Analytical strategy to reveal the in vivo process of multi-component herbal medicine: A pharmacokinetic study of licorice using liquid chromatography coupled with triple quadrupole mass spectrometry

Qiao, Xue; Ye, Min; Cheng, Xiang; Wang, Qing; Liu, Chunfang; Miao, Wenjuan; Guo, Dan

doi:10.1016/j.chroma.2012.08.041

Cited by 87 publications

(88 citation statements)

References 40 publications

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“…Among them, only the following compounds were prevalent in licorice extract: liquiritigenin (9), isoliquiritigenin (20), glycycoumarin (23), semilicoisoflavone B (24), kumatakenin (25), licoisoflavone A (26), licoricone (27), glycyrol (30), licoflavonol (32), topazolin (33), glycyrin (34), and licoisoflavone B (C15) ( Fig. 1 and ESM Fig.…”

Section: Discussionmentioning

confidence: 99%

“…However, key licorice components for P450 inhibition are not limited to the above compounds. According to the metabolic fates of licorice compounds (19,20), some hydrophilic glycosides could be metabolized into less polar aglycones. For instance, liquiritin (4), liquiritin apioside (3), isoliquiritin (6), and isoliquiritin apioside (5) could all be converted into liquiritigenin (9), isoliquiritigenin (20), and davidigenin (18) after oral administration of licorice water extract (19).…”

Section: Discussionmentioning

confidence: 99%

“…Chemical structures of licorice compounds (isolated from Glycyrrhiza uralensis Fisch.). The compounds were 4-hydroxybenzoic acid (1), phloretic acid (2), liquiritin apioside (3), liquiritin (4), isoliquiritin apioside (5), isoliquiritin (6), ononin (7), 4′,7-dihydroxyflavone (8), liquiritigenin (9), licoricesaponin A3 (10), licopyranocoumarin (11), echinatin (12), naringenin (13), genistein (14), licorice-saponin G2 (15), licorice-saponin E2 (16), 3-methylkaempferol (17), davidigenin (18), glycyrrhizic acid (19), isoliquiritigenin (20), 7,4′-dihydroxy-3′-methoxyisoflavan (21), formononetin (22), glycycoumarin (23), semilicoisoflavone B (24), kumatakenin (25), licoisoflavone A (26), licoricone (27), isolicoflavonol (28), lupiwighteone (29), glycyrol (30), glyurallin A (31), licoflavonol (32), topazolin (33), glycyrin (34), gancaonin I (35), angustone A (36), isoangustone A (37), gancaonin G (38), 6,8-diprenylgenistein (39), and 18β-glycyrrhetinic acid (40). Api apinose, GluA glucuronic acid, Glc glucose, Prenyl isoprenoid.…”

Section: Lc/ms/ms Assaymentioning

confidence: 99%

“…Potent 2C19 inhibitors mainly included prenylated flavonoids and coumarins substituted with -OH or -OMe (27, 31, 32, 33, 36, 38, 39), or compounds containing m-dihydroxybenzene substructure (12,14,20,24). Compounds 23, 26, and 34 contain both structural features, and showed IC 50 of 0.70±0.2, 2.52±0.9, and 0.65±0.1 μM.…”

Section: P450 Inhibition Assay For 40 Licorice Compoundsmentioning

confidence: 99%

“…Furthermore, chemical-bioactivity fingerprints were established to examine the occurrence of licorice compounds with their bioactivities. Combining the results of in vitro bioactivity, in vivo metabolism (19,20) and natural occurrence, the key licorice compounds which interact with cytochrome P450 were elucidated.…”

Section: Introductionmentioning

confidence: 99%

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Identification of Key Licorice Constituents Which Interact with Cytochrome P450: Evaluation by LC/MS/MS Cocktail Assay and Metabolic Profiling

Qiao

et al. 2013

AAPS J

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Abstract. Licorice has been shown to affect the activities of several cytochrome P450 enzymes. This study aims to identify the key constituents in licorice which may affect these activities. Bioactivity assay was combined with metabolic profiling to identify these compounds in several complex licorice extracts. Firstly, the inhibition potencies of 40 pure licorice compounds were tested using an liquid chromatography/tandem mass spectrometry cocktail method. Significant inhibitors of human P450 isozymes 1A2, 2C9, 2C19, 2D6, and 3A4 were then selected for examination of their structural features by molecular docking to determine their molecular interaction with several P450 isozymes. Based on the present in vitro inhibition findings, along with our previous in vivo metabolic studies and the prevalence of individual compounds in licorice extract, we identified several licorice constituents, viz., liquiritigenin, isoliquiritigenin, together with seven isoprenylated flavonoids and arylcoumarins, which could be key components responsible for the herb-drug interaction between cytochrome P450 and licorice. In addition, hydrophilic flavonoid glycosides and saponins may be converted into these P450 inhibitors in vivo. These studies represent a comprehensive examination of the potential effects of licorice components on the metabolic activities of P450 enzymes.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Lc/ms/ms Assaymentioning

confidence: 99%

Section: P450 Inhibition Assay For 40 Licorice Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Identification of Key Licorice Constituents Which Interact with Cytochrome P450: Evaluation by LC/MS/MS Cocktail Assay and Metabolic Profiling

Qiao

et al. 2013

AAPS J

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Comparative pharmacokinetics and tissue distribution of cryptotanshinone, tanshinone IIA, dihydrotanshinone I, and tanshinone I after oral administration of pure tanshinones and liposoluble extract of Salvia miltiorrhiza to rats

Wang

Cao

et al. 2020

Biopharm & Drug Disp

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Salvia miltiorrhiza is one of the most commonly used traditional Chinese medicines in the treatment of cardiovascular and cerebrovascular diseases. Cryptotanshinone (CTS), tanshinone IIA (Tan IIA), dihydrotanshinone I (diTan I), and tanshinone I (Tan I) are the main active compounds in the liposoluble extract of Salvia miltiorrhiza. The differences in the pharmacokinetic and tissue distribution behaviors of the four tanshinones after oral administration of the liposoluble extract of Salvia miltiorrhiza and pure compounds are not clear. This study aims to compare the pharmacokinetics and tissue distribution of the four tanshinones after oral administration of pure tanshinone monomers and the liposoluble extract of Salvia miltiorrhiza. An ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) analysis method was developed for the determination of the four tanshinones. Theresults showed that the AUC and C max of tanshinones in rats receiving the extract of Salvia miltiorrhiza were significantly increased compared with those receiving the pure tanshinones. In the tissue distribution experiments, the AUC of the four tanshinones in the extract was much greater than the AUC of the monomers in the lung, heart, kidney, liver, and brain, and the coexisting constituents particularly promoted the distribution of tanshinones into tissues that the drug cannot sufficiently penetrate. These findings suggested that the coexisting constituents in the liposoluble extract of Salvia miltiorrhiza play an important role in the alteration of plasma concentration and tissue distribution of the four tanshinones. Understanding these differences could be of significance for the development and application of Salvia miltiorrhiza extract and tanshinone components.

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Evaluation of liquid chromatography–ion trap–time of flight hybrid mass spectrometry on the quantitative analysis for ginsenosides

Xing

Xie

Liang

et al. 2014

Biomedical Chromatography

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It is ideal and desirable for a single instrument to meet the requirement of both qualitative and quantitative analysis of complicated components in pharmacokinetic research for herbal medicine. Liquid chromatography combined with hybrid ion trap and time-of-flight mass spectrometry (LCMS-IT-TOF) was recently confirmed as a very powerful tool for the qualitative analysis of both target and nontarget components in herbal medicines. The present study was designed to investigate the feasibility of LCMS-IT-TOF on quantitative analysis of ginsenosides in biological matrices. A simple liquid-liquid extraction procedure was followed by injection of the extracts onto a C₁₈ column with gradient elution and detection based on LCMS-IT-TOF system in negative scan mode. The developed method was validated with respect to the limit of quantification, linear dynamic range, precision, accuracy, matrix effects and stabilities. All the results suggested that the presently developed method was sufficiently sensitive and robust enough to simultaneously monitor 15 ginsenosides with diverse properties and a large range of concentration differences. Therefore, this method would be expected to be highly useful for comprehensive studies of ginsenosides in complicated matrix.

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Analytical strategy to reveal the in vivo process of multi-component herbal medicine: A pharmacokinetic study of licorice using liquid chromatography coupled with triple quadrupole mass spectrometry

Cited by 87 publications

References 40 publications

Identification of Key Licorice Constituents Which Interact with Cytochrome P450: Evaluation by LC/MS/MS Cocktail Assay and Metabolic Profiling

Identification of Key Licorice Constituents Which Interact with Cytochrome P450: Evaluation by LC/MS/MS Cocktail Assay and Metabolic Profiling

Comparative pharmacokinetics and tissue distribution of cryptotanshinone, tanshinone IIA, dihydrotanshinone I, and tanshinone I after oral administration of pure tanshinones and liposoluble extract of Salvia miltiorrhiza to rats

Evaluation of liquid chromatography–ion trap–time of flight hybrid mass spectrometry on the quantitative analysis for ginsenosides

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