Lumiquinone A, an α‑Aminomalonate-Derived Aminobenzoquinone from Photorhabdus luminescens

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...

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Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 78; no. 6; pp. 1437 - 1441
Main Authors Park, Hyun Bong, Crawford, Jason M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.06.2015
Amer Chemical Soc
Subjects
Anti-Infective Agents - chemistry
Anti-Infective Agents - isolation & purification
Anti-Infective Agents - pharmacology
Bacillus subtilis - drug effects
Benzoquinones - chemistry
Benzoquinones - isolation & purification
Benzoquinones - pharmacology
Chemistry, Medicinal
Dose-Response Relationship, Drug
Life Sciences & Biomedicine
Malonates - chemistry
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacology & Pharmacy
Photorhabdus - chemistry
Plant Sciences
Polyketide Synthases - metabolism
Saccharomyces cerevisiae - drug effects
Science & Technology
DRUG
IN-VITRO
ANTIBIOTICS
NATURAL-PRODUCTS
BIOSYNTHESIS
ECOLOGY
UNITS
DISCOVERY
SYMBIONTS
PATHOGENS
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Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ObjectType-Feature-2
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ISSN:0163-3864
1520-6025
DOI:10.1021/np500974f