Amphidinolide W, a new 12-membered macrolide from dinoflagellate Amphidinium sp.

被引：36

作者：

Shimbo, K ^{[1
]}

Tsuda, M ^{[1
]}

Izui, N ^{[1
]}

Kobayashi, J ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 03期

关键词：

D O I：

10.1021/jo016089o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new cytotoxic 12-membered macrolide, amphidinolide W (1), has been isolated from a marine dinoflagellate Amphidinium sp., and the structure was elucidated by spectroscopic data including C-13-C-13 INADEQUATE correlations for its C-13-enriched sample. The absolute stereochemistry of 1 was assigned by combination of J-based configuration analysis and modified Mosher method. Amphidinolide W (1) is the first macrolide without an exomethylene unit among all amphidinolides obtained so far.

引用

页码：1020 / 1023

页数：4

共 9 条

[1]

DERICCARDIS F, 1993, GAZZ CHIM ITAL, V123, P79

[2] NOVEL MARINE POLYHYDROXYLATED STEROIDS FROM THE STARFISH MYXODERMA-PLATYACANTHUM [J].

FINAMORE, E ;

MINALE, L ;

RICCIO, R ;

RINALDO, G ;

ZOLLO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1146-1153

[3] Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp and the biosynthesis of amphidinolide T1 [J].

Kobayashi, J ;

Kubota, T ;

Endo, T ;

Tsuda, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :134-142

[4] Colopsinol A, a novel polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp. [J].

Kobayashi, J ;

Kubota, T ;

Takahashi, M ;

Ishibashi, M ;

Tsuda, M ;

Naoki, H .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1478-1482

[5] AMPHIDINOLIDE-G AND AMPHIDINOLIDE-H - NEW POTENT CYTOTOXIC MACROLIDES FROM THE CULTURED SYMBIOTIC DINOFLAGELLATE AMPHIDINIUM SP [J].

KOBAYASHI, J ;

SHIGEMORI, H ;

ISHIBASHI, M ;

YAMASU, T ;

HIROTA, H ;

SASAKI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5221-5224

[6] Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products [J].

Matsumori, N ;

Kaneno, D ;

Murata, M ;

Nakamura, H ;

Tachibana, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :866-876

[7] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[8] HETERONUCLEAR FILTERS IN 2-DIMENSIONAL [H-1, H-1] NMR-SPECTROSCOPY - COMBINED USE WITH ISOTOPE LABELING FOR STUDIES OF MACROMOLECULAR CONFORMATION AND INTERMOLECULAR INTERACTIONS [J].

OTTING, G ;

WUTHRICH, K .

QUARTERLY REVIEWS OF BIOPHYSICS, 1990, 23 (01) :39-96

[9] SYMMETRICAL PHASE-ALTERNATING COMPOSITE PULSES [J].

SHAKA, AJ ;

PINES, A .

JOURNAL OF MAGNETIC RESONANCE, 1987, 71 (03) :495-503

← 1 →