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

被引:39
作者
Kobayashi, J [1 ]
Kubota, T
Takahashi, M
Ishibashi, M
Tsuda, M
Naoki, H
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Suntory Inst Bioorgan Res, Shimamoto, Osaka 6188503, Japan
关键词
D O I
10.1021/jo981882b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:1478 / 1482
页数:5
相关论文
共 18 条
[1]   4 NEW BIOACTIVE POLYHYDROXYLATED STEROLS FROM THE BLACK CORAL ANTIPATHES-SUBPINNATA [J].
AIELLO, A ;
FATTORUSSO, E ;
MENNA, M .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (03) :321-325
[2]   PATELLAZOLE-B - A NOVEL CYTO-TOXIC THIAZOLE-CONTAINING MACROLIDE FROM THE MARINE TUNICATE LISSOCLINUM-PATELLA [J].
CORLEY, DG ;
MOORE, RE ;
PAUL, VJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7920-7922
[3]   IMPROVED MULTIPLET EDITING OF PROTON-DETECTED, HETERONUCLEAR SHIFT-CORRELATION SPECTRA [J].
DAVIS, DG .
JOURNAL OF MAGNETIC RESONANCE, 1991, 91 (03) :665-672
[4]   Luteophanol A, a new polyhydroxyl compound from symbiotic marine dinoflagellate Amphidinium sp. [J].
Doi, Y ;
Ishibashi, M ;
Nakamichi, H ;
Kosaka, T ;
Ishikawa, T ;
Kobayashi, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3820-3823
[5]  
Fukushi E, 1998, MAGN RESON CHEM, V36, P741, DOI 10.1002/(SICI)1097-458X(199810)36:10<741::AID-OMR360>3.0.CO
[6]  
2-F
[7]  
Ishibashi M, 1997, HETEROCYCLES, V44, P543
[8]   Studies on the macrolides from marine dinoflagellate Amphidinium sp.: Structures of amphidinolides R and S and a succinate feeding experiment [J].
Ishibashi, M ;
Takahashi, M ;
Kobayashi, J .
TETRAHEDRON, 1997, 53 (23) :7827-7832
[9]  
KALINNOWSKI HO, 1988, CARBON 13 NMR SPECTR, P442
[10]   THEONEZOLIDE-A - A NOVEL POLYKETIDE NATURAL PRODUCT FROM THE OKINAWAN MARINE SPONGE THEONELLA SP [J].
KOBAYASHI, J ;
KONDO, K ;
ISHIBASHI, M ;
WALCHLI, MR ;
NAKAMURA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6661-6665