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

J Nat Prod. 2015 Jun 26;78(6):1437-41. doi: 10.1021/np500974f. Epub 2015 May 19.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Benzoquinones / chemistry
  • Benzoquinones / isolation & purification*
  • Benzoquinones / pharmacology
  • Dose-Response Relationship, Drug
  • Malonates / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Photorhabdus / chemistry*
  • Polyketide Synthases / metabolism
  • Saccharomyces cerevisiae / drug effects

Substances

  • Anti-Infective Agents
  • Benzoquinones
  • Malonates
  • lumiquinone A
  • Polyketide Synthases