4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

  1. Dandan LiORCID Logo,
  2. Naoya OkuORCID Logo,
  3. Yukiko Shinozaki,
  4. Yoichi Kurokawa and
  5. Yasuhiro Igarashi

Submitting author affiliation: Toyama Prefectural University, Toyama, Japan

Beilstein Arch. 2020, 202048. https://doi.org/10.3762/bxiv.2020.48.v1

Published 14 Apr 2020

  • Preprint


4-Hydroxy-3-methyl-2(1H)-quinolone (1), an old synthetic molecule and recently discovered from a plant without providing sufficient evidence to support the structure, was isolated from a fermentation extract of Burkholderia sp. 3Y-MMP isolated from a soil by a Zn2+ enrichment culture. Detailed spectroscopic analyses by MS and NMR, combined with 13C chemical shift comparison with literature values of the related compounds and a synthetic preparation of 1, allowed its first full NMR characterization and identification of 4-hydroxy-2-quinolone but not 4-hydroxy-2-quinolinol as the preferred tautomer for this heterocyclic system. While the metal-chelating activity was negligible, 1 at 100 mM quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86%. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response in the host organisms.

Keywords: antioxidant; Burkholderia sp.; quinolone; soil bacterium; Zn2+ enrichment culture

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Li, D.; Oku, N.; Shinozaki, Y.; Kurokawa, Y.; Igarashi, Y. Beilstein Arch. 2020, 202048. doi:10.3762/bxiv.2020.48.v1

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