New sulfated polyhydroxysteroids from the Antarctic ophiuroid Astrotoma agassizii

被引:25
作者
Roccatagliata, AJ [1 ]
Maier, MS [1 ]
Seldes, AM [1 ]
机构
[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
来源
JOURNAL OF NATURAL PRODUCTS | 1998年 / 61卷 / 03期
关键词
D O I
10.1021/np970429c
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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-2 beta,3 alpha,21-triol 2,21-disulfate (1), (20R)-5 alpha-cholest-24-ene-2 beta,3 alpha,21-triol 3,21-disulfate (3), and (20R)-cholesta-5,24-diene-2 alpha,3 alpha,4 beta,21-tetrol 3,21-disulfate (5). Analysis of the nonsulfated sterol fraction has shown the presence of cholest-5-en-3 beta-ol, cholesta-5,24-dien-3 beta-ol and (22E) cholesta-5,22-dien-3 beta-ol as the major sterols.
引用
收藏
页码:370 / 374
页数:5
相关论文
共 17 条
[11]   H-1-NMR AND MOLECULAR MECHANICS STUDIES OF EPIMERIC ETHYL-ESTERS OF 20(R, S)-HYDROXY-23-NORCHOLANOIC ACIDS [J].
MAIER, MS ;
SELDES, AM ;
GROS, EG .
MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (02) :137-142
[12]   HIV-INHIBITORY NATURAL-PRODUCTS .11. COMPARATIVE-STUDIES OF SULFATED STEROLS FROM MARINE-INVERTEBRATES [J].
MCKEE, TC ;
CARDELLINA, JH ;
RICCIO, R ;
DAURIA, MV ;
IORIZZI, M ;
MINALE, L ;
MORAN, RA ;
GULAKOWSKI, RJ ;
MCMAHON, JB ;
BUCKHEIT, RW ;
SNADER, KM ;
BOYD, MR .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (06) :793-797
[13]   Halistanol disulfate B, a novel sulfated sterol from the sponge Pachastrella sp: Inhibitor of endothelin converting enzyme [J].
Patil, AD ;
Freyer, AJ ;
Breen, A ;
Carte, B ;
Johnson, RK .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (06) :606-608
[14]   2 NEW STEROIDAL GLYCOSIDE SULFATES, LONGICAUDOSIDE-A AND LONGICAUDOSIDE-B, FROM THE MEDITERRANEAN OPHIUROID OPHIODERMA-LONGICAUDUM [J].
RICCIO, R ;
DAURIA, MV ;
MINALE, L .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :533-536
[15]   A novel marine steroidal sulfate from the starfish Luidia ludwigi [J].
Roccatagliata, AJ ;
Maier, MS ;
Seldes, AM .
JOURNAL OF NATURAL PRODUCTS, 1995, 58 (12) :1941-1944
[16]   Antiviral sulfated steroids from the ophiuroid Ophioplocus januarii [J].
Roccatagliata, AJ ;
Maier, MS ;
Seldes, AM ;
Pujol, CA ;
Damonte, EB .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (09) :887-889
[17]   220-MHZ NMR-SPECTRA OF PHYTOSTEROLS [J].
RUBINSTEIN, I ;
GOAD, LJ ;
CLAGUE, ADH ;
MULHEIRN, LJ .
PHYTOCHEMISTRY, 1976, 15 (01) :195-200