ISOLATION, STRUCTURE ELUCIDATION, AND PARTIAL SYNTHESIS OF XESTOSTEROL, A BIOSYNTHETICALLY SIGNIFICANT STEROL FROM THE SPONGE XESTOSPONGIA-MUTA

被引:31
作者
KOKKE, WCMC [1 ]
TARCHINI, C [1 ]
STIERLE, DB [1 ]
DJERASSI, C [1 ]
机构
[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
关键词
D O I
10.1021/jo01333a023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The major component of the sterol constituents of the Carribean sponge Xestospongia muta is a new C30 sterol-xestosterol-characterized by the “elongated” side chain depicted by structure 6, as was confirmed by partial synthesis. The probable biological function of 6 or similar sterols in sponges is emphasized. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:3385 / 3388
页数:4
相关论文
共 19 条
[1]  
BORTOLOTTO M, 1978, B SOC CHIM BELG, V87, P539
[2]  
CARLSON RMK, PURE APPL CHEM
[3]   METABOLISM IN PORIFERA .1. SOME STUDIES ON BIOSYNTHESIS OF FATTY-ACIDS, STEROLS AND BROMO-COMPOUNDS BY SPONGE VERONGIA-AEROPHOBA [J].
DEROSA, M ;
MINALE, L ;
SODANO, G .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY, 1973, 45 (4B) :883-893
[4]   RECENT ADVANCES IN MASS-SPECTROMETRY OF STEROIDS [J].
DJERASSI, C .
PURE AND APPLIED CHEMISTRY, 1978, 50 (03) :171-184
[5]  
DJERASSI C, PURE APPL CHEM
[6]   SEPARATION OF STERYL ACETATES BY SILVER ION CHROMATOGRAPHY [J].
IDLER, DR ;
SAFE, LM .
STEROIDS, 1972, 19 (03) :315-&
[7]   MINOR AND TRACE STEROLS IN MARINE-INVERTEBRATES .12. OCCURRENCE OF 24(R+S)-ISOPROPENYLCHOLESTEROL, 24(R+S)-METHYLCHOLESTA-5,25-DIEN-3-BETA-OL, AND 24(R+S)-METHYLCHOLESTA-7,25-DIEN-3-BETA-OL IN THE CARIBBEAN SPONGE, VERONGIA-CAULIFORMIS [J].
KOKKE, WCMC ;
PAK, CS ;
FENICAL, W ;
DJERASSI, C .
HELVETICA CHIMICA ACTA, 1979, 62 (04) :1310-1318
[8]  
KOKKE WCMC, 1978, TETRAHEDRON LETT, P4373
[9]   STRUCTURAL AND STEREOCHEMICAL APPLICATIONS OF MASS-SPECTROMETRY IN THE MARINE STEROL FIELD .252. SYNTHESIS AND ELECTRON-IMPACT INDUCED MASS-SPECTRAL FRAGMENTATION OF DELTA-24-3-BETA-HYDROXY-DELTA-5 AND "DELTA-24(28)-3-BETA-HYDROXY-DELTA-5 STEROLS [J].
MASSEY, IJ ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2448-2457
[10]  
MINALE L, 1977, MARINE NATURAL PRODU, P87