title: Novel triterpene oxidizing activity of Arabidopsis thaliana CYP716A subfamily enzymes.
abstract: Triterpenoids have diverse chemical structures and bioactivities. Cytochrome P450 monooxygenases play a key role in their structural diversification. In higher plants, CYP716A subfamily enzymes are triterpene oxidases. In this study, Arabidopsis thaliana CYP716A1 and CYP716A2 were characterized by heterologously expressing them in simple triterpene-producing yeast strains. In contrast to the C-28 oxidative activity of CYP716A1 shown in several CYP716A subfamily enzymes, remarkably, CYP716A2 displayed 22α-hydroxylation activity against α-amyrin that has not been previously reported, which produces the cytotoxic triterpenoid, 22α-hydroxy-α-amyrin. Our results contribute to the enrichment of the molecular toolbox that allows for the combinatorial biosynthesis of diverse triterpenoids.
authors.affiliation: Department of Biotechnology, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan.
authors.forename: Shuhei
authors.initials: S
authors.lastname: Yasumoto
authors.affiliation: Department of Biotechnology, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan.|Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan.
authors.forename: Ery O
authors.initials: EO
authors.lastname: Fukushima
authors.affiliation: Department of Biotechnology, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Seki
authors.affiliation: Department of Biotechnology, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan.
authors.forename: Toshiya
authors.initials: T
authors.lastname: Muranaka
mesh_terms: D017360:Arabidopsis / Q000201:enzymology*; D029681:Arabidopsis Proteins / Q000145:classification / Q000235:genetics / Q000378:metabolism*; D003577:Cytochrome P-450 Enzyme System / Q000145:classification / Q000235:genetics / Q000378:metabolism*; D006900:Hydroxylation; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D010084:Oxidation-Reduction; D010802:Phylogeny; D012441:Saccharomyces cerevisiae / Q000235:genetics / Q000378:metabolism; D014315:Triterpenes / Q000378:metabolism*
chemical_list: D029681:Arabidopsis Proteins; D014315:Triterpenes; D009828:Oleanolic Acid; D003577:Cytochrome P-450 Enzyme System; C000609476:cytochrome P-450 716A1, Arabidopsis; C000609477:cytochrome P-450 716A2, Arabidopsis; C036380:beta-amyrin
keywords: 22α-hydroxylation; Arabidopsis thaliana; CYP716A; combinatorial biosyn-thesis; cytochrome P450 monooxygenase; triterpenoids