Metabolites identification of glycyrin and glycyrol, bioactive coumarins from licorice

Wang, Qi; Qiao, Xue; Qian, Yi; Yang, Yanfang; Ji, Shuai; Li, Jun; Guo, Dan; Ye, Min

doi:10.1016/j.jchromb.2014.12.028

Cited by 23 publications

(8 citation statements)

References 18 publications

(23 reference statements)

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“…Isoliquiritigenin protects cells from the toxicity of arachidonic acid plus (Qiao et al, 2014;Xu et al, 2013), glycyrrhizic acid , licorice-saponin A3 Qiao et al, 2014), licorice-saponin G2 (Qiao et al, 2014), licorice-saponin E2 (Qiao et al, 2014) Flavanones Liquiritigenin, liquiritin , liquiritin apioside (Xu et al, 2013) Chalcones Isoliquiritigenin (Simmler et al, 2014), isoliquiritigenin apioside (Simmler et al, 2014), isoliquiritin (Simmler et al, 2014), neoisoliquiritin (Zhang and Ye, 2009), licochalcone A and B (Zhang and Ye, 2009) Flavones (flavonols) Licoflavonol (Qiao et al, 2014;Zhang and Ye, 2009), isolicoflavonol (Qiao et al, 2014;Zhang and Ye, 2009) Isoflavones Licoisoflavone (Zhang and Ye, 2009;Qiao et al, 2014), licoricone (Zhang and Ye, 2009;Qiao et al, 2014), gancaonin (Zhang and Ye, 2009;Qiao et al, 2014), angustone (Zhang and Ye, 2009;Qiao et al, 2014), isoangustone (Zhang and Ye, 2009;Qiao et al, 2014), glabrone (Zhang and Ye, 2009) Isoflavans Glabridin (Zhang and Ye, 2009), hispaglabridin A and B (Zhang and Ye, 2009) Isoflavenes Glabrene (Zhang and Ye, 2009) Coumarins Glycycoumarin (Qiao et al, 2014), licopyranocoumarin (Qiao et al, 2014), glycyrin, glycyrol (Wang et al, 2015) Figure 1. Chemical structure of some active constituents of licorice.…”

Section: Antioxidative Activitiesmentioning

confidence: 99%

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Pharmacological Effects ofGlycyrrhizaspp. and Its Bioactive Constituents: Update and Review

2015

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The roots and rhizomes of various species of the perennial herb licorice (Glycyrrhiza) are used in traditional medicine for the treatment of several diseases. In experimental and clinical studies, licorice has been shown to have several pharmacological properties including antiinflammatory, antiviral, antimicrobial, antioxidative, antidiabetic, antiasthma, and anticancer activities as well as immunomodulatory, gastroprotective, hepatoprotective, neuroprotective, and cardioprotective effects. In recent years, several of the biochemical, molecular, and cellular mechanisms of licorice and its active components have also been demonstrated in experimental studies. In this review, we summarized the new phytochemical, pharmacological, and toxicological data from recent experimental and clinical studies of licorice and its bioactive constituents after our previous published review.

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Section: Antioxidative Activitiesmentioning

confidence: 99%

“…Glycycoumarin (Qiao et al, 2014), licopyranocoumarin (Qiao et al, 2014), glycyrin, glycyrol (Wang et al, 2015) Figure 1. Chemical structure of some active constituents of licorice.…”

Section: Coumarinsmentioning

confidence: 99%

Pharmacological Effects ofGlycyrrhizaspp. and Its Bioactive Constituents: Update and Review

2015

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“…Peak 46 was tentatively characterized as glycyrol, a licorice coumarin, because of its [M − H] − ion at m / z 365.1028 and the fragmentation at m / z 307.0244 ([M − H − C 4 H 10 ] − ) and m / z 295.0244 ([M − H − C 5 H 10 ] − ), which were the same as those of glycyrol [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

Application of High-Performance Liquid Chromatography Coupled with Linear Ion Trap Quadrupole Orbitrap Mass Spectrometry for Qualitative and Quantitative Assessment of Shejin-Liyan Granule Supplements

Huang

et al. 2018

Molecules

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A method for high-performance liquid chromatography coupled with linear ion trap quadrupole Orbitrap high-resolution mass spectrometry (HPLC-LTQ-Orbitrap MS) was developed and validated for the qualitative and quantitative assessment of Shejin-liyan Granule. According to the fragmentation mechanism and high-resolution MS data, 54 compounds, including fourteen isoflavones, eleven ligands, eight flavonoids, six physalins, six organic acids, four triterpenoid saponins, two xanthones, two alkaloids, and one licorice coumarin, were identified or tentatively characterized. In addition, ten of the representative compounds (matrine, galuteolin, tectoridin, iridin, arctiin, tectorigenin, glycyrrhizic acid, irigenin, arctigenin, and irisflorentin) were quantified using the validated HPLC-LTQ-Orbitrap MS method. The method validation showed a good linearity with coefficients of determination (r2) above 0.9914 for all analytes. The accuracy of the intra- and inter-day variation of the investigated compounds was 95.0–105.0%, and the precision values were less than 4.89%. The mean recoveries and reproducibilities of each analyte were 95.1–104.8%, with relative standard deviations below 4.91%. The method successfully quantified the ten compounds in Shejin-liyan Granule, and the results show that the method is accurate, sensitive, and reliable.

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“…Seven compounds were suspended in 1% sodium carboxymethyl cellulose to obtain suspension (2 mg/ml for each compound). Rats ( n = 2) were orally given 40 mg/kg, while the control group was orally given the same amount of normal saline ( Wang et al, 2014 ).…”

Section: Methodsmentioning

confidence: 99%

Surface-Enhanced Raman Spectroscopy Analysis of Astragalus Saponins and Identification of Metabolites After Oral Administration in Rats by Ultrahigh-Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry Analysis

Kong

Liu

et al. 2022

Front. Pharmacol.

Self Cite

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Astragalus mongholicus Bunge (Fabaceae) is an ancient Chinese herbal medicine, and Astragalus saponins are the main active components, which have a wide range of biological activities, such as immunomodulation, antioxidation, and neuroprotection. In this study, silver nanoparticles obtained by sodium borohydride reduction were used as the enhanced substrate to detect astragaloside I (1), astragaloside II (2), astragaloside III (3), astragaloside IV (4), isoastragaloside I (5), and isoastragaloside II (6) in the phloem, xylem, and cork by surface-enhanced Raman spectroscopy (SERS). In the SERS spectrum of Astragalus slices, the characteristic peaks were observed at 562, 671, 732, 801, 836, 950, 1,026, 1,391, and 1,584 cm−1, among which 950 cm−1 and 1,391 cm−1 were strong SERS signals. Subsequently, the metabolites of the six kinds of Astragalus saponins were identified by UPLC/ESI/Q-TOF-MS. Totally, 80, 89, and 90 metabolites were identified in rat plasma, urine, and feces, respectively. The metabolism of saponins mainly involves dehydration, deacetylation, dihydroxylation, dexylose reaction, deglycosylation, methylation, deacetylation, and glycol dehydration. Ten metabolites (1-M2, 1-M11, 2-M3, 2-M12, 3-M14, 4-M9, 5-M2, 5-M17, 6-M3, and 6-M12) were identified by comparison with reference standards. Interestingly, Astragalus saponins 1, 2, 5, and 6 were deacetylated to form astragaloside IV (4), which has been reported to have good pharmacological neuroprotective, liver protective, anticancer, and antidiabetic effects. Six kinds of active Astragalus saponins from different parts of Astragalus mongholicus were identified by SERS spectroscopy. Six kinds of active Astragalus saponins from different parts of Astragalus mongholicus were identified by SERS spectrum, and the metabolites were characterized by UPLC/ESI/Q-TOF-MS, which not only provided a new method for the identification of traditional Chinese medicine but also provided a theoretical basis for the study of the pharmacodynamic substance basis of Astragalus mongholicus saponins.

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Metabolites identification of glycyrin and glycyrol, bioactive coumarins from licorice

Cited by 23 publications

References 18 publications

Pharmacological Effects ofGlycyrrhizaspp. and Its Bioactive Constituents: Update and Review

Pharmacological Effects ofGlycyrrhizaspp. and Its Bioactive Constituents: Update and Review

Application of High-Performance Liquid Chromatography Coupled with Linear Ion Trap Quadrupole Orbitrap Mass Spectrometry for Qualitative and Quantitative Assessment of Shejin-Liyan Granule Supplements

Surface-Enhanced Raman Spectroscopy Analysis of Astragalus Saponins and Identification of Metabolites After Oral Administration in Rats by Ultrahigh-Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry Analysis

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