Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria

Zhang, Dongdong; Shi, Yanhong; Li, Jingyi; Ruan, Deqing; Jia, Qi; Zhu, Weiliang; Chen, Kaixian; Li, Yiming; Wang, Rui

doi:10.3390/molecules24224033

Cited by 27 publications

(11 citation statements)

References 30 publications

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“…1). This compound was recently reported from the root of woad (Isatis tinctoria) with no details of structure characterization [14]. Here we describe isolation, unequivocal structure characterization, and antioxidant activity of 1.…”

Section: Introductionmentioning

confidence: 82%

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

Li¹,

Oku²,

Shinozaki³

et al. 2020

Preprint

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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.

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Section: Introductionmentioning

confidence: 82%

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

Li¹,

Oku²,

Shinozaki³

et al. 2020

Preprint

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show abstract

“…3Y-MMP, isolated from soil by an exhaustive enrichment culture under Zn 2+ -load, was selected for a detailed chemical study, which resulted in the isolation of 4-hydroxy-3-methyl-2(1H)quinolone (1, Figure 1). This compound was recently reported from the root of woad (Isatis tinctoria, family Brassicaceae) with no details of structure characterization [17]. Herein we describe the isolation, unequivocal structure characterization, and antioxidant activity of compound 1.…”

mentioning

confidence: 89%

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

Oku

Shinozaki

et al. 2020

Beilstein J. Org. Chem.

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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.

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“…3Y-MMP [66]. This compound was previously isolated as a plant metabolite from Isatis tinctoria (Brassicaceae) and displayed anti-tuberculosis activity with an IC 90 of 6.8 µM [66][67][68]. An extensive isolation report in 2020 described the isolation of six new HAQs, including the highly unusual sulfide and benzyl derivatives H3a and H7b, in addition to fifteen known AQs, three AQNOs, and the tetrhydroquinoline T7 [24].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

2020

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The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the Pseudomonas and Burkholderia genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from Pseudomonas aeruginosa. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in Pseudomonas aeruginosa. Many of the best-studied examples contain simple hydrocarbon side-chains, but more recent studies have revealed a wide range of structurally diverse examples from multiple bacterial genera, including those with aromatic, isoprenoid, or sulfur-containing side-chains. In addition to their well-known antimicrobial properties, alkylquinolones have been reported with antimalarial, antifungal, antialgal, and antioxidant properties. Here we review the structural diversity and biological activity of these intriguing metabolites.

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Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria

Cited by 27 publications

References 30 publications

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

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

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

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

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