Identification of major α-glucosidase inhibitors in Radix Astragali and its human microsomal metabolites using ultrafiltration HPLC-DAD-MSn

Journal of Pharmaceutical and Biomedical Analysis

Volumn 104, Issue , 2015, Pages 31-37

  Zhao, Huading ^a   Zhang, Yuping ^a   Guo, Ying ^b   Shi, Shuyun ^a,b  

^a CENTRAL SOUTH UNIVERSITY   (China)

^b CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

Isoflavonoid; Microsomal metabolite; Radix Astragali; Ultrafiltration; Glucosidase

Indexed keywords

10 HYDROXY 3,9 DIMETHOXY PTEROCARPAN; 2' HYDROXY 7,3',4' TRIMETHOXYISOFLAVAN; 3 HYDROXY 9,10 DIMETHOXYPTEROCARPAN; 3',6 DIMETHOXY 4' HYDROXYISOFLAVONE 7 O BETA DEXTRO GLUCOPYRANOSIDE; AGLYCONE; ALPHA GLUCOSIDASE INHIBITOR; ASTRAGALUS EXTRACT; CALYCOSIN; CALYCOSIN 7 O BETA DEXTRO GLUCOPYRANOSIDE; FORMONONETIN; FORMONONETIN 7 O BETA DEXTRO GLUCOPYRANOSIDE; FORMONONETIN 7 O BETA DEXTRO GLUCOPYRANOSIDE 6'' ACETATE; ISOFLAVONOID; ISOMUCRONULATON; LIGAND; ODORATIN 7 O BETA DEXTRO GLUCOPYRANOSIDE; ODORATION; PRATENSEIN 7 O BETA DEXTRO GLUCOPYRANOSIDE; SALICYLIC ACID; UNCLASSIFIED DRUG; GLYCOSIDASE INHIBITOR; HERBACEOUS AGENT; HUANG QI;

ARTICLE; ASTRAGALUS PLANT; BINDING AFFINITY; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STRUCTURE; ENZYMATIC ASSAY; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; IN VIVO STUDY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAFILTRATION; CHEMISTRY; LIVER MICROSOME; METABOLISM; PROCEDURES;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG EVALUATION, PRECLINICAL; DRUGS, CHINESE HERBAL; GLYCOSIDE HYDROLASE INHIBITORS; HUMANS; MASS SPECTROMETRY; MICROSOMES, LIVER; ULTRAFILTRATION;

EID: 84913530176     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2014.09.029     Document Type: Article

References (35)

1. Van de Laar F.A., Lucassen P.L., Akkermans R.P., van de Lisdonk F.H., Rutten G.E., van Weel C. Alpha-glucosidase inhibitors for patients with type 2 diabetes: results from a Cochrane systematic review and meta-analysis. Diab. Care 2005, 28:154-163.
2. Saito N., Sakai H., Sekihara H., Yajima Y. Effect of an α-glucosidase inhibitor (voglibose), in combination with sulphonilureas, on glycaemic control in type 2 diabetes patients. J. Int. Med. Res. 1998, 26:219-232.
3. Muraoka O., Morikawa T., Miyake S., Akaki J., Ninomiya K., Yoshikawa M. Quantitative determination of potent α-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry. J. Pharmaceut. Biomed. Anal. 2010, 52:770-773.
4. Zheng K.Y.Z., Choi R.C.Y., Guo A.J.Y., Bi C.W.C., Zhu K.Y., Du C.Y.Q., Zhang Z.X., Lau D.T.W., Dong T.T.X., Tsim K.W.K. The membrane permeability of Astragali Radix-derived formononetin and calycosin is increased by Angelicae Sinensis Radix in Caco-2 cells: a synergistic action of an ancient herbal decoction Danggui Buxue Tang. J. Pharmaceut. Biomed. Anal. 2012, 70:671-679.
5. Chu C., Qi L.W., Li B., Gao W., Li P. Radix Astragali (Astragalus): latest advancements and trends in chemistry, analysis, pharmacology and pharmacokinetics. Curr. Org. Chem. 2010, 14:1792-1807.
6. Lau K.M., Lai K.K., Liu C.L., Tam J.C., To M.H., Kwok H.F., Lau C.P., Ko C.H., Leung P.C., Fung K.P., Poon S.K., Lau C.B. Synergistic interaction between Astragali Radix and Rehmanniae Radix in a Chinese herbal formula to promote diabetic wound healing. J. Ethnopharmacol. 2012, 141:250-256.
7. Lee J.S., Kim H.G., Han J.M., Kim D.W., Yi M.H., Son S.W., Kim Y.A., Lee J.S., Choi M.K., Son C.G. Ethanol extract of Astragali Radix and Salviae Miltiorrhizae Radix, Myelophil, exerts anti-amnesic effect in a mouse model of scopolamine-induced memory deficits. J. Ethnopharmacol. 2014, 153:782-792.
8. Zhang Q., Fong C.C., Yu W.K., Chen Y., Wei F., Koon C.M., Lau K.M., Leung P.C., Lau C.B.S., Fung K.P. Herbal formula Astragali Radix and Rehmanniae Radix exerted wound healing effect on human skin fibroblast cell line Hs27 via the activation of transformation growth factor (TGF-beta) pathway and promoting extracellular matrix (ECM) deposition. Phytomedicine 2012, 20:9-16.
9. Zhang Y.P., Nie M.K., Shi S.Y., You Q.P., Guo J.F., Liu L.L. Integration of magnetic solid phase fishing and off-line two-dimensional high-performance liquid chromatography-diode array detector-mass spectrometry for screening and identification of human serum albumin binders from Radix Astragali. Food Chem. 2014, 146:56-64.
10. Hu F.L., Deng C.H., Zhang X.M. Development of high performance liquid chromatography with immobilized enzyme onto magnetic nanospheres for screening enzyme inhibitor. J. Chromatogr. B 2008, 871:67-71.
11. Choi C.W., Choi Y.H., Cha M.R., Yoo D.S., Kim Y.S., Yon G.H., Hong K.S., Kim Y.H., Ryu S.Y. Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternatives to acarbose. J. Agric. Food Chem. 2010, 58:9988-9993.
12. Rao R.N., Prasad K.G. LC-Q-TOF-MS/MS determination of darunavir and its metabolites in rat serum and urine: application to pharmacokinetics. J. Pharmaceut. Biomed. Anal. 2014, 94:92-98.
13. Xu F., Zhang Y., Xiao S.Y., Lu X.W., Yang D.H., Yang X.D., Li C.L., Shang M.Y., Tu P.F., Cai S.Q. Absorption and metabolism of Astragali Radix decoction: in silico, in vitro, and a case study in vivo. Drug Metabo. Dispos. 2006, 34:913-924.
14. n technique. J. Pharmaceut. Biomed. Anal. 2012, 70:425-439.
15. Wen X.D., Qi L.W., Li B., Li P., Yi L., Wang Y.Q., Liu E.H., Yang X.L. Microsomal metabolism of calycosin, formonetin and drug-drug interactions by dynamic microdialysis sampling and HPLC-DAD-MS analysis. J. Pharmaceut. Biomed. Anal. 2009, 50:100-105.
16. Chen L., Li Z., Tang Y., Cui X., Luo R., Guo S., Zheng Y., Huang C. Isolation, identification and antiviral activities of metabolites of calycosin-7-O-β-d-glucopyranoside. J. Pharmaceut. Biomed. Anal. 2011, 56:382-389.
17. Wen D.X., Liu E.H., Yang J., Li C.Y., Gao W., Qi L.W., Zhang C.Z., Yuan C.S., Li P. Identification of metabolites of Buyang Huawu decotion in rat urine using liquid chromatography-quadrupole time-of-flight mass spectrometry. J. Pharmaceut. Biomed. Anal. 2012, 67-78(67):114-120.
18. Yang D.H., Ren X.L., Xu F., Ma X.Q., Liu G.X., Li C.H., Li C., Cai S.Q. Absorptive constituents and their metabolites in drug-containing urine samples from WUZHI Shan miniature pigs orally administered with Buyang Huanwu decoction. J. Nat. Med. 2014, 6:11-21.
19. n. Chromatographia 2013, 76:767-780.
20. Shi S.Y., Peng M.J., Zhang Y.P., Peng S. Combination of preparative HPLC and HSCCC methods to separate phosphodiesterase inhibitors from Eucommia ulmoides bark guided by ultrafiltration-based ligand screening. Anal. Bioanal. Chem. 2013, 405:4213-4223.
21. Zhang Y.P., Shi S.Y., Chen X.Q., Peng M.J. Functionalized magnetic nanoparticles coupled with mass spectrometry for screening and identification of cyclooxygenase-1inhibitors from natural products. J. Chromatogr. B 2014, 960:126-132.
22. Zhang Y.P., Shi S.Y., Guo J.F., You Q.P., Feng D.S. On-line surface plasmon resonance-high performance liquid chromatography-tandem mass spectrometry for analysis of human serum albumin binders from Radix Astragali. J. Chromatogr. A 2013, 1293:92-99.
23. Choi Y., Jermihov K., Nam S.J., Sturdy M., Maloney K., Qiu X., Chadwick L.R., Main M., Chen S.N., Mesecar A.D., Farnsworth N.R., Pauli G.F., Fenical W., Pezzuto J.M., van Breemen R.B. Screening natural products for inhibitors of quinine reductase-2 using ultrafiltration LC-MS. Anal. Chem. 2011, 83:1048-1052.
24. Delavenne X., Montbel A., Hodin S., Zufferey P., Basset T. Quantification of total and unbound tranexamic acid in human plasma by ultrafiltration liquid chromatography/tandem mass spectrometry: application to pharmacokinetic analysis. J. Pharmaceut. Biomed. Anal. 2014, 91:32-36.
25. Jensen B.P., Chin P.K.L., Begg E.J. Quantification of total and free concentrations of R- and S-warfarin in human plasma by ultrafiltration and LC-MS/MS. Anal. Bioanal. Chem. 2011, 40:2187-2193.
26. n. Anal. Bioanal. Chem. 2013, 405:7437-7445.
27. Yang D., Zhao J.D., Liu S., Song F.R., Liu Z.Q. The screening of potential α-glucosidase inhibitors from the Polygonum multiflorum extract using ultrafiltration combined with liquid chromatography-tandem mass spectrometry. Anal. Meth. 2014, 6:3353-3359.
28. n. Phytochem. Anal. 2011, 24:315-323.
29. n. Chin. J. Nat. Med. 2010, 8:202-207.
30. de Rijke E., Zappey H., Ariese F., Gooijer C., Brinkman U.A.T. Liquid chromatography with atmospheric pressure chemical ionization and electrospray ionization mass spectrometry of flavonoids with triple-quadrupole and ion-trap instruments. J. Chromatogr. A 2003, 984:45-58.
31. Umeda M., Amagaya S., Ogihara Y. Effects of certain herbal medicines on the biotransformation of arachidonic acid: a new pharmacological testing method using serum. J. Ethnopharmacol. 1988, 23:91-98.
32. Anhut S., Zinsmeister D., Mues R., Barz W., Mackenbrock K., Köster J., Markham K.R. The first identification of isoflavones from a bryophyte. Phytochemistry 1984, 23:1073-1075.
33. Day A.J., DuPont M.S., Ridley S., Rhodes M., Rhodes M.J.C., Morgan M.R.A., Willianson G. Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver β-glucosidase activity. FEBS Lett. 1998, 436:71-75.
34. Yuk H.J., Lee J.H., Curtis-Long M.J., Lee J.W., Kim Y.S., Ryu H.W., Park C.G., Jeong T.S., Park K.H. The most abundant polyphenol of soy leaves, coumestrol, displays potent α-glucosidase inhibitory activity. Food Chem. 2011, 126:1057-1063.
35. Yuk H.J., Curtis-Long M.J., Ryu H.W., Jang K.C., Seo W.D., Kim J.Y., Kang K.Y., Park K.H. Pterocarpan profiles for soybean leaves at different growth stages and investigation of their glycosidase inhibitions. J. Agric. Food Chem. 2011, 59:12683-12690.