C-24 stereochemistry of marine sterols: (22E)-24-(isopropenyl)-22- dehydrocholesterol and 24-isopropenylcholesterol

Chemical and Pharmaceutical Bulletin

Volumn 54, Issue 10, 2006, Pages 1473-1477

  Echigo, Shizue ^a   Hara, Noriyuki ^a   Carderon, Gladys Jeanette ^b   Duque, Carmenza ^b   Fujimoto, Yoshinori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

24 isopropenyl 22 dehydrocholesterol; 24 isopropenylcholesterol; Marine sterol; Nervesterol; Topsentia ophiraphidites

Indexed keywords

24 ISOPROPENYLCHOLEST 5 EN 3BETA OL; 24 ISOPROPENYLCHOLESTA 5,22 DIEN 3BETA OL; 7 DEHYDROCHOLESTEROL; ISOPROPENYLCHOLESTEROL; STEROL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOCHEMISTRY; SYNTHESIS;

ANIMALS; DEHYDROCHOLESTEROLS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PORIFERA; REFERENCE STANDARDS; SENSITIVITY AND SPECIFICITY; SPECIES SPECIFICITY; STEREOISOMERISM; STEROLS;

EID: 33749418108     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.54.1473     Document Type: Article

References (16)

1. Calderon G. J., Castellanos L., Duque C., Echigo S., Hara N., Fujimoto Y., Steroids, 69, 93-100 (2004).
2. Echigo S., Calderon G. J., Castellanos L., Duque C., Hara N., Fujimoto Y., Steroids, 72 (2007), in press.
3. Wiersig J. R., Waespe-Sarcevic N., Djerassi C., J. Org. Chem., 44, 3374-3382 (1979).
4. Sucrow W., Schubert B., Richter W., Slopianka M., Chem. Ber., 104, 3689-3703 (1971).
5. Khripach V. A., Zhabinskii V. N., Konstantinova O. V., Khripach N. B., Antonchick A. P., Schneider B., Steroids, 67, 597-603 (2002).
6. Wright J. L. C., McInnes A. G., Shimizu S., Smith D. G., Walter J. A., Idler D., Khalil W., Can. J. Chem., 56, 1898-1903 (1978).
7. Kikuchi T., Kadota S., Suehara H., Namba T., Chem. Pharm. Bull., 33, 2235-2242 (1985).
8. Tam Ha T. B., Kokke W. C. M. C., Proudfoot J. R., Djerassi C., Steroids, 45, 263-276 (1985).
9. Kadota S., Sima T., Kikuchi T., Chem. Pharm. Bull., 35, 200-210 (1987).
10. Catalan C. A. N., Thompson J. E., Kokke W. C. M. C., Djerassi C., Tetrahedron, 41, 1073-1085 (1985).
11. The sterol was originally reported as a C-24 epimeric mixture, but later revised as a stereochemically pure material. Kokke W. C. M. C., Pak C. S., Fenical W., Djerassi C., Helv. Chim. Acta, 62, 1310-1318 (1979).
12. Kokke W. C. M. C., Shoolery J. N., Fenical W., Djerassi C., J. Org. Chem., 49, 3742-3752 (1984).
13. Ito A., Yasumoto K., Kasai R., Yamasaki K., Phytochemistry, 36, 1465-1467 (1994).
14. Selvi S. T., Mohan P. S., Indian J. Chem., 36B, 1082-1083 (1997).
15. Stoilov I., Thompson J. E., Djerassi C., Tetrahedron, 42, 4147-4160 (1986).
16. The spectra (higher field region) are reported in ref. 10.