title: Biosynthetic origins of the epoxyquinone skeleton in epoxyquinols A and B.
abstract: The biosynthetic origins of epoxyquinols A (1) and B (2) produced by an unidentified fungus have attracted considerable interest because these compounds could be assembled from a biosynthetic precursor, epoxycyclohexenone aldehyde (3), via an electrocyclization/intermolecular Diels-Alder dimerization cascade reaction. Furthermore, very little is known about the biosynthetic origins of naturally occurring epoxyquinone moieties. We herein describe the incorporation of (13)C at specific positions within the structure of a shunt product, epoxycyclohexenone (4), using stable isotope feeding experiments with sodium [1-(13)C]-acetate and sodium [1,2-(13)C2]-acetate. The results of these experiments strongly suggest that the epoxyquinone skeleton is assembled by a polyketide synthase.
authors.affiliation: Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Katsuki
authors.initials: K
authors.lastname: Fujita
authors.forename: Fumihiro
authors.initials: F
authors.lastname: Ishikawa
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kakeya
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry*; D006873:Hydroquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D048630:Polyketide Synthases / Q000378:metabolism*; D012988:Soil Microbiology
chemical_list: D004852:Epoxy Compounds; D006873:Hydroquinones; C455959:epoxyquinol A; C469247:epoxyquinol B; D048630:Polyketide Synthases