THE NATURAL POLYPROPIONATE-DERIVED ESTERS OF THE MOLLUSK ONCHIDIUM SP

被引:43
作者
RODRIGUEZ, J
RIGUERA, R
DEBITUS, C
机构
[1] UNIV SANTIAGO,FAC QUIM,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN
[2] ORSTOM,NOUMEA,NEW CALEDONIA
关键词
D O I
10.1021/jo00043a018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Eight new polypropionate-derived esters (5-8 and 10-13) have been isolated from pulmonate molluscs of the genus Onchidium collected in the South Pacific. The structures of these compounds were determined spectroscopically in particular by one- and two-dimensional NMR and low and high EIMS. The absolute of the seven asymmetric centers was determined by using the Trost-Mosher methodology. Saponification afforded two triols named onchitriol I and II (4 and 9, respectively). Compounds 4-13 displayed in vitro antitumor activity against several cell lines. Onchitriol I and II had antiviral activity also.
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页码:4624 / 4632
页数:9
相关论文
共 21 条
  • [1] NOVEL SPONGE-DERIVED AMINO-ACIDS .11. THE ENTIRE ABSOLUTE STEREOCHEMISTRY OF THE BENGAMIDES
    ADAMCZESKI, M
    QUINOA, E
    CREWS, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 240 - 242
  • [2] SYNTHETIC STUDIES ON FULLY SUBSTITUTED GAMMA-PYRONE-CONTAINING NATURAL-PRODUCTS - SYNTHESIS OF GAMMA-PYRONE DERIVATIVES OBTAINED BY DECOMPOSITION OF PERONIATRIOLS
    ARIMOTO, H
    NISHIYAMA, S
    YAMAMURA, S
    [J]. TETRAHEDRON LETTERS, 1990, 31 (38) : 5491 - 5494
  • [3] SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY
    BAX, A
    SUBRAMANIAN, S
    [J]. JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) : 565 - 569
  • [4] BAX A, 1986, J AM CHEM SOC, V108, P8096
  • [5] CYTO-TOXIC METABOLITES FROM THE MOLLUSK PERONIA-PERONII
    BISKUPIAK, JE
    IRELAND, CM
    [J]. TETRAHEDRON LETTERS, 1985, 26 (36) : 4307 - 4310
  • [6] Breitmaier E., 1987, CARBON 13 NMR SPECTR
  • [7] NOVEL MARINE POLYHYDROXYLATED STEROIDS FROM THE STARFISH MYXODERMA-PLATYACANTHUM
    FINAMORE, E
    MINALE, L
    RICCIO, R
    RINALDO, G
    ZOLLO, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1146 - 1153
  • [8] THE DENTICULATINS, 2 POLYPROPIONATE METABOLITES FROM THE PULMONATE SIPHONARIA-DENTICULATA
    HOCHLOWSKI, JE
    FAULKNER, DJ
    MATSUMOTO, GK
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (25) : 7413 - 7415
  • [9] HOWCHOLOWSKI JE, 1984, J AM CHEM SOC, V106, P6748
  • [10] HOWCHOLOWSKI JE, 1983, TETRAHEDRON LETT, V24, P1917