Verrucosin-a and -b, ichthyotoxic diterpenoic acid glycerides with a new carbon skeleton from the dorid nudibranch doris verrucosa

作者: G. Cimino , M. Gavagnin , G. Sodano , R. Puliti , C.A. Mattia

DOI: 10.1016/S0040-4020(01)81739-7

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摘要: Abstract The dorid nudibranch Doris verrucosa contains in its skin extracts two glycerides (2-3)linked to diterpenoid acid residues. terpenoids show a rearranged tricyclic skeleton. structures, inferred from spectral and chemical evidence, were unambiguously determined by X-ray diffraction analysis of 3. Both 2 3 are highly ichthyotoxic.

参考文章(16)
Paul J. Scheuer, Bioorganic Marine Chemistry ,(1988)
M. Poje, I. Perina, I. Vicković, M. Bruvo, The stereostructure of trimers of biacetyl Tetrahedron. ,vol. 41, pp. 1985- 1987 ,(1985) , 10.1016/S0040-4020(01)96564-0
L. Gunthorpe, A. M. Cameron, Bioactive properties of extracts from Australian dorid nudibranchs Marine Biology. ,vol. 94, pp. 39- 43 ,(1987) , 10.1007/BF00392898
JC Coll, S La Barre, PW Sammarco, WT Williams, GJ Bakus, Chemical defences in soft corals (Coelenterata: Octocorallia) of the Great Barrier Reef: a study of comparative toxicities Marine Ecology Progress Series. ,vol. 8, pp. 271- 278 ,(1982) , 10.3354/MEPS008271
D. Cremer, J. A. Pople, General definition of ring puckering coordinates Journal of the American Chemical Society. ,vol. 97, pp. 1354- 1358 ,(1975) , 10.1021/JA00839A011
G. Cimino, D. De Rosa, S. De Stefano, L. Minale, Isoagatholactone, a diterpene of a new structural type from the sponge Spongia officinalis Tetrahedron. ,vol. 30, pp. 645- 649 ,(1974) , 10.1016/S0040-4020(01)97059-0
Kirk Gustafson, Raymond J. Andersen, Marie H.M. Chen, Jon Clardy, Jill E. Hochlowski, Terpenoic acid glycerides from the dorid nudibranch Tetrahedron Letters. ,vol. 25, pp. 11- 14 ,(1984) , 10.1016/S0040-4039(01)91135-9
Ernest Wenkert, Adriano Afonso, Peter Beak, Richard W. J. Carney, P. W. Jeffs, James D. McChesney, The Proton Magnetic Resonance Spectral Characteristics of Tricyclic Diterpenic Substances Journal of Organic Chemistry. ,vol. 30, pp. 713- 722 ,(1965) , 10.1021/JO01014A014
G. Cimino, A. Crispino, S. De Stefano, M. Gavagnin, G. Sodano, A naturally-occurring analog of methylthioadenosine (MTA) from the nudibranch molluscDoris verrucosa Experientia. ,vol. 42, pp. 1301- 1302 ,(1986) , 10.1007/BF01946433
Kirk Gustafson, Raymond J. Andersen, Chemical studies of british columbia nudibranchs Tetrahedron. ,vol. 41, pp. 1101- 1108 ,(1985) , 10.1016/S0040-4020(01)96478-6