Identification of a Xanthine Oxidase-inhibitory Component from <i>Sophora Flavescens</i> using NMR-based Metabolomics

Suzuki, Ryuichiro; Hasuike, Yuka; Hirabayashi, Moeka; Fukuda, Tatsuo; Okada, Yoshihito; Shirataki, Yoshiaki

doi:10.1177/1934578x1300801017

Cited by 3 publications

(5 citation statements)

References 15 publications

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“…In a previous study, we used methanol (MeOH) to extract samples of Sophora f lavescens Aiton for NMR-based metabolomics analyses. 16 In the present study, MeOH was also used for extraction because it is a highly polar solvent. We prepared a MeOH extract of a lichen sample and then redissolved the dried extract residue with DMSO to an appropriate concentration for MS analysis.…”

Section: ■ Resultsmentioning

confidence: 99%

“…Natural biological samples are ideal materials for use in developing metabolomics methods due to the many constituents they contain. In a previous study, we used methanol (MeOH) to extract samples of Sophora flavescens Aiton for NMR-based metabolomics analyses . In the present study, MeOH was also used for extraction because it is a highly polar solvent.…”

Section: Resultsmentioning

confidence: 99%

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Establishment of a Direct-Injection Electron Ionization-Mass Spectrometry Metabolomics Method and Its Application to Lichen Profiling

et al. 2017

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Direct-injection electron ionization-mass spectrometry (DI-EI-MS) is a multivariate analysis method useful for characterizing biological materials. We demonstrated the use of DI-EI-MS for metabolic profiling using several closely related lichen species: Cladonia krempelhuberi, C. gracilis, C. pseudogymnopoda, and C. ramulosa. The methodology involves conversion of total ion chromatograms to integrated chromatograms and assessment of reproducibility. The qualitative DI-EI-MS method was used to profile the major and/or minor constituents in extracts of lichen samples. It was possible to distinguish each lichen sample by altering the electron energy in DI-EI-MS and examining the resulting data using one-way analysis of variance. Previously undetectable peaks, which are easy to fragment could be revealed by varying the electron energy. Our results suggest that metabolic profiling using DI-EI-MS would be useful for discriminating between subgroups within the same species. This is the first study to report the use of DI-EI-MS in a metabolomics application.

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Section: ■ Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Establishment of a Direct-Injection Electron Ionization-Mass Spectrometry Metabolomics Method and Its Application to Lichen Profiling

et al. 2017

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“…Xanthine oxidase is an important drug target used for gout, hyperuricemia, ischemic tissue/vascular injuries, inflammation related diseases, and myocardial infarction. Suzuki et al (2013) studied the xanthine oxidase inhibition potential of kurarinone. The result showed that kurarinone was active against the enzyme only at a higher concentration (100 µM) ( Suzuki et al, 2013 ).…”

Section: Introductionmentioning

confidence: 99%

“… Suzuki et al (2013) studied the xanthine oxidase inhibition potential of kurarinone. The result showed that kurarinone was active against the enzyme only at a higher concentration (100 µM) ( Suzuki et al, 2013 ).…”

Section: Introductionmentioning

confidence: 99%

Five-Decade Update on Chemopreventive and Other Pharmacological Potential of Kurarinone: a Natural Flavanone

et al. 2021

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In the present article we present an update on the role of chemoprevention and other pharmacological activities reported on kurarinone, a natural flavanone (from 1970 to 2021). To the best of our knowledge this is the first and exhaustive review of kurarinone. The literature was obtained from different search engine platforms including PubMed. Kurarinone possesses anticancer potential against cervical, lung (non-small and small), hepatic, esophageal, breast, gastric, cervical, and prostate cancer cells. In vivo anticancer potential of kurarinone has been extensively studied in lungs (non-small and small) using experimental xenograft models. In in vitro anticancer studies, kurarinone showed IC50 in the range of 2–62 µM while in vivo efficacy was studied in the range of 20–500 mg/kg body weight of the experimental organism. The phytochemical showed higher selectivity toward cancer cells in comparison to respective normal cells. kurarinone inhibits cell cycle progression in G2/M and Sub-G1 phase in a cancer-specific context. It induces apoptosis in cancer cells by modulating molecular players involved in apoptosis/anti-apoptotic processes such as NF-κB, caspase 3/8/9/12, Bcl2, Bcl-XL, etc. The phytochemical inhibits metastasis in cancer cells by modulating the protein expression of Vimentin, N-cadherin, E-cadherin, MMP2, MMP3, and MMP9. It produces a cytostatic effect by modulating p21, p27, Cyclin D1, and Cyclin A proteins in cancer cells. Kurarinone possesses stress-mediated anticancer activity and modulates STAT3 and Akt pathways. Besides, the literature showed that kurarinone possesses anti-inflammatory, anti-drug resistance, anti-microbial (fungal, yeast, bacteria, and Coronavirus), channel and transporter modulation, neuroprotection, and estrogenic activities as well as tyrosinase/diacylglycerol acyltransferase/glucosidase/aldose reductase/human carboxylesterases 2 inhibitory potential. Kurarinone also showed therapeutic potential in the clinical study. Further, we also discussed the isolation, bioavailability, metabolism, and toxicity of Kurarinone in experimental models.

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“…We previously reported the use of multivariate analysis, such as PCA with 1 H-NMR data in a chosen range, to analyze the cultivating places or the biological activities of various natural extracts. 4,5) Several other studies have employed 13 C-NMR data and multivariate analysis to distinguish the components of complex mixtures such as soy sauce. 6,7) However, very little experimental work has combined multivariate analysis with 13 C chemical shift data to establish predictive models.…”

Section: Introductionmentioning

confidence: 99%

Use of <sup>13</sup>C-NMR Chemical Shifts; Application of Principal Component Analysis for Categorizing Structurally Similar Methoxyflavones and Correlation Analysis between Chemical Shifts and Cytotoxicity

Suzuki

Uesawa

Okada

et al. 2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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The 13 C-NMR spectral data for the 15-carbon flavonoid skeleton in eleven methoxyflavones isolated from Kaempferia parviflora (Zingiberaceae) were processed by principal component analysis (PCA). Based on the PCA score plots, the methoxyflavones were categorized into three groups according to their structural features. The cytotoxicities of the methoxyflavones toward 3T3-L1 murine preadipocyte cells were evaluated by 3-(4,5-dimethylthiazole-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTT) assay and found to differ according to structure. The relationship between the 13 C-NMR chemical shifts of the methoxyflavones and their cytotoxicities was investigated using Pearson's correlation analysis. The 13 C-NMR signal at C-10, a quaternary carbon, was correlated with cytotoxicity. Based on these results, a structural design which lowers the 13 C-NMR chemical shift at C-10 would be important for the development of cytotoxic compounds. Although quantitative structure-activity and structure-property relationships are well established paradigms for predicting trends among a series of compounds, quantitative property-activity relationships have been relatively unstudied. This approach offers a new strategy for directing structure-activity relationship research.

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Identification of a Xanthine Oxidase-inhibitory Component from Sophora Flavescens using NMR-based Metabolomics

Cited by 3 publications

References 15 publications

Establishment of a Direct-Injection Electron Ionization-Mass Spectrometry Metabolomics Method and Its Application to Lichen Profiling

Establishment of a Direct-Injection Electron Ionization-Mass Spectrometry Metabolomics Method and Its Application to Lichen Profiling

Five-Decade Update on Chemopreventive and Other Pharmacological Potential of Kurarinone: a Natural Flavanone

Use of <sup>13</sup>C-NMR Chemical Shifts; Application of Principal Component Analysis for Categorizing Structurally Similar Methoxyflavones and Correlation Analysis between Chemical Shifts and Cytotoxicity

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