Lamm, A.S; Reynolds, W.F; Reese, Paul .B
Author Affiliation, Ana.
Bioconversion of Stemodia maritima diterpenes and derivatives by Cunninghamella echinulata var. elegans and Phanerochaete chrysosporium
Date of Publication
Stemodane and stemarane diterpenes isolated from the plant Stemodia maritima and their dimethylcarbamate derivatives were fed to growing cultures of the fungi Cunninghamella echinulata var. elegans ATCC 8688a and Phanerochaete chrysosporium ATCC 24725. C. echinulata transformed stemodin (1) to its 7*-hydroxy- (2) 7â-hydroxy- (3) and 3â-hydroxy- (4) analogues. 2* -(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) gave 2* -(N,N-dimethylcarbamoxy)-6* ,13-dihydroxystemodane (7) and 2 * -(N,N-(,-dimethylcarbamoxy)-7*, 13-dihydroxystemodane (8). Stemodinone (9) yielded 14-hydroxy-(10) and 7â-hydroxy- (11) congeners along with 1, 2 and 3. Stemarin (13) was converted to the hitherto unreported 6 * ,13-dihydroxystemaran-19-oic acid (18). 19-(N,N-Dimethylcarbamoxy)-13-hydroxystemarane (14) yielded 13-hydroxystemaran-19-oic acid (17) along with the two metabolites: 19-(N,N-dimethylcarbamoxy)-2â,13-dihydroxystemarane (15) and 19-(N,N-dimethylcarbamoxy)-2â,8,13-trihydroxystemarane (16). P. chrysosporium converted 1 into 3, 4 and 2*, 11â,13-trihydroxystemodane (5). The dimethylcarbamate (6) was not transformed by this microorganism. Stemodinone (9) was hydroxylated at C-19 to give 12. Both stemarin (13) and its dimethylcarbamate (14) were recovered unchanged after incubation with Phanerochaete.....