MYCOTHIAZOLE, A POLYKETIDE HETEROCYCLE FROM A MARINE SPONGE

被引：121

作者：

CREWS, P ^{[1
]}

KAKOU, Y ^{[1
]}

QUINOA, E ^{[1
]}

机构：

[1] UNIV CALIF SANTA CRUZ, INST MARINE SCI, SANTA CRUZ, CA 95064 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1988年 / 110卷 / 13期

关键词：

D O I：

10.1021/ja00221a042

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The structure of an annual thiazole containing compound, mycorthiazole (1), was established after extensive NMR analysis. It was further confirmed by exhaustive interpretation of a HREIMS spectrum. Mycothiazole was isolated from Spongia mycofijiensis collected from Vanuatu and it exhibited anthelminthic activity (in vitro) while high toxicity was observed in mice. Even though the disubstituted thiazole ring system that is present in 1 has not been previously observed in natural products chemistry, comparisons of its carbon skeleton to that of latrunculin B suggest a possible route for its biogenesis.

引用

页码：4365 / 4368

页数：4

共 30 条

[1]

ADAMCZESKI M, IN PRESS J AM CHEM S

[2] MODERN PULSE METHODS IN HIGH-RESOLUTION NMR-SPECTROSCOPY [J].

BENN, R ;

GUNTHER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (05) :350-380

[3]

BRYCROFT BW, 1978, J CHEM SOC CHEM COMM, P256

[4] STRUCTURE OF ALTHIOMYCIN, A HIGHLY MODIFIED PEPTIDE ANTIBIOTIC [J].

BYCROFT, BW ;

PINCHIN, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (04) :121-122

[5] JASPLAKINOLIDE, A CYCLODEPSIPEPTIDE FROM THE MARINE SPONGE, JASPIS SP [J].

CREWS, P ;

MANES, LV ;

BOEHLER, M .

TETRAHEDRON LETTERS, 1986, 27 (25) :2797-2800

[6] TOTAL SYNTHESIS OF (+)-DEMETHYLDYSIDENIN AND (-)-DEMETHYLISODYSIDENIN, HEXACHLORINATED AMINO-ACIDS FROM THE MARINE SPONGE DYSIDEA-HERBACEA - ASSIGNMENT OF ABSOLUTE STEREOCHEMISTRY [J].

DELASZLO, SE ;

WILLIARD, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) :199-203

[7] CONTRIBUTIONS TO THE STUDY OF SOME HETEROCYCLES .58. MASS-SPECTRA OF 2-PHENYL-4-CARBOXY-THIAZOLE AND 5-CARBOXY-THIAZOLE [J].

DEMIAN, H ;

SIMITI, I ;

PALIBRODA, N .

ORGANIC MASS SPECTROMETRY, 1984, 19 (04) :196-197

[8]

DEPAIRE H, 1977, TETRAHEDRON LETT, P1395

[9] C-13 NUCLEAR MAGNETIC-RESONANCE OF POLY-HETERO-ATOMIC PENTAGONAL HETEROCYCLES - THIAZOLES AND THIAZOLO [2,3-E]TETRAZOLES [J].

FAURE, R ;

GALY, JP ;

VINCENT, EJ ;

ELGUERO, J .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (01) :46-55

[10] MARINE TOXINS OF LATRUNCULIA-MAGNIFICA [J].

GROWEISS, A ;

SHMUELI, U ;

KASHMAN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3512-3516

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