title: Lumiquinone A, an α-Aminomalonate-Derived Aminobenzoquinone from Photorhabdus luminescens.
abstract: Lumiquinone A (1), an unusual aminobenzoquinone member within the phenylpropanoid class of natural products, together with the known compound 3,5-dihydroxy-4-isopropyl-trans-stilbene (2), was isolated from the entomopathogenic bacterium Photorhabdus luminescens TT01. On the basis of the analysis of extensive 2D NMR and high-resolution ESI-QTOF-MS spectral data, the structure of 1 was determined to be a 2-amino-5-hydroxy-1,4-benzoquinone substituted with (E)-2-phenylvinyl and isopropyl functional groups. Free α-aminomalonate medium supplementation significantly enhanced production of 1 relative to 2 in a dose-dependent manner, suggesting that promiscuous polyketide synthase processing of malonate- versus α-aminomalonate-derived substrates represents a competitive route for polyketide structural diversification. Metabolites 1 and 2 were active against Bacillus subtilis and Saccharomyces cerevisiae.
authors.affiliation: †Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.|‡Chemical Biology Institute, Yale University, West Haven, Connecticut 06516, United States.
authors.forename: Hyun Bong
authors.initials: HB
authors.lastname: Park
authors.affiliation: †Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.|‡Chemical Biology Institute, Yale University, West Haven, Connecticut 06516, United States.|§Department of Microbial Pathogenesis, Yale School of Medicine, New Haven, Connecticut 06536, United States.
authors.forename: Jason M
authors.initials: JM
authors.lastname: Crawford
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D008314:Malonates / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D020637:Photorhabdus / Q000737:chemistry*; D048630:Polyketide Synthases / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000187:drug effects
chemical_list: D000890:Anti-Infective Agents; D016227:Benzoquinones; D008314:Malonates; C000601158:lumiquinone A; D048630:Polyketide Synthases