First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa

Steroids

Volumn 73, Issue 11, 2008, Pages 1123-1127

  Boonananwong, Suthinee ^a   Kongkathip, Boonsong ^a   Kongkathip, Ngampong ^a  

^a KASETSART UNIVERSITY   (Thailand)

Author keywords

Anticancer activity; Biological activity; Polyoxygenated cholestanes; Steroid synthesis

Indexed keywords

16,20 DIHYDROCHOLESTAN 3 ONE; 20 HYDROXYCHOLEST 1 ENE 3,16 DIONE; 20 HYDROXYCHOLEST 4 ENE 3,16 DIONE; 20 HYDROXYCHOLESTANE 3,6 DIONE; 3,16,20 POLYOXYGENATED CHOLESTANE DERIVATIVE; CHOLESTANE DERIVATIVE; CYTOTOXIC AGENT; SAPONIN DERIVATIVE; TIGOGENIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CORAL; CULTURE MEDIUM; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; INFRARED SPECTROSCOPY; LEPTOGORGIA SARMENTOSA; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

ADENOCARCINOMA; ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CARCINOMA, SMALL CELL; CARCINOMA, SQUAMOUS CELL; CELL LINE, TUMOR; CHOLESTANES; CNIDARIA; CYTOTOXINS; DRUG EVALUATION, PRECLINICAL; HUMANS; INHIBITORY CONCENTRATION 50; LUNG NEOPLASMS; MOLECULAR STRUCTURE; MOUTH NEOPLASMS; STEROIDS;

GORGONIA; LEPTOGORGIA SARMENTOSA;

EID: 46949087664     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.04.013     Document Type: Article

References (17)

1. Mayer A.M.S., and Gustafson R.K. Marine pharmacology in 2000: antitumor and cytotoxic compounds. Int J Cancer 105 (2003) 291-299
2. D'Auria M.V., Minale L., and Riccio R. Polyoxygenated steroids of marine origin. Chem Rev 93 (1993) 1839-1895
3. Cimino G., De Rosa S., De Stefano S., Scognamiglio G., and Sodano G. Cholest-4,14-dien-15,20ξ-diol-3,16-dione, a novel polyoxygenated marine steroid that easily loses the side chain. Tetrahedron Lett 22 (1981) 3013-3016
4. Benvegnu R., Cimino G., De Rosa S., and De Stefano S. Guggulsterol-like steroids from the Mediterranean gorgonian Leptogorgia sarmentosa. Experientia 38 (1982) 1443-1444
5. Cimino G., De Rosa S., De Stefano S., and Sodano G. C-18 hydroxy steroids from the Mediterranean gorgonian Leptogorgia sarmentosa. Experientia 40 (1984) 246-248
6. Aiello A., Fattorusso E., and Menna M. Five new polar sterols from the black coral Antipathes subpinnata. Steroids (1991) 56513-56517
7. Aiello A., Fattorusso E., and Menna M. Four new bioactive polyhydroxylated sterols from the black coral Antipathes subpinnata. J Nat Prod 55 (1992) 321-325
8. Garrido L., Zubia E., Ortega M.J., and Salva J. Isolation and structure elucidation of new cytotoxic steroids from the gorgonian Leptogargia sarmentosa. Steroids 65 (2000) 85-88
9. Beauvoir MG. Process for obtaining sapogenin particularly hecogenin from plant material such as Agave sisalana leaves. US Patent 3,981,867; 1976.
10. Vogel A.I. Vogel's textbook of practical organic chemistry. 5th ed. (1989), Longman Group UK Ltd., London p. 871
11. Barton DHR, Motherwell WB. Dehydrogenation agents based on derivatives of selenium and their use in the dehydrogenation in the 1,4-position of steroids. US Patent 4,434,080; 1984.
12. Cameron A.F.B., Evans R.M., Hamlet J.C., Hunt J.S., Jones P.G., and Long A.G. Studies in the synthesis of cortisone. Part XII. Improvements in the conversion of sapogenins into pregnan-20-ones. J Chem Soc 77 (1955) 2807-2816
13. Brien J.O., Wilson I., Orton T., and Pognan F. Investigation of the alamar blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur J Biochem 267 (2000) 5421-5426
14. Mićović V., Ivanovic M.D., and Piatak D.M. Simplified preparation of 16-dehydropregnenol-one acetate. Synthesis 7 (1990) 591-592
15. Kim S., Sutton S.C., Guo C., LaCour T.G., and Fuchs P.L. Synthesis of the north 1 cephalostatin family from hecogenin acetate. J Am Chem Soc 121 (1999) 2056-2070
16. Nes W.R., and Varkey T.E. Conformatonal analysis of the 17(20) bond of 20-keto steroids. J Org Chem 41 (1976) 1652-1653
17. Nes W.R., Varkey T.E., Crump D.R., and Gut M. (Z)-17(20)-Dehydrocholesterol. A new sterol with C-21 and C-22 spatially fixed. J Org Chem 4 (1976) 3429-3433