Importance of oxygen functions in the biological hydroxylation of flavonoids by Absidia blackesleeana.
1. The synthesis and microbiological transformation of 2-phenyl-1-tetralone (compound 3, 1-deoxyisoflavanone), 3-phenyl-1-tetralone (compound 4, 1-deoxyflavanone), 2-phenylchroman (compound 7, 4-deoxyflavanone), 3-phenylchroman (compound 8, 4-deoxyisoflavanone) and 1,2-dihydro-3-phenylnaphthalene (compound 10, 1,4-dideoxy-dehydroflavanone) by Absidia blackesleeana are described. 2. Compounds 3, 4, 7 and 8 were hydroxylated at the 4'-position while compound 10 was not utilized as a substrate. The two phenylchroman analogues 7 and 8 gave approximately the same yield (22% and 26%, respectively) of the 4'-hydroxylation products, while the phenyltetralone analogues 3 and 4 showed significant differences in 4'-hydroxylation (2% and 47%, respectively).
Abul-Hajj
Y J
YJ
Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis 55455.
Ghaffari
M A
MA
Mehrotra
S
S
D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D006899:Mixed Function Oxygenases / Q000378:metabolism; D009090:Mucorales / Q000201:enzymology / Q000378:metabolism*; D010100:Oxygen / Q000378:metabolism*
D005419:Flavonoids; D006899:Mixed Function Oxygenases; D010100:Oxygen