Login Register Cart 0
Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
General Review Article

Detection, Identification and Structural Elucidation of Flavonoids using Liquid Chromatography Coupled to Mass Spectrometry

Author(s): Krzysztof Kamil Wojtanowski* and Tomasz Mroczek

Volume 24, Issue 1, 2020

Page: [104 - 112] Pages: 9

DOI: 10.2174/1385272824666200123104815

Price: $65

Abstract

Flavonoids are one of the most common secondary metabolites occurring in plants. Their activity in the Central Nervous System (CNS) including sedative, anxiolytic, anti-convulsive, anti-depressant and neuro-protective actions is well known and documented. The most popular methods for detection, identification and structural elucidation of flavonoids are these based on Nuclear Magnetic Resonance (NMR) and mass spectrometry (MS). NMR allows rapid, high throughput analysis of crude extracts and also gives stereochemical details about identified substances. However, these methods are expensive and less sensitive than MS-based techniques. Combining High Performance Liquid Chromatography (HPLC) with MS detection gives the most powerful tool for analysis of flavonoids occurring in plants. There is a lot of different approaches to use LC/MS based techniques for identification of flavonoids and this short review shows the most important.

Keywords: Flavonoids, mass spectrometry, HPLC, LC-MS, CNS, analysis.

« Previous Next »
Graphical Abstract

[1]
Jäger, A.K.; Saaby, L. Flavonoids and the CNS. Molecules, 2011, 16(2), 1471-1485.
[http://dx.doi.org/10.3390/molecules16021471] [PMID: 21311414]
[2]
Fernández, S.P.; Wasowski, C.; Loscalzo, L.M.; Granger, R.E.; Johnston, G.A.R.; Paladini, A.C.; Marder, M. Central nervous system depressant action of flavonoid glycosides. Eur. J. Pharmacol., 2006, 539(3), 168-176.
[http://dx.doi.org/10.1016/j.ejphar.2006.04.004] [PMID: 16698011]
[3]
Pinheiro, F.P.; Justino, G.C. Structural analysis of flavonoids and related compounds – a review of spectroscopic applications.Phytochemicals - A Global Perspective of Their Role in Nutrition and Health; Venketeshwer, R., Ed.; 33-56.
[4]
McNaught, A.D.; Wilkinson, A. IUPAC, Compendium of Chemical Terminology, Electronic version (2006) of IUPAC. In: Compendium of Chemical Terminology, 2nded. (The “Gold Book”);,
[5]
Middleton, E., Jr Effect of plant flavonoids on immune and inflammatory cell function In: Flavonoids in the living system. Adv. Exp. Med. Biol., 1998, 439, 175-182.
[http://dx.doi.org/10.1007/978-1-4615-5335-9_13] [PMID: 9781303]
[6]
Gould, K.S.; Lister, C. Flavonoid functions in plants. In:Flavonoids Chemistry, Biochemistry and Application; Andersen, O.M.; Markham, K.R., Eds.; CRC Press: Boca Raton, FL, 2005, pp. 397-441.
[7]
Boudet, A.M. Evolution and current status of research in phenolic compounds. Phytochemistry, 2007, 68(22-24), 2722-2735.
[http://dx.doi.org/10.1016/j.phytochem.2007.06.012] [PMID: 17643453]
[8]
Németh, K.; Plumb, G.W.; Berrin, J.G.; Juge, N.; Jacob, R.; Naim, H.Y.; Williamson, G.; Swallow, D.M.; Kroon, P.A. Deglycosylation by small intestinal epithelial cell beta-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans. Eur. J. Nutr., 2003, 42(1), 29-42.
[http://dx.doi.org/10.1007/s00394-003-0397-3] [PMID: 12594539]
[9]
Spencer, J.P.E. The impact of fruit flavonoids on memory and cognition. Br. J. Nutr., 2010, 104(Suppl. 3), S40-S47.
[http://dx.doi.org/10.1017/S0007114510003934] [PMID: 20955649]
[10]
Carrasco-Pancorbo, A.; Neusüss, C.; Pelzing, M.; Segura-Carretero, A.; Fernández-Gutiérrez, A. CE- and HPLC-TOF-MS for the characterization of phenolic compounds in olive oil. Electrophoresis, 2007, 28(5), 806-821.
[http://dx.doi.org/10.1002/elps.200600382] [PMID: 17315149]
[11]
Valls, J.; Millán, S.; Martí, M.P.; Borràs, E.; Arola, L. Advanced separation methods of food anthocyanins, isoflavones and flavanols. J. Chromatogr. A, 2009, 1216(43), 7143-7172.
[http://dx.doi.org/10.1016/j.chroma.2009.07.030] [PMID: 19691963]
[12]
Fisher, J.F.; Wheaton, T. High pressure liquid chromatographic for the resolution and quantitation of naringin rutinoside in grapefruit juice. J. Agric. Food Chem., 1976, 24, 890-898.
[http://dx.doi.org/10.1021/jf60206a026]
[13]
Wulf, L.W.; Nagel, C.W. High pressure liquid chromatographic separation of anthocyanins of Vitis vinifera. Am. J. Enol. Vitic., 1978, 29, 42-49.
[14]
Gruz, J.; Novak, O.; Strnad, M. Rapid analysis of phenolic acids in beverages by UPLC-MS/MS. Food Chem., 2008, 111(3), 789-794.
[http://dx.doi.org/10.1016/j.foodchem.2008.05.014]
[15]
Daigle, D.J.; Conkerton, E.J. Analysis of flavonoids by HPLC: an update. J. Liq. Chromatogr., 1988, 11(2), 309-325.
[http://dx.doi.org/10.1080/01483918809349942]
[16]
Lea, A.G.H. High performance liquid chromatography of cider proanthocyanidins. Journal of science agriculture and food, 1979, 30, 833-838.
[17]
Stefova, M.; Stafilov, T.; Kulevanova, S. HPLC analysis of flavonoids In: Encyclopedia of Chromatography, Marcel Dekker; Cazes, J., 2003, pp. 113- 119.
[18]
Huck, C.W.; Bonn, G.K. Evaluation of detection methods for the reversed-phase HPLC determination of 3′,4′,5′-trimethoxyflavone in different phytopharmaceutical products and in human serum. Phytochem. Anal., 2001, 12(2), 104-109.
[http://dx.doi.org/10.1002/pca.547] [PMID: 11705238]
[19]
de Rijke, E.; Out, P.; Niessen, W.M.; Ariese, F.; Gooijer, C.; Brinkman, U.A. Analytical separation and detection methods for flavonoids. J. Chromatogr. A, 2006, 1112(1-2), 31-63.
[http://dx.doi.org/10.1016/j.chroma.2006.01.019] [PMID: 16480997]
[20]
Abad-García, B.; Berrueta, L.A.; Garmón-Lobato, S.; Gallo, B.; Vicente, F. A general analytical strategy for the characterization of phenolic compounds in fruit juices by high-performance liquid chromatography with diode array detection coupled to electrospray ionization and triple quadrupole mass spectrometry. J. Chromatogr. A, 2009, 1216(28), 5398-5415.
[http://dx.doi.org/10.1016/j.chroma.2009.05.039] [PMID: 19500791]
[21]
Mabry, T.J.; Markham, K.R. Mass spectrometry of flavonoids In: Encyclopedia of Chromatography, Marcel Dekker;, Habrone, J.B.; Mabry, T.J.; Mabry, H., Eds.; The flavonoids, Academic Press: New York. 1975, pp. 79- 126.
[22]
Schels, H.; Zinsmeister, H.D.; Pfleger, K. Mass spectrometry of silylated flavone and flavanone glycosides. Phytochemistry, 1978, 17, 523-526.
[http://dx.doi.org/10.1016/S0031-9422(00)89352-8]
[23]
Pikulski, M.; Brodbelt, J.S. Differentiation of flavonoid glycoside isomers by using metal complexation and electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom., 2003, 14(12), 1437-1453.
[http://dx.doi.org/10.1016/j.jasms.2003.07.002] [PMID: 14652191]
[24]
Beckey, H.D. Field ionization mass spectrometry. Res. Dev., 1969, 20(11), 26-29.
[25]
Hunt, D.F.; Shabanowitz, J.; Botz, K.; Brent, D.A. Chemical ionization mass spectrometry of salts ant thermally labile organics with field desorption emitters as solid probes. Anal. Chem., 1977, 49, 1160-1163.
[http://dx.doi.org/10.1021/ac50016a025]
[26]
Barber, M.; Bordoli, R.S.; Sedgwick, R.D.; Tyler, A.N.; Tyler, A. Fast atom bombardment mass spectrometry of the angiotensin peptides. Biomed. Mass Spectrom., 1982, 9(5), 208-214.
[http://dx.doi.org/10.1002/bms.1200090506] [PMID: 7093442]
[27]
Aberth, W.; Burlingame, A.L. Comparison of three geometries for a cesium primary beam liquid secondary ion mass spectrometry source. Anal. Chem., 1984, 56(14), 2915-2918.
[http://dx.doi.org/10.1021/ac00278a066] [PMID: 6524663]
[28]
Stobiecki, M. Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry, 2000, 54(3), 237-256.
[http://dx.doi.org/10.1016/S0031-9422(00)00091-1] [PMID: 10870178]
[29]
Blakley, C.R.; Vestal, M.L. Thermospray interface for liquid chromatography/mass spectrometry. Anal. Chem., 1983, 55, 750-754.
[http://dx.doi.org/10.1021/ac00255a036] [PMID: 6638513]
[30]
Koropchak, J.A.; Veber, M.; Browner, R.F. Thermospray sample introduction to atomic spectrometry. Crit. Rev. Anal. Chem., 1992, 23(3), 113-141.
[http://dx.doi.org/10.1080/10408349208050851]
[31]
Hempel, J.; Böhm, H. Quality and quantity of prevailing flavonoid glycosides of yellow and green French beans (Phaseolus vulgaris L.). J. Agric. Food Chem., 1996, 44(8), 2114-2116.
[http://dx.doi.org/10.1021/jf9507001]
[32]
Baldi, A.; Rosen, R.T.; Fukuda, E.K.; Ho, C.T. Identification of non-volatile components in lemon peel by high-performance liquid chromatography with confirmation by mass spectrometry and diode-array detection. J. Chromatogr. A, 1995, 718(1), 89-97.
[http://dx.doi.org/10.1016/0021-9673(95)00676-1] [PMID: 7620574]
[33]
Rodriguez, S.; Wolfender, J-L.; Odontuya, G.; Purev, O.; Hostettmann, K. Xanthones, secoiridoids, and flavonoids from Helenia corniculata. Phytochemistry, 1995, 40(4), 1265-1272.
[http://dx.doi.org/10.1016/0031-9422(95)00402-S]
[34]
Holčapek, M.; Jirásko, R.; Lísa, M. Recent developments in liquid chromatography-mass spectrometry and related techniques. J. Chromatogr. A, 2012, 1259, 3-15.
[http://dx.doi.org/10.1016/j.chroma.2012.08.072] [PMID: 22959775]
[35]
Prasain, J.K.; Wang, C-C.; Barnes, S. Mass spectrometric methods for the determination of flavonoids in biological samples. Free Radic. Biol. Med., 2004, 37(9), 1324-1350.
[http://dx.doi.org/10.1016/j.freeradbiomed.2004.07.026] [PMID: 15454273]
[36]
Fang, X.; Wang, J.; Hao, J.; Li, X.; Guo, N. Simultaneous extraction, identification and quantification of phenolic compounds in Eclipta prostrata using microwave-assisted extraction combined with HPLC-DAD-ESI-MS/MS. Food chemistry., 2015, 188(1), 527-536.
[37]
Ramešova, Š.; Sokolovà, R.; Degano, I. The study of the oxidation of the natural flavonol fisetin confirmed quercetin oxidation mechanism. Electrochim. Acta, 2015, 182(10), 544-549.
[http://dx.doi.org/10.1016/j.electacta.2015.09.144]
[38]
Neugart, S.; Rohn, S.; Schreiner, M. Identification of complex, naturally, occurring flavonoid glycosides in Vica faba and Pisum sativum leaves by HPLC-DAD-ESI-MSn and the genotypic effect on their flavonoid profile. Food Res. Int., 2015, 76(1), 114-121.
[http://dx.doi.org/10.1016/j.foodres.2015.02.021]
[39]
Ly, H.; Wang, X.; He, Y.; Wang, H.; Suo, Y. Identification and quantification in flavonoid aglycones in rape bee pollen from Qinghai-Tibetan Plateau by HPLC-DAD-APCI/MS. J. Food Compos. Anal., 2015, 38, 49-54.
[http://dx.doi.org/10.1016/j.jfca.2014.10.011]
[40]
Özbek, H.; Güvenalp, Z.; Kuruüzüm-Uz, A.; Kakaz, C.; Demirezer, L.Ö. Trinrguaian and germacradiene type sesquiterpenes along with flavonoids from herb of Pimpinella cappadocica Boiss. & Bal. Phytochem. Lett., 2015, 11, 74-79.
[http://dx.doi.org/10.1016/j.phytol.2014.11.017]
[41]
Santos, J.; Herrero, M.; Mendiola, J.A.; Oliva-Teles, M.T.; Ibàñez, E.; Delerue-Matos, C. Oliveira M.B.P.P. Assesment of nutrional and metabolic profiles of pea shots: the new ready-to-eat baby-leaf vegetable. Food Res. Int., 2014, 58, 105-111.
[http://dx.doi.org/10.1016/j.foodres.2014.01.062]
[42]
Homoki, J.R.; Nemes, A.; Fazekas, E.; Gyémánt, G.; Balogh, P.; Gál, F.; Al-Asri, J.; Mortier, J.; Wolber, G.; Babinszky, L.; Remenyik, J. Anthocyanin composition, antioxidant efficiency, and α-amylase inhibitor activity of different Hungarian sour cherry varieties (Prunus cerasus L.). Food Chem., 2016, 194(17926), 222-229.
[http://dx.doi.org/10.1016/j.foodchem.2015.07.130] [PMID: 26471548]
[43]
Oliveira, J.; Alhinho da Silva, M.; Teixeira, N.; De Freitas, V.; Salas, E. Screening of anthocyanin-derived pigments in red wine grape pomace using LC-DAD/MS and MALDI-TOF techniques. J. Agric. Food Chem., 2015, 63(35), 7636-7644.
[http://dx.doi.org/10.1021/acs.jafc.5b00256] [PMID: 25912410]
[44]
Brunnée, C. The ideal mass analyzer: fact or fiction? Int. J. Mass Spectrom. Ion Process., 1987, 76(2), 125-237.
[http://dx.doi.org/10.1016/0168-1176(87)80030-7]
[45]
Syed, S.U.; Maher, S.; Taylor, S. Quadrupole mass filter operation under the influence of magnetic field. J. Mass Spectrom., 2013, 48(12), 1325-1339.
[http://dx.doi.org/10.1002/jms.3293] [PMID: 24338888]
[46]
Hvattum, E.; Ekeberg, D. Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry. J. Mass Spectrom., 2003, 38(1), 43-49.
[http://dx.doi.org/10.1002/jms.398] [PMID: 12526005]
[47]
Davis, B.D.; Brodbelt, J.S. Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry. J. Am. Soc. Mass Spectrom., 2004, 15(9), 1287-1299.
[http://dx.doi.org/10.1016/j.jasms.2004.06.003] [PMID: 15337509]
[48]
Grant, D.C.; Helleur, R.J. Rapid screening of anthocyanins in berry samples by surfactant-mediated matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom., 2008, 22(2), 156-164.
[http://dx.doi.org/10.1002/rcm.3351] [PMID: 18072192]
[49]
Jia, B-X.; Huangfu, Q.Q.; Ren, F-X.; Jia, L.; Zhang, Y-B.; Liu, H-M.; Yang, J.; Wang, Q. Identification and quantification of flavonoids and chromes in Baeckea frutescens by using HPLC coupled with diode-array detection and quadruple time-of-flight mass spectrometry. Nat. Prod. Res., 2015, 29(9), 800-806.
[http://dx.doi.org/10.1080/14786419.2014.987144] [PMID: 25466282]
[50]
Gu, W-Y.; Li, N.; Leung, E.L-H.; Zhou, H.; Luo, G-A.; Liu, L.; Wu, J-L. Metabolites software-assisted flavonoid hunting in plants using ultra-high performance liquid chromatography-quadrupole-time of flight mass spectrometry. Molecules, 2015, 20(3), 3955-3971.
[http://dx.doi.org/10.3390/molecules20033955] [PMID: 25738538]
[51]
Park, S.K.; Jin, D.E.; Park, C.H.; Seung, T.W.; Guo, T.J.; Song, J.W.; Kim, J.H.; Kim, D.O.; Heo, H.J. Ameliorating effects of ethyl acetate fraction from onion (Allium cepa L.) flesh and peel in mice following trimethyltin-induced learning and memory impairment. Food Res. Int., 2015, 75, 53-60.
[http://dx.doi.org/10.1016/j.foodres.2015.05.038] [PMID: 28454972]
[52]
Myjavcova, R.; Bednar, P.; Srovnalova, A.; Papouskova, B. Ultra-performance liquid chromatography/mass spectrometry study of metabolism of 5-methylopyranopelargonidin. Chromatographia, 2015, 78(3-4), 189-201.
[http://dx.doi.org/10.1007/s10337-014-2832-4]
[53]
Perry, R.H.; Cooks, R.G.; Noll, R.J. Orbitrap mass spectrometry: instrumentation, ion motion and applications. Mass Spectrom. Rev., 2008, 27(6), 661-699.
[http://dx.doi.org/10.1002/mas.20186] [PMID: 18683895]
[54]
Teixeira, N.; Azevedo, J.; Mateus, N.; de Freitas, V. Proanthocyanidin screening by LC-ESI-MS of Portuguese red wines made with teinturier grapes. Food Chem., 2016, 190, 300-307.
[http://dx.doi.org/10.1016/j.foodchem.2015.05.065] [PMID: 26212974]
[55]
Ferreira, F.P.; Morais, S.R.; Bara, M.T.; Conceição, E.C.; Paula, J.R.; Carvalho, T.C.; Vaz, B.G.; Costa, H.B.; Romão, W.; Rezende, M.H. Eugenia calycina Cambess extracts and their fractions: Their antimicrobial activity and the identification of major polar compounds using electrospray ionization FT-ICR mass spectrometry. J. Pharm. Biomed. Anal., 2014, 99, 89-96.
[http://dx.doi.org/10.1016/j.jpba.2014.07.003] [PMID: 25108373]
[56]
Zhang, J.; Xu, X.J.; Xu, W.; Huang, J.; Zhu, D.Y.; Qiu, X.H. Rapid characterization and identification of flavonoids in Radix astragali by ultra-high-pressure liquid chromatography coupled with linear ion trap-orbitrap mass spectrometry. J. Chromatogr. Sci., 2015, 53(6), 945-952.
[http://dx.doi.org/10.1093/chromsci/bmu155] [PMID: 25501118]
[57]
Zhang, J.Y.; Wang, F.; Zhang, H.; Lu, J.Q.; Qiao, Y.J. Rapid identification of polymethoxylated flavonoids in traditional Chinese medicines with a practical strategy of stepwise mass defect filtering coupled to diagnostic product ions analysis based on a hybrid LTQ-Orbitrap mass spectrometer. Phytochem. Anal., 2014, 25(5), 405-414.
[http://dx.doi.org/10.1002/pca.2508] [PMID: 24596165]
[58]
de Hoffman, E.; Strobant, V. Mass Spectrometry - Principles and Applications, 3rd ed; Wiley: Great Britain, 2007.
[59]
Prasain, J.K.; Barnes, S. Metabolism and bioavailability of flavonoids in chemoprevention: current analytical strategies and future prospectus. Mol. Pharm., 2007, 4(6), 846-864.
[http://dx.doi.org/10.1021/mp700116u] [PMID: 18052086]
[60]
de Hoffman, E. Tandem Mass Spectrometry: A Primer. Journal of Mass Spectrometry., 1996, 31, 129-137.
[http://dx.doi.org/10.1002/(SICI)1096-9888(199602)31:2<129:AID-JMS305>3.0.CO;2-T]
[61]
de Rijke, E.; Zappey, H.; Ariese, F.; Gooijer, C.; Brinkman, U.A.Th. 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(1), 45-58.
[http://dx.doi.org/10.1016/S0021-9673(02)01868-X] [PMID: 12564675]
[62]
Cuyckens, F.; Claeys, M. Optimization of a liquid chromatography method based on simultaneous electrospray ionization mass spectrometric and ultraviolet photodiode array detection for analysis of flavonoid glycosides. Rapid Commun. Mass Spectrom., 2002, 16(24), 2341-2348.
[http://dx.doi.org/10.1002/rcm.861] [PMID: 12478580]
[63]
Cuyckens, F.; Claeys, M. Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom., 2004, 39(1), 1-15.
[http://dx.doi.org/10.1002/jms.585] [PMID: 14760608]
[64]
Ma, Y.L.; Li, Q.M.; Van den Heuvel, H.; Claeys, M. Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom., 1997, 11, 1357-1364.
[http://dx.doi.org/10.1002/(SICI)1097-0231(199708)11:12<1357:AID-RCM983>3.0.CO;2-9]
[65]
Domon, B.; Costello, C.E. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj. J., 1988, 5, 397-409.
[http://dx.doi.org/10.1007/BF01049915]
[66]
Wolfender, J.L.; Waridel, P.; Ndjoko, K.; Hobby, K.R.; Major, H.J.; Hostettmann, K. Evaluation of Q-TOF-MS/MS and multiple stage IT-MSn for the dereplication of flavonoids and related compounds in crude plant extracts. Analusis, 2000, 28, 895-906.
[http://dx.doi.org/10.1051/analusis:2000280895]
[67]
Zhang, Y.; Zhang, P.; Cheng, Y. Structural characterization of isoprenylated flavonoids from Kushen by electrospray ionization multistage tandem mass spectrometry. J. Mass Spectrom., 2008, 43(10), 1421-1431.
[http://dx.doi.org/10.1002/jms.1423] [PMID: 18464298]
[68]
Zhou, D.Y.; Xu, Q.; Xue, X.Y.; Zhang, F.F.; Jing, Y.; Liang, X.M. Rapid qualitative and quantitative analyses of flavanone aglycones in Fructus aurantii by HPLC ion-trap MS. J. Sep. Sci., 2007, 30(6), 858-867.
[http://dx.doi.org/10.1002/jssc.200600466] [PMID: 17536731]
[69]
Kuhn, F.; Oehme, M.; Romero, F.; Abou-Mansour, E.; Tabacchi, R. Differentiation of isomeric flavone/isoflavone aglycones by MS2 ion trap mass spectrometry and a double neutral loss of CO. Rapid Commun. Mass Spectrom., 2003, 17(17), 1941-1949.
[http://dx.doi.org/10.1002/rcm.1138] [PMID: 12913857]
[70]
Nowakowska, Z.; Pankiewicz, R. (E)-4-alkoxycarbonylalkylthiochalcones: differentiation of isomeric derivatives by electron ionization mass spectrometry. Rapid Commun. Mass Spectrom., 2008, 22(15), 2301-2306.
[http://dx.doi.org/10.1002/rcm.3614] [PMID: 18613297]
[71]
Cuyckens, F.; Ma, Y.L.; Pocsfalvi, G.; Claeys, M. Tandem mass spectral strategies for structural characterization of flavonoid glycosides. Analusis, 2000, 28(10), 888-895.
[http://dx.doi.org/10.1051/analusis:2000280888]
[72]
Vukics, V.; Guttman, A. Structural characterization of flavonoid glycosides by multi-stage mass spectrometry. Mass Spectrom. Rev., 2010, 29(1), 1-16.
[PMID: 19116944]
[73]
Ferreres, F.; Gil-Izquierdo, A.; Andrade, P.B.; Valentão, P.; Tomás-Barberán, F.A. Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A, 2007, 1161(1-2), 214-223.
[http://dx.doi.org/10.1016/j.chroma.2007.05.103] [PMID: 17602695]
[74]
Li, Q.M.; Claeys, M. Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom., 1994, 23(7), 406-416.
[http://dx.doi.org/10.1002/bms.1200230705] [PMID: 8068736]
[75]
Geng, P.; Sun, J.; Zhang, M.; Li, X.; Harnly, J.M.; Chen, P. Comprehensive characterization of C-glycosyl flavones in wheat (Triticum aestivum L.) germ using UPLC-PDA-ESI/HRMSn and mass defect filtering. J. Mass Spectrom., 2016, 51(10), 914-930.
[http://dx.doi.org/10.1002/jms.3803] [PMID: 27373213]
[76]
Marczak, Ł.; Stobiecki, M.; Jasiński, M.; Oleszek, W.; Kachlicki, P. Fragmentation pathways of acylated flavonoid diglucuronides from leaves of Medicago truncatula. Phytochem. Anal., 2010, 21(3), 224-233.
[http://dx.doi.org/10.1002/pca.1189] [PMID: 19950391]
[77]
Kazuno, S.; Yanagida, M.; Shindo, N.; Murayama, K. Mass spectrometric identification and quantification of glycosyl flavonoids, including dihydrochalcones with neutral loss scan mode. Anal. Biochem., 2005, 347(2), 182-192.
[http://dx.doi.org/10.1016/j.ab.2005.09.020] [PMID: 16269127]
[78]
Abrankó, L.; García-Reyes, J.F.; Molina-Díaz, A. In-source fragmentation and accurate mass analysis of multiclass flavonoid conjugates by electrospray ionization time-of-flight mass spectrometry. J. Mass Spectrom., 2011, 46(5), 478-488.
[http://dx.doi.org/10.1002/jms.1914] [PMID: 21500306]
[79]
Kachlicki, P.; Einhorn, J.; Muth, D.; Kerhoas, L.; Stobiecki, M. Evaluation of glycosylation and malonylation patterns in flavonoid glycosides during LC/MS/MS metabolite profiling. J. Mass Spectrom., 2008, 43(5), 572-586.
[http://dx.doi.org/10.1002/jms.1344] [PMID: 18074333]
[80]
Markham, K.R. Techniques of flavonoids identification; Academic Press: London, 1982, p. 144.
[81]
Awouafack, M.D.; Tane, P.; Morita, H. Isolation and Structure Characterization of Flavonoids In; Flavonoids - From Biosynthesis to Human Health, 2017, pp. 46-59.

Rights & Permissions Print Cite
Article Metrics
18
© 2024 Bentham Science Publishers | Privacy Policy