MYCOTHIAZOLE, A POLYKETIDE HETEROCYCLE FROM A MARINE SPONGE

被引：120
|
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
收藏
页码：4365 / 4368
页数：4
相关论文
共 50 条
  • [41] Trisphaerolide A, a novel polyketide from the Dominican sponge Erylus trisphaerus
    van Altena, I
    van Soest, R
    Roberge, M
    Andersen, RJ
    JOURNAL OF NATURAL PRODUCTS, 2003, 66 (04): : 561 - 563
  • [42] Polyketide Synthase Genes from Marine Dinoflagellates
    R. V. Snyder
    P. D. L. Gibbs
    A. Palacios
    L. Abiy
    R. Dickey
    J. V. Lopez
    K. S. Rein
    Marine Biotechnology, 2003, 5 : 1 - 12
  • [43] Polyketide synthase genes from marine dinoflagellates
    Snyder, RV
    Gibbs, PDL
    Palacios, A
    Abiy, L
    Dickey, R
    Lopez, JV
    Rein, KS
    MARINE BIOTECHNOLOGY, 2003, 5 (01) : 1 - 12
  • [44] Synthesis of a syn,syn,syn,syn-stereopentad precursor of the marine sponge polyketide callystatin A
    Marshall, JA
    Fitzgerald, RN
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12): : 4477 - 4481
  • [45] TRICHOHARZIN, A NEW POLYKETIDE PRODUCED BY THE IMPERFECT FUNGUS TRICHODERMA-HARZIANUM SEPARATED FROM THE MARINE SPONGE MICALE-CECILIA
    KOBAYASHI, M
    UEHARA, H
    MATSUNAMI, K
    AOKI, S
    KITAGAWA, I
    TETRAHEDRON LETTERS, 1993, 34 (49) : 7925 - 7928
  • [46] NEW TETRAHYDROPYRANS FROM A MARINE SPONGE
    CAPON, RJ
    GHISALBERTI, EL
    JEFFERIES, PR
    TETRAHEDRON, 1982, 38 (11) : 1699 - 1703
  • [47] Novel polyketide metabolites from a species of marine fungi
    Smith, CJ
    Abbanat, D
    Bernan, VS
    Maiese, WM
    Greenstein, M
    Jompa, J
    Tahir, A
    Ireland, CM
    JOURNAL OF NATURAL PRODUCTS, 2000, 63 (01): : 142 - 145
  • [48] Metagenomic Exploration of the Marine Sponge Mycale hentscheli Uncovers Multiple Polyketide-Producing Bacterial Symbionts
    Storey, Mathew A.
    Andreassend, Sarah K.
    Bracegirdle, Joe
    Brown, Alistair
    Keyzers, Robert A.
    Ackerley, David F.
    Northcote, Peter T.
    Owen, Jeremy G.
    MBIO, 2020, 11 (02):
  • [49] STUDIES ON THE STEROIDS OF MARINE SPONGE .4. STEROIDS FROM THE MARINE SPONGE BIEMNA SP
    ZENG, Z
    SU, JY
    ZENG, LM
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 1995, 11 (03): : 185 - 188
  • [50] A Tetrachloro Polyketide Hexahydro-1H-isoindolone, Muironolide A, from the Marine Sponge Phorbas sp Natural Products at the Nanomole Scale
    Dalisay, Doralyn S.
    Morinaka, Brandon I.
    Skepper, Colin K.
    Molinski, Tadeusz F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) : 7552 - +
12345