Regio- and stereoselective reductions of dehydrocholic acid

Steroids
Giancarlo CravottoStefano Chimichi

Abstract

Dehydrocholic acid (DHCA), an unnatural bile acid, is manufactured by oxidation of cholic acid. Its biotransformation by two basidiomycetes (Trametes hirsuta and Collybia velutipes) is reported. These mycelia showed different affinities for the substrate and selectivities of attack: T. hirsuta in particular regio- and stereoselectively reduced the 3-keto group to yield 3 alpha-hydroxy-7,12-diketo-5 beta-cholan-24-oic acid (7,12-diketolithocolic acid) as the main product. A number of different chemical reductions were carried out on DHCA; among them hydrogenation with Raney Nickel in water under high-intensity ultrasound proved highly regio- and stereoselective, yielding 7,12-diketolithocolic acid exclusively. (1)H and (13)C resonances were assigned in details thanks to a series of 1D and 2D NMR runs including DEPT, NOESY, H-H COSY, gHSQC and gHMBC.

References

Nov 1, 1993·Phytochemistry·S B Mahato, I Majumdar
Nov 4, 2000·Expert Opinion on Investigational Drugs·P B Savage, C Li
Dec 1, 2001·Steroids·Alessandro MediciRoberto Pellicciari
Jul 29, 2003·Hepatology : Official Journal of the American Association for the Study of Liver Diseases·Tuvia GilatFred M Konikoff
Jan 1, 1994·Biotechnology Advances·S B MahatoS Banerjee
Jan 30, 2004·Biochemical Society Transactions·A Leikin-FrenkelF M Konikoff
Feb 21, 2004·Toxicological Sciences : an Official Journal of the Society of Toxicology·Anabela P RoloKendall B Wallace
Jun 9, 2004·Hepatology : Official Journal of the American Association for the Study of Liver Diseases·Marieke H SchoemakerHan Moshage
Oct 20, 2004·Ultrasonics Sonochemistry·Giancarlo CravottoLivio Stevanato

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Citations

Nov 23, 2007·Natural Product Reports·James R Hanson
Aug 18, 2012·Applied Microbiology and Biotechnology·Luo LiuRolf D Schmid
Dec 14, 2011·Journal of Colloid and Interface Science·Amr Ali Mohamed, Egon Matijević
Sep 12, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Klara ČebularStojan Stavber
May 29, 2021·RSC Medicinal Chemistry·Bojana R VasiljevićKsenija J Pavlović

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