title: A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway.
abstract: The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: Yan-Long
authors.initials: YL
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Zhou
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: Gang
authors.initials: G
authors.lastname: Du
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: Ke-Na
authors.initials: KN
authors.lastname: Feng
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China.|School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, 430074, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Feng
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China.
authors.forename: Xiao-Li
authors.initials: XL
authors.lastname: Fu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China. jkliu@mail.kib.ac.cn.|School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, 430074, China. jkliu@mail.kib.ac.cn.
authors.forename: Ji-Kai
authors.initials: JK
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, China. biochem@mail.kib.ac.cn.
authors.forename: Ying
authors.initials: Y
authors.lastname: Zeng
mesh_terms: D001487:Basidiomycota / Q000737:chemistry / Q000201:enzymology* / Q000378:metabolism; D053898:Biosynthetic Pathways; D003653:Decarboxylation; D006873:Hydroquinones / Q000378:metabolism; D007783:Lactones / Q000032:analysis / Q000378:metabolism*; D006899:Mixed Function Oxygenases / Q000378:metabolism*; D010226:Parabens / Q000378:metabolism
chemical_list: D006873:Hydroquinones; D007783:Lactones; D010226:Parabens; C522315:vibralactone; D006899:Mixed Function Oxygenases; C038193:4-hydroxybenzoic acid; C031927:hydroquinone
keywords: biosynthesis; decarboxylation; enzymes; meroterpenoid; natural products