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

被引：64
作者：
KOKKE, WCMC [1 ]
PAK, CS [1 ]
FENICAL, W [1 ]
DJERASSI, C [1 ]
机构：
[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
来源：
HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 04期
关键词：
D O I：
10.1002/hlca.19790620444
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In addition to the two new sterols verongulasterol 11 and 25‐dehydroaplysterol 13 of Verongia cauliformis3), which were reported earlier [2] [3], the minor and trace sterols of this sponge include five new sterols listed in the title (with the exception of the known 24 S‐methyl‐cholesta‐5, 25‐dien‐3β‐ol (codisterol, 1b). The isolation of the 24(R)‐epimer of codisterol is of interest, as this compound is a possibly biosynthetic precursor for aplysterol 12, 25‐dehydroaplysterol 13, and verongulasterol 11 (all 24R) which occur in the same sponge [2]. A partial synthesis from fucosterol (4) of 24 (R + S)‐isopropenylcholesterol (9), and of 24‐isopropylcholesterol (10) is described. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim
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页码：1310 / 1318
页数：9
相关论文
共 21 条
[11]  
LUCA PD, 1973, J CHEM SOC CHEM COMM, P825
[12]   METABOLISM IN PORIFERA .7. CONVERSION OF [7,7-H-3(2)]-FUCOSTEROL INTO CALYSTEROL BY SPONGE CALYX-NICEAENSIS [J].
MINALE, L ;
RICCIO, R ;
SCALONA, O ;
SODANO, G ;
FATTORUSSO, E ;
MAGNO, S ;
MAYOL, L ;
SANTACROCE, C .
EXPERIENTIA, 1977, 33 (12) :1550-1552
[13]   MASS-SPECTROMETRY IN STRUCTURAL AND STEREOCHEMICAL PROBLEMS .249. ELUCIDATION OF COURSE OF CHARACTERISTIC RING D-FRAGMENTATION OF UNSATURATED STEROIDS [J].
PARTRIDGE, LG ;
MIDGLEY, I ;
DJERASSI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (23) :7686-7695
[14]   MINOR AND TRACE STEROLS IN MARINE-INVERTEBRATES .1. GENERAL METHODS OF ANALYSIS [J].
POPOV, S ;
CARLSON, RMK ;
WEGMANN, A ;
DJERASSI, C .
STEROIDS, 1976, 28 (05) :699-732
[15]  
ROSA MD, 1973, COMP BIOCHEM PHYS B, V46, P823
[16]   STEROLS OF SIPHONOUS MARINE ALGA CODIUM-FRAGILE [J].
RUBINSTEIN, I ;
GOAD, LJ .
PHYTOCHEMISTRY, 1974, 13 (02) :481-484
[17]   220-MHZ NMR-SPECTRA OF PHYTOSTEROLS [J].
RUBINSTEIN, I ;
GOAD, LJ ;
CLAGUE, ADH ;
MULHEIRN, LJ .
PHYTOCHEMISTRY, 1976, 15 (01) :195-200
[18]   MINOR AND TRACE STEROLS IN MARINE-INVERTEBRATES .8. ISOLATION, STRUCTURE ELUCIDATION, AND PARTIAL SYNTHESIS OF 2 NOVEL STEROLS - STELLIFERASTEROL AND ISOSTELLIFERASTEROL [J].
THEOBALD, N ;
WELLS, RJ ;
DJERASSI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7677-7684
[19]   CARBONIMIDIC DICHLORIDES FROM MARINE SPONGE PSEUDAXINYSSA-PITYS [J].
WRATTEN, SJ ;
FAULKNER, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) :7367-7368
[20]  
WYLLIE S, 1968, J ORG CHEM, V33, P1305
123