Fragmentation Characterization and Differentiation of Isomeric Diglycosyl Flavonoids Using Ultra-High-Performance Liquid Chromatography Electrospray Ionization Quadrupole Time-of-Flight Tandem Mass Spectrometry in Negative Ion Mode
Available accessResearch articleFirst published online February, 2013
Fragmentation Characterization and Differentiation of Isomeric Diglycosyl Flavonoids Using Ultra-High-Performance Liquid Chromatography Electrospray Ionization Quadrupole Time-of-Flight Tandem Mass Spectrometry in Negative Ion Mode
Flavonoids exhibit a wide range of biological activities and the fragmentation characterization and differentiation of isomeric diglycosyl flavonoids is an important area of research. In this study, ultra-high-performance liquid chromatography electrospray ionization quadrupole time-of-flight tandem mass spectrometry was used to identify two pairs of isomeric diglycosyl flavonoids: naringin/narirutin and neohesperidin/hesperidin. The two pairs of flavonoids were identified by product ion tandem mass spectra of the precursor ions [M – H]−. The results showed that characteristic product ions distinguishing flavonoids glycosylated with rhamnosyl-(α1 α 2)-glucosyl from isomeric flavonoids glycosylated with rhamnosyl-(α1 α 6)-glucosyl were the precursor ion [M – H]− and its characteristic product ions Y0− and [0,2X0 – H]−.
ErlundI., “Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology”, Nutr. Res.24, 851 (2004). doi: 10.1016/j.nutres.2004.07.005
2.
GuoX.F.YueY.D.MengZ.F.TangF.WangJ.YaoX., “Antioxidant properties of major flavonoids and subfractions of the extract of Phyllostachys pubescens leaves”, J. Food Biochem.37, (2013). doi: 10.1111/j.1745-4514.2012.00655.x
3.
HalliwellB.RafterJ.JennerA., “Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: Direct or indirect effects? Antioxidant or not?”, Am. J. Clin. Nutr.81, 268S (2005).
4.
ManachC.WilliamsonG.MorandC.ScalbertA.RemesyC., “Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies”, Am. J. Clin. Nutr.81, 230S–242S (2005).
5.
RobardsK.AntolovichM., “Analytical chemistry of fruit bioflavonoids—a review”, Analyst122, 11R (1997). doi: 10.1039/A606499J
6.
JeongH.J.RyuY.B.ParkS.J.KimJ.H.KwonH.J.KimJ.H.ParkK.H.RhoM.C.LeeW.S., “Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities”, Bioorg. Med. Chem.17, 6816 (2009). doi: 10.1016/j.bmc.2009.08.036
7.
KayC.D.HooperL.KroonP.A.RimmE.B.CassidyA., “Relative impact of flavonoid composition, dose and structure on vascular function: A systematic review of randomised controlled trials of flavonoid-rich food products”, Mol. Nutr. Food Res.56, 1605 (2012). doi: 10.1002/mnfr.201200363
SánchezI.Gómez-GaribayF.TaboadaJ.RuizB.H., “Antiviral effect of flavonoids on the Dengue virus”, Phytother. Res.14, 89 (2000). doi: 10.1002/(SICI)1099-1573(200003)
10.
ZhengX.ShiP.ChengY.QuH., “Rapid analysis of a Chinese herbal prescription by liquid chromatography time-of-flight tandem mass spectrometry”, J. Chromatogr. A1206, 140 (2008). doi: 10.1016/j.chroma.2008.08.038
11.
PiersonJ.T.DietzgenR.G.ShawP.N.Roberts-ThomsonS.J.MonteithG.R.GidleyM.J., “Major Australian tropical fruits biodiversity: Bioactive compounds and their bioactivities”, Mol. Nutr. Food Res.56, 357 (2012). doi: 10.1002/mnfr.201100441
12.
WyattR.M.HodgesL.D.KalafatisN.WrightP.F.A.WynneP.M.MacridesT.A., “Phytochemical analysis and biological screening of leaf and twig extracts from Kunzea ericoides”, Phytother. Res.19, 963 (2005). doi: 10.1002/ptr.1767
13.
MaY.L.LiQ.M.van den HeuvelH.ClaeysM., “Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry”, Rapid Commun. Mass Spectrom.11, 1357 (1997). doi: 10.1002/(SICI)1097-0231(199708)
14.
DomonB.CostelloC.E., “A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates”, Glycoconj. J.5, 397–409 (1988). doi: 10.1007/BF01049915
15.
StobieckiM., “Application of mass spectrometry for identification and structural studies of flavonoid glycosides”, Phytochemistry54, 237 (2000). doi: 10.1016/S0031-9422(00)00091-1
16.
GuoX.F.YueY.D.TangF.WangJ.YaoX., “A comparison of C-glycosidic flavonoid isomers by electrospray ionization quadrupole time-of-flight tandem mass spectrometry in negative and positive ion mode”, Int. J. Mass Spectrom.333, 59 (2013). doi: 10.1016/j.ijms.2012.08.035
17.
AblajanK., “A study of characteristic fragmentation of isoflavonoids by using negative ion ESI-MSn”, J. Mass. Spectrom.46, 77 (2011). doi: 10.1002/jms.1867
18.
YanC.Y.LiuS.Y.ZhouY.H.SongF.R.CuiM.LiuZ.Q., “A study of isomeric diglycosyl flavonoids by SORI CID of fourier transform ion cyclotron mass spectrometry in negative ion mode”, J. Am. Soc. Mass Spectrom.18, 2127 (2007). doi: 10.1016/j.jasms.2007.09.012
19.
HvattumE.EkebergD., “Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry”, J. Mass Spectrom.38, 43 (2003). doi: 10.1002/jms.398
20.
KerhoasL.AouakD.CingozA.RoutaboulJ.M.LepiniecL.EinhornJ.BirlirakisN., “Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds”, J. Agr. Food Chem.54, 6603 (2006). doi: 10.1021/jf061043n
21.
RobardsK.LiX.AntolovichM.BoydS., “Characterisation of citrus by chromatographic analysis of flavonoids”, J. Sci. Food Agr.75, 87 (1997). doi: 10.1002/(SICI)1097-0010(199709)
22.
CuyckensF.RozenbergR.de HoffmannE.ClaeysM., “Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry”, J. Mass Spectrom.36, 1203 (2001). doi: 10.1002/jms.224
23.
FranskiR.BednarekP.WojtaszekP.StobieckiM., “Identification of flavonoid diglycosides in yellow lupin (Lupinus luteus I.) with mass spectrometric techniques”, J. Mass Spectrom.34, 486–495 (1999). doi: 10.1002/(SICI)1096-9888(199905)
