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10.3762/bjoc.16.124

http://scihub22266oqcxt.onion/10.3762/bjoc.16.124
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C7323622!7323622!32647550
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suck abstract from ncbi


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pmid32647550      Beilstein+J+Org+Chem 2020 ; 16 (ä): 1489-94
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  • 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 #MMPMID32647550
  • Li D; Oku N; Shinozaki Y; Kurokawa Y; Igarashi Y
  • Beilstein J Org Chem 2020[]; 16 (ä): 1489-94 PMID32647550show ga
  • 4-Hydroxy-3-methyl-2(1H)-quinolone (1), a molecule known for a long time and recently discovered from a Brassicaceae plant Isatis tinctoria 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 2-quinolone but not 2-quinolinol (2) as the preferred tautomer for this heterocyclic system. While the metal-chelating activity was negligible, compound 1 at 10 ?M, a concentration lower than that in liquid production cultures, 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.
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