Qualitative and quantitative studies on chemical constituents of Ling-gui-zhu-gan decoction: In vitro and in vivo.

Fourier transform ion cyclotron resonance mass spectrometry Ling-gui-zhu-gan decoction chemical constituents identification metabolite

Journal

Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554

Informations de publication

Date de publication:
Oct 2023
Historique:
revised: 29 07 2023
received: 27 06 2023
accepted: 02 08 2023
pubmed: 12 8 2023
medline: 12 8 2023
entrez: 11 8 2023
Statut: ppublish

Résumé

Ling-gui-zhu-gan decoction has significant therapeutic effects in the treatment of diseases related to phlegm and fluid retention. In this study, we aimed to qualitatively characterize the chemical constituents of Ling-gui-zhu-gan decoction in vitro and in vivo by HPLC coupled to Fourier transform ion cyclotron resonance MS, and quantitively determine the contents of typical chemical constituents by HPLC method. As a result, a total of 75 chemical constituents were discovered including 37 flavonoids and their glycosides, 20 saponins, 9 sterols, 3 organic acids and their derivatives, 3 lactones, 2 coumarins, and 1 alcohol. Among them, 17 chemical constituents were specifically identified. Subsequently, an HPLC method was established for simultaneous determination of seven chemical constituents. Finally, a total of 40 prototype components were initially detected by HPLC-MS method in the biological samples of rats after their water extract was orally administrated. Among them, 29, 27, 12, and 32 prototype components were detected in plasma, bile, urine, and feces, respectively. Moreover, 34 metabolites, including 16 phase II metabolites, were detected for the first time. In conclusion, this study lays the foundation for the identification of chemical components in vitro and in vivo and the elucidation of the potential pharmacodynamic components of Ling-gui-zhu-gan decoction.

Identifiants

pubmed: 37568255
doi: 10.1002/jssc.202300465
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e2300465

Subventions

Organisme : National Natural Science Foundation of China
ID : 82274077
Organisme : Natural Science Foundation of Liaoning Province
ID : 2021-MS-220
Organisme : Career Development Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University
ID : ZQN2018007
Organisme : Career Development Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University
ID : ZQN202204

Informations de copyright

© 2023 Wiley-VCH GmbH.

Références

Wang L, Shi H, Huang JL, Xu S, Liu PP. Linggui zhugan decoction inhibits ventricular remodeling after acute myocardial infarction in rats by suppressing TGF-1β/Smad signaling pathway. Chin J Integr Med. 2019;26:345-52.
Zhang JJ, Huang YJ, Ke B, Liu LP, Shangguan JJ, Meng J, et al. Effect of alternate-day fasting therapy combined with Linggui Zhugan decoction on hepatic oxidative stress in hyperlipidemic rat. Chin J Integr Med. 2015:1672-0415.https://doi.org/10.1007/s11655-014-1999-8
Sun S, Xun G, Zhang J, Gao YH, Ge JC, Liu FF, et al. An integrated approach for investigating pharmacodynamic material basis of Lingguizhugan decoction in the treatment of heart failure. J Ethnopharmacol. 2022;295:115366.
Wang X, Gao Y, Tian Y, Liu X, Zhang G, Wang Q, et al. Integrative serum metabolomics and network analysis on mechanisms exploration of Ling-Gui-Zhu-Gan decoction on doxorubicin-induced heart failure mice(Article). J Ethnopharmacol. 2020;250:112397.
Wang X, Gao YH, Zhang J, Zhang HX, Sun S, Su SW, et al. Revealment study on the regulation of lipid metabolism by Lingguizhugan decoction in heart failure treatment based on integrated lipidomics and proteomics. Biomed Pharmacother. 2022;158:114066.
Li YM, Wu HQ, Zhang BX, Xu X, Wang YJ, Song QQ, Efficacy and safety of Linggui Zhugan decoction in the treatment of chronic heart failure with Yang deficiency: a protocol for systematic review and meta-analysis. Medicine. 2021;100:e26012.
Chen X, Huang WX, Lv HM, Qin J, Ke B, Shen WZ. Identification of Cald1 as a novel regulator of Linggui Zhugan decoction for improving insulin resistance in vivo and in vitro. J Tradit Chin Med. 2021;41:706-16.
Chen JM, Zhou CX. Advances in pharmacological mechanism of Linggui Zhugan tang. Chin J ETMF. 2019;25:222-7.
Tang TJ, Wang X, Zhou P, Wang L, Shi H, Huang JL. Effect of Linggui Zhugan decoction-containing serum on mitochondrial oxidative stress in cardiomyocytes: an exploration based on Nrf2/BNIP3 signaling pathway. China J Chin Mater Med. 2022;47:3303-11.
Zhou P, Zhang M, Zhao XN, Tang TJ, Wang X, Huang LL, et al. Exploring the mechanism of Ling-Gui-Zhu-Gan decoction in ventricular remodeling after acute myocardial infarction based on UPLC and in vivo experiments. Evid-Based Compl Alt Med. 2022;2002:1-14.
Xi FF, Sang F, Zhou CX, Ling Y. Protective effects of Lingguizhugan decoction on amyloid-beta peptide (25-35)-induced cell injury: anti-inflammatory effects, J Neural Regen Res. 2012;7:2867-73.
Sang F, Zhou CX. Experimental research on the effect of Ling Gui Zhu Gan decoction on the pathogenesis of AD. J Tradit Chin Med. 2011;6:685-7.
Han J, Zhang HT, Zhang Y, Zhang Z, Yu MM, Wang SJ, et al. Lingguizhugan decoction protects PC12 cells against Aβ25-35-induced oxidative stress and neuroinflammation by modulating NF-κB/MAPK signaling pathways. J Ethnopharmacol. 2022;292:115194.
Dong W, Hao XJ, Wang CZ, Guo LN, Pan H, Lin Y, et al. Serum pharmacochemistry of honey-fried Stemona tuberosa Lour. by UHPLC-QTOF/MS and MetaboLynx analysis. Acta Pharm Sin. 2016;51:1458-63.
Zhang AH, Sun H, Yan GL, Han Y, Wang XJ. Establishment of three-dimensional integrated “serum pharmacochemistry-pharmacokinetics (pharmacodynamics)-systems biology” for research of traditional Chinese medicine prescription and its application in Yinchenhao Tang. China J Chin Mater Med. 2013;38:3786-9.
Zhou J, Yi H, Zhao ZX, Shang XY, Zhu MJ, Kuang GJ, et al. Simultaneous qualitative and quantitative evaluation of Ilex kudingcha C. J. tseng by using UPLC and UHPLC-qTOF-MS/MS. J Pharm Biomed Anal. 2018;155:15-26.
Lin P, Wang Q, Liu YH, Jiang H, Lv WH, Lan TH, et al. Qualitative and quantitative analysis of the chemical profile for Gualou-Xiebai-Banxia decoction, a classical traditional Chinese medicine formula for the treatment of coronary heart disease, by UPLC-Q/TOF-MS combined with chemometric analysis. J Pharm Biomed Anal. 2021;197:113950.
Salleh WMNHW, Shakri NM, Jauri MH, Nafiah MA. Alkaloids and flavonoids from Polyalthia cauliflora. Chem Nat Compounds. 2022;58:986-8.
Wang Z, Sun B, Yang R, Jia AQ. Flavonoids and other phenolics from Camellia nitidissima chi flowers. Nat Prod Res. 2023;37:180-7.
Liu S, Meng ZL, Zhang HY, Chu YX, Qiu YY, Jin B, et al. Identification and characterization of thirteen gene families involved in flavonoid biosynthesis in Ginkgo biloba. Ind Crops Prod. 2022;188:115576.
Sun M, Yang FF, Hou WY, Jiang SF, Yang RQ, Zhang W, et al. Dynamic variation of amino acid contents and identification of sterols in Xinyang Mao Jian green tea. Molecules. 2022;27:3562.
Yan Y, Abdulla R, Liu X, Li S, Aisa HA. Comprehensive chemical profile and quantitative analysis of the Shabyar tablet, a traditional ethnic medicine prescription, by ultra-high-performance liquid chromatography with quadrupole-orbitrap high-resolution mass spectrometry. J Sep Sci. 2022;45:2148-60.
Wei Z, Yu X, Zhang Y, Wang Y, Zhang H, Wang S, et al. Studies on chemical constituents of Flos Puerariae-Semen Hoveniae medicine pair by HPLC and Fourier transform ion cyclotron resonance mass spectrometry. J Sep Sci. 2022;45:477-91.
Liu WJ, Li W, Zhang PJ, Gong XC, Tu PF, Tang L, et al. Quality structural annotation for the metabolites of chlorogenic acid in rat. Food Chem. 2022;379:132134.
Zhao Y, Lu H, Wang Q, Liu H, Shen H, Xu W, et al. Rapid qualitative profiling and quantitative analysis of phenolics in Ribes meyeri leaves and their antioxidant and antidiabetic activities by HPLC-QTOF-MS/MS and UHPLC-MS/MS. J Sep Sci. 2021;44:1404-20.
Moscovitz JE, Aleksunes LM. Establishment of metabolism and transport pathways in the rodent and human fetal liver. Int J Mol Sci. 2013;14:23801-27.
Holcapek M, Kolárová L, Nobilis M. High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites. Anal Bioanal Chem. 2008;391:59-78.
Herbert M. Forensic relevance of glucuronidation in phase-II-metabolism of alcohols and drugs. Leg Med. 2009;11:S22-6.
Kampe T, König A, Schroeder H, Hengstler JG, Niemeyer CM. Modular microflfluidic system for emulation human phase I/phase II metabolism. Anal Chem. 2014;86:3068-74.
Mullen W, Boitier A, Stewart AJ, Crozier A. Flavonoid metabolites in human plasma and urine after the consumption of red onions: analysis by liquid chromatography with photodiode array and full scan tandem mass spectrometric detection. J Chromatogr A. 2004;1058:163-8.
Miners JO, Smith PA, Sorich MJ, McKinnon RA, Mackenzie PI. Predicting human drug glucuronidation parameters: application of in vitro and in silico modeling approaches. Annu Rev Pharmacol Toxicol. 2004;44:1-25.
Wang SN, Sun LJ, Gu LQ, Zhang YY, Zhao SM, Zhao LS, et al. The comparative pharmacokinetics of four bioactive ingredients after administration of Ramulus Cinnamomi-Radix Glycyrrhizae herb pair extract, Ramulus Cinnamomi extract and Radix Glycyrrhizae extract. Biomed Chromatogr. 2016;30:1270-7.
Huang L, Nikolic D, van Breemen RB. Hepatic metabolism of licochalcone A, a potential chemopreventive chalcone from licorice (Glycyrrhiza inflflata),determined using liquid chromatography-tandem mass spectrometry. AnalBioanal Chem. 2017;409:6937-48.
Li SM, Wang ZY, Sang SM, Huang MT, Ho CT. Identification of nobiletin metabolites in mouse urine. Mol Nutr Food Res. 2006;50:291-9.
Xu LL, He YQ, Guo X, Lu YH, Wang CH, Wang ZT. Metabolites characterization of chamaechromone in vivo and in vitro by using ultra-performance liquid chromatography/Xevo G2 quadrupole time-of-flight tandem mass spectrometry. J Ethnopharmacol. 2011;151:242-52.
Lin L, Liu XB, Zhou QY, Liu SS, Zuo MT, Zeng JG, et al. Characterization of in vitro metabolites of three tetrahydroprotoberberine alkaloids in rat liver S9 by high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2018;32:1540-8.
Luo KW, Feng F. Identification of absorbed components and metabolites of Zhi-Zi-Hou-Po decoction in rat plasma after oral administration by an untargeted metabolomics-driven strategy based on LC-MS. Anal Bioanal Chem. 2016;408:5723-35.
Xu TT, Yang M, Li YF, Chen X, Wang QR, Deng WP, et al. An integrated exact mass spectrometric strategy for comprehensive and rapid characterization of phenolic compounds in licorice. Rapid Commun Mass Spectrom. 2013;27:2297-309.
Xu H, Li YL, Che X, Tian HC, Fan HY, Liu K. Metabolism of salvianolic acid A and antioxidant activities of its methylated metabolites. Drug Metab Dispos. 2014;42: 274-81.
Wei Y, Li P, Wang C, Peng YR, Shu L, Jia XB, et al. Metabolism of tanshinone IIA, cryptotanshinone and tanshinone I from Radix Salvia miltiorrhiza in zebrafifish. Molecules. 2012;17:8617-32.
Sun JH, Yang M, Han J, Wang BR, Ma XC, Xu M, et al. Profiling the metabolic difference of seven tanshinones using high-performance liquid chromatography/multi-stage mass spectrometry with data-dependent acquisition. Rapid Commun Mass Spectrom. 2007;21:2211-26.

Auteurs

Siyue Li (S)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Yutong Gao (Y)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Xue Wang (X)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Zhe Wang (Z)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Nan Li (N)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Yonglin Shang (Y)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Fei Han (F)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Jia Yu (J)

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

Classifications MeSH