41943-80-0Relevant articles and documents
Biotransformation of diterpenes and diterpene derivatives by Beauveria bassiana ATCC 7159
Buchanan, Greg O.,Reese, Paul B.
, p. 141 - 151 (2001)
The biohydroxylation of stemodin and stemodinone by Beauveria hassiana ATCC 7159 gave exclusively 2α,13,18-trihydroxystemodane and l3,18-dihydroxystemodan-2-one respectively. Stemarin was converted to the novel 1β,13,19-trihydroxystemarane and 13-hydroxys
Stemodin-derived analogues with lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation inhibitory activities
Russell, Floyd A.,Mulabagal, Vanisree,Thompson, Dwayne R.,Singh-Wilmot, Marvadeen A.,Reynolds, William F.,Nair, Muraleedharan G.,Langer, Vratislav,Reese, Paul B.
, p. 2361 - 2368 (2011)
A series of analogues, derived from the antiviral and cytotoxic diterpene stemodin, were prepared and evaluated for their lipid peroxidation (LPO), cyclooxygenase enzyme-1 (COX-1) and -2 (COX-2), and tumour cell proliferation inhibitory activities. Oxidation of stemodin produced stemodinone, which was then converted to stemod-12-en-2-one. Reaction of the latter under Petrow conditions (bromine; silver acetate/pyridine) yielded mainly dibrominated abeo-stachanes. Solvolysis of the dibromo compounds gave products of hydrolysis, some with rearranged skeleta. In the lipid peroxidation inhibitory assay three of the compounds exhibited prominent activity. Interestingly, all the analogues showed higher COX-1 enzyme inhibition than COX-2. Although a few of the diterpenes limited the growth of some human tumour cell lines, most compounds induced proliferation of such cells.
Bioconversion of Stemodia maritima diterpenes and derivatives by Cunninghamella echinulata var. elegans and Phanerochaete chrysosporium
Lamm, Andrew S.,Reynolds, William F.,Reese, Paul B.
, p. 1088 - 1093 (2008/02/10)
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 7α-hydroxy- (2), 7β-hydroxy- (3) and 3β-hydroxy- (4) analogues. 2α-(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) gave 2α-(N,N-dimethylcarbamoxy)-6α,13-dihydroxystemodane (7) and 2α-(N,N-dimethylcarbamoxy)-7α,13-dihydroxystemodane (8). Stemodinone (9) yielded 14-hydroxy-(10) and 7β-hydroxy- (11) congeners along with 1, 2 and 3. Stemarin (13) was converted to the hitherto unreported 6α,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)-2β,13-dihydroxystemarane (15) and 19-(N,N-dimethylcarbamoxy)-2β,8,13-trihydroxystemarane (16). P. chrysosporium converted 1 into 3, 4 and 2α,11β,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.
