New 9,10‐Secosteroids from Biotransformations of Hyodeoxycholic Acid with Rhodococcus spp. |
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| Authors: | Stefania Costa Pier Paolo Giovannini Giancarlo Fantin Alessandro Medici Paola Pedrini |
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| Affiliation: | 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 hyodeoxycholic acid with various Rhodococcus spp. are reported. Some strains (i.e., Rhodococcus zopfii, Rhodococcus ruber, and Rhodococcus aetherivorans) are able to partially degrade the side chain at C(17) to afford 6α‐hydroxy‐3‐oxo‐23,24‐dinor‐5β‐cholan‐22‐oic acid ( 2 ; 23%) and 6α‐hydroxy‐3‐oxo‐23,24‐dinorchol‐1,4‐dien‐22‐oic acid ( 3 ; 23–30%), together with two new 9,10‐secosteroids 4 and 5 (10–45%), still bearing the partial side chain at C(17) and adopting an intramolecular hemiacetal form. In addition, the 9,10‐secosteroid 5 showed an unprecedented C(4)‐hydroxylation. The new secosteroids were fully characterized by MS, IR, NMR, and 2D‐NMR analyses. |
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| Keywords: | Steroids 9,10‐Secosteroids Rhodococcus species Hyodeoxycholic acid Biotransformation |
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