Analysis and improved characterization of minor antioxidants from leaves of Malus doumeri using a combination of major constituents' knockout with high-performance liquid chromatography-diode array detector-quadrupole time-of-flight tandem mass spectrometry

Journal of Chromatography A

Volumn 1398, Issue , 2015, Pages 57-65

  Zhao, Huading ^a   Hu, Xin ^a   Chen, Xiaoqin ^a   Shi, Shuyun ^a   Jiang, Xinyu ^a   Liang, Xuejuan ^b   Chen, Wei ^b   Zhang, Shuihan ^b  

^a CENTRAL SOUTH UNIVERSITY   (China)

^b Hunan Academy of Chinese Medicine   (China)

Author keywords

Antioxidant; DPPH HPLC; HSCCC; Knockout; Malus doumeri

Indexed keywords

DRUG PRODUCTS; FLAVONOIDS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PLANTS (BOTANY); ULTRAVIOLET SPECTROSCOPY;

1 ,1-DIPHENYL-2-PICRYLHYDRAZYL; DPPH-HPLC; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY-DIODE ARRAY DETECTORS; HSCCC; KNOCKOUT; MALUS DOUMERI; QUADRUPOLE TIME-OF-FLIGHT TANDEM MASS SPECTROMETRIES; STEPWISE HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHIES;

ANTIOXIDANTS;

3 HYDROXYPHLORIDZIN; 3,5 DIHYDROXYPHLORIDZIN; 3,5 DIHYDROXYTRILOBATIN; 4',6' DIHYDROXYHYDROCHALCONE 2' O BETA GLUCOPYRANOSIDE; APIGENIN; AUREUSIDIN O BETA GLUCOPYRANOSIDE; AURONE; CAFFEIC ACID; CHALCONE DERIVATIVE; CHRYSIN 5 O BETA GLUCOPYRANOSIDE; COUMARIC ACID; DIHYDROCAFFEIC ACID; DIHYDROCHALCONE; ERIODICTYOL 5 O BETA GLUCOPYRANOSIDE; FERULIC ACID; FLAVANONE; FLAVONE DERIVATIVE; FLAVONOL DERIVATIVE; HYPERIN; ISOQUERCITRIN; METHYL 3,5 DIHYDROXYPHLORIDZIN; NATURAL PRODUCT; PHENOLIC ACID; PHLORETIC ACID; PHLORIZIN; PROTOCATECHUIC ACID; QUERCETIN; SYRINGIC ACID 4 O BETA GLUCOPYRANOSIDE; TRIBLOBATIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTIOXIDANT; PLANT EXTRACT;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; COUNTER CURRENT CHROMATOGRAPHY; DIODE ARRAY DETECTOR; DPPH RADICAL SCAVENGING ASSAY; GENE INACTIVATION; GENERAL DEVICE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALUS; MALUS DOUMERI; NONHUMAN; PLANT LEAF; PRIORITY JOURNAL; QUADRUPOLE MASS SPECTROMETRY; SIGNAL PROCESSING; STRUCTURE ANALYSIS; TAIWAN; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; MASS SPECTROMETRY; PROCEDURES;

MALUS DOUMERI;

ANTIOXIDANTS; CHEMISTRY TECHNIQUES, ANALYTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MALUS; MASS SPECTROMETRY; PLANT EXTRACTS; PLANT LEAVES; TANDEM MASS SPECTROMETRY;

EID: 84929269948     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2015.04.018     Document Type: Article

References (46)

1. O'Connor C.J., Beckmann H.S.G., Spring D.R. Diversity-oriented synthesis: producing chemical tools for dissecting biology. Chem. Soc. Rev. 2012, 41:4444-4456.
2. Shi S.Y., Zhou H.H., Zhang Y.P., Jiang X.Y., Chen X.Q., Huang K.L. Coupling HPLC to on-line, post-column (bio)chemical assays for high-resolution screening of bioactive compounds from complex mixtures. Trends Anal. Chem. 2009, 28:865-877.
3. Newman D.J., Cragg G.M. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 2012, 75:311-335.
4. Qiu F., Cai G., Jaki B.U., Lankin D.C., Franzblau S.G., Pauli G.F. Quantitativepurity-activity relationships of natural products: the case of anti-tuberculosisactive triterpenes from Oplopanax horridus. J. Nat. Prod. 2013, 76:413-419.
5. Jaki B.U., Franzblau S.G., Chadwick L.R., Lankin D.C., Zhang F.Q., Wang Y., Pauli G.F. Purity-activity relationships of natural products: the case of anti-TB activeursolic acid. J. Nat. Prod. 2008, 71:1742-1748.
6. Li D.Q., Zhao J., Li S.P. High-performance liquid chromatography coupled with post-column dual-bioactivity assay for simultaneous screening of xanthine oxidase inhibitors and free radical scavengers from complex mixture. J. Chromatogr. A 2014, 1345:50-56.
7. Zhang Y.P., Shi S.Y., Xiong X., Chen X.Q., Peng M.J. Comparative evaluation of three methods based on high-performance liquid chromatography analysis combined with a 2,2'-diphenyl-1-picrylhydrazyl assay for the rapid screening of antioxidants from Pueraria lobata flowers. Anal. Bioanal. Chem. 2012, 402:2965-2976.
8. Montero L., Herrero M., Ibáñez E., Cifuentes A. Profiling of phenolic compounds from different apple varieties using comprehensive two-dimensional liquid chromatography. J. Chromatogr. A 2014, 1313:275-283.
9. Qiu Y.K., Chen F.F., Zhang L.L., Yan X., Chen L., Fang M.J., Wu Z. Two-dimensional preparative liquid chromatography system for preparative separation of minor amount components from complicated natural products. Anal. Chim. Acta 2014, 820:176-186.
10. Qiao X., Song W., Ji S., Li Y.J., Wang Y., Li R., An R., Guo D.A., Ye M. Separation and detection of minor constituents in herbal medicines using a combination of heart-cutting and comprehensive two-dimensional liquid chromatography. J. Chromatogr. A 2014, 1362:157-167.
11. 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.
12. Rodríguez-Cabo T., Rodríguez I., López P., Ramil M., Cela R. Investigation of liquid chromatography quadrupole time-of-flight mass spectrometry performance for identification for identification and determination of hydroxylated stilbene antioxidants in wine. J. Chromatogr. A 2014, 1337:162-170.
13. Ling Y., Liu K.Y., Zhang Q., Liao L., Lu Y.H. High performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight-mass spectrometry as a powerful strategy for systematic analysis and improved characterization of the major bioactive constituents from Radix Dipsaci. J. Pharm. Biomed. Anal. 2014, 98:120-129.
14. Dugo P., Cacciola F., Donato P., Jacques R.A., Caramao E.B., Mondello L. High efficiency liquid chromatography techniques coupled to mass spectrometry for the characterization of mate extracts. J. Chromatogr. A 2009, 1216:7213-7221.
15. Bordbar A., Monk J.M., King Z.A., Palsso B.O. Constraint-based models predict metabolic and associated cellular functions. Nat. Rev. Genet. 2014, 15:107-120.
16. 2S production in Pakinson's disease gene knockout astrocytes. J. Am. Chem. Soc. 2013, 135:9915-9923.
17. Chen J.Y., Ge Z.Z., Zhu W., Xu Z., Li C.M. Screening of key antioxidant compounds of longan (Dimocarpus longan Lour.) seed extract by combining online fishing/knockout, activity evaluation, Fourier transform ion cyclotron resonance mass spectrometry, and high-performance liquid chromatography electrospray ionization mass spectrometry methods. J. Agric. Food Chem. 2014, 62:9744-9750.
18. Jin J., Li Y.B., Tanui E.K., Han L.W., Jia Y., Zhang L., Wang Y.M., Zhang X.X., Zhang Y.J. Fishing and knockout of bioactive compounds using a combination of high-speed counter-current chromatography (HSCCC) and preparative HPLC for evaluating the holistic efficacy and interaction of the components of Herba Epimedii. J. Ethnopharmacol. 2013, 147:357-365.
19. Liu Y., Zhou J.L., Liu P., Sun S., Li P. Chemical markers' fishing and knockout for holistc activity and interaction evaluation of the components in herbal medicines. J. Chromatogr. A 2010, 1217:5239-5245.
20. Uto T., Morinaga O., Tanaka H., Shoyama Y. Analysis of the synergistic effect of glycyrrhizin and other constituents in licorice extract on lipopolysaccharide-induced nitric oxide producton using knock-out extract. Biochem. Biophys. Res. Commun. 2012, 417:473-478.
21. Kao M.T. Popular Herbal Remedies of Taiwan 1996, 54. SMC Publishing Inc., Taipei.
22. Lin Y.P., Hsu F.L., Chen C.S., Chern J.W., Lee M.H. Constituents from the Formosan apple reduce tyrosinase activity in human epidermal melanocytes. Phytochemistry 2007, 68:1189-1199.
23. Leu S.J., Lin Y.P., Lin R.D., Wen C.L., Cheng K.T., Hsu F.L., Lee M.H. Phenolic constituents of Malus doumeri var. formosana in the Field of skin care. Biol. Pharm. Bull. 2006, 29:740-745.
24. Lin Y.P., Hsu F.L., Chen C.S., Chern J.W., Lee M.H. Constituents from the Formosan apple reduce tyrosinase activity in human epidermal melanocytes. Phytochemistry 2007, 68:1189-1199.
25. Jerz G., Gebers N., Szot D., Szalenier M., Winterhalter P., Wybraniec S. Separation of amaranthinetype betacyanins by ion-pair high-speed countercurrent chromatography. J. Chromatogr. A 2014, 1344:42-55.
26. Regalado E.L., Tolle S., Pino J.A., Winterhalter P., Menendez R., Morales A.R., Rodríguez J.L. Isolation and identification of phenolic compounds from rum aged in oak barrels by high-speed countercurrent chromatography/high-performance liquid chromatography-diode array detection-electrospray ionization mass spectrometry and screening for antioxidant activity. J. Chromatogr. A 2011, 1218:7358-7364.
27. Zhou X.L., Liang J.S., Zhang Y., Zhao H.D., Guo Y., Shi S.Y. Separation and purification of α-glucosidase inhibitors from Polygonatum odoratum by stepwise high-speed counter-current chromatography combined with Sephadex LH-20 chromatography target-guided by ultrafiltration-HPLC screening. J. Chromatogr. B 2015, 985:149-154.
28. Pérez-Bonilla M., Salido S., van Beek T.A., Linares-Palomino P.J., Altarejos J., Nogueras M., Sánchez A. Isolation and identification of radical scavengers in olive tree (Olea europaea) wood. J. Chromatogr. A 2006, 1112:311-318.
29. Liu Q., Zeng H.L., Jiang S.J., Zhang L., Yang F.Z., Chen X.Q., Yang H. Separation of polyphenols from leaves of Malus hupehensis (Pamp.) Rehder by off-line two-dimensional High Speed Counter-Current Chromatography combined with recycling elution mode. Food Chem. 2014, 10.1016/j.foodchem.2014.09.037.
30. Dick A.J., Redden P.R., DeMarco A.C., Lidster P.D., Grindley T.B. Flavonoid glycosides of Spartan apple peel. J. Agric. Food Chem. 1987, 35:529-531.
31. Williams A.H. Dibenzoylmethanes and flavones of Malus. Phytochemistry 1979, 18:1897-1898.
32. Liang X.J., Zhang Y.P., Chen W., Cai P., Zhang S.H., Chen X.Q., Shi S.Y. High-speed counter-current chromatography coupled online to high performance liquid chromatography-diode array detector-mass spectrometry for purification, analysis and identification of target compounds from natural products. J. Chromatogr. A 2015, 1385:69-76.
33. 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.
34. Sun L., Li H.K., Willson K., Breidinger S., Rizk M.L., Wenning L., Woolf E.J. Ultrasensitive liquid chromatography-tandem mass spectrometric methodologies for quantification of five HIV-1 integrase inhibitors in plasma for a microdose clinical trial. Anal. Chem. 2012, 84:8614-8621.
35. Portet B., Fabre N., Rozenberg R., Habib-Jiwan J., Moulis C., Quetin-Leclercq J. Analysis of minor flavonoids in Piper hostmannianum var. Berbicense using liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry. J. Chromatogr. A 2008, 1210:45-54.
36. Fang N., Yu S., Prior R.L. LC/MS/MS characterization of phenolic constituents in dried plums. J. Agric. Food Chem. 2002, 50:3579-3585.
37. Shi S.Y., Zhao Y., Zhou H.H., Zhang Y.P., jiang X.Y., Huang K.L. Identification of antioxidants from Taraxacum mongolicum by high-performance liquid chromatography-diode array detection-radical-scavenging detection-electrospray ionization mass spectrometry and nuclear magnetic resonance experiments. J. Chromatogr. A 2008, 1209:145-152.
38. Lu Y.R., Foo L.Y. Identification and quantification of major polyphenols in apple pomace. Food Chem. 1997, 59:187-194.
39. Aladedunye F., Matthäus B. Phenolic extracts from Sorbus aucuparia (L.) and Malus baccata (L.) berries: antioxidant activity and performance in rapeseed oil during frying and storage. Food Chem. 2014, 159:273-281.
40. Ramirez-Ambrosi M., Abad-Garcia B., Viloria-Bernal M., Garmon-Lobato S., Berrueta L.A., Gallo B. A new ultrahigh performance liquid chromatography with diode array detection coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry analytical strategy for fast analysis and improved characterization of phenolic compounds in apple products. J. Chromatogr. A 2013, 1316:78-91.
41. Dong H.Q., Li M., Zhu F., Liu F.L., Huang J.B. Inhibitory potential of trilobatin from Lithocarpus polystachyus Rehd against α-glucoside and α-amylase linked to type 2 diabetes. Food Chem. 2012, 130:261-266.
42. Fabre N., Rustan I., de Hoffmann E., Quetin-Leclercq J. Determination of flavones, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J. Am. Mass Spectrom. 2001, 12:707-715.
43. 18 column. J. Chromatogr. A 2008, 1185:117-129.
44. Masao H., Teruo S. Flavanoids of various Prunus species. V. The flavanoids in the wood of Prunus verecunda. J. Am. Chem. Soc. 1957, 79:450-452.
45. Lommen A., Godejohann M., Venema D.P., Hollman P.C.H., Spraul M. Application of directly coupled HPLC-NMR-MS to the identification and confirmation of quercetin glycosides and phloretin glycosides in apple peel. Anal. Chem. 2000, 72:1793-1797.
46. Morikawa T., Wang L.B., Nakamura S., Ninomiya K., Yokoyama E., Matsuda H., Muraoka O., Wu L.J., Yoshikawa M. Medicinal flowers. XXVII. New flavanone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-α inhibitors from everlasting, flowers of Helichrysum arenarium. Chem. Pharm. Bull. 2009, 57:361-367.