Rapid Screening and Identification of Bioactive Compounds Specifically Binding to Beta 2-adrenoceptor from San-ao Decoction Using Affinity Magnetic Fine Particles Coupled with High-performance Liquid Chromatography-mass Spectrometry

Overview

Journal Chin Med

Publisher Biomed Central

Specialty Biomedical Engineering

Date 2018 Sep 28

PMID 30258489

Citations 2

Authors

Fuhuan Fei

Huanmei Sun

Xixi Cheng

Jiajun Liu

Jing Wang

Qian Li

Yajun Zhang

Affiliations

Soon will be listed here.

Abstract

Background: San-ao decoction (SAD) has been widely used in Chinese medicine against respiratory diseases, such as asthma and rhinallergosis. The bioactive compounds for such pharmacological action remain unknown.

Methods: We developed a methodology to isolate the bioactive compounds of SAD. The assay involved the immobilization of beta 2-adrenoceptor ( -AR) onto magnetic fine particles, the capture of target compounds by the immobilized receptor, the identification of the receptor bound compounds by reversed-phase high-performance liquid chromatography coupled with tandem mass spectrometry.

Results: Vicenin, shaftoside, isoshaftoside, liquiritin apioside and isoliquiritin apioside were identified as -AR ligands in SAD extract. The binding of these compounds to -AR occurred on serine, serine and phenylalanine of the receptor.

Conclusions: The developed methodology has high stability and specificity for recognizing and isolating target compounds. It is an alternative method for rapidly screening bioactive compounds of immobilized receptor from Chinese prescriptions.

Citing Articles

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Exploring new targets and chemical space with affinity selection-mass spectrometry.

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References

Yang Y, Zhang W, Yang F, Zhou B, Zeng D, Zhang N . Ru nanoparticles dispersed on magnetic yolk-shell nanoarchitectures with FeO core and sulfoacid-containing periodic mesoporous organosilica shell as bifunctional catalysts for direct conversion of cellulose to isosorbide. Nanoscale. 2018; 10(5):2199-2206. DOI: 10.1039/c7nr07875g. View

Wang Z, Li X, Chen M, Liu F, Han C, Kong L . A strategy for screening of α-glucosidase inhibitors from Morus alba root bark based on the ligand fishing combined with high-performance liquid chromatography mass spectrometer and molecular docking. Talanta. 2018; 180:337-345. DOI: 10.1016/j.talanta.2017.12.065. View

Liu G, Wang P, Li C, Wang J, Sun Z, Zhao X . Confirming therapeutic target of protopine using immobilized β -adrenoceptor coupled with site-directed molecular docking and the target-drug interaction by frontal analysis and injection amount-dependent method. J Mol Recognit. 2017; 30(7). DOI: 10.1002/jmr.2613. View

Qinga L, Xue Y, Zheng Y, Xiong J, Liao X, Ding L . Ligand fishing from Dioscorea nipponica extract using human serum albumin functionalized magnetic nanoparticles. J Chromatogr A. 2010; 1217(28):4663-8. PMC: 2955990. DOI: 10.1016/j.chroma.2010.05.009. View

Marszall M, Bucinski A . A protein-coated magnetic beads as a tool for the rapid drug-protein binding study. J Pharm Biomed Anal. 2009; 52(3):420-4. DOI: 10.1016/j.jpba.2009.06.023. View

Bagdas D, Muldoon P, AlSharari S, Carroll F, Negus S, Damaj M . Expression and pharmacological modulation of visceral pain-induced conditioned place aversion in mice. Neuropharmacology. 2015; 102:236-43. PMC: 5574195. DOI: 10.1016/j.neuropharm.2015.11.024. View

Zeng K, Li Q, Wang J, Yin G, Zhang Y, Xiao C . One-step methodology for the direct covalent capture of GPCRs from complex matrices onto solid surfaces based on the bioorthogonal reaction between haloalkane dehalogenase and chloroalkanes. Chem Sci. 2018; 9(2):446-456. PMC: 5868316. DOI: 10.1039/c7sc03887a. View

Li Z, Liu T, Liao J, Ai N, Fan X, Cheng Y . Deciphering chemical interactions between Glycyrrhizae Radix and Coptidis Rhizoma by liquid chromatography with transformed multiple reaction monitoring mass spectrometry. J Sep Sci. 2017; 40(6):1254-1265. DOI: 10.1002/jssc.201601054. View

Wang J, Li F, Zeng K, Li Q, Zhao X, Zheng X . Bioactive compounds of Shuang-Huang-Lian prescription and an insight into its binding mechanism by β -adrenoceptor chromatography coupled with site-directed molecular docking. J Sep Sci. 2017; 40(22):4357-4365. DOI: 10.1002/jssc.201700522. View

10.

Zhao X, Li Q, Xiao C, Zhang Y, Bian L, Zheng J . Oriented immobilisation of histidine-tagged protein and its application in exploring interactions between ligands and proteins. Anal Bioanal Chem. 2014; 406(12):2975-85. DOI: 10.1007/s00216-014-7723-x. View

11.

Newman D, Cragg G . Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod. 2012; 75(3):311-35. PMC: 3721181. DOI: 10.1021/np200906s. View

12.

Li L, Zhou X, Li N, Sun M, Lv J, Xu Z . Herbal drugs against cardiovascular disease: traditional medicine and modern development. Drug Discov Today. 2015; 20(9):1074-86. DOI: 10.1016/j.drudis.2015.04.009. View

13.

Ren L, Xue X, Zhang F, Xu Q, Liang X . High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs. J Sep Sci. 2007; 30(6):833-42. DOI: 10.1002/jssc.200600246. View

14.

Tu Y . The discovery of artemisinin (qinghaosu) and gifts from Chinese medicine. Nat Med. 2011; 17(10):1217-20. DOI: 10.1038/nm.2471. View

15.

Ma C, Qian Y, Fan X, Shang E, Yao X, Ma S . Using UPLC-QTOF-MS to analyze the chemical changes between traditional and dispensing granule decoctions of San-Ao-Tang. J Chromatogr Sci. 2013; 52(4):277-92. DOI: 10.1093/chromsci/bmt026. View

16.

Johnson M . Beta2-adrenoceptors: mechanisms of action of beta2-agonists. Paediatr Respir Rev. 2005; 2(1):57-62. DOI: 10.1053/prrv.2000.0102. View

17.

Wubshet S, Brighente I, Moaddel R, Staerk D . Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae. J Nat Prod. 2015; 78(11):2657-65. PMC: 5036580. DOI: 10.1021/acs.jnatprod.5b00603. View

18.

Li Z, Gao H, Li J, Zhang Y . Identification of bioactive compounds in Shaoyao-Gancao decoction using β2-adrenoceptor affinity chromatography. J Sep Sci. 2017; 40(12):2558-2564. DOI: 10.1002/jssc.201700113. View

19.

Can K, Ozmen M, Ersoz M . Immobilization of albumin on aminosilane modified superparamagnetic magnetite nanoparticles and its characterization. Colloids Surf B Biointerfaces. 2009; 71(1):154-9. DOI: 10.1016/j.colsurfb.2009.01.021. View

20.

Ciesla L, Moaddel R . Comparison of analytical techniques for the identification of bioactive compounds from natural products. Nat Prod Rep. 2016; 33(10):1131-45. PMC: 5042860. DOI: 10.1039/c6np00016a. View