Biotransformation of 21-O-acetyl-deoxycorticosterone by cell suspension cultures of Digitalis lanata (strain W.1.4)

Abstract

Cell cultures of Digitalis species are known to accept exogenous substrates for biotransformation reactions. We here report the biotransformation of 21-O-acetyl-deoxycorticosterone (1) by cell suspension cultures of Digitalis lanata strain W.1.4. Nine derivatives of 1 were obtained and their chemical structures determined by spectroscopic methods. 2β-Hydroxylation and C-21-glucosylation of the steroidal nucleus were described for the first time in suspension-cultured plant cells. Steroid 5α- and 5β-reduction products were also observed. Among the compounds isolated and structures elucidated were 2β,3β,21-trihydroxy-4-pregnen-20-one, 2β,3α,21-trihydroxy-4-pregnen-20-one and 3β,21-dihydroxy-5α-pregnan-20-one-3β-O-β-glucoside.