Stemodane and stemarane diterpenoid hydroxylation by Mucor plumbeus and Whetzelinia sclerotiorum

Incubation of stemodin (1) with Mucor plumbeus ATCC 4740 resulted in the formation of 2alpha,6beta,13-trihydroxystemodane (2), 2alpha,3beta,13-trihydroxystemodane (3), 2alpha,11beta,13-trihydroxystemodane (4) and 2alpha,13,14-trihydroxystemodane (5), while stemodinone (7) afforded 6alpha,13-dihydroxystemodan-2-one (8) and 6alpha,12alpha,13-trihydroxystemodan-2-one (9). Metabolites obtained from the bioconversion of stemarin (11) were 8,13,19-trihydroxystemarane (12) and 2alpha,13,19-trihydroxystemarane (13). 19-N,N-Dimethylcarbamoxy-13-hydroxystemarane (14) was not transformed by the fungus. Stemodin (1) was incubated with Whetzelinia sclerotiorum ATCC 18687 to produce 2alpha,7beta,13-trihydroxystemodane (6) and 2alpha,11beta,13-trihydroxystemodane (4). Stemodinone (7) was converted to 7beta,13-dihydroxystemodan-2-one (10). Compounds 2, 4, 9, 10, 12 and 13 have not been previously reported.