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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.
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-06-26 , DOI: 10.3762/bjoc.16.124
Dandan Li 1 , Naoya Oku 1 , Yukiko Shinozaki 2 , Yoichi Kurokawa 3 , Yasuhiro Igarashi 1
Affiliation  

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 μM, 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.

中文翻译:

最初从十字花科植物中发现的4-羟基-3-甲基-2(1H)-喹诺酮是由Burkholderia sp。属的土壤细菌生产的:测定优选的互变异构体和抗氧化活性。

从发酵提取物中分离出4-羟基-3-甲基-2(1 H)-喹诺酮(1),该分子是长期已知的,最近在十字花科植物Istiss tinctoria中发现,但没有提供足够的证据来支持该结构。的伯克霍尔德氏菌。通过Zn 2+富集培养从土壤中分离出的3Y-MMP 。通过MS和NMR光谱的详细分析,结合13与相关化合物和的合成制备的文献值C化学位移的比较1,允许其第一个完整NMR表征和鉴定2-喹诺酮的但不是2-羟基喹啉(2)作为该杂环系统的首选互变异构体。尽管金属螯合活性可忽略不计,但浓度为10μM(低于液体生产培养物中的浓度)的化合物1使由鲁米诺发出的羟自由基诱导的化学发光猝灭了86%。由于某些伯克霍尔德菌对植物和动物具有致病性,因此上述结果表明1是一种潜在的抗氧化剂,可以抵消宿主生物中基于活性氧的免疫反应。
更新日期:2020-06-26
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