New 9,10‐Secosteroids from Biotransformations of Bile Acids with Rhodococcus ruber |
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| Authors: | Stefania Costa Pier Paolo Giovannini Giancarlo Fantin Alessandro Medici Paola Pedrini |
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| Institution: | 1. Dipartimento di Scienze della Vita e Biotecnologie, Università di Ferrara, Via L. Borsari 46, IT‐44121 Ferrara (phone +39?0532?455700;2. fax +39?0532?455715);3. Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Ferrara, Via Fossato di Mortara 17?–?27, IT‐44121 Ferrara |
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| Abstract: | The biotransformations of cholic, deoxycholic, and hyocholic acids with Rhodococcus ruber are reported. In all biotransformations, the C17‐side chain is partially degraded, and the new 9,10‐secosteroids 4a (54%) and 4b (55%) are obtained from cholic and deoxycholic acids, respectively. The loss of H2O from C(11)? C(12) of secosteroids 4a and 4b affords the compounds 5a (5%) and 5b (20%), respectively. On the other hand, in the biotransformation of hyocholic acid with R. ruber the 9,10‐secosteroid 4c is not detected, but, rearranging to an intramolecular hemiacetal form, it evolves to the final furan derivative 6c (35%) by easy elimination of two molecules of H2O. The new secosteroids were characterized by IR, NMR, and 2D‐NMR spectroscopy, and mass spectroscopy. |
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| Keywords: | 9 10‐Secosteroids Rhodococcus ruber Steroids Cholic acid Deoxycholic acid Hyocholic acid |
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