Functional diversity of cytochrome P450s of the white-rot fungus Phanerochaete chrysosporium.
The functional diversity of cytochrome P450s (P450s) of the white-rot basidiomycete, Phanerochaete chrysosporium, was studied. A series of compounds known to be P450 substrates of other organisms were utilized for metabolic studies of P. chrysosporium. Metabolic conversions of benzoic acid, camphor, 1,8-cineol, cinnamic acid, p-coumaric acid, coumarin, cumene, 1,12-dodecanediol, 1-dodecanol, 4-ethoxybenzoic acid, and 7-ethoxycoumarin were observed with P. chrysosporium for the first time. 1-Dodecanol was hydroxylated at seven different positions to form 1,12-, 1,11-, 1,10-, 1,9-, 1,8-, 1,7-, and 1,6-dodecandiols. The effect of piperonyl butoxide, a P450 inhibitor, on the fungal conversion of 1-dodecanol was also investigated, indicating that hydroxylation reactions of 1-dodecanol were inhibited by piperonyl butoxide in a concentration-dependent manner. With 11 substrates, 23 hydroxylation reactions and 2 deethylation reactions were determined and 6 products were new with the position of hydroxyl group incorporated. In conclusion, fungal P450s were shown to have diverse and unique functions.
Matsuzaki
Fumiko
F
Faculty of Agriculture, Kyushu University, Fukuoka 812-8581, Japan.
Wariishi
Hiroyuki
H
D000473:Alkanes / Q000737:chemistry / Q000378:metabolism; D000890:Anti-Infective Agents / Q000378:metabolism; D000925:Anticoagulants / Q000378:metabolism; D000935:Antifungal Agents / Q000378:metabolism; D001555:Benzene Derivatives / Q000378:metabolism; D019817:Benzoic Acid / Q000378:metabolism; D002164:Camphor / Q000378:metabolism; D002934:Cinnamates / Q000378:metabolism; D003373:Coumaric Acids / Q000378:metabolism; D003374:Coumarins / Q000737:chemistry / Q000378:metabolism; D003511:Cyclohexanols / Q000378:metabolism; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D000077591:Eucalyptol; D005656:Fungal Proteins / Q000378:metabolism*; D039821:Monoterpenes / Q000378:metabolism; D010226:Parabens / Q000378:metabolism; D020075:Phanerochaete / Q000201:enzymology*; D011422:Propionates
D000473:Alkanes; D000890:Anti-Infective Agents; D000925:Anticoagulants; D000935:Antifungal Agents; D001555:Benzene Derivatives; D002934:Cinnamates; D003373:Coumaric Acids; D003374:Coumarins; D003511:Cyclohexanols; D005656:Fungal Proteins; D039821:Monoterpenes; D010226:Parabens; D011422:Propionates; C007548:n-dodecane; C029010:cinnamic acid; D002164:Camphor; C015763:cumene; D019817:Benzoic Acid; D003577:Cytochrome P-450 Enzyme System; C030123:coumarin; C495469:p-coumaric acid; C038193:4-hydroxybenzoic acid; D000077591:Eucalyptol