Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145.
A new stemodinoside, stemodin-alpha-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2 alpha,7 beta,13(S)-trihydroxystemodane (17) and 2 alpha,3 beta,13(S),16 alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6 alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2 beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2 beta,7 beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7 beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion.
Martin
Glenroy D A
GD
Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica.
Reynolds
William F
WF
Reese
Paul B
PB
D001089:Arabinose / Q000031:analogs & derivatives; D001711:Biotransformation; D004224:Diterpenes / Q000737:chemistry* / Q000378:metabolism*; D006900:Hydroxylation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012233:Rhizopus / Q000235:genetics / Q000378:metabolism*; D028083:Scrophulariaceae / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry
D004224:Diterpenes; D014315:Triterpenes; C074341:stemodin; D001089:Arabinose