The biotransformations of hyodeoxycholic acid with various Rhodococcus spp. are reported. Some strains (i.e. Rhodococcus zopfii, Rhodococcus ruber and Rhodococcus atherovorans) are able to partially degrade the C17-side chain affording 6α-hydroxy-3-oxo-5β-23,24-dinorcholan-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 C17-side chain and adopting an intramolecular hemiacetal form. In addition, the 9,10 secosteroid 5 shows an unprecedented reported C(4)-hydroxylation. The new secosteroids were fully characterized through MS, IR, NMR and 2D NMR spectroscopy.
New 9,10-Secosteroids from Biotransformations of Hyodeoxycholic Acid with Rhodococcus spp.
COSTA, Stefania;GIOVANNINI, Pier Paolo;FANTIN, Giancarlo;MEDICI, Alessandro;PEDRINI, Paola
2013
Abstract
The biotransformations of hyodeoxycholic acid with various Rhodococcus spp. are reported. Some strains (i.e. Rhodococcus zopfii, Rhodococcus ruber and Rhodococcus atherovorans) are able to partially degrade the C17-side chain affording 6α-hydroxy-3-oxo-5β-23,24-dinorcholan-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 C17-side chain and adopting an intramolecular hemiacetal form. In addition, the 9,10 secosteroid 5 shows an unprecedented reported C(4)-hydroxylation. The new secosteroids were fully characterized through MS, IR, NMR and 2D NMR spectroscopy.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
