A novel D-ring unsaturated A-nor sterol from the Indonesian sponge, Axinella carteri Dendy

Natural Product Research

Volumn 22, Issue 15, 2008, Pages 1339-1343

  Gallimore, Winklet A ^a   Cabral, Chelsea ^a   Kelly, Michelle ^b   Scheuer, Paul J ^a  

^a UNIVERSITY OF HAWAII   (United States)

^b NATIONAL INSTITUTE OF WATER AND ATMOSPHERIC RESEARCH   (New Zealand)

Author keywords

3 (hydroxymethyl) A nor 5 ( cholest 14 en 16 one; A nor sterol; Axinella carteri; Dibromoisophakellin

Indexed keywords

3BETA (HYDROXYMETHYL) A NOR 5ALPHA CHOLEST 14 EN 16 ONE; ALKALOID; AXINELLA CARTERI EXTRACT; DIBROMOISOPHAKELLIN; NATURAL PRODUCT; STEROL; UNCLASSIFIED DRUG;

ARTICLE; AXINELLA CARTERI; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; FREEZE DRYING; HUMAN; HUMAN CELL; INDONESIA; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); TUMOR CELL LINE;

ANIMALS; AXINELLA; CHOLESTENONES; INDONESIA; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEROLS;

AXINELLA; AXINELLA CARTERI; AXINELLIDAE; DEMOSPONGIAE; HALICHONDRIDA;

EID: 57049151696     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410601132279     Document Type: Article

References (14)

1. Aknin, M., Gaydou, E., Boury-Esnault, N., Costantino, V., Fattorusso, E. and Mangoni, A. (1996) Nor-sterols in Axinella proliferans, sponge from the Indian Ocean. Comparative Biochemistry Physiology, 113, p. 845.
2. Bergquist, P., Hofheinz, W. and Oesterhelt, G. (1980) Sterol composition and the classification of the Demospongiae. Biochemical Systematics and Ecology, 8, p. 423.
3. Bibolino, L., Minale, L. and Sodano, G. (1978) Investigations on the ring contraction step in the biosynthesis of 6-nor-stanols by the sponge Axinella verrucosa. Journal of the Chemical Society Chemical Communications, p. 524.
4. Bohlin, L., Sjostrand, U., Djerassi, C. and Sullivan, B. (1981) Two new sterols with modified nucleus and side chain from Teichaxinella moprchella. Journal of the Chemical Society Perkin Transactions 1, p. 1023.
5. Bohlin, L., Sjostrand, U., Sodano, G. and Djerassi, C. (1982) Five new 3 from the Red Sea sponge Acanthella auranthiaca. Journal of Organic Chemistry, 47, p. 5309.
6. Ciminiello, P., Fattorusso, E., Magno, S., Mangoni, A. and Pansini, M. (1992) Three new D-ring unsaturated sterols from the Mediterranean sponge Topsentia aurantiaca: Structure determination and complete nuclear magnetic resonance assignment. Steroids, 57, p. 62.
7. De Nanteuil, G., Ahond, A., Poupat, C., Potier, P., Pusset, N. Pusset, J. et al. (1985) Isolation and identification of eleven nor-A from Pseudaxinyssa cantharella α sterols with a hydroxymethyl-3. Tetrahedron, 41, p. 6035.
8. Eggersdorfer, M., Kokke, W., Crandell, C., Hochlowsky, J. and Djerassi, C. (1982) Isolation of -cholest-15-ene, the first naturally occurring sterolα-(hydroxymethyl)-A-nor-5β3 with a 15-16 double bond in sponge Homaxinella trachys. Journal of Organic Chemistry, 47, p. 5304.
9. Fedoreyev, S., Utkina, N., Ilyin, S., Reshetnyak, M. and Maximov, O. (1986) Structure of dibromoisophakellin from the marine sponge Acanthella carteri. Tetrahedron Letters, 27, p. 3177.
10. Kalidindi, R., Rao, B., Akihisa, T., Tamura, T. and Matsumoto, T. (1988) Sterols of Spirastrella inconstans (Dendy) and Axinella sp. from the Indian Ocean. Indian Journal of Chemistry, 27, p. 160.
11. Kokke, W., Fenical, W. and Djerassi, C. (1981) Sterols with unusual nuclear unsaturation from three cultured marine dinoflagellates. Phytochemistry, 20, p. 127.
12. Minale, L. and Riccio, R. (1978) Starfish saponins 1: -cholesta-8,14-dien-23-one: The major genin from the stafish α-Hydroxy-5β3 Echinaster sepositus. Tetrahedron Letters, p. 2609.
13. Minale, L. and Sodano, G. (1974) Marine sterols: Unique -hydroxymethyl-A-nor-5a-steranes from the sponge Axinella verrucosaβ3. Journal of the Chemical Society. Perkin Transactions 1, p. 2380.
14. Teshima, S., Kanazawa, A. and Yamada, L. (1984) A novel A-nor sterol, 3-cholestane in the sponge Acanthella α-hydroxymethyl-24Z- ethylidene-A-nor-5 cristagalli. Nippon Suisan Gakkaishi, 50, p. 545.