treated with another V-ATPase inhibitor, bafilomycin A(1). Because IEJLs did not inhibit actin polymerization in vitro, these results suggest that the primary target of IEJL-C, as well as IEJL-A and -B, is V-ATPase, and actin reorganizations are probably caused by the disruption of pH homeostasis via V-ATPase inhibition.

    DOI: 10.1248/bpb.b14-00548

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  • Amphidinins C-F, amphidinolide Q analogues from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Takahiro Iwai, Kanae Sakai, Tohru Gonoi, Jun'ichi Kobayashi

    Organic Letters   16 ( 21 )   5624 - 5627   2014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  

    Four new polyketides, amphidinins CF (14), have been isolated from the culture broth of symbiotic dinoflagellate Amphidinium sp. The analysis of their spectral data revealed that amphidinins CF (14) were 4,5-seco-analogues of amphidinolide Q (5). The absolute configurations of the new compounds were elucidated by the combination of J-based configuration analysis, modified Moshers method, and chemical derivatization. Amphidinins D (2) and F (4) are the first glycosides related to amphidinolides. Amphidinins CF (14) showed antimicrobial activity against bacteria and/or fungi.

    DOI: 10.1021/ol502685z

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  • Absolute configuration of amphidinin A 査読

    Takahiro Iwai, Takaaki Kubota, Jun'Ichi Kobayashi

    Journal of Natural Products   77 ( 6 )   1541 - 1544   2014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  

    The absolute configurations at six stereogenic centers in amphidinin A (1), a cytotoxic linear polyketide isolated from a symbiotic marine dinoflagellate, Amphidinium sp., were elucidated to be 2R, 4R, 6S, 9R 11R, and 12S by the combination of J-based configuration analysis, modified Mosher's method, and density-functional theory calculations.

    DOI: 10.1021/np5003065

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  • Nagelamide I and 2,2'-Didebromonagelamide B, new dimeric bromopyrrole-imidazole alkaloids from a marine sponge agelas sp 査読

    Takahiro Iwai, Takaaki Kubota, Jane Fromont, Junichi Kobayashi

    Chemical and Pharmaceutical Bulletin   62 ( 2 )   213 - 216   2014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:PHARMACEUTICAL SOC JAPAN  

    New dimeric bromopyrrole-imidazole alkaloids, nagelamide I (1) and 2,2'-didebromonagelamide B (2), have been isolated from an Okinawan marine sponge Agelas species. The structures of 1 and 2 were elucidated based on analyses of the spectral data. Nagelamide I (1) was the first symmetric dimeric bromopyrrole-imidazole alkaloid consisting of two subunits connected with a single bond.

    DOI: 10.1248/cpb.c13-00821

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  • Nakijiquinone S and nakijinol C, new meroterpenoids from a marine sponge of the family spongiidae 査読

    Haruna Suzuki, Takaaki Kubota, Azusa Takahashi-Nakaguchi, Jane Fromont, Tohru Gonoi, Junichi Kobayashi

    Chemical and Pharmaceutical Bulletin   62 ( 2 )   209 - 212   2014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:PHARMACEUTICAL SOC JAPAN  

    New meroterpenoids, nakijiquinone S (1) and nakijinol C (2), have been isolated from an Okinawan marine sponge of the family Spongiidae. The gross structures and relative stereochemistries of 1 and 2 were elucidated on the basis of their spectral data. Nakijiquinone S (1) and nakijinol C (2) were new meroterpenoids consisting of a clerodane-type decalin ring connected to a 2-butoxy-5-hydroxy-benzoquinone unit or methyl 2,3,4-trihydroxybenzoate unit through a methylene, respectively. Nakijiquinone S (1) and nakijinol C (2) showed antimicrobial activities against several bacteria and fungi.

    DOI: 10.1248/cpb.c13-00810

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  • Taurospongins B and C, new acetylenic fatty acid derivatives possessing a taurine amide residue from a marine sponge of the family Spongiidae 査読

    Takaaki Kubota, Haruna Suzuki, Azusa Takahashi-Nakaguchi, Jane Fromont, Tohru Gonoi, Jun'Ichi Kobayashi

    RSC Advances   4 ( 22 )   11073 - 11079   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  

    Two new acetylenic fatty acid derivatives possessing a taurine amide residue, taurospongins B (1) and C (2), have been isolated from an Okinawan marine sponge of the family Spongiidae. The gross structures of 1 and 2 were elucidated on the basis of their spectral data, especially 2D NMR and FABMS/MS data. The absolute configurations for 1 and 2 were established by chemical means. Taurospongin C (2) showed inhibitory activity against Cryptococcus neoformans.

    DOI: 10.1039/c3ra47796g

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  • Hyrtimomines D and E, bisindole alkaloids from a marine sponge Hyrtios sp. 査読

    Naonobu Tanaka, Rei Momose, Yohei Takahashi, Takaaki Kubota, Azusa Takahashi-Nakaguchi, Tohru Gonoi, Jane Fromont, Jun'Ichi Kobayashi

    Tetrahedron Letters   54 ( 31 )   4038 - 4040   2013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)  

    Two new alkaloids, hyrtimomines D (1) and E (2), were isolated from an Okinawan marine sponge Hyrtios sp. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis. Hyrtimomines D (1) and E (2) are structurally unique bisindole alkaloids possessing the canthin-6-one skeleton with a hydroxyindole and an imidazolium units. Hyrtimomines D (1) and E (2) exhibited antimicrobial activity. © 2013 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2013.05.073

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  • Revised structure and stereochemical assignments of amphidinolide N 査読

    Yohei Takahashi, Takaaki Kubota, Misako Imachi, Markus R. Wälchli, Jun'ichi Kobayashi

    Journal of Antibiotics   66 ( 5 )   277 - 279   2013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)  

    DOI: 10.1038/ja.2012.117

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  • Stereochemistry of theonezolides A-C 査読

    Kohei Nozawa, Masashi Tsuda, Naonobu Tanaka, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Jun'Ichi Kobayashi

    Tetrahedron Letters   54 ( 8 )   783 - 787   2013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  

    Theonezolides A-C (1-3) are cytotoxic 37-membered macrolides with a long side chain isolated from an Okinawan marine sponge Theonella sp. The relative stereochemistry of 1-3 was investigated by combination of NMR analysis including application of a JBCA method, a Universal NMR database, and a C-13-acetonide method. Furthermore, the absolute configurations at 14 chiral centers in 1-3 were found to be 19S, 22R, 24S, 28S, 44S, 45S, 47R, 49S, 53R, 55S, 57S, 59S, 60S, and 63S by application of a modified Mosher's method. (C) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2012.11.120

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  • Zamamiphidin A, a new manzamine related alkaloid from an Okinawan marine sponge amphimedon sp. 査読

    Takaaki Kubota, Yuki Kamijyo, Azusa Takahashi-Nakaguchi, Jane Fromont, Tohru Gonoi, Jun'Ichi Kobayashi

    Organic Letters   15 ( 3 )   610 - 612   2013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  

    A manzamine related alkaloid, zamamiphidin A (1), consisting of a new heptacyclic ring system has been isolated from an Okinawan marine sponge Amphimedon sp. The structure of 1 including the relative stereochemistry was elucidated on the basis of the spectroscopic data. Compound 1 showed antibacterial activity against Staphylococcus aureus (MIC, 32 mu g/mL).

    DOI: 10.1021/ol3034274

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  • Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp. 査読

    Takaaki Kubota, Ken'Ichi Kura, Jane Fromont, Jun'Ichi Kobayashi

    Tetrahedron   69 ( 1 )   96 - 100   2013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:PERGAMON-ELSEVIER SCIENCE LTD  

    Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an alpha,beta-unsaturated 3,5-disubstituted gamma-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells. (C) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2012.10.062

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  • Inhibitory effects of metachromins L-Q and its related analogs against receptor tyrosine kinases EGFR and HER2 査読

    Yohei Takahashi, Takaaki Kubota, Sunao Yamamoto, Jun'Ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   23 ( 1 )   117 - 118   2013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)  

    Metachromins are a series of sesquiterpenoid quinones isolated from Okinawan marine sponges. Inhibitory effects of metachromins L-Q (1-6), sesquiterpenoid quinones with an amino acid residue, and their related analogs (7-18) prepared from metachromins A (19) and C (20) against receptor tyrosine kinases EGFR and HER2 were investigated. Two analogs 11 and 12 showed relatively stronger inhibitory activity against EGFR, while metachromins L-Q (1-6) and seven analogs (8, 10, 11, and 15-18) showed inhibitory activities against HER2.

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  • Manzamenones L-N, new dimeric fatty-acid derivatives from an Okinawan marine sponge Plakortis sp. 査読

    Takaaki Kubota, Yuichiro Ishiguro, Azusa Takahashi-Nakaguchi, Jane Fromont, Tohru Gonoi, Jun'Ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   23 ( 1 )   244 - 247   2013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:PERGAMON-ELSEVIER SCIENCE LTD  

    Three new polyketides, manzamenones L-N (1-3), have been isolated from an Okinawan marine sponge of the genus Plakortis. The structures of 1-3 were elucidated on the basis of spectroscopic data. Manzamenones L-N (1-3) were new dimeric fatty-acid derivatives consisting of a tetrahydroindenone with three carboxy groups and two hexadecanyl chains. Manzamenones M (2) and N (3) showed antimicrobial activity against several bacteria and fungi. (c) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2012.10.109

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  • Tyrokeradines C-F, new bromotyrosine alkaloids from the Verongid sponges 査読

    Takaaki Kubota, Shinya Watase, Hiroya Mukai, Jane Fromont, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   60 ( 12 )   1599 - 1601   2012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:PHARMACEUTICAL SOC JAPAN  

    Four new bromotyrosine alkaloids, tyrokeradines C-F (1-4), have been isolated from Okinawan marine sponges of the order Verongidae. The structures of 1-4 were elucidated on the basis of spectroscopic data. Tyrokeradines C (1) and D (2) are new bromotyrosine alkaloids possesing an imidazole ring, while tyrokeradines E (3) and F (4) are new bromotyrosine alkaloids possesing a cyano group.

    DOI: 10.1248/cpb.c12-00785

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  • Agelasines O-U, new diterpene alkaloids with a 9-N-methyladenine unit from a marine sponge Agelas sp. 査読

    Takaaki Kubota, Takahiro Iwai, Azusa Takahashi-Nakaguchi, Jane Fromont, Tohru Gonoi, Jun'Ichi Kobayashi

    Tetrahedron   68 ( 47 )   9738 - 9744   2012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  

    New diterpene alkaloids, agelasines O-U (1-7), have been isolated from an Okinawan marine sponge Agelas sp. The gloss structures and relative stereochemistries of 1-7 were elucidated from the spectroscopic data. Agelasines O-R (1-4) were the third examples of diterpene alkaloid with a 9-N-methyladenine and a pyrrole units. Agelasine O (1) has a halimane skeleton, while agelasines P-R (2-4) have a clerodane skeleton. Agelasines S-U (5-7) were new diterpene alkaloids with a 9-N-methyladenine unit consisting of a halimane skeleton, a labdane skeleton, and a clerodane skeleton, respectively. Agelasines O-R (1-4) and T (6) showed antimicrobial activities against several bacteria and fungi. (c) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2012.09.040

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  • Heteroaromatic alkaloids, nakijinamines, from a sponge Suberites sp. 査読

    Yohei Takahashi, Naonobu Tanaka, Takaaki Kubota, Haruaki Ishiyama, Azusa Shibazaki, Tohru Gonoi, Jane Fromont, Jun'Ichi Kobayashi

    Tetrahedron   68 ( 41 )   8545 - 8550   2012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:PERGAMON-ELSEVIER SCIENCE LTD  

    The structures of seven new secondary metabolites isolated from an Okinawan marine sponge Suberites sp., nakijinamines A (1), B (2), and F-I (3-6) and 6-bromoconicamin (7), have been elucidated on the basis of spectroscopic analysis, chemical conversion, and conformational analysis. These analyses disclosed that 1-6 were heteroaromatic alkaloids having the hybrid structures of an aaptamine-type alkaloid and an indole alkaloid, while 7 was a bromoindole alkaloid. Nakijinamine I (6) is the first example of an aaptamine-type alkaloid possessing a 1,4-dioxane ring. Antimicrobial activities of 1-7 were evaluated. (C) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2012.08.018

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  • Halichonadins K and L, new dimeric sesquiterpenoids from a sponge Halichondria sp. 査読

    Naonobu Tanaka, Shohei Suto, Haruaki Ishiyama, Takaaki Kubota, Akihito Yamano, Motoo Shiro, Jane Fromont, Jun'Ichi Kobayashi

    Organic Letters   14 ( 13 )   3498 - 3501   2012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  

    Two new structurally unique dimeric sesquiterpenoids, halichonadins K (1) and L (2), were isolated from an Okinawan marine sponge Halichondria sp. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis including a single crystal X-ray diffraction analysis and chemical conversion. Halichonadins K (1) and L (2) are homodimers of the eudesmane sesquiterpene linked with a piperidine ring through amide bonds. Halichonadin K (1) showed moderate cytotoxicity against KB cells.

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  • Eudistomidins H-K, new β-carboline alkaloids from the Okinawan marine tunicate Eudistoma glaucus. 査読

    Suzuki T, Kubota T, Kobayashi J

    Bioorganic & medicinal chemistry letters   21 ( 14 )   4220 - 4223   2011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:14  

    DOI: 10.1016/j.bmcl.2011.05.072

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  • Nakijinamines C-E, new heteroaromatic alkaloids from the sponge suberites species 査読

    Yohei Takahashi, Takaaki Kubota, Azusa Shibazaki, Tohru Gonoi, Jane Fromont, Jun'Ichi Kobayashi

    Organic Letters   13 ( 12 )   3016 - 3019   2011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  

    Three new heteroaromatic alkaloids, nakijinamines C-E (1-3), which are a hybrid of the aaptamine-type and bromoindole alkaloids possessing a taurine- or histidine-derived residue, have been isolated from an Okinawan marine sponge Suberites species. The structures of 1-3 were elucidated on the basis of spectroscopic data and chemical conversions. Nakijinamines C (1) and E (3) are the first natural products possessing a 1H-oxazolo[4',5':4,5]benzo[1,2,3-de][1,6]naphthyridine ring system.

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  • Hyrtioseragamines A and B, new alkaloids from the sponge hyrtios species 査読 国際誌

    Yohei Takahashi, Yoshiro Iinuma, Takaaki Kubota, Masashi Tsuda, Mitsuhiro Sekiguchi, Yuzuru Mikami, Jane Fromont, Jun'Ichi Kobayashi

    Organic Letters   13 ( 4 )   628 - 631   2011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:4  

    Two novel alkaloids with a furo[2,3-b]pyrazin-2(1H)-one moiety and a guanidino group, hyrtioseragamines A (1) and B (2), have been isolated from an Okinawan marine sponge Hyrtios species. The structures of 1 and 2 were elucidated on the basis of spectroscopic data and chemical conversions. Compounds 1 and 2 are the first natural products possessing a furo[2,3-b]pyrazine-related moiety.

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  • Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum 査読

    Kan'Ichiro Ishiuchi, Takaaki Kubota, Haruaki Ishiyama, Shigeki Hayashi, Toshiro Shibata, Koichiro Mori, Yutaro Obara, Norimichi Nakahata, Jun'Ichi Kobayashi

    Bioorganic and Medicinal Chemistry   19 ( 2 )   749 - 753   2011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:PERGAMON-ELSEVIER SCIENCE LTD  

    Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmc.2010.12.025

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  • Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum 査読

    Kan'ichiro Ishiuchi, Takaaki Kubota, Haruaki Ishiyama, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

    Tetrahedron Letters   52 ( 2 )   289 - 292   2011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:PERGAMON-ELSEVIER SCIENCE LTD  

    New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C(16)N(2)-type Lycopodium alkaloid possessing unique fused-tetracyclic ring system consisting of a cycloheptene ring fused to a decahydroquinoline and pyridone rings. Lyconadin F (2) possesses a primary amide moiety in its molecular, which is the first example of Lycopodium alkaloids. Biogenetically, lyconadins C (1) and F (2) might be related to lyconadins A (4) and B (5). The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute stereochemistry of 2 was elucidated by chemical correlations with lyconadin B (5) through hemiaminal form of lyconadin F (3). (C) 2010 Elsevier Ltd. All rights reserved.

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  • Pyrinodemins e and F, new 3-alkylpyridine alkaloids from sponge Amphimedon sp. 査読

    Ken'Ichi Kura, Takaaki Kubota, Jane Fromont, Jun'Ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   21 ( 1 )   267 - 270   2011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:PERGAMON-ELSEVIER SCIENCE LTD  

    Two new 3-alkylpyridine alkaloids, pyrinodemins E(1) and F(2), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1 and 2 were elucidated on the basis of spectroscopic data. Pyrinodemins E(1) and F(2) were novel 3-alkylpyridine alkaloids possessing a 4-(methoxyamino)piperidinone moiety and an indol-3-glyoxylamide moiety, respectively. Pyrinodemin E (1) showed cytotoxicity against P388 and L1210 murine leukemia cells. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2010.11.020

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  • Amphidinolide C3, a new cytotoxic 25-membered macrolide from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Akiko Suzuki, Mika Yamada, Shigeyuki Baba, Jun'ichi Kobayashi

    Heterocycles   82 ( 1 )   333 - 338   2010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  

    A new cytotoxic 25-membered macrolide, amphidinolide C3 (1), has been isolated from marine dinoflagellate Amphidinium sp. (Y-56 strain), and the structure of 1 was elucidated on the basis of spectroscopic data and chemical means.

    DOI: 10.3987/COM-10-S(E)3

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  • Untenolide A, a new polyketide from an Okinawan marine sponge Plakortis sp. 査読

    Yuichiro Ishiguro, Takaaki Kubota, Jane Fromont, Motoo Shiro, Jun'ichi Kobayashi

    Tetrahedron Letters   51 ( 31 )   4023 - 4026   2010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  

    A new polyketide, untenolide A (1), has been isolated from an Okinawan marine sponge Plakortis species, and the structure was elucidated from spectroscopic data and X-ray analysis. Untenolide A (1) is a new polyketide possessing a fused-pentacyclic skeleton with two hexadecanyl chains. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2010.05.085

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  • Ceratinadins A-C, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp. 査読

    Yuji Kon, Takaaki Kubota, Azusa Shibazaki, Tohru Gonoi, Jun'Ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   20 ( 15 )   4569 - 4572   2010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  

    Three new bromotyrosine alkaloids, ceratinadins A-C (1-3), were isolated from an Okinawan marine sponge Pseudoceratina sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Ceratinadin A (1) was a novel bromotyrosine alkaloid possessing an N-imidazolyl-quinolinone moiety. Ceratinadins A (1) and B (2) showed antifungal activity. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2010.06.015

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  • Eudistomidin G, a new β-carboline alkaloid from the Okinawan marine tunicate Eudistoma glaucus and structure revision of eudistomidin B 査読

    Yohei Takahashi, Haruaki Ishiyama, Takaaki Kubota, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   20 ( 14 )   4100 - 4103   2010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  

    A new beta-carboline alkaloid, eudistomidin G (1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B (2), which has been isolated from the same tunicate, was revised from 2a to 2b by detailed analyses of spectroscopic data. Asymmetric synthesis of the revised structure (2b) of eudistomidin B (2) and its (1S, 10S)-diastereomer (2c) has been accomplished with the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of eudistomidin B (2) was confirmed to be 2b possessing (1R, 10S)-configuration, from comparison of the (1)H NMR data, CD spectra, [a] D values, and HPLC analysis of 2b, 2c, and natural eudistomidin B. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2010.05.071

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  • Nakijiquinones J-R, sesquiterpenoid quinones with an amine residue from okinawan marine sponges 査読

    Yohei Takahasbi, Masahiro Ushio, Takaaki Kubota, Sunao Yamamoto, Jane Fromont, Ju N.Ichi Kobayashi

    Journal of Natural Products   73 ( 3 )   467 - 471   2010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  

    Nine new sesquiterpenoid quinones, nakijiquinones J-R (1 -9), have been isolated from three collections of Okinawan marine sponges of the family Spongiidae, and the structures and configurations were elucidated from the spectroscopic data and chemical correlations. Nakijiquinones J-L (1-3), M and N (4 and 5, respectively), 0 (6), 11 and Q (7 and 8, respectively), and R (9) are new sesquiterpenoid quinones possessing (S)-2-methylbutylamine, isopentylamine, isobutylamine, phenethylamine, and taurine residues, respectively, attached to each quinone ring.

    DOI: 10.1021/np900470e

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  • Platisidines A-C, N-methylpyridinium alkaloids from an okinawan marine sponge of Plakortis species 査読

    Takaaki Kubota, Yuichiro Ishiguro, Sunao Yamamoto, Jane Fromont, Jun'Ichi Kobayashi

    Heterocycles   80 ( 2 )   1407 - 1412   2010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  

    Three new N-methyl pyridinium alkaloids, platisidines A-C (1-3), were isolated from an Okinawan marine sponge of the genus Plakortis, and the structures were elucidated from spectroscopic data. The structures of platisidines A-C (1-3) were elucidated to be N-methyl nicotinic acid derivatives with a n-hexadecanoyl chain. Platisidines A-C (1-3) showed inhibitory activity against acetylcholinesterase.

    DOI: 10.3987/COM-09-S(S)131

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  • Bioactive metabolites from marine dinoflagellates 査読

    Jun'ichi Kobayashi, Takaaki Kubota

    Comprehensive Natural Products II: Chemistry and Biology   2   263 - 325   2010年3月

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    掲載種別:論文集(書籍)内論文  

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  • Biyouxanthones A - D, prenylated xanthones from roots of Hypericum chinense 査読

    Naonobu Tanaka, Takuji Mamemura, Shuhei Abe, Kiyoshi Imabayashi, Yoshiki Kashiwada, Yoshihisa Takaishi, Tetsuro Suzuki, Yutaka Takebe, Takaaki Kubota, Jun'ichi Kobayashi

    Heterocycles   80 ( 1 )   613 - 621   2010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:PERGAMON-ELSEVIER SCIENCE LTD  

    Four new prenylated xanthones, biyouxanthones A - D (1 - 4), were isolated from roots of Hypericum chinense. The gross structures of 1 - 4 were elucidated from spectroscopic data, and 2 was assigned as a racemate by chiral HPLC analysis. Biyouxanthones A (1) and B (2) exhibited anti-viral activity against hepatitis C virus (HCV).

    DOI: 10.3987/COM-09-S(S)28

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  • Benzosceptrin C, a new dimeric bromopyrrole alkaloid from sponge Agelas sp. 査読

    Takaaki Kubota, Atsushi Araki, Tetsuro Yasuda, Masashi Tsuda, Jane Fromont, Kazuki Aoyama, Yuzuru Mikami, Markus R. Wälchli, Jun'ichi Kobayashi

    Tetrahedron Letters   50 ( 52 )   7268 - 7270   2009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  

    A new dimeric bromopyrrole alkaloid possessing a benzocyclobutane ring, benzosceptrin C (1), has been isolated from an Okinawan marine sponge of the genus Agelas (SS-956), and the structure and relative stereochemistry were elucidated from spectroscopic data. Benzosceptrin C (1) showed antimicrobial activity. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.10.017

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  • Lycopladine H, a novel alkaloid with fused-tetracyclic skeleton from Lycopodium complanatum 査読

    Kan'Ichiro Ishiuchi, Takaaki Kubota, Shigeki Hayashi, Toshiro Shibata, Jun'Ichi Kobayashi

    Tetrahedron Letters   50 ( 47 )   6534 - 6536   2009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  

    A novel Lycopodium alkaloid, lycopladine H (1), with a fused-tetracyclic ring system consisting of an azocane ring connected to a [2.2.2]-bicyclooctane ring and a 3-piperidone ring, was isolated from the club moss lycopodium complanatum. The structure and relative stereochemistry of I were elucidated on the basis of spectroscopic data (C) 2009 Elsevier Ltd All rights reserved

    DOI: 10.1016/j.tetlet.2009.09.035

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  • Petiolins F-I, Benzophenone Rhamnosides from Hypericum pseudopetiolatum var. kiusianum

    Naonobu Tanaka, Takaaki Kubota, Yoshiki Kashiwada, Yoshihisa Takaishi, Jun'ichi Kobayashi

    CHEMICAL & PHARMACEUTICAL BULLETIN   57 ( 10 )   1171 - 1173   2009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:PHARMACEUTICAL SOC JAPAN  

    Four new benzophenone-O-rhamnosides, petiolins F-I (1-4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and chemical means.

    DOI: 10.1248/cpb.57.1171

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  • Petiolins F-I, benzophenone rhamnosides from Hypericum pseudopetiolatum var. kiusianum 査読

    Naonobu Tanaka, Takaaki Kubota, Yoshiki Kashiwada, Yoshihisa Takaishi, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   57 ( 10 )   1171 - 1173   2009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:PHARMACEUTICAL SOC JAPAN  

    Four new benzophenone-O-rhamnosides, petiolins F-I (1-4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and chemical means.

    DOI: 10.1248/cpb.57.1171

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  • Yezo’otogirins A-C, new tricyclic terpenoids from Hypericum yezoense 査読

    TANAKA Naonobu, KAKUGUCHI Yuka, ISHIYAMA Haruaki, KUBOTA Takaaki, KOBAYASHI Jun’ichi

    Tetrahedron Lett.   50 ( 33 )   4747 - 4750   2009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)  

    DOI: 10.1016/j.tetlet.2009.06.021

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  • Lannotinidines H-J, new Lycopodium alkaloids from Lycopodium annotinum

    Kan'ichiro Ishiuchi, Shihomi Kodama, Takaaki Kubota, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   57 ( 8 )   877 - 881   2009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:PHARMACEUTICAL SOC JAPAN  

    Three new Lycopodium alkaloids, lannotinidines H-J (1-3), were isolated from the club moss Lycopodium annotinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data and the absolute stereochemistry of 2 was assigned by chemical correlation. Lannotinidine H (1) is the first Lycopodium alkaloid possessing a lycopodane skeleton with an additional C-3 unit.

    DOI: 10.1248/cpb.57.877

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  • Lannotinidines H-J, New Lycopodium Alkaloids from Lycopodium annotinum 査読

    Kan'ichiro Ishiuchi, Shihomi Kodama, Takaaki Kubota, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

    CHEMICAL & PHARMACEUTICAL BULLETIN   57 ( 8 )   877 - 881   2009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:PHARMACEUTICAL SOC JAPAN  

    Three new Lycopodium alkaloids, lannotinidines H-J (1-3), were isolated from the club moss Lycopodium annotinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data and the absolute stereochemistry of 2 was assigned by chemical correlation. Lannotinidine H (1) is the first Lycopodium alkaloid possessing a lycopodane skeleton with an additional C-3 unit.

    DOI: 10.1248/cpb.57.877

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    その他リンク: http://orcid.org/0000-0002-3553-5844

  • Lycopladines F and G, new C<inf>16</inf>N<inf>2</inf>-type alkaloids with an additional C<inf>4</inf>N unit from Lycopodium complanatum 査読

    Kan'ichiro Ishiuchi, Takaaki Kubota, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

    Tetrahedron Letters   50 ( 29 )   4221 - 4224   2009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  

    Two new Lycopodium alkaloids, lycopladines F (1) and G (2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistries of I and 2 were elucidated on the basis of spectroscopic data. Lycopladine F (1) is a rare C16N2-type Lycopodium alkaloid possessing an amino acid residue (C4N) (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.04.139

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  • Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp. 査読

    Yuichiro Ishiguro, Takaaki Kubota, Kan'ichiro Ishiuchi, Jane Fromont, Jun'ichi Kobayashi

    Tetrahedron Letters   50 ( 26 )   3202 - 3204   2009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  

    A new piperidine alkaloid plakoridine C (1) has been isolated from an Okinawan marine sponge Plakortis species, and the structure was elucidated from spectroscopic data. Plakoridine C (1) is a new alkaloid possessing a piperidine ring connected to a beta-keto-gamma-lactone through a double bond. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.01.135

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  • Serratezomines D and E, new Lycopodium alkaloids from Lycopodium serratum var. serratum 査読

    Takaaki Kubota, Hiroko Yahata, Sunao Yamamoto, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   19 ( 13 )   3577 - 3580   2009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  

    Two new Lycopodium alkaloids, serratezomines D (1) and E (2), were isolated from the club moss Lycopodium serratum var. serratum. Serratezomine D (1) is a new lucidine-type alkaloid, while serratezomine E (2) is a new phlegmarane-type alkaloid. The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. Serratezomine D (1) exhibited an inhibitory activity against acetylcholinesterase. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2009.04.146

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  • The Daphniphyllum alkaloids 査読

    Jun'Ichi Kobayashi, Takaaki Kubota

    Natural Product Reports   26 ( 7 )   936 - 962   2009年7月

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    About two hundred Daphniphyllum alkaloids have so far been isolated from thirteen species of the genus Daphniphyllum. This comprehensive review summarizes all the research into the isolation and structure elucidation of these alkaloids reported since investigations began in 1966. The structures of the Daphniphyllum alkaloids are classified based on six Daphniphyllum alkaloids (daphniphylline, secodaphniphylline, yuzurimine, daphnilactone A, daphnilactone B and yuzurine); there are also a number of newly found skeletons. The biosynthetic pathways, total syntheses, and bioactivities of the Daphniphyllum alkaloids are also described.

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  • Daphnezomines T-V, Alkaloids from Daphniphyllum humile 査読

    Takaaki Kubota, Teppei Suzuki, Kan'ichiro Ishiuchi, Taiga Kuhara, Jun'ichi Kobayashi

    CHEMICAL & PHARMACEUTICAL BULLETIN   57 ( 5 )   504 - 507   2009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:PHARMACEUTICAL SOC JAPAN  

    Three new Daphniphyllum alkaloids, daphnezomines T-V (1-3), were isolated from the leaves and branches of Daphniphyllum humile (Daphniphyllaceae). The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Daphnezomine T (1) is the first alkaloid without a branched C-1 unit at C-5 among all Daphiniphyllum alkaloids reported so far.

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  • Daphnezomines T-V, alkaloids from Daphniphyllum humile

    Takaaki Kubota, Teppei Suzuki, Kan'ichiro Ishiuchi, Taiga Kuhara, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   57 ( 5 )   504 - 507   2009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:PHARMACEUTICAL SOC JAPAN  

    Three new Daphniphyllum alkaloids, daphnezomines T-V (1-3), were isolated from the leaves and branches of Daphniphyllum humile (Daphniphyllaceae). The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Daphnezomine T (1) is the first alkaloid without a branched C-1 unit at C-5 among all Daphiniphyllum alkaloids reported so far.

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  • Total synthesis of amphidinolactone A and its absolute configuration 査読

    Masahiro Hangyou, Haruaki Ishiyama, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi

    Tetrahedron Letters   50 ( 13 )   1475 - 1477   2009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  

    Asymmetric synthesis of amphidinolactone A, a cytotoxic macrolide from the Cultured dinoflagellate Amphidinium sp., has been accomplished. Absolute configuration of amphidinolactone A was concluded to be 1 from comparison of the NMR data and vertical bar x vertical bar(D) values of synthetic and natural amphidinolactone A. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.01.065

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  • Total synthesis and biological evaluation of amphidinolide v and analogues 査読

    Alois Fürstner, Susanne Flügge, Oleg Larionov, Yohei Takahashi, Takaaki Kubota, Juńichi Kobayashi

    Chemistry - A European Journal   15 ( 16 )   4011 - 4029   2009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:WILEY-V C H VERLAG GMBH  

    A sequence of ring-closing alkyne metathesis followed by an intermolecular enyne metathesis of the resulting cycloalkyne with ethene was used to forge the macrocyclic skeleton and to set the vicinal exo-methylene branches characteristic for the cytotoxic marine natural product amphidinolide V (1). Comparison of the synthetic material with all authentic sample of this extremely scarce metabolite isolated from a dinoflagellate of the Amphidinium sp. eliminated any, doubts about its structure and allowed the absolute configuration of amphidinolide V to be determined as 8R,9S,10S,13R. Moreover, the flexibility inherent to the underlying Synthesis blueprint also opened access to a comprehensive set of diastereomers of I as well as to synthetic analogues differing from the natural lead in the lipophilic chains appended to the macrocyclic core. This set of designed analogues gave first insights into structure-activity relationships, which revealed that the stereo-structure Of the macrolactone is a highly critical parameter, whereas the examined alterations of the side chain did not diminish the cytotoxicity, of the compounds to any notable extent.

    DOI: 10.1002/chem.200802068

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  • Petiolins D and E, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum 査読

    Naonobu Tanaka, Takaaki Kubota, Haruaki Ishiyama, Yoshiki Kashiwada, Yoshihisa Takaishi, Junji Ito, Yuzuru Mikami, Motoo Shiro, Jun'ichi Kobayashi

    Heterocycles   79 ( C )   917 - 924   2009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  

    A new phloroglucinol derivative possessing citran skeleton, petiolin D (1), and a new chromone glucoside, petiolin E (2), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The structures of I and 2 were elucidated by spectroscopic data, and a single-crystal X-ray diffraction analysis of 1 revealed that 1 was a racemic mixture.

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  • Nagelamides Q and R, novel dimeric bromopyrrole alkaloids from sponges agelas sp 査読

    Atsushi Araki, Takaaki Kubota, Kazuki Aoyama, Yuzuru Mikami, Jane Fromont, Ju N.Ichi Kobayashi

    Organic Letters   11 ( 8 )   1785 - 1788   2009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 dimeric bromopyrrole alkaloids, nagelamides Q (1) and R (2), have been isolated from Okinawan marine sponges of the genus Agelas (SS-1134 and SS-956, respectively), and the structures and stereochemistry were elucidated from spectroscopic data. Nagelamide Q (1) is a rare dimeric bromopyrrole alkaloid possessing a pyrrolidine ring, while nagelamide R (2) is the first bromopyrrole alkaloid having an oxazoline ring. Nagelamides Q (1) and R (2) showed antimicrobial activity.

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  • Naucleamide F, a new monoterpene indole alkaloid from Nauclea Latifolia 査読

    Yuka Kakuguchi, Haruaki Ishiyama, Takaaki Kubota, Jun'ichi Kobayashi

    Heterocycles   79 ( C )   765 - 771   2009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  

    A new monoterpene indole alkaloid, naucleamide F (1), has been isolated from the bark and wood of Nauclea latifolia, and the structure and stereochemistry were elucidated on the basis of the spectral data. Naucleamide F (1) is a new monoterpene indole alkaloid consisting of a tetrahydro-beta-carboline ring fused to a pyridone ring, and a 1,3,5-trioxepane ring fused to a dihydropyran ring and a glucose unit.

    DOI: 10.3987/COM-08-S(D)41

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  • Bromopyrrole alkaloids from marine sponges of the genus agelas 査読

    Tetsuro Yasuda, Atsushi Araki, Takaaki Kubota, Junji Ito, Yuzuru Mikami, Jane Fromont, Ju N.Ichi Kobayashi

    Journal of Natural Products   72 ( 3 )   488 - 491   2009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  

    Four new bromopyrrole alkaloids, nagelamides O (1) and P (2) and mukanadins E (3) and F (4), were isolated from three collections of Okinawan marine sponges of the genus Agelas. The structures and sterectchemistry of 1-4 were elucidated on the basis of their spectroscopic data.

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  • Nakijiquinones E and F, new dimeric sesquiterpenoid quinones from marine sponge 査読

    Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry   17 ( 6 )   2185 - 2188   2009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  

    Two new dimeric sesquiterpenoid quinones, nakijiquinones E (1) and F (2), have been isolated from an Okinawan marine sponge, and the structures and relative stereochemistry of 1 and 2 were elucidated on the basis of the spectral data. Nakijiquinones E (1) and F (2) were the first dimeric sesquiterpenoid quinones possessing a 3-aminobenzoate moiety. (C) 2008 Elsevier Ltd. All rights reserved.

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  • Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp. 査読

    Mika Yamada, Yohei Takahashi, Takaaki Kubota, Jane Fromont, Aki Ishiyama, Kazuhiko Otoguro, Haruki Yamada, Satoshi Omura, Jun'ichi Kobayashi

    Tetrahedron   65 ( 11 )   2313 - 2317   2009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  

    New manzamine alkaloids, zamamidine C (1), 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2), and 3,4-dihydromanzamine J N-oxide (3). have been isolated from an Okinawan marine sponge Amphimedon species. The Structures and stereochemistries of 1-3 were elucidated from the spectroscopic data and chemical derivatization. Zamamidine C (1) is a new manzamine alkaloid possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine D, while 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2) is the first manzamine alkaloid possessing an epoxide ring at C-10 and C-11. Zamamidine C (1) showed significant antitrypanosomal activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and antimalarial activity against Plasmodium falciparum, the causative agent of malaria in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2009.01.032

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  • Tyrokeradines A and B, new bromotyrosine alkaloids with an imidazolyl-quinolinone moiety from a Verongid sponge 査読

    Hiroya Mukai, Takaaki Kubota, Kazuki Aoyama, Yuzuru Mikami, Jane Fromont, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry Letters   19 ( 5 )   1337 - 1339   2009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  

    Two new bromotyrosine alkaloids, tyrokeradines A (1) and B (2), with an imidazolyl-quinolinone moiety have been isolated from an Okinawan marine sponge of the order Verongida. The structures of 1 and 2 were elucidated on the basis of spectroscopic data. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2009.01.056

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  • Zamamidines A and B, new manzamine alkaloids from the sponge Amphimedon species 査読

    Yohei Takahashi, Takaaki Kubota, Jane Fromont, Jun'ichi Kobayashi

    Organic Letters   11 ( 1 )   21 - 24   2009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  

    New manzamine alkaloids, zemamidines A (1) and B (2), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistry of 1 and 2 were elucidated from the spectroscopic data and conformational analysis. Zamamidines A (1) and B (2) are the first manzamine alkaloids possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine H and 1,2,3,4-tetrahydromanzamine B, respectively.

    DOI: 10.1021/ol802251q

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  • Calyciphyllines N-P, alkaloids from Daphniphyllum calycinum 査読

    Hiroko Yahata, Takaaki Kubota, Jun'ichi Kobayashi

    Journal of Natural Products   72 ( 1 )   148 - 151   2009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  

    Three new Daphniphyllum alkaloids, calyciphyllines N-P (1-3), were isolated from the leaves and stems of Daphniphyllum calycinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data.

    DOI: 10.1021/np800515s

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  • Nagelamides M and N, new bromopyrrole alkaloids from sponge Agelas species 査読

    Takaaki Kubota, Atsushi Araki, Junji Ito, Yuzuru Mikami, Jane Fromont, Jun'ichi Kobayashi

    Tetrahedron   64 ( 48 )   10810 - 10813   2008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  

    Two new bromopyrrole alkaloids, nagelamides M (1) and N (2), have been isolated from an Okinawan marine sponge Agelas species, and the structures and stereochemistry were elucidated from the spectroscopic data. Nagelamide M (1) is a novel bromopyrrole alkaloid possessing a 2-amino-octahydropyrrolo[2,3-d]imidazole ring with a taurine unit, while nagelamide N (2) is a new bromopyrrole alkaloid possessing a 2-amino-tetrahydroimidazole-4-one ring with a taurine unit and 3-(dibromopyrrole-2-carboxamido)propanoic acid moiety. Nagelamides M (1) and N (2) exhibited antimicrobial activity. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2008.09.039

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  • Xestosaprol C, a new pentacyclic hyroquinone sulfate from a marine sponge xestospongia sapra 査読

    Takaaki Kubota, Yuji Kon, Jun'ichi Kobayashi

    Heterocycles   76 ( 2 )   1571 - 1575   2008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  

    A new pentacyclic hydroquinone sulfate with a 2,5-dihydro-2,5-furandiol ring, xestosaprol C (1), has been isolated from an Okinawan marine sponge Xestospongia sapra. The structure of I was elucidated by the spectroscopic data.

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  • Absolute stereochemistry of amphidinolide Q 査読

    Yohei Takahashi, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Jun'ichi Kobayashi

    Organic Letters   10 ( 17 )   3709 - 3711   2008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  

    The absolute configurations at five chiral centers in amphidinolide Q (1), a cytotoxic 12-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were elucidated to be 4R, 7R, 9S, 11 R, and 13R on the basis of NMR analyses and a modified Mosher&apos;s method.

    DOI: 10.1021/ol8013123

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  • Nakijiquinones G-I, new sesquiterpenoid quinones from marine sponge 査読

    Yohei Takahashi, Takaaki Kubota, Junji Ito, Yuzuru Mikami, Jane Fromont, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry   16 ( 16 )   7561 - 7564   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:PERGAMON-ELSEVIER SCIENCE LTD  

    Three new sesquiterpenoid quinones, nakijiquinones G-I (1-3), containing a different amino group derived from amino acids have been isolated from Okinawan marine sponges of the family Spongiidae, and the structures and relative stereochemistry of 1-3 were elucidated on the basis of the spectral data. Nakijiquinones G-I (1-3) showed modest cytotoxicity and inhibitory activity against HER2 kinase, while nakijiquinone H (2) exhibited antimicrobial activity. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmc.2008.07.028

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  • Nagelamides K and L, dimeric bromopyrrole alkaloids from sponge Agelas species 査読

    Atsushi Araki, Takaaki Kubota, Masashi Tsuda, Yuzuru Mikami, Jane Fromont, Jun'ichi Kobayashi

    Organic Letters   10 ( 11 )   2099 - 2102   2008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  

    Two new dimeric bromopyrrole alkaloids, nagelamides K (1) and L (2), have been isolated from Okinawan marine sponges Agelas species, and the structures and stereochemistry were elucidated from spectroscopic data. Nagelamide K (1) is a bromopyrrole alkaloid possessing a rare piperidinoiminoimidazolone ring with an aminoimidazole ring and a taurine unit, while nagelamide L (2) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamides K (1) and L (2) exhibited antimicrobial activity.

    DOI: 10.1021/ol8003904

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  • Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum 査読

    Naonobu Tanaka, Takaaki Kubota, Haruaki Ishiyama, Atsushi Araki, Yoshiki Kashiwada, Yoshihisa Takaishi, Yuzuru Mikami, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry   16 ( 10 )   5619 - 5623   2008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:PERGAMON-ELSEVIER SCIENCE LTD  

    Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A ( 1) and B ( 2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C ( 3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C ( 3) exhibited antifungal activity. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmc.2008.03.076

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  • Nakinadines B-F, new pyridine alkaloids with a β-amino acid moiety from sponge Amphimedon sp. 査読

    Nishi T, Kubota T, Fromont J, Sasaki T, Kobayashi J

    Tetrahedron   64 ( 14 )   3127 - 3132   2008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.tet.2008.01.111

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  • Calyciphyllines H-M, new Daphniphyllum alkaloids from Daphniphyllum calycinum 査読

    Shizuka Saito, Hiroko Yahata, Takaaki Kubota, Yutaro Obara, Norimichi Nakahata, Jun'ichi Kobayashi

    Tetrahedron   64 ( 8 )   1901 - 1908   2008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  

    Six new Daphniphyllum alkaloids, calyciphyllines H-M (1-6), were isolated from the leaves and stems of Daphniphyllum calycinum (Daphniphyllaceac). The structures and relative stereochemistry of 1-6 were elucidated on the basis of spectroscopic data, and the absolute stereochemistry of 3 was assigned by PGME method. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2007.11.087

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  • Seragadine A, a β-carboline alkaloid from marine sponge 査読

    Nozawa K, Tsuda M, Kubota T, Fromont J, Kobayashia J

    Heterocycles   74 ( C )   849 - 853   2007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)  

    DOI: 10.3987/com-07-s(w)77

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  • Lycopladine E, a new C<inf>16</inf>N<inf>1</inf>-type alkaloid from lycopodium complanatum 査読

    Takaaki Kubota, Hiroko Yahata, Kan'ichiro Ishiuchi, Yutaro Obara, Norimichi Nakahat, Jun'ichi Kobayashi

    Heterocycles   74 ( C )   843 - 848   2007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  

    A new C(16)N(1)-type alkaloid, lycopladine E (1), has been isolated from the club moss Lycopodium complanatum, and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical correlation.

    DOI: 10.3987/com-07-s(w)76

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  • Nitrogen-containing verticillene diterpenoids from the Taiwanese soft coral Cespitularia taeniata 査読

    Ya Ching Shen, Yuan Bin Cheng, Jun'ichi Kobayashi, Takaaki Kubota, Yohei Takahashi, Yuzuru Mikami, Junji Ito, Yun Sheng Lin

    Journal of Natural Products   70 ( 12 )   1961 - 1965   2007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  

    Extensive column chromatography of the ethanolic extract of the soft coral Cespitularia taeniata collected in Taiwan has resulted in the isolation of eight new nitrogen-containing verticillene diterpenes, designated cespitulactams D-K (1-8), together with three known diterpenes, cespitulactams A (9) and B (10) and cespitularin F. In addition, one new derivative, 6-O-acetyleespitulactam F (11), was prepared from compound 3. The structures of these compounds were elucidated on the basis of spectroscopic analyses, especially HRMS and 2D NMR experiments. The cytotoxicity against human oral epidermoid carcinoma (KB) and murine L1210 leukemia cell lines and antimicrobial activities of 1-8 and 11 were tested and evaluated. A biogenetic pathway for these novel diterpene alkaloids was also proposed.

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  • Metachromins R-T, new sesquiterpenoids from marine sponge Spongia sp. 査読

    Yohei Takahashi, Mika Yamada, Takaaki Kubota, Jane Fromont, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   55 ( 12 )   1731 - 1733   2007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:PHARMACEUTICAL SOC JAPAN  

    Three new sesquiterpenoids, metachromins R-T (1-3), have been isolated from an Okinawan marine sponge Spongia sp. The structures and stereochemistry of 1-3 were elucidated on the basis of the spectroscopic data. Metachromins S (2) and T (3) showed modest cytotoxicity.

    DOI: 10.1248/cpb.55.1731

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  • Sarusubine A, a new dimeric Lythraceae alkaloid from Lagerstroemia subcostata 査読

    Kozue Watanabe, Takaaki Kubota, Takakazu Shinzato, Junji Ito, Yuzuru Mikami, Jun'ichi Kobayashi

    Tetrahedron Letters   48 ( 42 )   7502 - 7504   2007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:PERGAMON-ELSEVIER SCIENCE LTD  

    A new dimeric Lythraceac alkaloid with a cyclobutane ring, sarusubine A (1), has been isolated from the leaves of Lagerstroemia subcostata, and the structure and stereochemistry were elucidated by spectroscopic data. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2007.08.059

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  • Metachromins L-Q, new sesquiterpenoid quinones with an amino acid residue from sponge Spongia sp. 査読

    Yohei Takahashi, Takaaki Kubota, Jane Fromont, Jun'ichi Kobayashi

    Tetrahedron   63 ( 36 )   8770 - 8773   2007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:PERGAMON-ELSEVIER SCIENCE LTD  

    Six new sesquiterpenoid quinones with an amino acid residue, metachromins L-Q (1-6), have been isolated from an Okinawan marine sponge Spongia sp. The structures and stereochemistry of 1-6 were elucidated on the basis of the spectroscopic data and chemical correlations. Metachromins L (1) and M (2) showed modest cytotoxicity. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2007.06.031

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  • Calyciphylline G, a novel alkaloid with an unprecedented fused-hexacyclic skeleton from Daphniphyllum calycinum 査読

    Shizuka Saito, Takaaki Kubota, Jun'ichi Kobayashi

    Tetrahedron Letters   48 ( 32 )   5693 - 5695   2007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  

    Calyciphylline G (1), a novel Daphniphyllum alkaloid with an unprecedented fused-hexacyclic skeleton containing a 5-azatricyclo[6.2.1.0(1,5)]undecane ring, has been isolated from the stem of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2007.05.172

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  • Nakinadine A, a novel bis-pyridine alkaloid with a β-amino acid moiety from sponge Amphimedon sp 査読

    KUBOTA Takaaki, NISHI Takami, FUKUSHI Eri, KAWABATA Jun, FROMONT Jane, KOBAYASHI Jun’ichi

    Tetrahedron. Lett.   48 ( 29 )   4983 - 4985   2007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)  

    DOI: 10.1016/j.tetlet.2007.05.121

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  • Nagelamide J, a novel dimeric bromopyrrole alkaloid from a sponge agelas species 査読

    Atsushi Araki, Masashi Tsuda, Takaaki Kubota, Yuzuru Mikami, Jane Fromont, Ju N.ichi Kobayashi

    Organic Letters   9 ( 12 )   2369 - 2371   2007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 novel dimeric bromopyrrole alkaloid, nagelamide J (1), with antimicrobial activity has been isolated from an Okinawan marine sponge Agelas species, and the structure and stereochemistry were elucidated from spectroscopic data. Nagelamide J (1) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring.

    DOI: 10.1021/ol0707867

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  • Amphidinolactone B, a new 26-membered macrolide from dinoflagellate Amphidinium sp. 査読

    Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi

    Journal of Antibiotics   60 ( 6 )   376 - 379   2007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:JAPAN ANTIBIOTICS RESEARCH ASSOC  

    A new 26-membered macrolide, amphidinolactone 13, has been isolated from a marine dinoflagellate Amphidinium sp., and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. Amphidinolactone B (1) showed modest cytotoxicity.

    DOI: 10.1038/ja.2007.51

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  • Calyciphyllines E and F, novel hepta- and pentacyclic alkaloids from Daphniphyllum calycinum 査読

    Shizuka Saito, Takaaki Kubota, Jun'ichi Kobayashi

    Tetrahedron Letters   48 ( 22 )   3809 - 3812   2007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:PERGAMON-ELSEVIER SCIENCE LTD  

    Two new Daphniphyllum alkaloids, calyciphyllines E (1) and F (2), have been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data. (C) 2007 Elsevier Ltd. All rights reserved.

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  • Amphidinolactone a, a new 13-membered macrolide from dinoflagellate Amphidinium sp. 査読

    Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi

    Heterocycles   72   567 - 572   2007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  

    A new 13-membered macrolide, amphidinolactone A (1), has been isolated from a marine dinoflagellate Amphidinium sp., and the structure and relative stereochemistry were elucidated by spectroscopic data. Amphidinolactone A (1) is the first macrolide without a branched methyl or an exomethylene among all the macrolides isolated from the dinoflagellates so far.

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  • Calyciphylline D, a novel alkaloid with an unprecedented fused-pentacyclic skeleton from daphniphyllum calycinum 査読

    Shizuka Saito, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Huiping Zhang, Jun'ichi Kobayashi

    Organic Letters   9 ( 7 )   1207 - 1209   2007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  

    Calyciphylline D (1), a novel Daphniphyllum alkaloid with an unprecedented fused-pentacyclic skeleton containing a 8-azatricyclo[4.2.1.0.(4,8)]nonane ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

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  • Bioactive macrolides and polyketides from marine dinoflagellates of the genus Amphidinium 査読

    Jun'ichi Kobayashi, Takaaki Kubota

    Journal of Natural Products   70 ( 3 )   451 - 460   2007年3月

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

    Marine microorganisms such as bacteria, cyanobacteria, dinoflagellates, and others have attracted many natural product chemists as the real producers of marine toxins such as fish and algal poisons as well as bioactive substances isolated from marine invertebrates such as sponges and tunicates. Among marine microorganisms, dinoflagellates have proved to be important sources of marine toxins and have been investigated worldwide by natural product chemists. We have continued investigations on chemically interesting and biologically significant secondary metabolites from Amphidinium spp., of a genus of symbiotic marine dinoflagellates separated from inside cells of Okinawan marine flatworms. This review covers the results described in our recent publications on a series of cytotoxic macrolides, designated amphidinolides, and long-chain polyketides isolated from Amphidinium spp. In this review, topics include the isolation, structure elucidation, synthesis, biosynthesis, and bioactivity of amphidinolides and long-chain polyketides.

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  • Calyciphylline C, a novel Daphniphyllum alkaloid from Daphniphyllum calycinum 査読

    Shizuka Saito, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Huiping Zhang, Jun'ichi Kobayashi

    Tetrahedron Letters   48 ( 9 )   1587 - 1589   2007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  

    Calyciphylline C (1), a novel Daphniphyllum alkaloid with unprecedented fused-hexacyclic ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. (c) 2007 Elsevier Ltd. All rights reserved.

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  • Complanadines C and D, new dimeric alkaloids from Lycopodium complanatum 査読

    Kan'ichiro Ishiuchi, Takaaki Kubota, Yuzuru Mikami, Yutaro Obara, Norimichi Nakahata, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry   15 ( 1 )   413 - 417   2007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:PERGAMON-ELSEVIER SCIENCE LTD  

    Two new dimeric Lycopodium alkaloids, complanadines C (1) and D (2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistry of I and 2 were elucidated on the basis of the spectral data. Complanadine D (2) enhanced mRNA expression for NGF. (c) 2006 Elsevier Ltd. All rights reserved.

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  • Pyrinadines B-G, new bis-pyridine alkaloids with an azoxy moiety from sponge Cribrochalina sp. 査読

    Yuuko Kariya, Takaaki Kubota, Jane Fromont, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry   14 ( 24 )   8415 - 8419   2006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  

    Six new cytotoxic bis-3-alkylpyridine alkaloids with an azoxy moiety, pyrinadines B-G (1-6), have been isolated from an Okinawan marine sponge Cribrochalma sp., and the structures were elucidated by spectroscopic data and chemical means. (c) 2006 Elsevier Ltd. All rights reserved.

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  • Lycovatine A, a C<inf>16</inf>N-type quaternary alkaloid from Lycopodium clavatum var. Robustum 査読

    Takaaki Kubota, Tomoe Sunaura, Hiroshi Morita, Yuzuru Mikami, Tomohiro Hoshino, Yutaro Obara, Norimichi Nakahata, Jun'ichi Kobayashi

    Heterocycles   69 ( 1 )   469 - 474   2006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  

    A new C16N-type quaternary alkaloid, lycovatine A (1), has been isolated from the club moss Lycopodium clavatum var. robustum, and the structure including the relative stereochemistry was elucidated on the basis of spectroscopic data.

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  • Brasilicardin A, a Natural Immunosuppressant, Targets Amino Acid Transport System L 査読

    Takeo Usui, Yoko Nagumo, Ai Watanabe, Takaaki Kubota, Kazusei Komatsu, Jun'ichi Kobayashi, Hiroyuki Osada

    Chemistry and Biology   13 ( 11 )   1153 - 1160   2006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:CELL PRESS  

    Lymphocytes in T cell activation require extracellular nutrients to provide energy for cellular proliferation and effector functions. Therefore, inhibitors of nutrient transporters are expected to be a new class of immunosuppressant. Here, we report that the molecular target of brasilicardin A (BraA), an immunosuppressive compound, is the amino acid transporter system L. BraA inhibited the cell-cycle progression of murine T cell lymphocyte CTLL-2 cells in G1 phase, and potently inhibited the uptake of amino acids that are substrates for amino acid transport system L. Moreover, BraA stimulated the GCN2 activation and, subsequently, the phosphorylation of eIF2 alpha. These results suggest that the immunosuppressive activity of BraA is induced by amino acid deprivation via the inhibition of system L and that the amino acid transporter is a target for immunosuppressant.

    DOI: 10.1016/j.chembiol.2006.09.006

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  • Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare 査読

    Toshinori Kagata, Shizuka Saito, Hideyuki Shigemori, Ayumi Ohsaki, Haruaki Ishiyama, Takaaki Kubota, Jun'ichi Kobayashi

    Journal of Natural Products   69 ( 10 )   1517 - 1521   2006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  

    Four new oxindole alkaloids, paratunamides A-D (1-4), containing a secologanin unit, were isolated from the bark of Cinnamodendron axillare, and their structures and relative configurations were elucidated by spectroscopic data. The absolute configuration at C-7 in 1-4 was assigned as S, S, R, and S, respectively, on the basis of the CD spectra.

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  • Lycopladines B-D and lyconadin B, new alkaloids from Lycopodium complanatum 査読

    Kan'ichiro Ishiuchi, Takaaki Kubota, Tomohiro Hoshino, Yutaro Obara, Norimichi Nakahata, Jun'ichi Kobayashi

    Bioorganic and Medicinal Chemistry   14 ( 17 )   5995 - 6000   2006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:PERGAMON-ELSEVIER SCIENCE LTD  

    Four new alkaloids, lycopladines B-D (1-3) and lyconadin B (4), have been isolated from the club moss Lycopodium complanatum and the structures including the stereochemistry were elucidated on the basis of spectral data and modified Mosher's method. Lyconadin B (4) elevated NGF mRNA expression in 1321N1 human astrocytoma cells. (c) 2006 Elsevier Ltd. All rights reserved.

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  • Determination of the cryptic stereochemistry of the first PKS chain-extension step in ansamitocin biosynthesis by Actinosynnema pretiosum 査読

    Takaaki Kubota, Marco Brünjes, Thomas Frenzel, Jun Xu, Andreas Kirschning, Heinz G. Floss

    ChemBioChem   7 ( 8 )   1221 - 1225   2006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:WILEY-V C H VERLAG GMBH  

    The biosynthesis of the antitumor antibiotic, ansamitocin, involves the assembly of a linear octaketide on the ansamitocin (asm) polyketide synthase (PKS), which is then cyclized to proansamitocin and further modified to the final product. In the first chain-extension step on the asm PKS, a stereocenter is generated which is then obliterated in a subsequent double-bond migration. The cryptic configuration at this stereocenter was determined by first synthesizing the two enantiomers of the intermediate diketide as their N-acetylcysteamine (SNAC) thioesters. These were then used to demonstrate that only the R enantiomer complements a 3-amino-5-hydroxybenzoic acid (AHBA) deficient mutant of Actinosynnema pretiosum to restore ansomitocin formation. The low efficiency of complementation by the diketide, compared to AHBA, is due to inefficient loading onto the PKS and not the inhibition of the enzyme. A presumed next chain-extension intermediate-the triketide with an unrearranged double bond-was also synthesized as its SNAC ester, but did not complement the AHBA(-) mutant.

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  • Amphidinin B, a new polyketide metabolite from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Tetsuya Endo, Yohei Takahashi, Masashi Tsuda, Jun'ichi Kobayashi

    Journal of Antibiotics   59 ( 8 )   512 - 516   2006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:JAPAN ANTIBIOTICS RESEARCH ASSOC  

    A new polyketide metabolite, amphidinin B (1), has been isolated from a marine dinoflagellate Amphidinium sp. and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical means.

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  • Amphidinin B, a new polyketide metabolite from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Tetsuya Endo, Yohei Takahashi, Masashi Tsuda, Jun&apos;ichi Kobayashi

    JOURNAL OF ANTIBIOTICS   59 ( 8 )   512 - 516   2006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:JAPAN ANTIBIOTICS RESEARCH ASSOC  

    A new polyketide metabolite, amphidinin B (1), has been isolated from a marine dinoflagellate Amphidinium sp. and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical means.

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    その他リンク: http://orcid.org/0000-0002-3553-5844

  • Cloning of polyketide synthase genes from amphidinolide-producing dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Yoshiro Iinuma, Jun'ichi Kobayashi

    Biological and Pharmaceutical Bulletin   29 ( 7 )   1314 - 1318   2006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:PHARMACEUTICAL SOC JAPAN  

    Cloning of polyketide synthase (PKS) gene for amphidinolide biosynthesis was attempted from a dinoflagellate Amphidinium sp. (strain Y-42). Fourteen beta-ketoacyl synthase gene fragments were obtained by Polymerase Chain Reaction (PCR) amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences of beta-ketoacyl synthase domains in known type I PKSs. The PCR analysis using primer sets designed from these fourteen beta-ketoacyl synthase gene fragments revealed that these DNA sequences exist only in the dinoflagellates producing amphidinolides. The DNA sequence of the positive clone, which was isolated from genomic DNA library of Amphidinium sp. (strain Y-42) by PCR detection using the specific primer set, was analyzed by shotgun sequencing. The deduced gene products in the positive clone showed similarity with beta-ketoacyl synthase (KS), acyl transferase (AT), dehydratase (DH), ketoreductase (KR), and acyl carrier protein (ACP) in known type I PKSs and thioesterase (TE).

    DOI: 10.1248/bpb.29.1314

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  • Amphezonol A, a novel polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Yusuke Sakuma, Kazutaka Shimbo, Masashi Tsuda, Michiko Nakano, Yasuhiro Uozumi, Jun'ichi Kobayashi

    Tetrahedron Letters   47 ( 26 )   4369 - 4371   2006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  

    Amphezonol A (1), a novel polyhydroxyl linear carbon-chain metabolite, has been isolated from the cultured marine dinoflagellate Amphidinium sp., which was isolated from an Okinawan marine acoel flatworm Amphiscolops sp. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Amphezonol A (1) possesses one tetrahydrofuran ring, two tetrahydropyran rings, and twenty-one hydroxyl groups on C-60-linear aliphatic chain with one exo-methylene and one methyl branch. Amphezonol A (1) exhibited a modest inhibitory activity against DNA polymerase alpha. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.04.094

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  • Iejimalides show anti-osteoclast activity via V-ATPase inhibition 査読

    Sayaka Kazami, Makoto Muroi, Makoto Kawatani, Takaaki Kubota, Takeo Usui, Jun'ichi Kobayashi, Hiroyuki Osada

    Bioscience, Biotechnology and Biochemistry   70 ( 6 )   1364 - 1370   2006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:TAYLOR & FRANCIS LTD  

    Iejimalides (IEJLs), 24-membered macrolides, are potent antitumor compounds, but their molecular targets remain to be revealed. In the course of screening, we identified IEJLs as potent osteoclast inhibitors. Since it is known that osteoclasts are sensitive to vacuolar H+-ATPase (V-ATPase) inhibitor, we investigated the effect of IEJLs on V-ATPases. IEJLs inhibited the V-ATPases of both mammalian and yeast cells in situ, and of. yeast V-ATPases in vitro. A bafilomycin-resistant yeast mutant conferred IEJL resistance, suggesting that IEJLs bind a site similar to the bafilomycins/concanamycins-binding site. These results indicate that IEJLs are novel V-ATPase inhibitors, and that antitumor and antiosteporotic activities are exerted via V-ATPase inhibition.

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  • Daphtenidines A–D, new Daphniphyllum alkaloids from Daphniphyllum teijsmannii 査読

    KUBOTA Takaaki, MATSUNO Yosuke, MORITA Hiroshi, SHINZATO Takakazu, SEKIGUCHI Mitsuhiro, KOBAYASHI Jun’ichi

    Tetrahedron   62 ( 20 )   4743 - 4748   2006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)  

    DOI: 10.1016/j.tet.2006.03.040

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  • Lycopladine A, a new C<inf>16</inf>N alkaloid from Lycopodium complanatum 査読

    Kan'ichiro Ishiuchi, Takaaki Kubota, Hiroshi Morita, Jun'ichi Kobayashi

    Tetrahedron Letters   47 ( 19 )   3287 - 3289   2006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:PERGAMON-ELSEVIER SCIENCE LTD  

    A new C16N type alkaloid, lycopladine A (1), has been isolated from the club moss Lycopodium complanatum, and the structure and relative stereochemistry of 1 were elucidated on the basis of spectral data. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.03.027

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  • Manzamenones inhibit T-cell protein tyrosine phosphatase 査読

    Yusuke Wakuda, Takaaki Kubota, Hiroshi Shima, Tadashi Okada, Shinya Mitsuhashi, Naohito Aoki, Kunimi Kikuchi, Jun'ichi Kobayashi

    Marine Drugs   4 ( 1 )   9 - 14   2006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:MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL  

    Manzamenones A similar to C (1 similar to 3) and E similar to F (5 similar to 6), unique oxylipin metabolites isolated from a marine sponge Plakortis sp., have been found to exhibit inhibitory activity against T-cell protein tyrosine phosphatase (TCPTP). The inhibitory activity of 2 and 5 against TCPTP was 4 times more potent than that against protein tyrosine phosphatase-1B (PTP1B).

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  • Pyrinadine A, a novel pyridine alkaloid with an azoxy moiety from sponge Cribrochalina sp. 査読

    Yuuko Kariya, Takaaki Kubota, Jane Fromont, Jun'ichi Kobayashi

    Tetrahedron Letters   47 ( 6 )   997 - 998   2006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 novel cytotoxic bis-3-alkylpyridine alkaloid with an azoxy moiety, pyrinadine A (1), has been isolated from an Okinawan marine sponge Cribrochalina sp. (SS-1115), and the structure was elucidated by spectroscopic data and chemical means. (c) 2005 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2005.11.163

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  • Luteophanol D, new polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Ayako Takahashi, Masashi Tsuda, Jun'ichi Kobayashi

    Marine Drugs   3 ( 4 )   113 - 118   2005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:MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL  

    Luteophanol D ( 1), a new polyhydroxyl linear carbon-chain metabolite, has been isolated from the cultured marine dinoflagellate Amphidinium sp., which was isolated from Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Luteophanol D ( 1) possesses two tetrahydropyran rings and twenty-three hydroxyl groups on C-63-linear aliphatic chain with one exo-methylene and two methyl branches.

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  • Amphidinolide C2, new macrolide from marine dinoflagellate amphidinium species 査読

    Takaaki Kubota, Yusuke Sakuma, Masashi Tsuda, Jun’Ichi Kobayashi

    Marine Drugs   2 ( 3 )   83 - 87   2004年9月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI} {AG  

    A new cytotoxic 25-membered macrolide, amphidinolide C2 (1), has been isolated from marine dinoflagellate Amphidinium sp. (Y-71 strain), and the structure 1 was elucidated on the basis of spectroscopic data and chemical means.

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  • Absolute stereochemistry of amphidinolide C: Synthesis of C-1-C-10 and C-17-C-29 segments 査読

    Takaaki Kubota, Masashi Tsuda, Jun'ichi Kobayashi

    Tetrahedron   59 ( 10 )   1613 - 1625   2003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  

    Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(03)00142-X

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  • Bioactive macrolides and polyketides from marine dinoflagellates 査読

    Jun'ichi Kobayashi, Kazutaka Shimbo, Takaaki Kubota, Masashi Tsuda

    Pure and Applied Chemistry   75 ( 2-3 )   337 - 342   2003年

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    記述言語:英語   掲載種別:研究論文(国際会議プロシーディングス)   出版者・発行元:Walter de Gruyter GmbH  

    Absolute stereochemistry of amphidinolides G and H, potent cytotoxic 27- and 26-membered macrolides, respectively, isolated from a marine dinofiagellate Amphidinium sp., was determined by X-ray diffraction analysis, synthesis of a degradation product, and chemical interconversion. Six new macrolides, amphidinolides H2∼H5, G2, G3, and W, have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42), and the structures were elucidated by 2D NMR data and chemical means. The structure-activity relationship of amphidinolide H-type macrolides for cytotoxicity was examined. The biosynthetic origins of amphidinolides B, C, H, J, T1, and W were investigated on the basis of 13C NMR data of 13C-enriched samples obtained by feeding experiments with [1-13C], [2-13C], and [1,2-13C2] sodium acetates in cultures of the dinoflagellates. Five novel long-chain polyhydroxyl compounds, colopsinols A∼E, were obtained from the Amphidinium sp. (strain Y-5).

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    その他リンク: http://orcid.org/0000-0002-3553-5844

  • Absolute stereochemistry of amphidinolide E 査読

    Takaaki Kubota, Masashi Tsuda, Jun'ichi Kobayashi

    Journal of Organic Chemistry   67 ( 5 )   1651 - 1656   2002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  

    The absolute configurations at eight chiral centers in amphidinolide E (1), a cytotoxic 19-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were determined to be 2R, 7R, 8R, 13S, 16S, 17R, 18R, and 19R on the basis of detailed analysis of NMR data and by chemical means.

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  • Biosynthetic study of amphidinolide B 査読

    M. Tsuda, T. Kubota, Y. Sakuma, J. Kobayashi

    Chemical and Pharmaceutical Bulletin   49 ( 10 )   1366 - 1367   2001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:PHARMACEUTICAL SOC JAPAN  

    The biosynthetic origins of amphidinolide B (1) were investigated on the basis of C-13-NMR data of C-13-enriched samples obtained by feeding experiments with [1-C-13], [2-C-13], and [1,2-C-13(2)] sodium acetates in cultures of a dinoflagellate Amphidinium sp. These incorporation patterns suggested that 1 was generated from three successive polyketide chains, an isolated C-1 unit from C-2 of acetates, six branched C-1 units from C-2 of acetates, and an "m-m" and an "m-m-m" unit derived only from C-2 of acetates. The labeling patterns of amphidinolide B (1) were different from those of amphidinolide H (2), a 26-membered macrolide closely related to 1.

    DOI: 10.1248/cpb.49.1366

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  • Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1 査読

    Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro, Jun'Ichi Kobayashi

    Tetrahedron   57 ( 29 )   6175 - 6179   2001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  

    Amphidinolide T5 (1), a new 19-membered macrolide related to amphidinolide T1 (2), has been isolated from a marine dinoflagellate Amphidinium sp. The structure of 1 was elucidated on the basis of spectroscopic data and chemical means. The stereostructure of amphidinolide T1 (2) was confirmed by a single crystal X-ray diffraction analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(01)00591-9

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  • Biosynthetic study of amphidinolide C 査読

    Takaaki Kubota, Masashi Tsuda, Jun'ichi Kobayashi

    Tetrahedron   57 ( 28 )   5975 - 5977   2001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 biosynthetic origins of amphidinolide C (1) were investigated on the basis of C-13 NMR data of C-13 enriched samples obtained by feeding experiments with [1-C-13], [2-C-13], and [1,2-(13)C2] sodium acetates in cultures of a dinoflagellate Amphidinium sp. These incorporation patterns suggested that amphidinolide C (1) was generated from four diketide chains, four acetate units, five isolated C-1 unit from C-2 of acetates, seven branched C-1 units from C-2 of acetates, and a 'm-m' and a 'm-m-m' units derived only from C-2 of acetates. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(01)00556-7

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  • Absolute stereochemistry of amphidinolide C 査読

    Takaaki Kubota, Masashi Tsuda, Jun'ichi Kobayashi

    Organic Letters   3 ( 9 )   1363 - 1366   2001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  

    [GRAPHICS]
    The absolute configurations at 12 chiral centers in amphidinolide C (1), a potent cytotoxic 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp,, were determined to be 3S, 4R, 6R, 7R, 8R, 12R 135, 16S, 20R, 23R, 24R, and 29S by combination of NMR analyses, degradation experiments, and synthesis of the C-1-C-7 segment.

    DOI: 10.1021/ol015741z

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  • Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp. and the biosynthesis of amphidinolide T1 査読

    J. Kobayashi, T. Kubota, T. Endo, M. Tsuda

    Journal of Organic Chemistry   66 ( 1 )   134 - 142   2001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  

    Three new 19-membered macrolides, amphidinolides T2 (2), T3 (3), and T4 (4), structurally related to amphidinolide T1 (1) have been isolated from two strains of marine dinoflagellates of the genus Amphidinium. The structures of 2-4 were elucidated on the basis of spectroscopic data. The absolute configurations at C-7, C-8, and C-10 of 1-4 were determined by comparison of NMR data of their C-1-C-12 segments with those of synthetic model compounds for the tetrahydrofuran portion. The biosynthetic origins of amphidinolide TI (1) were investigated on the basis of C-13 NMR data of a C-13 enriched sample obtained by feeding experiments with [1-C-13], [2-C-13], and [1,2-C-13(2)] sodium acetates and C-13-labeled sodium bicarbonstte in the cultures of the dinoflagellate. These incorporation patterns suggested that amphidinolide T1 (1) was generated from four successive palyketide chains, an isolated C-1 unit formed from C-2 of acetates, and three unusual Ct units derived only from C-2 of acetates. Furthermore, it is noted that five oxygenated carbons of C-l, C-7, C-12, C-13, and C-18 were not derived from the C-1 carbonyl, but from the C-2 methyl of acetates.

    DOI: 10.1021/jo005607c

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  • Ma'edamines A and B, cytotoxic bromotyrosine alkaloids with a unique 2(1H)pyrazinone ring from sponge Suberea sp. 査読

    Keiko Hirano, Takaaki Kubota, Masashi Tsuda, Kenji Watanabe, Jane Fromont, Jun'ichi Kobayashi

    Tetrahedron   56 ( 41 )   8107 - 8110   2000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:PERGAMON-ELSEVIER SCIENCE LTD  

    Two new cytotoxic bromotyrosine alkaloids, ma'edamines A (1) and B (2), with a unique 2(1H)pyrazinone ring have been isolated from the Okinawan marine sponge Suberea sp. The structures were elucidated on the basis of spectroscopic data. (C) 2000 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(00)00732-8

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  • Colopsinols D and E, new polyhydroxyl linear carbon chain compounds from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Masashi Tsuda, Miho Takahashi, Masami Ishibashi, Seiko Oka, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   48 ( 10 )   1447 - 1451   2000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:PHARMACEUTICAL SOC JAPAN  

    Colopsinols D (1) and E (2), two new polyhydroxyl linear carbon chain compounds, have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated on the basis of two-dimensional NMR and FAB-MS/MS data.

    DOI: 10.1248/cpb.48.1447

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  • Pyrinodemins B-D, potent cytotoxic bis-pyridine alkaloids from marine sponge Amphimedon sp.

    K Hirano, T Kubota, M Tsuda, Y Mikami, J Kobayashi

    CHEMICAL & PHARMACEUTICAL BULLETIN   48 ( 7 )   974 - 977   2000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:PHARMACEUTICAL SOC JAPAN  

    New bis-pyridine alkaloids, pyrinodemins B-D (1-3), have been isolated together with pyrinodemin A (4) and related 3-alkyl pyridine alkaloids 5-8 from the Okinawan marine sponge Amphimedon sp. and the structures were elucidated from spectroscopic data. Pyrinodemins B-D (1-3) showed potent cytotoxicity, while compounds 5-8 exhibited antimicrobial activity.

    DOI: 10.1248/cpb.48.974

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  • Pyrinodemins B - D, potent cytotoxic bis-pyridine alkaloids from marine sponge Amphimedon sp. 査読

    Keiko Hirano, Takaaki Kubota, Masashi Tsuda, Yuzuru Mikami, Jun'ichi Kobayashi

    Chemical and Pharmaceutical Bulletin   48 ( 7 )   974 - 977   2000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:PHARMACEUTICAL SOC JAPAN  

    New bis-pyridine alkaloids, pyrinodemins B-D (1-3), have been isolated together with pyrinodemin A (4) and related 3-alkyl pyridine alkaloids 5-8 from the Okinawan marine sponge Amphimedon sp. and the structures were elucidated from spectroscopic data. Pyrinodemins B-D (1-3) showed potent cytotoxicity, while compounds 5-8 exhibited antimicrobial activity.

    DOI: 10.1248/cpb.48.974

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  • Amphidinolide V, novel 14-membered macrolide from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Masashi Tsuda, Jun'ichi Kobayashi

    Tetrahedron Letters   41 ( 5 )   713 - 716   2000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:PERGAMON-ELSEVIER SCIENCE LTD  

    A novel 14-membered polyene macrolide, amphidinolide V (1), has been isolated from a marine dinoflagellate Amphidinium sp., and the structure was elucidated by spectroscopic data. The relative stereochemistry of C-8, C-9, C-10, and C-13 was elucidated by NOESY correlations. Amphidinolide V (1) possessing five exo-methylenes and one epoxide exhibited cytotoxicity against tumor cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(99)02170-X

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  • Colopsinols B and C, new long chain polyhydroxy compounds from cultured marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Masashi Tsuda, Miho Takahashi, Masami Ishibashi, Hideo Naoki, Jun'ichi Kobayashi

    Journal of the Chemical Society - Perkin Transactions 1   ( 23 )   3483 - 3487   1999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:ROYAL SOC CHEMISTRY  

    Colopsinols B (1) and C (2), unique polyhydroxy compounds consisting of a C-53-linear aliphatic chain with three C-1 branches, three ether rings, six hydroxy groups, a glucoside moiety, and a sulfate ester have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques as well as FABMS/MS data of the peroxide (3) of 2.

    DOI: 10.1039/a906296c

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  • Two theonellapeptolide congeners from marine sponge Theonella sp. 査読

    Masashi Tsuda, Kazutaka Shimbo, Takaaki Kubota, Yuzuru Mikami, Jun'ichi Kobayashi

    Tetrahedron   55 ( 34 )   10305 - 10314   1999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  

    Two new theonellapeptolide-related cyclic depsipeptides (1 and 2) have been isolated from an Okinawan marine sponge Theonella sp. and the structures were elucidated on the basis of the 2D NMR data, PSD analysis of MALDI-TOFMS, and chemical means. Compound 1 was a theonellapeptolide congener possessing a methylsulfinylacetyl group at the N-terminus, while 2 was another theonellapeptolide congener having an acetyl group at the N-terminus. Compounds 1 and 2 exhibited antimicrobial activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(99)00586-4

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  • Pyrinodemin A, a cytotoxic pyridine alkaloid with an isoxazolidine moiety from sponge Amphimedon sp. 査読

    Masashi Tsuda, Keiko Hirano, Takaaki Kubota, Jun'ichi Kobayashi

    Tetrahedron Letters   40 ( 26 )   4819 - 4820   1999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  

    A novel cytotoxic pyridine alkaloid, pyrinodemin A (1), with a unique cis-cyclopent[c]isoxazolidine moiety has been isolated from the Okinawan marine sponge Amphimedon sp., and the structure was elucidated from 2D NMR data and EIMS fragmentation. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(99)00852-7

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  • Pyrinodemin A, a cytotoxic pyridine alkaloid with an isoxazolidine moiety from sponge Amphimedon sp. 査読

    M Tsuda, K Hirano, T Kubota, J Kobayashi

    TETRAHEDRON LETTERS   40 ( 26 )   4819 - 4820   1999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  

    A novel cytotoxic pyridine alkaloid, pyrinodemin A (1), with a unique cis-cyclopent[c]isoxazolidine moiety has been isolated from the Okinawan marine sponge Amphimedon sp., and the structure was elucidated from 2D NMR data and EIMS fragmentation. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(99)00852-7

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    その他リンク: http://orcid.org/0000-0002-3553-5844

  • Colopsinol A, a novel polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp. 査読

    Jun'ichi Kobayashi, Takaaki Kubota, Miho Takahashi, Masami Ishibashi, Masashi Tsuda, Hideo Naoki

    Journal of Organic Chemistry   64 ( 5 )   1478 - 1482   1999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  

    Colopsinol A (1), a novel polyhydroxyl compound, has been isolated from the cultured marine dinoflagellate Amphidiniun sp., from which a number of cytotoxic macrolides, amphidinolides, have been obtained to date, and the gross structure of 1 was elucidated on the basis of extensive spectroscopic analyses including recent 2D NMR techniques of CH2-seIected editing HSQC as well as FABMS/MS experiments and chemical means. Colopsinol A (1), C71H119O25SNa, is the first member of a new class of polyketide natural products possessing a gentiobioside moiety and a sulfate eater. The polyketide aglycon consisted of a C-56-linear aliphatic chain with one exo-methylene and two methyl branches as well as two ketones, five hydroxyl groups, and a tetrahydropyran and two epoxide rings.

    DOI: 10.1021/jo981882b

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  • Colopsinols B and C, new long chain polyhydroxy compounds from cultured marine dinoflagellate Amphidinium sp.

    T Kubota, M Tsuda, M Takahashi, M Ishibashi, H Naoki, J Kobayashi

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   40 ( 23 )   3483 - 3487   1999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  

    Colopsinols B (1) and C (2), unique polyhydroxy compounds consisting of a C-53-linear aliphatic chain with three C-1 branches, three ether rings, six hydroxy groups, a glucoside moiety, and a sulfate ester have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques as well as FABMS/MS data of the peroxide (3) of 2.

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  • Luteophanols B and C, new polyhydroxyl compounds from marine dinoflagellate Amphidinium sp. 査読

    Takaaki Kubota, Masashi Tsuda, Yukiko Doi, Ayako Takahashi, Hiroko Nakamichi, Masami Ishibashi, Eri Fukushi, Jun Kawabata, Jun'ichi Kobayashi

    Tetrahedron   54 ( 48 )   14455 - 14464   1998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  

    Luteophanols B (1) and C (2), new polyhydroxyl linear carbon-chain compounds, have been isolated from the cultured marine dinoflagellate Amphidinium sp. The structures of 1 and 2 were elucidated by detailed analyses of two-dimensional NMR data containing HMBC, HMQC-RELAY, CH2-selected E-HSQC, and CH2-selected E-HSQC, TOCSY. (C) 1998 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(98)00898-9

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▼全件表示

書籍等出版物

  • Comprehensive Natural Products II: Chemistry and Biology

    Elsevier Science  2010年 

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  • Cooperation of Bio and Nano Sciences, II. Application to New Life Sciences

    Hokkaido University Publisher  2007年 

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  • パートナー天然物化学

    久保田 高明( 担当: 共著)

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MISC

  • 沖縄産Agelas属海綿から単離した新規ジテルペンアルカロイドの構造

    近藤和幸, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020年

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  • 沖縄産Amphimedon属海綿から単離した新規マンザミン関連アルカロイドの構造

    栗本慎一郎, 鈴木祥一, 上野真由美, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020年

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  • 沖縄産Halichondria属海綿から単離した新規ステロイドの構造

    森光希, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020年

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  • 構造活性相関研究に向けたセスキテルペノイドキノン誘導体の調製

    島田祐莉奈, 小川実華, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020年

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  • 沖縄産Spongiidae科海綿から単離したセスキテルペノイドキノンの構造

    猪俣実加, 小川実華, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020年

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  • 渦鞭毛藻Symbiodinium sp.から単離した新規マクロリドの構造

    石田理紗, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019年

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  • 沖縄産Suberea属海綿から単離した新規ブロモチロシンアルカロイドの構造

    清野皐月, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019年

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  • 沖縄産Stylissa属海綿から単離した新規環状ペプチドの構造

    大山英将, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019年

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  • 渦鞭毛藻Amphidinium sp.から単離した新規ポリケチドの構造

    坂根美和子, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019年

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  • 沖縄産Plakortis属海綿から単離した新規ポリケチドの構造

    木村悠登, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019年

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  • 沖縄産Hyrtios属海綿から単離した新規β-カルボリンアルカロイドの構造

    高橋秀彰, 栗本慎一郎, 小林淳一, 久保田高明

    天然薬物の開発と応用シンポジウム講演要旨集   22nd   2018年

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  • 沖縄産Hyrtios属海綿から単離した新規Canthin-6-oneアルカロイドの構造

    高橋秀彰, 栗本慎一郎, 小林淳一, 久保田高明

    日本生薬学会年会講演要旨集   65th   2018年

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  • 沖縄産Dysidea属海綿から単離した新規ポリヒドロキシステロールの構造

    武田郁恵, 栗本慎一郎, 小林淳一, 久保田高明

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  • 沖縄産Hyrtios属海綿から単離した新規インドールアルカロイドの構造

    高橋秀彰, 栗本慎一郎, 小林淳一, 久保田高明

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  • 沖縄産Pseudoceratina属海綿から単離した新規ブロモチロシンアルカロイドの構造

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    日本薬学会年会要旨集(CD-ROM)   138th   2018年

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  • 沖縄産Amphimedon属海綿から単離した新規マンザミンアルカロイドZamamiphidin AおよびZamamidine D

    久保田高明, 栗本慎一郎, 上條優樹, 中村健太, 酒井香奈江, 高橋梓, 穗苅玲, 石山亜紀, 岩月正人, 乙黒一彦, 五ノ井透, 大村智, 小林淳一

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  • 沖縄産Hyrtios属海綿由来新規アゼピノインドールアルカロイドhyrtinadine CおよびDの構造

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    日本薬学会年会要旨集(CD-ROM)   137th   2017年

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  • New polyketides from dinoflagellate Amphidinium sp.

    T. Kubota, T. Iwai, H. Sato, J. Kobayashi

    PLANTA MEDICA   82   2016年12月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:GEORG THIEME VERLAG KG  

    DOI: 10.1055/s-0036-1596659

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  • 沖縄産Stylissa属海綿から単離した新規環状ペプチドの構造

    栗本慎一郎, 中村健太, 久保田高明, 小林淳一

    天然薬物の開発と応用シンポジウム講演要旨集   21st   2016年

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  • New polyketides from marine dinoflagellate Amphidinium sp.

    T. Kubota, T. Iwai, J. Kobayashi

    PLANTA MEDICA   80 ( 10 )   765 - 765   2014年7月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:GEORG THIEME VERLAG KG  

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  • 沖縄産Agelas属海綿から単離した新規ジテルペンアルカロイドagelasine O‐Uの構造

    岩井隆宏, 久保田高明, 片倉賢, 小林淳一

    天然薬物の開発と応用シンポジウム講演要旨集   19th   110 - 112   2012年10月

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  • 沖縄産ホヤEudistoma glaucus由来の新規β‐カルボリンアルカロイドEudistomidn H‐Kの構造

    久保田高明, 鈴木哲平, 小林淳一

    日本薬学会年会要旨集   132nd ( 2 )   194   2012年3月

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  • 嫌われ者の藍藻に期待!(バイオミディア)

    久保田 高明

    生物工学会誌 : seibutsu-kogaku kaishi   89 ( 10 )   2011年10月

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    記述言語:日本語   出版者・発行元:公益社団法人日本生物工学会  

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  • 嫌われ者の藍藻に期待!

    久保田高明

    生物工学会誌   89 ( 10 )   617   2011年10月

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  • 沖縄産Plakortis属海綿由来の新規ポリケタイドUntenolide Aの構造

    久保田高明, 石黒悠一朗, 城始勇, 小林淳一

    日本薬学会年会要旨集   131st ( 2 )   230   2011年3月

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  • 沖縄産海綿由来新規アルカロイドnakijinamine類の構造

    高橋洋平, 久保田高明, 小林淳一

    天然有機化合物討論会講演要旨集   52nd   661-666   2010年9月

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  • アスヒカズラより単離した新規アルカロイドの構造

    石内勘一郎, 久保田高明, 林茂樹, 柴田敏郎, 小林淳一

    日本薬学会年会要旨集   130th ( 2 )   239   2010年3月

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  • ナガサキオトギリより単離した新規benzophenone rhamnosideの構造

    田中直伸, 久保田高明, 柏田良樹, 高石喜久, 小林淳一

    日本薬学会年会要旨集   130th ( 2 )   233   2010年3月

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  • 沖縄産海綿由来の新規ピリジニウムアルカロイドPlatisidine A〜Cの構造

    久保田高明, 石黒悠一朗, 山本淳, 小林淳一

    日本薬学会年会要旨集   130th ( 2 )   221   2010年3月

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  • スギカズラ(Lycoposiumannotinum)より単離した新規アルカロイドの構造

    石内勘一郎, 児玉志保美, 久保田高明, 小林淳一, 林茂樹, 柴田敏郎

    日本生薬学会年会講演要旨集   56th   141   2009年9月

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  • エゾオトギリHypericum yezoenseより単離したyezo’otogirin A‐Cの構造

    田中直伸, 格口ゆか, 石山玄明, 久保田高明, 小林淳一

    日本生薬学会年会講演要旨集   56th   256   2009年9月

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  • 海綿由来の新規マンザミンアルカロイドzamamidine A〜Cの構造と生物活性

    高橋洋平, 山田美香, 久保田高明, 石山亜紀, 乙黒一彦, 山田陽城, 大村智, 小林淳一

    天然有機化合物討論会講演要旨集   51st   581-586   2009年9月

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  • アスヒカズラ(Lycopodium complanatum)由来新規アルカロイドの構造

    石内勘一郎, 久保田高明, 林茂樹, 柴田敏郎, 小林淳一

    天然有機化合物討論会講演要旨集   51st   19-24   2009年9月

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  • Corrigendum to "Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp." [Tetrahedron 65 (2009) 2313-2317] (DOI:10.1016/j.tet.2009.01.032)

    Mika Yamada, Yohei Takahashi, Takaaki Kubota, Jane Fromont, Aki Ishiyama, Kazuhiko Otoguro, Haruki Yamada, Satoshi Omura, Jun'ichi Kobayashi

    Tetrahedron   65 ( 31 )   6263 - 6263   2009年8月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    DOI: 10.1016/j.tet.2009.05.081

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  • 渦鞭毛藻由来マクロリド・Amphidinolactone Aの全合成による立体化学の解明

    萩行正博, 石山玄明, 高橋洋平, 久保田高明, 小林淳一

    次世代を担う有機化学シンポジウム講演要旨集   7th   38-39   2009年5月

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  • 沖縄産海綿由来の新規ブロモチロシンアルカロイドTyrokeradine AおよびBの構造

    久保田高明, 向井裕也, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   179   2009年3月

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  • 渦鞭毛藻由来マクロリド・Amphidinolactone Aの全合成と立体化学の解明

    萩行正博, 石山玄明, 高橋洋平, 久保田高明, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   95   2009年3月

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  • アスヒカズラより単離した新規リコポジウムアルカロイドの構造

    石内勘一郎, 久保田高明, 柴田敏郎, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   97   2009年3月

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  • ビヨウヤナキより単離した新規xanthone誘導体の構造

    田中直伸, 大豆村拓自, 久保田高明, 今林潔, 柏田良樹, 高石喜久, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   172   2009年3月

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  • アカネ科植物由来の新規モノテルペンインドールアルカロイド・Naucleamide Fの構造

    石山玄明, 格口ゆか, 高橋洋平, 久保田高明, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   179   2009年3月

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  • 沖縄産Agelas属海綿より単離した新規ブロモピロールアルカロイドの構造

    荒木敦, 久保田高明, 三上襄, 小林淳一

    天然薬物の開発と応用シンポジウム講演要旨集   17th   79-80   2008年11月

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  • 沖縄産海綿より単離したnakijiquinone/metachromin類の構造と生物活性

    高橋洋平, 久保田高明, 三上襄, 小林淳一

    天然有機化合物討論会講演要旨集   50th   59-64   2008年9月

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  • 6 沖縄産海綿より単離したnakijiquinone/metachromin類の構造と生物活性(口頭発表の部)

    高橋 洋平, 久保田 高明, 三上 襄, 小林 淳一

    天然有機化合物討論会講演要旨集   0 ( 50 )   59 - 64   2008年9月

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会  

    Sesquiterpenoid quinines and hydroquinones are representative marine natural products with unique structures and interesting biological activities. In our continuous search for bioactive compounds having unique structures from Okinawan marine sponges, we have isolated new sesquiterpenoid quinones, nakijiquinones E〜I (1〜5) and metachromins L-Q (6〜11), from three collections of Okinawan marine sponges. The structures of 1〜5 were elucidated on the basis of 2D NMR data, while those of 6〜11 were established by chemical correlations. Furthermore, biological activities for 1〜11 and synthetic metac...

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  • P-33 沖縄産海綿由来の新規ブロモピロールアルカロイドの構造(ポスター発表の部)

    荒木 敦, 安田 鉄郎, 久保田 高明, 三上 襄, 小林 淳一

    天然有機化合物討論会講演要旨集   0 ( 50 )   361 - 366   2008年9月

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会  

    Bromopyrrole alkaloids are known to be one of the most common metabolites contained in marine sponges. During our search for bioactive substances from marine organisms, we have isolated bromopyrrole alkaloids with unique cyclic skeletons from sponges of the genus Agelas or Hymeniacidon. Recently, three new bromopyrrole alkaloids, nagelamides K, M, and N (1-3), have been isolated from an Okinawan marine sponge Agelas sp. (SS-1134). The structures and relative stereochemistry of 1〜3 were elucidated on the basis of spectroscopic data. Nagelamide K (1) is a new dimeric bromopyrrole alkaloid pos...

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  • ナガサキオトギリ由来の新規フロログルシノール誘導体petiolin Dの構造

    田中直伸, 久保田高明, 石山玄明, 小林淳一, 柏田良樹, 高石喜久, 伊藤淳二, 三上襄, 城始勇

    日本生薬学会年会講演要旨集   55th   188   2008年9月

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  • 沖縄産海綿由来の新規ブロモピロールアルカロイドの構造

    荒木敦, 安田鉄郎, 久保田高明, 三上襄, 小林淳一

    天然有機化合物討論会講演要旨集   50th   361-366   2008年9月

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  • シマサルスベリより単離した新規Lythraceaeアルカロイドの構造

    久保田高明, 渡辺梢, 小林淳一, 新里孝和, 伊藤淳二, 三上襄

    日本生薬学会年会講演要旨集   55th   219   2008年9月

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  • ナガサキオトギリより単離した新規フロログルシノール誘導体petiolin A‐Cの構造

    田中直伸, 久保田高明, 荒木敦, 柏田良樹, 高石喜久, 三上襄, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   11   2008年3月

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  • 沖縄産海綿Spongia sp.由来の新規テルペノイドMetachromin R〜Tの構造

    山田美香, 高橋洋平, 久保田高明, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   11   2008年3月

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  • ユズリハ科植物由来の新規アルカロイドCalyciphylline H〜Mの構造

    八幡弘子, 齊藤静夏, 久保田高明, 小原祐太郎, 中畑則道, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   12   2008年3月

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  • 沖縄産海綿Amphimedon sp.由来の新規アルカロイドNakinadine Aの構造

    久保田高明, 西貴美, 佐々木琢磨, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   12   2008年3月

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  • Multi Phenotypic Screeningによる生理活性物質の作用解析

    風見紗弥香, 風見紗弥香, 臼井健郎, 臼井健郎, 久保田高明, 小林淳一, 長田裕之, 長田裕之

    日本農芸化学会大会講演要旨集   2008   9   2008年3月

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  • アスヒカズラより単離した新規アルカロイドの構造

    久保田高明, 八幡弘子, 石内勘一郎, 小林淳一

    日本生薬学会年会講演要旨集   54th   226   2007年9月

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  • P-11 ユズリハ科植物由来の新規アルカロイドcalyciphylline C〜Gの構造と生物活性(ポスター発表の部)

    齊藤 静夏, 久保田 高明, 福士 江里, 川端 潤, 張 恵平, 小林 淳一

    天然有機化合物討論会講演要旨集   0 ( 49 )   271 - 276   2007年8月

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会  

    Daphniphyllum alkaloids are a structually diverse group of natural products with unique fused-heterocyclic skeletons, which are elaborated by trees of the genus Daphniphyllum (Daphniphyllaceae). These unusual ring systems have been challenging targets for total synthesis as well as biosynthetic studies. We have isolated novel types of Daphniphyllum alkaloids from Daphniphyllum macropodum, D. humile, D. teijsmanni, and D. glaucescense. In our continuing search for structually unique and biogenetically interesting new alkaloids, calyciphyllines C-G (1-5) have been isolated from D. calycinum, ...

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  • ユズリハ科植物由来の新規アルカロイドcalyciphylline C〜Gの構造と生物活性

    齊藤静夏, 久保田高明, 福士江里, 川端潤, ZHANG Huiping, 小林淳一

    天然有機化合物討論会講演要旨集   49th   271-276   2007年8月

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  • ケミカルバイオロジー研究のフロンティア 創薬リードとしての分子標的天然薬物の探索

    小林淳一, 久保田高明

    現代化学   ( 436 )   21-26   2007年7月

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  • 創薬リードとしての分子標的天然薬物の探索

    小林 淳一, 久保田 高明

    現代化学   0 ( 436 )   21 - 26   2007年7月

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    記述言語:日本語   出版者・発行元:東京化学同人  

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  • 渦鞭毛藻由来の新規amphidinolide関連化合物の構造

    高橋洋平, 久保田高明, 小林淳一

    次世代を担う有機化学シンポジウム講演要旨集   5th   6-7   2007年5月

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  • 免疫抑制物質brasilicardin Aの標的分子同定

    臼井健郎, 臼井健郎, 南雲陽子, 南雲陽子, 渡邉愛, 久保田高明, 小林淳一, 長田裕之

    日本農芸化学会大会講演要旨集   2007   98   2007年3月

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  • 1 Agelas属海綿由来の新規アルカロイドagesamide類およびnagelamide類の構造(口頭発表の部)

    安田 鉄郎, 荒木 敦, 津田 正史, 久保田 高明, 福士 江里, 川端 潤, 小林 淳一

    天然有機化合物討論会講演要旨集   49 ( 0 )   1 - 6   2007年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analysis. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. (SS-1056) so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated fromspectroscopic data. Furthermore, two new bromopyrrole alkaloids, nagelamides J (3) and K (4), have been isolated from another Okinawan marine sponge Agelas sp. (SS-1077), and the structures and relative stereochemistries were elucidated from spectroscopic data. Nagelamide J (3) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring and nagelamide K (4) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamide J (3) exhibited antimicrobial activity against Staphylococcus aureus (MIC, 8.35μg/ml) and antifungal activity against Cryptococcus neoformans (MIC, 16.7μg/ml), while nagelamide K (4) exhibited antimicrobial activity against Micrococcus luteus (MIC, 16.7μg/ml).

    DOI: 10.24496/tennenyuki.49.0_1

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  • 1 Agelas属海綿由来の新規アルカロイドagesamide類およびnagelamide類の構造(口頭発表の部)

    安田 鉄郎, 荒木 敦, 津田 正史, 久保田 高明, 福士 江里, 川端 潤, 小林 淳一

    天然有機化合物討論会講演要旨集   49 ( 0 )   1 - 6   2007年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analysis. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. (SS-1056) so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated fromspectroscopic data. Furthermore, two new bromopyrrole alkaloids, nagelamides J (3) and K (4), have been isolated from another Okinawan marine sponge Agelas sp. (SS-1077), and the structures and relative stereochemistries were elucidated from spectroscopic data. Nagelamide J (3) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring and nagelamide K (4) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamide J (3) exhibited antimicrobial activity against Staphylococcus aureus (MIC, 8.35μg/ml) and antifungal activity against Cryptococcus neoformans (MIC, 16.7μg/ml), while nagelamide K (4) exhibited antimicrobial activity against Micrococcus luteus (MIC, 16.7μg/ml).

    DOI: 10.24496/tennenyuki.49.0_1

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  • ユズリハ科植物(Daphniphynaceae)に含まれる新規アルカロイドの構造と推定生合成経路

    松野陽介, 岡本麻里子, 在間一将, 久保田高明, 小林淳一, 新里孝和, 森田博史

    薬学雑誌   126 ( Suppl.5 )   100-103   2006年11月

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  • 沖縄産ホヤ由来マクロリド・イエジマリド類の構造と生物活性

    久保田高明, 野沢耕平, 津田正史, 石山玄明, 風見紗弥香, 臼井健郎, 長田裕之, 小林淳一

    薬学雑誌   126 ( Suppl.5 )   222-225   2006年11月

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  • アスヒカズラLycopodium complanatum由来の新規アルカロイドの構造と生物活性

    石内勘一郎, 久保田高明, 森田博史, 星野智洋, 小原祐太郎, 中畑則道, 小林淳一

    天然有機化合物討論会講演要旨集   48th   493-498   2006年9月

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  • P-16 アスヒカズラLycopodium complanatum由来の新規アルカロイドの構造と生物活性(ポスター発表の部)

    石内 勘一郎, 久保田 高明, 森田 博史, 星野 智洋, 小原 祐太郎, 中畑 則道, 小林 淳一

    天然有機化合物討論会講演要旨集   0 ( 48 )   493 - 498   2006年9月

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会  

    Club moss (Lycopodiaceae) is known to be a rich source of Lycopodium alkaloids posessing unique heterocyclic ring systems such as C_&lt;16&gt;N, C_&lt;16&gt;N_2, and C_&lt;27&gt;N_3, which have attracted great interest from biogenetic, synthetic, and biological points of view. In our continuing efforts to find new Lycopodium alkaloids, lycopladines A-D (1-4), lyconadin B (5), and complanadines C (6), D (7) were isolated from the club moss Lycopodium complanatum. The structures for 1-7 were elucidated on the basis of spectral data. Lycopladine A (1) obtained as colorless amourphous solid, showed the pseudomol...

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  • ヒメユズリハ(Daphniphyllum teijsmannii)より単離した新規アルカロイドDaphtenidine A‐Dの構造

    松野陽介, 松野陽介, 久保田高明, 森田博史, 新里孝和, 関口光広, 小林淳一

    日本生薬学会年会講演要旨集   53rd   152   2006年9月

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  • アスヒカズラLycopodium complanatum由来の新規アルカロイドの構造と生物活性

    石内勘一郎, 久保田高明, 小林淳一, 森田博史, 星野智洋, 小原祐太郎, 中畑則道

    日本生薬学会年会講演要旨集   53rd   157   2006年9月

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  • 放線菌由来細胞毒性物質・ブラシリカルジン類の構造と活性

    小林淳一, 久保田高明

    日本癌学会学術総会記事   65th   466-467   2006年8月

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  • リコポジウムアルカロイドの構造の多様性と生物活性

    石内勘一郎, 久保田高明, 小林淳一, 森田博史

    万有生命科学振興国際交流財団札幌シンポジウム   18th   42   2006年7月

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  • 骨粗鬆症やがんの治療薬として期待のV‐ATPase阻害剤

    小林淳一, 久保田高明

    化学   61 ( 6 )   68-69   2006年6月

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  • 沖縄産海綿Cribrochalina sp.より単離した新規ピリジンアルカロイドPyrinadine Aの構造

    久保田高明, 仮屋佑子, 小林淳一

    日本薬学会年会要旨集   126th ( 4 )   86   2006年3月

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  • Iejimalidesの標的分子の同定

    風見紗弥香, 臼井健郎, 室井誠, 久保田高明, 小林淳一, 長田裕之

    日本農芸化学会大会講演要旨集   2006   11   2006年3月

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  • 沖縄産ホヤ由来マクロリド・イエジマリド類の構造と生物活性 (第16回 天然薬物の開発と応用シンポジウム講演要旨集)

    久保田 高明, 野沢 耕平, 津田 正史

    薬学雑誌   126 ( 0 )   222 - 225   2006年

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    記述言語:日本語   出版者・発行元:日本薬学会  

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  • 海洋渦鞭毛藻由来の新規ポリケチドの探索

    久保田高明, 佐久間裕介, 新保和高, 津田正史, 小林淳一

    マリンバイオテクノロジー学会大会講演要旨集   8th   109   2005年5月

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  • 27 海洋共生藻由来の新規長鎖ポリヒドロキシ化合物Amphezonol Aの構造と生合成研究(口頭発表の部)

    久保田 高明, 佐久間 祐介, 新保 和高, 津田 正史, 魚住 泰広, 小林 淳一

    天然有機化合物討論会講演要旨集   47 ( 0 )   151 - 156   2005年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Amphezonol A (1), a novel polyhydroxyl compound, was isolated from a marine dinoflagellate Amphidinium sp. (Y-72), and the structure was elucidated on the basis of 2D NMR data including HSQC-TOCSY and INADEQUATE spectra (920MHz) using the ^<13>C-enriched sample. Amphezonol A (1), C_<62>H_<114>O_<24>, was the first member of a new class of polyketide natural products consisting of a C_<60>-linear aliphatic chain with twenty-one hydroxyl groups, and two tetrahydropyran and a tetrahydrofuran rings. Cloning of polyketide synthase (PKS) gene from a dinoflagellate Amphidinium sp. was attempted and PKS gene fragments were obtained by PCR amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences in known type I PKSs. The PCR analysis, using primer sets designed from these PKS gene fragments, revealed that these DNA sequences exist only in the dinoflagellates producing polyketides.

    DOI: 10.24496/tennenyuki.47.0_151

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  • 27 海洋共生藻由来の新規長鎖ポリヒドロキシ化合物Amphezonol Aの構造と生合成研究(口頭発表の部)

    久保田 高明, 佐久間 祐介, 新保 和高, 津田 正史, 魚住 泰広, 小林 淳一

    天然有機化合物討論会講演要旨集   47 ( 0 )   151 - 156   2005年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Amphezonol A (1), a novel polyhydroxyl compound, was isolated from a marine dinoflagellate Amphidinium sp. (Y-72), and the structure was elucidated on the basis of 2D NMR data including HSQC-TOCSY and INADEQUATE spectra (920MHz) using the ^<13>C-enriched sample. Amphezonol A (1), C_<62>H_<114>O_<24>, was the first member of a new class of polyketide natural products consisting of a C_<60>-linear aliphatic chain with twenty-one hydroxyl groups, and two tetrahydropyran and a tetrahydrofuran rings. Cloning of polyketide synthase (PKS) gene from a dinoflagellate Amphidinium sp. was attempted and PKS gene fragments were obtained by PCR amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences in known type I PKSs. The PCR analysis, using primer sets designed from these PKS gene fragments, revealed that these DNA sequences exist only in the dinoflagellates producing polyketides.

    DOI: 10.24496/tennenyuki.47.0_151

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  • Amphidinolide Eの立体化学

    久保田高明, 津田正史, 小林淳一

    日本化学会講演予稿集   81st ( 2 )   707   2002年3月

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  • Amphidinolide類の生合成に関する研究

    津田正史, 久保田高明, 新保和高, 堀口健雄, 勝又和人, 小林淳一

    日本化学会講演予稿集   80th   3   2001年9月

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  • 沖縄産海綿Suberea sp.より単離した新規ブロモチロシンアルカロイドMa'edamine AとBの構造

    久保田 高明, 津田 正史, 平野 敬子, 渡部 賢二, 小林 淳一

    日本薬学会年会要旨集   121年会 ( 2 )   119 - 119   2001年3月

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    記述言語:日本語   出版者・発行元:(公社)日本薬学会  

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  • 17 Amphidinolide CおよびT1〜T5の立体構造(口頭発表の部)

    久保田 高明, 津田 正史, 遠藤 哲哉, 城 始勇, 小林 淳一

    天然有機化合物討論会講演要旨集   43 ( 0 )   97 - 102   2001年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Amphidinolide C (1) is a unique 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp. (strain Y-5). The gross structure of 1 has been elucidated by 2D-NMR data, whereas the stereochemistry remains undefined. During our search for bioactive metabolites from marine dinoflagellates, relatively large amounts of 1 have been recently isolated from two strains (Y-56 and Y-71) of the genus Amphidinium, which allowed us to investigate the stereochemistry of 1 Absolute configurations at C-12, C-13, C-20, C-23, C-24, and C-29 of amphidinolide C (1) were assigned by combination of NMR analyses including J-based configuration analysis and Mosher's method, while absolute configurations at C-7 and C-8 of 1 were assigned by application of Mosher's method for erythro glycol and comparison of ^1H-NMR data of natural specimen with those of synthetic C-1-C-10 segments. Absolute configurations at C-3, C-4, C-6, and C-16 of 1 were elucidated by comparison of NMR data of degradation products of 1 with synthetic C-1-C-7 and C-16-C-18 segments. On the other hand, five new 19-membered macrolides amphidinolides T1-T5 (2-6) have been isolated from the Y-56 and Y-71 strains of the genus Amphdinium. The gross structures were elucidated by 2D-NMR analyses. Absolute configurations at C-2, C-13, C-14, and C-18 of amphidinolide T1 (2) were assigned on the basis of NMR data of the MTPA esters of 2 and those of degradation products of 2, while absolute configurations at C-7, C-8, and C-10 of 2 were elucidated by comparison of ^1H-NMR data of C-1-C-12 segment with those of synthetic model compounds for tetrahydrofuran portion. The absolute stereochemistry of amphidinolides T2-T5 (3-6) were also elucidated by similar methods. The stereostructure of 2 was also confirmed by a single crystal X-ray diffraction analysis.

    DOI: 10.24496/tennenyuki.43.0_97

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  • 17 Amphidinolide CおよびT1〜T5の立体構造(口頭発表の部)

    久保田 高明, 津田 正史, 遠藤 哲哉, 城 始勇, 小林 淳一

    天然有機化合物討論会講演要旨集   43 ( 0 )   97 - 102   2001年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Amphidinolide C (1) is a unique 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp. (strain Y-5). The gross structure of 1 has been elucidated by 2D-NMR data, whereas the stereochemistry remains undefined. During our search for bioactive metabolites from marine dinoflagellates, relatively large amounts of 1 have been recently isolated from two strains (Y-56 and Y-71) of the genus Amphidinium, which allowed us to investigate the stereochemistry of 1 Absolute configurations at C-12, C-13, C-20, C-23, C-24, and C-29 of amphidinolide C (1) were assigned by combination of NMR analyses including J-based configuration analysis and Mosher's method, while absolute configurations at C-7 and C-8 of 1 were assigned by application of Mosher's method for erythro glycol and comparison of ^1H-NMR data of natural specimen with those of synthetic C-1-C-10 segments. Absolute configurations at C-3, C-4, C-6, and C-16 of 1 were elucidated by comparison of NMR data of degradation products of 1 with synthetic C-1-C-7 and C-16-C-18 segments. On the other hand, five new 19-membered macrolides amphidinolides T1-T5 (2-6) have been isolated from the Y-56 and Y-71 strains of the genus Amphdinium. The gross structures were elucidated by 2D-NMR analyses. Absolute configurations at C-2, C-13, C-14, and C-18 of amphidinolide T1 (2) were assigned on the basis of NMR data of the MTPA esters of 2 and those of degradation products of 2, while absolute configurations at C-7, C-8, and C-10 of 2 were elucidated by comparison of ^1H-NMR data of C-1-C-12 segment with those of synthetic model compounds for tetrahydrofuran portion. The absolute stereochemistry of amphidinolides T2-T5 (3-6) were also elucidated by similar methods. The stereostructure of 2 was also confirmed by a single crystal X-ray diffraction analysis.

    DOI: 10.24496/tennenyuki.43.0_97

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  • 沖縄産海綿Theonella sp.より単離した新規環状デプシペプチドの構造

    新保和高, 久保田高明, 津田正史, 小林淳一

    日本化学会講演予稿集   78th ( 2 )   849   2000年3月

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  • 渦鞭毛藻Amphidinium sp.より単離した新規14員環マクロリドAmphidinolide Vの構造

    久保田高明, 津田正史, 小林淳一

    日本化学会講演予稿集   78th ( 2 )   884   2000年3月

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  • 100(P48) 渦鞭毛藻Amphidinium sp.より単離した新規ポリヒドロキシ化合物Colopsinol AとBの構造(ポスター発表の部)

    久保田 高明, 津田 正史, 高橋 美穂, 石橋 正己, 小林 淳一, 直木 秀夫

    天然有機化合物討論会講演要旨集   41 ( 0 )   595 - 600   1999年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Marine dinoflagellates of the genus Amphidinium have been recognized as a rich source of novel bioactive substances with unique structures. We previously isolated a series of cytotoxic macrolides, designated amphidinolides, possessing unique structural features from several strains of the dinoflagellates Amphidinium sp., among which the strain Y-5 was the richest source of the amphidinolides. Further search for metabolites from the strain Y-5, which was a symbiont of Okinawan marine acoel flatworm Amphiscolops sp., resulted in the isolation of two novel polyhydoroxyl compounds, colopsinols A (1) and B (2), belonging to a new class of polyketide metabolites. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques including a newly developed 2D NMR experiments such as CH_2-selected editing HSQC (E-HSQC) as well as FABMS/MS data. Colopsinols A (1) and B (2) are new class of polyketide natural products consisting of C_<56> and C_<53>-liner carbon chains, respectively, possessing a gentiobioside (β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside) moiety and a sulfate ester. From this strain (Y-5), 13 cytotoxic macrolides, amphidinolides A-D, J, K, and M-S, have been isolated so far. Biosynthetically it is interesting that quite different type of polyketides such as colopsinols and amphidinolides are produced from the same dinoflagellate. Colopsinol A (1) showed inhibitory activity against DNA polymerase α and β with IC_<50> values of 13 and 7μM, respectively.

    DOI: 10.24496/tennenyuki.41.0_595

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  • 100(P48) 渦鞭毛藻Amphidinium sp.より単離した新規ポリヒドロキシ化合物Colopsinol AとBの構造(ポスター発表の部)

    久保田 高明, 津田 正史, 高橋 美穂, 石橋 正己, 小林 淳一, 直木 秀夫

    天然有機化合物討論会講演要旨集   41 ( 0 )   595 - 600   1999年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    Marine dinoflagellates of the genus Amphidinium have been recognized as a rich source of novel bioactive substances with unique structures. We previously isolated a series of cytotoxic macrolides, designated amphidinolides, possessing unique structural features from several strains of the dinoflagellates Amphidinium sp., among which the strain Y-5 was the richest source of the amphidinolides. Further search for metabolites from the strain Y-5, which was a symbiont of Okinawan marine acoel flatworm Amphiscolops sp., resulted in the isolation of two novel polyhydoroxyl compounds, colopsinols A (1) and B (2), belonging to a new class of polyketide metabolites. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques including a newly developed 2D NMR experiments such as CH_2-selected editing HSQC (E-HSQC) as well as FABMS/MS data. Colopsinols A (1) and B (2) are new class of polyketide natural products consisting of C_<56> and C_<53>-liner carbon chains, respectively, possessing a gentiobioside (β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside) moiety and a sulfate ester. From this strain (Y-5), 13 cytotoxic macrolides, amphidinolides A-D, J, K, and M-S, have been isolated so far. Biosynthetically it is interesting that quite different type of polyketides such as colopsinols and amphidinolides are produced from the same dinoflagellate. Colopsinol A (1) showed inhibitory activity against DNA polymerase α and β with IC_<50> values of 13 and 7μM, respectively.

    DOI: 10.24496/tennenyuki.41.0_595

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  • 渦鞭毛藻Amphidinium sp.より単離した新規ポリオール化合物Luteophanol Bの構造

    久保田高明, 津田正史, 土居由貴子, 中道寛子, 石橋正己, 小林淳一

    日本薬学会年会要旨集   118th ( 2 )   108   1998年3月

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  • 80(P63) 渦鞭毛藻由来の新規ポリヒドロキシ化合物Luteophanol BおよびCの構造(ポスター発表の部)

    久保田 高明, 津田 正史, 土居 由貴子, 高橋 彩子, 中道 寛子, 石橋 正己, 福士 江里, 川端 潤, 小林 淳一

    天然有機化合物討論会講演要旨集   40 ( 0 )   473 - 478   1998年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    During our continuing search for structurally unique secondary metabolites from marine dinoflagellates, we previously isolated a series of cytotoxic macrolides, amphidinolides, from dinoflagellates Amphidinium sp. Recently we investigated another strain of Amphidinium sp. (strain number Y-52), which was isolated from the inside cells of the Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris, and isolated two new polyhydroxyl compounds, luteophanols B (1) and C (2), both consisting of a C_<64>-linear aliphatic chain. The structure elucidation of 1 and 2 were elucidated on the basis of chemical degradation and newly developed 2D NMR experiments, E-HSQC and E-HSQC-TOCSY. E-HSQC and E-HSQC-TOCSY are very useful techniques for structure elucidations of complex natural products possessing many aliphatic methine and methylene carbons such as luteophanols B (1) and C (2). CH_2-selected E-HSQC-TOCSY^6 experiments seem to be suitable to assign very closely resonated carbon signals, since this method affords the high resolution in F_1 axis by limiting the F_1 spectral width, in which sp^2 methylene carbons are resonated.

    DOI: 10.24496/tennenyuki.40.0_473

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  • 80(P63) 渦鞭毛藻由来の新規ポリヒドロキシ化合物Luteophanol BおよびCの構造(ポスター発表の部)

    久保田 高明, 津田 正史, 土居 由貴子, 高橋 彩子, 中道 寛子, 石橋 正己, 福士 江里, 川端 潤, 小林 淳一

    天然有機化合物討論会講演要旨集   40 ( 0 )   473 - 478   1998年

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    記述言語:日本語   出版者・発行元:天然有機化合物討論会実行委員会  

    During our continuing search for structurally unique secondary metabolites from marine dinoflagellates, we previously isolated a series of cytotoxic macrolides, amphidinolides, from dinoflagellates Amphidinium sp. Recently we investigated another strain of Amphidinium sp. (strain number Y-52), which was isolated from the inside cells of the Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris, and isolated two new polyhydroxyl compounds, luteophanols B (1) and C (2), both consisting of a C_<64>-linear aliphatic chain. The structure elucidation of 1 and 2 were elucidated on the basis of chemical degradation and newly developed 2D NMR experiments, E-HSQC and E-HSQC-TOCSY. E-HSQC and E-HSQC-TOCSY are very useful techniques for structure elucidations of complex natural products possessing many aliphatic methine and methylene carbons such as luteophanols B (1) and C (2). CH_2-selected E-HSQC-TOCSY^6 experiments seem to be suitable to assign very closely resonated carbon signals, since this method affords the high resolution in F_1 axis by limiting the F_1 spectral width, in which sp^2 methylene carbons are resonated.

    DOI: 10.24496/tennenyuki.40.0_473

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産業財産権

  • 渦鞭毛藻由来のポリケチド合成酵素遺伝子

    久保田 高明, 小林 淳一

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    出願人:国立大学法人 北海道大学

    出願番号:特願2005-186086  出願日:2005年6月27日

    公開番号:特開2007-000104  公開日:2007年1月11日

    J-GLOBAL

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受賞

  • 学術貢献賞

    2016年   日本生薬学会  

    久保田 高明

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共同研究・競争的資金等の研究

  • 海産天然物をシーズとした核内受容体PXRアンタゴニストの開発

    研究課題/領域番号:20K07116  2020年04月 - 2023年03月

    日本学術振興会  科学研究費助成事業 基盤研究(C)  基盤研究(C)

    久保田 高明

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    配分額:4290000円 ( 直接経費:3300000円 、 間接経費:990000円 )

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  • 渦鞭毛藻ポリケチドをシーズとした新しいタイプの抗感染症薬の開発

    研究課題/領域番号:17K08345  2017年04月 - 2020年03月

    日本学術振興会  科学研究費助成事業 基盤研究(C)  基盤研究(C)

    久保田 高明

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    配分額:4810000円 ( 直接経費:3700000円 、 間接経費:1110000円 )

    渦鞭毛藻および海綿動物を素材として、新たな抗真菌および抗原虫物質の探索を行い、26個の新規天然有機化合物を単離した。構造が明らかになった化合物について生物活性を評価した結果、渦鞭毛藻由来の1個のマクロリドと海綿動物由来の2個のアルカロイドがマウス白血病細胞に対して細胞毒性を、海綿動物由来の1個のアルカロイドが抗マラリア原虫活性を示すことが明らかになった。現在、他の新規化合物および同時に単離した既知化合物について生物活性評価を進めている。

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  • 海産アルカロイドをシーズとした新しいトリパノソーマ症治療薬の開発

    研究課題/領域番号:25460115  2013年04月 - 2016年03月

    日本学術振興会  科学研究費助成事業 基盤研究(C)  基盤研究(C)

    久保田 高明, 小林 淳一, 片倉 賢, 五ノ井 透

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    配分額:5200000円 ( 直接経費:4000000円 、 間接経費:1200000円 )

    海洋生物を素材として、新たな抗トリパノソーマ物質の探索を行い、海綿動物および渦鞭毛藻から12個の新規化合物を単離、構造決定した。また、これまでに研究代表者らが見いだした抗トリパノソーマ物質の構造活性相関を明らかにする目的で、アナログ化合物を含むことが推定された海綿抽出物から、3個のアナログ化合物を含む5個の新規化合物を単離、構造決定した。これらのうち、十分な物質量が得られた化合物について、詳細な抗トリパノソーマ活性の評価を進めている。

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  • ブラシリカルジンAをリード化合物とした新しい抗腫瘍剤および免疫抑制剤の開発

    研究課題/領域番号:25670043  2013年04月 - 2015年03月

    日本学術振興会  科学研究費助成事業 挑戦的萌芽研究  挑戦的萌芽研究

    小林 淳一, 久保田 高明, 石山 玄明, 田中 直伸

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    配分額:3900000円 ( 直接経費:3000000円 、 間接経費:900000円 )

    天然物ライブラリーの拡充を目的に広範な生物資源を対象として新規生物活性物質の探索を行い60個の新規化合物を単離、構造決定した他、以前研究代表者が単離した数種の生物活性物質については、未解明だった立体化学や活性発現の機構を明らかにすることができた。拡充した天然物ライブラリーおよび新たに単離したブラシリカルジンAおよび関連化合物から化学変換により調製したアナログを用いて新規System L 阻害物質の探索を行ったが、ブラシリカルジンAより活性の強い化合物を見い出すことはできなかった。

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  • 渦鞭毛藻由来マクロリドの特異な生合成経路の解明

    研究課題/領域番号:23108502  2011年04月 - 2013年03月

    日本学術振興会  科学研究費助成事業 新学術領域研究(研究領域提案型)  新学術領域研究(研究領域提案型)

    久保田 高明

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    担当区分:研究代表者  資金種別:競争的資金

    配分額:6760000円 ( 直接経費:5200000円 、 間接経費:1560000円 )

    研究代表者らが海洋渦鞭毛藻Amphidinium sp.から単離、構造決定している一連の抗腫瘍性マクロリドであるアンフィジノリド類のポリケチド鎖は、13C標識酢酸の投与実験により、通常の酢酸-マロン酸経路だけでは説明できない特異な炭素鎖伸長経路により生合成されていることが分かっている。この特異な炭素鎖伸長経路は、他の属の渦鞭毛藻が生産するポリケチドの生合成にも関与していることが示唆されている。
    植物や菌類のポリケチド生合成酵素(PKS)は、酢酸由来の2炭素を直列に2炭素ずつポリケチド鎖を伸長する事しかできないが、渦鞭毛藻のPKSはポリケチド鎖を2炭素伸長させるだけでなく、酢酸のメチル基炭素を用いて1炭素のみ伸長させることも可能と考えられる。生合成工学的手法により、渦鞭毛藻のPKSを利用することが可能になれば、菌類に比べて培養が困難な渦鞭毛藻のポリケチドを、他のホストで効率よく生産させることが可能になるだけでなく、既知のPKSでは生産することができない多彩な炭素骨格の化合物を、酵素的に合成することも可能となる。しかし、この特異な1炭素伸長のメカニズムは不明である。
    本研究では、2011年に採取したアンフィジノリド生産株について、RNA-Seq解析によるmRNAの網羅的な解析を行った結果、アンフィジノリド類の生合成に関与している可能性のある遺伝子として、既知のPKSに見られる酵素や、β-メチル化に関与する酵素と相同性を示す酵素遺伝子の他、藍藻の生産するバルバミドの生合成において特異な炭素鎖伸長に関与している酵素と相同性を示す、非リボソームペプチド合成酵素に見られるドメインとPKSの混合したモジュール型酵素の遺伝子を取得した。

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  • 海洋生物由来の機能性天然分子の開発と創薬への利用

    研究課題/領域番号:20390001  2008年 - 2010年

    日本学術振興会  科学研究費助成事業 基盤研究(B)  基盤研究(B)

    小林 淳一, 久保田 高明, 石山 玄明

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:19760000円 ( 直接経費:15200000円 、 間接経費:4560000円 )

    わが国をはじめ欧米諸国では高齢化社会を向えつつあり、癌や骨粗しょう症、アルツハイマー病や認知症などに対して有効な薬剤の開発が早急に求められている。一方、癌などの分子標的に特異的に作用する薬剤(分子標的治療薬)の開発は、従来の化学療法との併用による作用増強、特異的な作用機序による毒性の軽減、患者のQOLの改善などが期待されている。本研究では、研究代表者が保持している、特異な構造を有する海洋生物由来の天然物ライブラリーに加え、新たに海洋生物(海綿、ホヤ、海洋由来真菌、渦鞭毛藻など)より新規な骨格を有する天然物を見い出し、これらの海洋天然物を用いて、癌、骨粗しょう症、アルツハイマー病、HIVや肝炎ウイルス等の感染症の治療に有効な新たな機能性天然分子の開発と創薬への利用を行うことを目的に研究を行った。その結果、沖縄で採取されたAgelas属の海綿より抗菌活性を示すブロモピロールアルカロイドのベンゾセプトリンCを、Plakortis属の海綿よりアセチルコリンエステラーゼ阻害活性を示すピリジニウムアルカロイドのプラティシジンA-Cを、Spongiidae科の海綿よりチロシンキナーゼ阻害活性を示すセスキテルペノイドキノンのナキジキノンJ-Rを、それぞれ単離した。また、以前に当研究室でAmphidinium属の渦鞭毛藻より単離した殺細胞活性を示すマクロライドのアンフィジノライドQの絶対立体配...

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  • 創薬素材としての細胞骨格系機能性分子の探索

    研究課題/領域番号:18032005  2006年 - 2007年

    日本学術振興会  科学研究費助成事業 特定領域研究  特定領域研究

    小林 淳一, 久保田 高明, 石山 玄明, 津田 正史

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:6200000円 ( 直接経費:6200000円 )

    本研究では、海洋生物、植物、微生物などの広範な天然資源を素材として、細胞骨格系において重要な役割を果たしているアクチンおよびチューブリン等を分子標的にしたスクリーニングを行うことにより、これらの蛋白質の重合・脱重合を阻害する新しい天然分子を見い出すとともに、これらの天然分子の構造活性相関を検討し、特異な重合阻害剤や脱重合阻害剤(重合促進剤)を開発する目的で研究を行った。以下に本年度の研究成果の概要を報告する。アクチンファイバーの安定化促進作用を有する渦鞭毛藻由来マクロリド化合物アンフィジノリドHの関連化合物として、渦鞭毛藻より、アンフィジノラクトンB、アンフィジノリドB6,B7およびイリオモテオリド1aを単離、構造決定した。イリオモテオリド1aについては、human Blymphocyte DG-75 cellsに対する作用を調べた結果、アンフィジノリドHと同程度の細胞毒性を示すこと見い出した。また、強力なチューブリン脱重合阻害作用と抗癌作用を示すイチイ科植物由来め化合物・タキソールの関連化合物として、日本産イチイよりタキセゾピジンOおよびPを単離、構造決定した。今回単離、構造解析した化合物については、分子標的に対する詳細な活性評価、および各種ヒト腫瘍パネルに対するin vitro、in vivoでの活性を評価し、開発した阻害剤あるいは促準剤の新しい癌治療薬等としての可能性を...

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  • フォトンフォース計測技術を用いた細胞系ダイナミック分析法の開発

    研究課題/領域番号:17034001  2005年 - 2006年

    日本学術振興会  科学研究費助成事業 特定領域研究  特定領域研究

    笹木 敬司, 久保田 高明, 山本 隆晴

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:4900000円 ( 直接経費:4900000円 )

    これまでに我々は、フォトンフォース(光の放射圧)を利用して単一徴粒子やマイクロ・ナノ構造体に作用するフェムトニュートンオーダーの力を計測し、表面電荷・吸収・粘弾性特性・吸着力等の物性を非接触・非破壊的に解析する新しい手法を提案するとともに、高精度かつ汎用性の高い計測システムを開発してきた。本特定領域研究では、フォトンフォース計測技術を単一細胞や複数細胞集団の新しい分析法として応用し、細胞系のダイナミック分析を実現することを目的として、a)新しいアイデアに基づく2ビームフォトンフォース計測システムを開発、b)単一細胞の粘弾性特性や表面修飾した徴粒子との相互作用ポテンシャルを計測、c)細胞間の接着特性や徴細構造を持つ基板への付着特性の解析、を課題として研究を展開した。細胞と徴粒子あるいは細胞間の相互作用ポテンシャルの解析を実現するために、偏光の異なる2つのパルスレーザービームを個々に照射し、透過散乱光を偏光で分離して同時3次元ポジションセンシングを可能とする新しいフォトンフォース計測システムを試作し、感度、精度について検証した上で、2つの微粒子間の相互作用の解析に応用した。また、フォース計測システムにより細胞の各ポジションの表面弾性や粘性を解析して、細胞が固有の形態で運動するメカニズムの解明を試みている。さらに、細胞間の選択的接着特性を解析するために、外部環境を変えながら細胞間の...

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  • 蛋白質リン酸化を標的とした新規抗腫瘍性シーズの探索

    研究課題/領域番号:17035004  2005年

    日本学術振興会  科学研究費助成事業 特定領域研究  特定領域研究

    津田 正史, 小林 淳一, 久保田 高明

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:3200000円 ( 直接経費:3200000円 )

    海洋生物からの生物活性物質探索の一環として、本研究では、海洋由来真菌Penicillium citrinum N055株より、新規4環性アルカロイドPerinadin Aを単離し、絶対立体配置を含む化学構造を明らかにした。同じくP.citrinum N059株より、5環性アルカロイドCitrinadin Aとともに新規化合物Citrinadin Bを単離し、Citrinadin AとBの絶対立体配置を含む化学構造を推定した。沖縄県辺戸岬沖にて採取したアオブダイの消化管より分離した真菌P.citrinum N05株の培養液の上清より、新規アルカロイドPerinadin Aを得た。Perinadin Aは、光学活性な無色の非結晶性固体として得られ、HRESIMSより分子式がC_<28>H_<37>NO_2であることが明らかとなった。2D NMRデータの詳細な解析に基づいて、Perinadin Aの相対立体配置を含む化学構造を帰属した。CDスペクトルの解析より、絶対立体配置を1S、3R、4R、2'R、3'Sであると帰属した。C-7'はエピ体の混合物であると推定した。沖縄県辺戸岬沖にて採取した紅藻より分離した真菌P.citrinum N059株の培養液の菌体より、新規アルカロイドCitrinadin Bを、既知関連化合物Citrinadin Aとともに単離した。2D NMRデータの詳...

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  • がん分子標的に特異的に作用する天然薬物の開発

    研究課題/領域番号:17016003  2005年

    日本学術振興会  科学研究費助成事業 特定領域研究  特定領域研究

    小林 淳一, 久保田 高明, 石山 玄明

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:3100000円 ( 直接経費:3100000円 )

    研究代表者らはこれまでに、広範な天然資源より種々の分子標的阻害物質を数多く見い出しており、そのいくつかは新しい医薬リード化合物として開発研究が展開される一方、生体機能解明のためのバイオプローブとして利用されている。本研究では、海洋生物、植物、微生物などの広範な天然資源を素材として、チューブリン、トポイソメラーゼ、ヒストンデアセチラーゼ、チロシンキナーゼ、等の分子標的に対するスクリーニングを行うことにより、新しいがん分子標的阻害物質を見い出すことを目的とし、以下の研究を行った。放線菌Nocardia brasiliensisより単離した免疫抑制物質ブラシリカルジンAのアナログを調製し構造活性相関について研究を行った。現在、ビオチン誘導体を用いて、分子標的の特定を行っている。一方、アクチンファイバーの安定化を促進させる作用を有する海洋共生渦鞭毛藻由来マクロリド化合物・アンフィジノリドHの溶液中のコンホメーション解析を行うとともに、関連抗腫瘍性マクロリドとしてアンフィジノリドB4およびB5を単離構造決定した。また、沖縄産群体ホヤEudistoma cf.rigidaより単離した抗腫瘍性マクロリド化合物・イエジマリド類の絶対立体配置を決定した。今後、活性を示した化合物については、構造活性相関を通じて、より特異性の高い分子標的阻害物質を分子設計する予定である。さらに、得られた分子標的阻...

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  • 抗腫瘍性マクロリド・イエジマリド類の真の生産微生物の解明

    研究課題/領域番号:16651104  2004年 - 2005年

    日本学術振興会  科学研究費助成事業 萌芽研究  萌芽研究

    小林 淳一, 津田 正史, 久保田 高明

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:2900000円 ( 直接経費:2900000円 )

    沖縄産群体ホヤEudistoma cf.rigidaより単離したイエジマリド類は、旅線菌などの二次代謝産物にみられるアミノ酸結合型ポリケチドであり、ホヤの体内に共生する微生物が生産しているものと推定される。そこで本研究では、共生微生物を含むホヤの全ゲノムDNAより、イエジマリド合成酵素遺伝子のクローニングを行い、イエジマリドの生合成経路の遺伝子レベルでの解明、および、分子マーカーと免疫学的手法を駆使してイエジマリド類の真の生産微生物の特定を目的として研究を行った。まず、これまで不確定であったイエジマリド類の立体化学について、NMRデータ解析、酸化分解生成物の立体選択的合成、化学相関実験により、全絶対立体配置を確定した。次にポリケチド合成酵素のKetosynthaseドメインに特異的な遺伝子プローブや、非リボゾーム型ペプチド合成酵素の遺伝子プローブを種々設計し、沖縄で採取したホヤについて、ゲノムDNAを分離精製するとともに、ホヤの全DNAよりコスミドライブラリーの作成を行った。作成した遺伝子プローブをプライマーとしてホヤゲノムDNAについてPCRを行い、PCR生成物よりプラスミドDNAを調製した。特異的なパターンを示す遺伝子については、DNAシークエンサーで塩基配列を決定し、その塩基配列に基づいた特異的な遺伝子プローブを設計した。今後これら特異的遺伝子プローブを用いて、コスミド...

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  • 細胞骨格系に作用する機能性天然分子の開発と創薬への利用

    研究課題/領域番号:16310143  2004年 - 2005年

    日本学術振興会  科学研究費助成事業 基盤研究(B)  基盤研究(B)

    小林 淳一, 津田 正史, 久保田 高明, 石山 玄明, 森田 博史

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    担当区分:連携研究者  資金種別:競争的資金

    配分額:13500000円 ( 直接経費:13500000円 )

    本研究では、広範な天然資源を素材として、アクチンおよびチューブリンを分子標的にしたスクリーニングを行うことにより、これらの蛋白質の重合・脱重合を阻害する新しい天然分子を見出すとともに、構造活性相関を検討することにより、特異な重合阻害剤や脱重合阻害剤(重合促進剤)を開発し、新しい癌治療薬等のリード化合物としての可能性を検討することを目的として以下の研究を行った。海洋生物、植物、微生物等の天然物資源を素材として、チューブリンとアクチンに特異的に作用する機能性天然分子を探索した結果、ラン科シランBletilla striataの根茎から単離した数種のスチルベン関連化合物が、IC_<50> 10μMでチューブリン重合阻害活性を示すことを見い出した。これらスチルベン関連化合物のチューブリンに対する活性は、bisbenzylの存在が重要であると推定される。これらのうち一つはSN-38のK562/BCRP cellに対する殺細胞活性を増強させる作用を示した。また、キョウチクトウ科コプシアKopsia singapurensisから単離されている、微小管脱重合阻害活性を持つアルカロイドrhazinilamの溶液中のコンホメーションと活性について計算化学により考察した。さらに、アクチンファイバーの安定化を促進させる作用を有する海洋共生渦鞭毛藻由来マクロリド化合物・アンフィジノリドHの溶液中のコ...

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  • 渦鞭毛藻由来マクロリドamphidinolide Cの立体化学と生合成経路の解明

    研究課題/領域番号:01J10818  2001年 - 2002年

    日本学術振興会  科学研究費助成事業 特別研究員奨励費  特別研究員奨励費

    久保田 高明

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    配分額:2000000円 ( 直接経費:2000000円 )

    海洋産の渦鞭毛藻Amphidinium sp.の培養藻体から単離した抗腫瘍性25員環マクロリド・Amphidinolide Cは、テトラヒドロフラン環、共役ジエン(S-cisおよびS-trans)、水酸基、エキソメチレン、エステルカルボニル基、ケトカルボニル基、といった多彩な官能基・部分構造を持ち、12個の不斉炭素を有するユニークで複雑な構造の化合物である。しかしながらこれまで、Amphidinolide Cの立体化学については、一部の相対立体配置の推定がなされているのみであり、作用メカニズムの解明および構造活性相関についての研究が展開できない状況にある。一方、Amphidinolide Cは奇数員環のマクロリドで、隣接するメチル基-エキソメチレン基を有するなど通常のポリケチド生合成経路では説明のつかない炭素骨格を有しており、その生合成経路についても興味が持たれる。本研究では、Amphidinolide Cの絶対立体配置を解明し、合成研究とそれに続く活性評価を可能にするとともに、生合成経路の解明を目的として研究を行った。
    1)Amphidinolide CのC-1〜C-10とC-17〜C29に相当するセグメントを合成し、天然物由来の反応生成物とスペクトルデータを比較により、3位、4位、6位、7位、8位、20位、23位および24位の絶対立体配置を決定した。
    2)Amphidinolide Eについて、NMRデータの解析、分解反応、セグメントの合成により、8個の不斉炭素の絶対立体配置を明らかにした。

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  • Search for bioactive natural products and its biosynthesis

    1995年

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    資金種別:競争的資金

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  • 生物活性天然物質の探索と生合成

    1995年

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    資金種別:競争的資金

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担当授業科目

  • 創薬化学 (2021年度) 第2学期  - 金5~6

  • 創薬化学 (2021年度) 第3学期  - 金5~6

  • 天然物化学概説 (2021年度) 特別  - その他

  • 天然物化学演習 (2021年度) 特別  - その他

  • 天然物化学1 (2021年度) 第1学期  - 木7,木8

  • 天然物化学1 (2021年度) 第1学期  - 木7,木8

  • 天然物化学2 (2021年度) 第2学期  - 木7,木8

  • 天然物化学2 (2021年度) 第2学期  - 木7,木8

  • 有機化学・天然物化学 (2021年度) 後期  - その他

  • 漢方薬学概論1 (2021年度) 第3学期  - 金5,金6

  • 漢方薬学概論1 (2021年度) 第3学期  - 金5,金6

  • 漢方薬学概論2 (2021年度) 第4学期  - 金5,金6

  • 漢方薬学概論2 (2021年度) 第4学期  - 金5,金6

  • 生薬学 (2021年度) 3・4学期  - 金1,金2

  • 生薬学 (2021年度) 3・4学期  - 金1,金2

  • 生薬学1 (2021年度) 第3学期  - 金1,金2

  • 生薬学1 (2021年度) 第3学期  - 金1,金2

  • 生薬学2 (2021年度) 第4学期  - 金1,金2

  • 生薬学2 (2021年度) 第4学期  - 金1,金2

  • 薬学ガイダンス (2021年度) 1・2学期  - [第1学期]水4, [第2学期]月1

  • 薬学ガイダンス (2021年度) 1・2学期  - [第1学期]水4, [第2学期]月1

  • 薬学ガイダンス (2021年度) 1・2学期  - [第1学期]水4, [第2学期]月1

  • 薬学ガイダンス (2021年度) 1・2学期  - [第1学期]水4, [第2学期]月1

  • 薬学基礎実習Ⅱ (2021年度) 1・2学期  - その他6~9

  • 薬学基礎実習Ⅱ (2021年度) 1・2学期  - その他6~9

  • 薬用天然物化学I (2021年度) 特別  - その他

  • 薬用天然物化学II (2021年度) 特別  - その他

  • 機能性天然素材学1 (2020年度) 第4学期  - その他

  • 機能性天然素材学1 (2020年度) 第4学期  - その他

  • 機能性天然素材学2 (2020年度) 第4学期  - その他

  • 機能性天然素材学2 (2020年度) 第4学期  - その他

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