New Sulfated Polyhydroxysteroids from the Antarctic Ophiuroid Astrotoma agassizii
- 20 February 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 61 (3) , 370-374
- https://doi.org/10.1021/np970429c
Abstract
Three new and two known sulfated steroidal polyols have been isolated from the Antarctic ophiuroid Astrotoma agassizii. All of the new steroids possess a terminal isopropenyl group and a C-21 sulfoxy moiety in the side chain but differ in the steroidal nuclei. The structures of these new steroids were established from spectral and chemical correlations with related steroids as (20R)-cholesta-5,24-diene-2β,3α,21-triol 2,21-disulfate (1), (20R)-5α-cholest-24-ene-2β,3α,21-triol 3,21-disulfate (3), and (20R)-cholesta-5,24-diene-2α,3α,4β,21-tetrol 3,21-disulfate (5). Analysis of the nonsulfated sterol fraction has shown the presence of cholest-5-en-3β-ol, cholesta-5,24-dien-3β-ol and (22E) cholesta-5,22-dien-3β-ol as the major sterols.Keywords
This publication has 11 references indexed in Scilit:
- Antiviral Sulfated Steroids from the Ophiuroid Ophioplocus januariiJournal of Natural Products, 1996
- A Novel Marine Steroidal Sulfate from the Starfish Luidia ludwigiJournal of Natural Products, 1995
- HIV-Inhibitory Natural Products. 11. Comparative Studies of Sulfated Sterols from Marine InvertebratesJournal of Medicinal Chemistry, 1994
- Isolation and Structure Characterization of Two Novel Bioactive Sulphated Polyhydroxysteroids from the Antarctic OphiuroidOphioderma longicaudumNatural Product Letters, 1993
- Polyoxygenated steroids of marine originChemical Reviews, 1993
- 1H NMR and molecular mechanics studies of epimeric ethyl esters of 20(R, S)-hydroxy-23-norcholanoic acidsMagnetic Resonance in Chemistry, 1991
- Modification of photochemical reactivity by cyclodextrin: difference in photobehavior between short-chain and long-chain benzoin alkyl ethers: conformational effectThe Journal of Organic Chemistry, 1987
- Two new steroidal glycoside sulfates, longicaudoside-A and B, from the Mediterranean ophiuroid Ophioderma longicaudumThe Journal of Organic Chemistry, 1986
- (20R)- and (20S)-Cholest-5-ene-3.beta.,21-diolThe Journal of Organic Chemistry, 1977
- The 220 MHz NMR spectra of phytosterolsPhytochemistry, 1976