Chen, Avril R. ; Ruddock, P.L.D. ; Lamm, A.S. ; Reynolds, W.F. ; Reese, Paul B
Author Affiliation, Ana.
Department of Chemistry
Stemodane and stemarane diterpenoid hydroxylation by Mucor plumbers and Whetzelina sclerotiorum
Date of Publication
Incubation of stemodin (1) with Mucor plumbeus ATCC 4740 resulted in the formation of 2a,6ß,13-trihydroxystemodane (2), 2a,3ß,13-trihydroxystemodane (3), 2a,11ß,13-trihydroxystemodane (4) and 2a,13,14-trihydroxystemodane (5), while stemodinone (7) afforded 6a,13-dihydroxystemodan-2-one (8) and 6a,12a,13-trihydroxystemodan-2-one (9). Metabolites obtained from the bioconversion of stemarin (11) were 8,13,19-trihydroxystemarane (12) and 2a,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 2a,7ß,13-trihydroxystemodane (6) and 2a,11ß,13-trihydroxystemodane (4). Stemodinone (7) was converted to 7ß,13-dihydroxystemodan-2-one (10). Compounds 2, 4, 9, 10, 12 and 13 have not been previously reported....