Biologically active quinoline and quinazoline alkaloids part II

Shang, Xiaofei; Morris‐Natschke, Susan L.; Yang, Guan‐Zhou; Liu, Ying‐Qian; Guo, Xiao; Xu, Xiaoshan; Goto, Masuo; Li, Juncai; Zhang, Jiyu; Lee, Kuo Hsiung̀

doi:10.1002/med.21492

Cited by 158 publications

(98 citation statements)

References 222 publications

(507 reference statements)

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“…Differential comparison also revealed that kanamycin resistant Y. pestis produces significantly lower amounts of 3-(2-chloro-5-hydroxyphenyl)-2-methylquinazolin-4-one and isopropylhydroxylamine, relative to the wildtype strain (~ 800 and 8,000 fold lower, respectively). The quinazolinone alkaloids are a large family of secondary metabolites produced by plants, fungi, and bacteria 28 – 30 . Alterations to primary metabolism is well known to alter production of secondary metabolites 31 .…”

Section: Resultsmentioning

confidence: 99%

VOC fingerprints: metabolomic signatures of biothreat agents with and without antibiotic resistance

Dailey

Saha

Zaidi

et al. 2020

Sci Rep

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Category A and B biothreat agents are deemed to be of great concern by the US Centers for Disease Control and Prevention (CDC) and include the bacteria Francisella tularensis, Yersinia pestis, Burkholderia mallei, and Brucella species. Underscored by the impact of the 2020 SARS-CoV-2 outbreak, 2016 Zika pandemic, 2014 Ebola outbreak, 2001 anthrax letter attacks, and 1984 Rajneeshee Salmonella attacks, the threat of future epidemics/pandemics and/or terrorist/criminal use of pathogenic organisms warrants continued exploration and development of both classic and alternative methods of detecting biothreat agents. Volatile organic compounds (VOCs) comprise a large and highly diverse group of carbon-based molecules, generally related by their volatility at ambient temperature. Recently, the diagnostic potential of VOCs has been realized, as correlations between the microbial VOC metabolome and specific bacterial pathogens have been identified. Herein, we describe the use of microbial VOC profiles as fingerprints for the identification of biothreatrelevant microbes, and for differentiating between a kanamycin susceptible and resistant strain. Additionally, we demonstrate microbial VOC profiling using a rapid-throughput VOC metabolomics method we refer to as 'simultaneous multifiber headspace solid-phase microextraction' (simulti-hSPME). Finally, through VOC analysis, we illustrate a rapid non-invasive approach to the diagnosis of BALB/c mice infected with either F. tularensis SCHU S4 or Y. pestis CO92. Category A and B biothreat agents include several bacteria, viruses, and toxins deemed to be of great concern by the US Centers for Disease Control and Prevention (CDC), due to their ease of dissemination/transmission, morbidity/mortality rates, and ability to cause public panic and disruption. Underscored by the impact of the 2020 SARS-CoV-2 outbreak, the 2016 Zika pandemic, the 2014 Ebola outbreak, the 2001 anthrax letter attacks, and the 1984 Rajneeshee Salmonella attacks, the threat of future epidemics/pandemics and/or terrorist use of pathogenic organisms warrants continued exploration and development of both classic and alternative methods of rapidly detecting agents of threat. Although sensitive and selective detection techniques such as polymerase chain reaction (PCR), microbial dichotomous keying, and/or enzyme-linked immunosorbent assays (ELISA) are well established 1 , these techniques are typically time consuming, laborious, and costly. Conversely, bacterial metabolome fingerprints, such as those derived through the use of techniques like Matrix-Assisted Laser Desorption Ionization (MALDI) coupled with mass spectrometry (MS), are rapid, reproducible, and cost effective 2,3. Using gas chromatography coupled with mass spectrometry (GC-MS), we have previously demonstrated the diagnostic potential of volatile organic compounds (VOCs) emanating from biological samples 4-7. VOCs comprise a large and highly diverse group of carbon-based molecules, generally related by their volatility at ambient temperature. A VOC-b...

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Section: Resultsmentioning

confidence: 99%

VOC fingerprints: metabolomic signatures of biothreat agents with and without antibiotic resistance

Dailey

Saha

Zaidi

et al. 2020

Sci Rep

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“…4-Hydroxy-2(1H)-quinolone is a unique structural motif mostly found in alkaloids from rutaceous plants (family Rutaceae) [1,2]. This motif has several tautomeric forms including 2,4-dihydroxyquinoline [3], although which tautomer to be taken seems not always be identified in some of the studies.…”

Section: Introductionmentioning

confidence: 99%

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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“…Quinolines are one of the most ubiquitous structural units in natural products, [1][2][3][4][5] biologically active compounds [6][7][8][9][10][11] and functionalized materials ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

An efficient 3-acylquinoline synthesis from acetophenones and anthranilviaC(sp³)–H bond activation mediated by Selectfluor

Gao

Hider

2019

RSC Adv.

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Biologically active quinoline and quinazoline alkaloids part II

Cited by 158 publications

References 222 publications

VOC fingerprints: metabolomic signatures of biothreat agents with and without antibiotic resistance

VOC fingerprints: metabolomic signatures of biothreat agents with and without antibiotic resistance

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

An efficient 3-acylquinoline synthesis from acetophenones and anthranilviaC(sp³)–H bond activation mediated by Selectfluor

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Biologically active quinoline and quinazoline alkaloids part II

Cited by 158 publications

References 222 publications

VOC fingerprints: metabolomic signatures of biothreat agents with and without antibiotic resistance

VOC fingerprints: metabolomic signatures of biothreat agents with and without antibiotic resistance

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

An efficient 3-acylquinoline synthesis from acetophenones and anthranilviaC(sp3)–H bond activation mediated by Selectfluor

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An efficient 3-acylquinoline synthesis from acetophenones and anthranilviaC(sp³)–H bond activation mediated by Selectfluor