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

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

Author information

1
†Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
2
‡Chemical Biology Institute, Yale University, West Haven, Connecticut 06516, United States.
3
§Department of Microbial Pathogenesis, Yale School of Medicine, New Haven, Connecticut 06536, United States.

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.

PMID:
25988621
PMCID:
PMC5055755
DOI:
10.1021/np500974f
[Indexed for MEDLINE]
Free PMC Article

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