Epoxidation of diosgenin, 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-ol

Molecules

Volumn 8, Issue 12, 2003, Pages 886-893

  Ma, Eunsook ^a   Kim, Jongwon ^a  

^a Catholic University of Daegu   (South Korea)

Author keywords

Diosgenin; H2O2; m Chloroperoxybenzoic acid; Stereoselective epoxidation

Indexed keywords

DIOSGENIN;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG ISOLATION; EPOXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 3342985699     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/81200886     Document Type: Article

References (17)

1. Dewick, P. M. Medicinal Natural Products, 2nd ed.; John Wiley & Sons: Chichester, U.K., 2002; pp. 237-289.
2. Laguna, J.; Gomez-Puyoy, A.; Pena, A.; Guzman-Garcia, J. Effect of diosgenin on cholesterol metabolism. J. Atheroscler. Res. 1962, 2, 459-470.
3. Peifer, J. J.; Guzman, J. Hypocholesterolemic effects of diosgenin in the rat. Circulation 1966, 34, III-25.
4. Accatino, L.; Pizarro, M.; Solis, N.; Koenig, C. S. Effects of diosgenin a plant-derived steroid, on bile secretion and hepatocellular cholestasis induced by estrogens in the rat. Hepatology 1998, 28, 129-140.
5. Cayen, M. N.; Dvornik, D. Effect of diosgenin on lipid metabolism in rats. J. Lipid Res. 1979, 20, 162-174.
6. Uchida, K.; Takase, H.; Nomura, Y.; Takeda, K.; Takeuchi, N.; Ishikawa, Y. Changes in biliary and fecal bile acids in mice after treatments with diosgenin and β-sitosterol. J. Lipid Res. 1984, 25, 236-245.
7. Datt, K.; Datta, S. K.; Datta, P. C. Pharmacognostic evaluation of potential yams Dioscorea. J. Econ.Taxon. Bot. 1984, 5, 181-196.
8. Noam, M.; Tamir, I.; Breuer, E.; Mechoulam, R. Conversion of ruscogenin into 1α- and 1β-hydroxycholesterol. Tetrahedron 1981, 37, 597-604.
9. Liu, M.; Yu, B.; Hui, Y. First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→ 3)-(β-D-glucopyranosyl-(1→2)-β-D- fucopyranoside, an Ophiopogonis saponin from the tuber of Liliope muscari (Decne.). Tetrahedron Lett. 1998, 39, 415-418.
10. 5-steroids by reduction of 1α,2α-epoxy-4,6-dien-3-ones with lithium in ammonia. Helv. Chim. Acta 1981, 64, 1870-1892.
11. Kobayashi, Y.; Taguchi, T.; Mitsuhashi, S.; Eguchi, T.; Ohshima, E.; Ikekawa, N. Studies on organic fluorine compounds. XXXIX. Studies on steroids. LXXIX. Synthesis of 1α,25-dihydroxy-26,26,26,27,27,27-hexafluorovitamin D. Chem. Pharm. Bull. 1982, 30, 4297-4303.
12. Araghiniknam, M.; Chung, S.; Tresa, N.-W.; Eskelson, C.; Watson, R. R. Antioxidant activity of dioscorea and dehydroepiandrosterone (DHEA) in older humans. Life Sci. 1996, 59, 147-157
13. Schulz, S.; Klann, R. C.; Schonfeld, S.; Nyce J. W. Mechanisms of cell growth inhibition and cell cycle arrest in human colonic adenocarcinoma cells by dehydroepiandrosterone: role of isoprenoid biosynthesis. Cancer Res. 1992, 52, 1372-1376.
14. Boros, L. G.; Puigjaner, J.; Cascante, M; Lee, W. N.; Brandes, J. L.; Brassilian, S. Oxythiamine and dehydroepiandrosterone inhibit the nonoxidative synthesis of ribose and tumor cell proliferation. Cancer Res. 1997, 57, 4242-4248.
15. Gao, H.; Dias J. R. Synthetic studies toward 1α-hydroxytestosterone from testosterone. Fourth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-4), 2000, September, 1-30.
16. Gamoh, K.; Hirayama, M.; Ikekawa, N. Stereocontrolled synthesis of Withanolide D and related compounds. J. Chem. Soc., Perkin Trans. I 1984, 440-454.
17. Sharpless, K. B.; Verhoeven, T. R. Metal-catalysed, highly selective oxygenations of olefins and acetylenes with tert-butyl hydroperoxide. Practical considerations and mechanisms. Aldrichim. Acta. 1979, 12, 63-75.