Analysis of flavonoids in foods and biological samples

Mini-Reviews in Medicinal Chemistry

Volumn 11, Issue 14, 2011, Pages 1239-1255

  Gonzalez Paramas A M ^a   Santos Buelga, C ^a   Duenas M ^a   Gonzalez Manzano S ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Analysis; Biological fluids; Flavonoid databases; Flavonoids; Food and beverages; Occurrence in food; Phenolic compounds

Indexed keywords

AGLYCONE; ANTHOCYANIN; BIOLOGICAL PRODUCT; CHALCONE DERIVATIVE; CYANIDIN 3 GLUCOSIDE; DELPHINIDIN; EPICATECHIN; EPIGALLOCATECIN; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; FOLIN CIOCALTEU REAGENT; HESPERETIN; ISOFLAVONE DERIVATIVE; KAEMPFEROL; MALVIDIN CHLORIDE; MYRICETIN; NARINGERIN; PLANT EXTRACT; PROANTHOCYANIDIN DERIVATIVE; PROCYANIDIN; QUERCETIN; REAGENT; UNCLASSIFIED DRUG;

ACIDIFICATION; ANALYSIS; BEVERAGE; BODY FLUID; CAPILLARY ELECTROPHORESIS; CHEMICAL STRUCTURE; DATA BASE; DIETARY INTAKE; DRUG DETERMINATION; ELECTROCHEMISTRY; EXTRACTION; FLUORESCENCE ANALYSIS; FOOD; FOOD COMPOSITION; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIGHT ABSORPTION; LIGHT EMITTING DIODE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METABOLITE; MICROWAVE ASSISTED EXTRACTION; NONHUMAN; PRESSURIZED LIQUID EXTRACTION; RED WINE; REVIEW; SUPERCRITICAL FLUID EXTRACTION; ULTRAVIOLET SPECTROSCOPY; VEGETABLE;

EID: 82955226081     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/13895575111091239     Document Type: Review

References (172)

1. Aherne, S.A.; O'Brien, N.M. Dietary Flavonols: Chemistry, FoodContent, and Metabolism. Nutrition, 2002, 18, 75-81.
2. Robards, K. Strategies for the determination of bioactive phenols inplants, fruit and vegetables. J Chromatog. A, 2003, 1000, 657-691.
3. Spencer, J.P.E.; El Mohsen, M.M.A.; Minihane, A.M.; Mathers, J.C. Biomarkers of the intake of dietary polyphenols: strengths, limitations and application in nutrition research. Br. J. Nutr., 2008, 99, 12-22.
4. Loke, W.M.; Jenner, A.M.; Proudfoot, J.M.; McKinley, A.J.;Hodgson, J.M.; Halliwell, B.; Croft, K.D. A Metabolite ProfilingApproach to Identify Biomarkers of Flavonoid Intake in Humans, J. Nutr., 2009, 139, 2309-2314.
5. Kroon, P.A.; Clifford, M.N.; Crozier, A.; Day, A.J.; Donovan, J.L.;Manach, C.; Williamson, G. How should we assess the effects ofexposure to dietary polyphenols in vitro? Am. J. Clin. Nutr., 2004, 80, 15-21.
6. Luthria, D.L. Significance of sample preparation in developinganalytical methodologies for accurate estimation of bioactivecompounds in functional foods. J. Sci. Food Agric., 2006, 86, 2266-2272.
7. Marston, A.; Hostettmann, K. In: Flavonoids: Chemistry, Biochemistry and Applications, Andersen, O.; Markham, K.R., Eds.; CRC Press: Boca Raton, 2006, pp1-36.
8. Escarpa, A.; Gonzalez, M. C. An overview of analytical chemistryof phenolic compounds in foods. Crit. Rev. Anal. Chem., 2001, 31, 57-139.
9. Santos-Buelga, C.; Gonzalez-Manzano, S.; Duenas, M.; Gonzalez-Paramas, A.M. (2011). In: Recent advances in polyphenolsresearch. Vol III, Quideau, S. and Cheynier, V. Eds.; Wiley-Blackwell, Oxford, UK. In Press.
10. Day, A.J.; Morgan, M.R.A. In: Methods in Polyphenol Analysis, Santos-Buelga, C.; Williamson, G. Eds. The Royal Society ofChemistry: Cambridge, 2003; pp. 17-47.
11. Andreasen, M.F.; Christensen, L.P.; Meyer, A.S.; Hansen, A. Release of hydroxycinnamic and hydroxybenzoic acids in rye bycommercial plant cell wall degrading enzyme preparations. J. Sci. Food Agric., 1999, 79, 411-1413.
12. Harborne, J. B. Plant polyphenols XIV. Characterisation offlavonoid glycosides by acidic and enzymic hydrolyses. Phytochemistry, 1965, 4, 107-120.
13. Hertog, M. G. L.; Hollman, P. C. H.; Venema, D. P. Optimizationof quantitative HPLC determination of potentially anticarcinogenicflavonoids in fruit and vegetables. J. Agric. Food. Chem., 1992, 40, 1591-1598.
14. Rivas-Gonzalo JC. In: Methods in polyphenol analysis, Santos-Buelga C and Williamson G (Eds.), The Royal Society ofChemistry, Cambridge, 2003, pp.338-358.
15. Nardini, N.; Cirillo, E.; Natella, F.; Mencarelli, D.; Comisso, A.;Scaccini, C. Detection of bound phenolic acids: prevention byascorbic acid and ethylenediaminetetraacetic acid of degradation ofphenolic acids during alkaline hydrolysis. Food Chem., 2002, 79, 119-124.
16. Escribano-Bailon, M.T.; Santos-Buelga, C. In: Methods inPolyphenol Analysis. Santos-Buelga C and Williamson G (Eds.), The Royal Society of Chemistry, Cambridge, 2003, pp.1-16.
17. Santos-Buelga, C.; García-Viguera, C.; Tomás-Barberán, F.A.(2003). In: Methods in Polyphenol Analysis. Santos-Buelga C andWilliamson G (Eds.), The Royal Society of Chemistry, Cambridge, 2003, pp.92-124.
18. Tomás-Barberán, F.A.; Gil-Izquierdo, A.; Ferreres, F.; Gil, M.I. In:Methods in Polyphenol Analysis, Santos-Buelga, C.; Williamson, G. Eds, The Royal Society of Chemistry: Cambridge; 2003, pp.359-371.
19. Luque de Castro, M.D.; Garcia-Ayuso, L.E. Soxhlet extraction ofsolid materials: an outdated technique with a promising innovativefuture. Anal. Chim. Acta, 1998, 369, 1-10.
20. Priego-Capote, F.; Luque de Castro, M.D. Ultrasound in analyticalchemistry. Anal. Bioanal. Chem., 2007, 387, 249-257.
21. Li, S.; Zhu, R.; Zhong, M.; Zhang, Y.; Huang, K.; Xu Zhi, X.; Fu, S. Effects of ultrasonic-assistant extraction parameters on totalflavones yield of Selaginella doederleinii, and its antioxidantactivity. J. Med. Plant. Res., 2010, 4, 1743-1750.
22. Ma, Y.Q.; Chen, J.C.; Liu, D.H.; Ye, X.Q. Simultaneous extractionof phenolic compounds of citrus peel extracts: Effect of ultrasound. Ultrason. Sonochem., 2009, 16, 57-62.
23. Chukwumah, Y.C.; Walker, L.T.; Verghese, M.; Ogutu, S. Effectof frequency and duration of ultrasonication on the extractionefficiency of selected isoflavones and trans-resveratrol frompeanuts (Arachis hypogaea). Ultrason. Sonochem., 2009, 16, 293-299.
24. Khan, M.K.; Abert-Vian, M.; Fabiano-Tixier, A.S.; Dangles, O.;Chemat, F. Ultrasound-assisted extraction of polyphenols(flavanone glycosides) from orange (Citrus sinensis, L.) peel. FoodChem., 2010, 119, 851-858.
25. Ghafoor, K.; Choi, Y.H.; Jeon, J.Y.; Jo, I.H. Optimization ofultrasound-assisted extraction of phenolic compounds, antioxidants, and anthocyanins from grape (Vitis vinifera) seeds. J. Agric. Food Chem., 2009, 57, 4988-4994.
26. Bai, X.L.; Yue, T.L.; Yuan, Y.H., Zhang, H.w. Optimization ofmicrowave-assisted extraction of polyphenols from apple pomaceusing response surface methodology and HPLC analysis. J. Sep. Sci., 2010, 33, 3751-3758.
27. Terigar, B.G.; Balasubranian, S.; Boldor, D.; Xu, Z.; Lima, M.;Sabliov, C.M. Continuous microwave-assisted isoflavoneextraction system: Design and performance evaluation. Biores. Technol., 2010, 101: 2466-2471.
28. Du, F.Y.; Xiao, X.H.; Luo, X.J.; Li, G.K. Application of ionicliquids in the microwave-assisted extraction of polyphenoliccompounds from medicinal plants. Talanta, 2009, 78, 1177-1184.
29. Proestos, C.; Komaitis, M. Application of microwave-assistedextraction to the fast extraction of plant phenolic compounds. LWTFoodSci. Technol., 2008, 41, 652-659.
30. Søltoft, M.; Christensen, J.H.; Nielsen, J.; Knuthsen, P. Pressurisedliquid extraction of flavonoids in onions. Method development andvalidation. Talanta, 2009, 80, 269-278.
31. Dobiáš, P.; Pavlíková, P.; Adam, M.; Eisner, A., Beñová, B.;Ventura, K. Comparison of pressurised fluid and ultrasonicextraction methods for analysis of plant antioxidants and theirantioxidant capacity. Cent. Eur. J. Chem., 2010, 8, 87-95.
32. Pineiro, Z.; Palma, M.; Barroso, C.G. Determination of catechinsby mean of extraction with pressurized liquids. J. Chromatogr. A., 2004, 1026, 19-23.
33. Luque-Rodriguez, J.M.; Luque de Castro, M.D.; Perez-Juan, P. Dynamic superheated liquid extraction of anthocyanins and otherphenolics from red grape skins of winemaking residues. Biores. Technol., 2007, 98, 2705-2713.
34. Monrad, J.K.; Howard, L.R.; King, J.W.; Srinivas, K.;Mauromoustakos, A. Subcritical solvent extraction of procyanidinsfrom dried red grape pomace. J. Agric. Food Chem., 2010, 58, 4014-4021.
35. Wijngaard, H.; Brunton, N. The optimization of extraction ofantioxidants from apple pomace by pressurized liquids. J. Agric. Food Chem., 2009, 57, 10625-10631. 57.
36. Howard, L.; Pandjaitan, N. Pressurized liquid extraction offlavonoids from spinach. J. Food Sci., 2008, 73, C151-157.
37. Shouqin, Z.; Jun, X.; Changzheng, W. High hydrostatic pressureextraction of flavonoids from propolis. J. Chem. Technol. Biotechnol., 2005, 80, 50-54.
38. Corrales, M.; Fernández García, A.; Butz, P.; Tauscher, B. Extraction of anthocyanins from grape skins assisted by highhydrostatic pressure. J. Food Eng., 2009, 90, 415-421.
39. Pereira, C.G.; Meireles, M.A.A. Supercritical fluid extraction ofbioactive compounds: fundamentals, applications and economicperspectives. Food Bioprocess. Technol., 2010, 3, 340-372.
40. Liu, E.H.; Qi, L.W.; Cao, J.; Li, P.; Li, C.Y.; Peng, Y.B. Advancesof modern chromatographic and electrophoretic methods inseparation and analysis of flavonoids. Molecules, 2008, 13, 2521-2544.
41. Scalia, S.; Giuffreda, L.; Pallado, P. Analytical and preparativesupercritical fluid extraction of Chamomile flowers and itscomparison with conventional methods. J. Pharmaceut. Biomed. Anal., 1999, 21, 549-558.
42. Klejdus, B.; Lojkova, L.; Lapcik, O.; Kovlovská, R.; Moravcová, J.; Kubán, V. Supercritical fluid extraction of isoflavones frombiological samples with ultra-fast high-performance liquidchromatography/mass spectrometry. J. Sep. Sci., 2005, 28, 1334-1346.
43. Novakova, L.; Vlckova, H. A review of current trends andadvances in modern bio-analytical methods: Chromatography andsample preparation. Anal. Chim. Acta, 2009, 656, 8-35.
44. Kalt, W.; MacKinnon, S.; McDonald, J.; Vinqvist, M.; Craft, C.;Howell, A. Phenolics of Vaccinium, berries and other fruit crops. J. Sci. Food Agric., 2008, 88, 68-76.
45. Wallace, T.C.; Giusti, M.M. Extraction and normal-phase HPLCfluorescence-electrospray MS characterization and quantificationof procyanidins in cranberry extracts. J. Food Sc. i, 2010, 75, C690-C696.
46. Zgorka, G.; Hajnos, A. The application of solid-phase extractionand reversed phase high-performance liquid chromatography forsimultaneous isolation and determination of plant flavonoids andphenolic acids. Chromatographia, 2003, 57: S77-S80.
47. Poole, C.F. New trends in solid-phase extraction. Trends Anal. Chem., 2003, 22, 362-373.
48. Fontanals, N.; Marce, R.M.; Borrull, F. New hydrophilic materialsfor solid-phase extraction. Trends Anal. Chem., 2005, 24, 394-406.
49. Waterhouse, A.L. Determination of total phenolics. Cur. Prot. Food Anal. Chem., 2002, I1.1.1-I1.1.8
50. Berend, S.; Grabarić, Z. Determination of total polyphenol contentin food with the flow-injection method. Arh. Hig. Rada Toksikol., 2008, 59, 205-212.
51. Graham, H.D. Stabilization of the Prussian blue color in thedetermination of polyphenols. J. Agric. Food Chem., 1992, 40, 801-805.
52. Markham, K.R. Techniques of Flavonoid Identification; Academicpress: London, 1982.
53. Broadhurst, R.B.; Jones, W.T. Analysis of condensed tannins usingacidified vanillin. J. Sci. Food Agric., 1978, 29, 788-794.
54. Delcour, J.A.; Varebeke, D.J. A new colorimetric assay forflavonoids in pilsner beers. J. Inst. Brew., 1985, 91, 37-40.
55. Santos-Buelga, C.; Scalbert, A. Proanthocyanidins and tannin-likecompounds: nature, occurrence, dietary intake and effects onnutrition and health. J. Food Sci. Agric., 2000, 80, 1094-1117.
56. Porter, L.J.; Hrstich, L.N.; Chan, B.G. The conversion ofprocyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry, 1986, 25, 223-230.
57. Ribereau-Gayon, P.; Stonestreet, E. Le dosage des anthocyanesdans le vins rouge. Bull. Soc. Chim., 1965, 9, 2649-2652.
58. Mabry, T.J.; Markham, K.R.; Thomas, M.B., Eds. The SystematicIdentification of Flavonoids, Springer-Verlag: New York; 1970.
59. Miller, C.E. In: Near Infrared Technology in the Agricultural andFood Industries, Williams, P.C.; Norris, K.H., Eds.; AmericanAssociation of Cereal Chemist: St. Paul, 2001; pp. 9-29.
60. Cozzolino, D. Near Infrared Spectroscopy in natural productsanalysis. Planta Med., 2009, 75, 746-756.
61. Luypaert, J.; Zhang, M.H.; Massart, D.L. Feasibility study for theuse of near infrared spectroscopy in the qualitative and quantitativeanalysis of green tea Camellia sinensis, (L). Anal. Chim. Acta, 2003, 478, 303-12.
62. Chen, Q.; Zhao, J.; Liu, M.; Cai, J.; Liu, J. Determination of totalpolyphenols content in green tea using FT-NIR spectroscopy anddifferent PLS algorithms. J. Pharmaceut. Biomed. Anal., 2008, 46, 568-73.
63. Yu, C.Y.; Tong, Z.K.; Huang, H.H.; Zhe, Y.Q. Quantification ofphenolic compound in Magnolia officinalis, by near infraredreflectance spectroscopy. J Zhejiang Forestry College, 2007; 24, 544-549.
64. Gishen, M.; Dambergs, R.G.; Cozzolino, D. Grape and wineanalysis-enhancing the power of spectroscopy withchemometrics. A review of some applications in the Australianwine industry. Aust. J. Grape Wine Res., 2005, 11, 296-305.
65. Zhou, X.; Xiang, B.; Wang, Z.; Zhang, M. Determination ofquercetin in extracts of Ginkgo biloba, L leaves by near infraredreflectance spectroscopy based on interval partial least squares(iPLS) model. Anal. Let., 2007, 40, 3383-3391.
66. Joubert, E.; Manley, M; Botha, M. Use of NIRS for quantificationof mangigerin and hesperidin contents of dried honeybush(Cyclopia genistoides) plant material. J. Agric. Food Chem., 2006;54: 5279-83.
67. de Rijke, E.; Out, P.; Niessen, W. M. A.; Ariese, F.; Gooijer, C;Brinkman, U. A. T. Analytical separation and detection methodsfor flavonoids. J. Chromatogr. A, 2006, 1112, 31-63.
68. Merken, H.M.; Beecher, G.R. Liquid chromatographic method forseparation and quantification of prominent flavonoid aglycones. JChromatogr. A., 2000, 897, 177-84.
69. Sakakibara, H.; Honda, Y.; Nakagawa, S.; Ashida, H.; Kanazawa, K. Simultaneous determination of all polyphenols in vegetables, fruits, and teas. J. Agric. Food Chem., 2003, 51, 571-81.
70. Fossen, T.; Andersen, O.M. In: Flavonoids: Chemistry, Biochemistry and Applications, Andersen, O.; Markham, K.R., Eds.; CRC Press: Boca Raton, 2006, pp37-142.
71. de Rijke, E.; Joshi, H.C.; Sanderse, H.R.; Ariese, F.; Brinkman, U.A. Th.; Gooijer, C. Natively fluorescent isoflavones exhibitinganomalous Stokes' shifts. Anal. Chim. Acta, 2002, 468, 3-11.
72. Stoggl, W.M.; Huck, C.W.; Bonn, G.K. Structural elucidation ofcatechin and epicatechin in sorrel leaf extracts using liquidchromatographycoupled to diode array-, fluorescence-, and massspectrometric detection. J. Sep. Sci., 2004, 27, 524-528.
73. Huck, C.W.; Bonn, G.K. Evaluation of detection methods for thereversed-phase HPLC determination of 3β, 4β, 5β-trimethoxyflavonein different phytopharmaceutical products and in human serum. Phytochem. Anal., 2001, 12, 104-109.
74. Hollman, P.C.H.; van Trijp, J.M.P.; Buysman, M.N.C.P. Fluorescence detection of flavonols in hplc by postcolumnchelation with aluminum. Anal. Chem., 1996, 68, 3511-3515.
75. Hollman, P.C.H.; Van Trijp, J.M.; Buysman, M.N.C.P.; Vander Gaag, M.S.; Mengelers, M.J.B.; de Vries, J.H.M.; Katan, M.B. Relative bioavailability of the antioxidant quercetin from variousfoods in man. FEBS Let., 1997, 418, 152-156.
76. de Vries, J.H.; Hollman, P.C.H.; Meyboom, S.; Buysman, M.N.;Zock, P.L.; van Staveren, W.A.; Katan, M.B. Plasmaconcentrations and urinary excretion of the antioxidant flavonolsquercetin and kaempferol as biomarkers for dietary intake. Am. J. Clin. Nutr., 1998, 68, 60-65.
77. Paulke, A.; Schubert-Zsilavecz, M.; Wurglics, M. Determination of St. John's wort flavonoid-metabolites in rat brain through highperformance liquid chromatography coupled with fluorescencedetection. J Chromatogr. B, 2006, 832, 109-113.
78. Morand, C.; Manach, C.; Donovan, J.; Remesy, C. Preparation andcharacterization of flavonoid metabolites present in biologicalsamples. Meth. Enzymol., 2001, 335, 115-121.
79. Manach, C. In: Methods in Polyphenol Analysis, Santos-Buelga, C.; Williamson, G., Eds; The Royal Society of Chemistry:Cambridge, 2003, pp. 63-91.
80. Piskula, M. K.; Terao, J. Accumulation of (α)-epicatechinmetabolites in rat plasma after oral administration and distributionof conjugated enzymes in rat tissues. J. Nutr., 1998, 128, 1172-1178.
81. Piskula M. K.; Terao J. Quercetin's solubility affects itsaccumulation in rat plasma after oral administration. J. Agric. FoodChem., 1998, 46, 4313-4317.
82. Manach, C.; Texier, O.; Morand, C.; Crespy, V.; Regerat, F.;Demigne, C.; Remesy, C. Comparison of the bioavailability ofquercetin and catechin in rats. Free Rad. Biol. Med., 1999, 27, 1259-1266.
83. Jones, D.J.L.; Lim, C.K.; Ferry, D.R.; Gescher, A.A. Determinationof quercetin in human plasma by HPLC with spectrophotometric orelectrochemical detection. Biomed. Chromatogr., 1998, 12, 232-235.
84. Erlund, I.; Alfthan, G.; Siren, H.; Ariniemi, K.; Aro, A. Validatedmethod for the quantitation of quercetin from human plasma usinghigh-performance liquid chromatography with electrochemicaldetection. J. Chromatogr. B, 1999, 727, 179-189.
85. Lee, M.J.; Prabhu, S.; Meng, X.; Li, C.; Yang, C. S. An improvedmethod for the determination of green and black tea polyphenols inbiomatrices by highperformance liquid chromatography withcoulometric array detection. Anal. Biochem., 2000, 279, 164-169.
86. Donovan, J.L.; Manach, C.; Rios, L.; Morand, C.; Scalbert, A.;Remesy, C. Procyanidins are not bioavailable in rats fed a singlemeal containing a grapeseed extract or the procyanidin dimer B3. Br. J. Nutr., 2002, 87, 299-306.
87. Azuma, K.; Ipposhui, K.; Ito, H.; Horie, H.; Terao J. Enhancingeffect of lipids and emulsifiers on the accumulation of quercetinmetabolites in blood plasma after the short-term ingestion of onionby rats. Biosc. Biotechnol. Biochem., 2003, 67, 2548-2555.
88. Chu K.O.; Wang C.C.; Chu C.Y.; Rogers M.S.; Choy K.W.; PengC.P. Determination of catechins and catechin gallates in tissues byliquid chromatography with coulometric array detection andselective solid phase extraction. J. Chromatogr. B, 2004, 810, 187-195.
89. Bolarinwa A.; Linseisen J. Validated application of a new highperformanceliquid chromatographic method for the determinationof selected flavonoids and phenolic acids in human plasma usingelectrochemical detection. J. Chromatogr. B, 2005, 823, 143-51.
90. Careri, M.; Bianchi, F.; Corradini, C. Recent advances in theapplication of mass spectrometry in food-related analysis. J. Chromatogr. A, 2002, 970, 3-64.
91. Bureau, S.; Renard, C.M.G.C.; Reich, M.; Ginies, C.; Audergon, J.M. Change in anthocyanin concentrations in red apricot fruitsduring ripening. Food Sci. Technol., 2009, 42, 372-377.
92. Boué, S.M.; Carter-Wientjes, C.H.; Shih, B.Y.; Cleveland, T.E. Identification of flavone aglycones and glycosides in soybean podsby liquid chromatography-tandem mass spectrometry. J. Chromatogr. A, 2003, 991, 61-68.
93. Fulcrand, H.; Remy, S.; Souquet, J.M.; Cheynier, V.; Moutounet, M. Study of wine tannin oligomers by on-line liquidchromatography electrospray ionization mass spectrometry. J. Agric. Food Chem., 1999, 47, 1023-1028.
94. Grant, D.C.; Helleur, R.J. Rapid screening of anthocyanins in berrysamples by surfactant-mediated matrix-assisted laserdesorption/ionization time-of-flight mass spectrometry. RapidCommun. Mass Spectrom., 2008, 22, 156-164.
95. Monagas, M.; Quintanilla-López, J.E.; Carmen Gómez-Cordovés, C.; Bartolomé, B.; Lebrón-Aguilar, R. MALDI-TOF MS analysisof plant proanthocyanidins. J. Pharmaceut. Biomed. Anal., 2010, 51, 358-372.
96. Stobiecki M. Application of mass spectrometry for identificationand structural studies of flavonoid glycosides. Phytochemistry, 2000, 54, 237-256.
97. Prasain, J.K.; Wang, C.C.; Barnes, S. Mass spectrometric methodsfor the determination of flavonoids in biological samples. FreeRad. Biol. Med., 2004, 37, 1324-1350.
98. Xing, J.; Xie, C.; Lou, H. Recent applications of liquidchromatography-mass spectrometry in natural products bioanalysis. J. Pharmaceut. Biomed. Anal., 2007, 44, 368-378.
99. Cuyckens, F., Claeys, M. Mass spectrometry in the structuralanalysis of flavonoids. J. Mass Spectrom., 2004, 39, 1-15.
100. March, R.E.; Lewars, E.G.; Stadey, C.J.; Miao, X.S.; Zhao, X.;Metcalfe, C.D. A comparison of flavonoid glycosides byelectrospray tandem mass spectrometry. Int. J. Mass Spectrom., 2006, 248, 61-85.
101. Vukics, V.; Guttman, A. Structural characterization of flavonoidglycosides by multi-stage mass spectrometry. Mass Spectrom. Rev., 2010, 29, 1-16.
102. Gómez-Romero, M.; Zurek, G.; Schneider, B.; Baessmann, C. Segura-Carretero, A.; Fernández-Gutiérrez, A. Automatedidentification of phenolics in plant-derived foods by using librarysearch approach. Food Chem., 2011, 124, 379-386.
103. Frazier, R. A.; Papadopoulou, A. Recent advances in theapplication of capillary electrophoresis for food analysis. Electrophoresis, 2003, 24, 4095-4105.
104. Caridi, D.; Trenerry, V. C.; Rochfort, S.; Duong, S.; Laugher, D.;Jones, R. Profiling and quantifying quercetin glucosides in onion(Allium cepa, L.) varieties using capillary zone electrophoresis andhigh performance liquid chromatography. Food Chem., 2007, 105, 691-699.
105. Wang, S.; Huang, K. Determination of flavonoids by highperformance liquid chromatography and capillary electrophoresis. J. Chromatogr. A, 2004, 1032, 273-279.
106. Vaher, M.; Koel, M. Separation of polyphenol compoundsextracted from plant matrices using capillary electrophoresis. J. Chromatogr. A, 2003, 900, 225-230.
107. Bridle, P.; García-Viguera, C.; Tomas-Barberan, F. A. Analysis ofanthocyanins by capillary zone electrophoresis. J. LiquidChromatogr. Rel. Techn., 1996, 19, 537-545.
108. Bednar, P.; Papouskova, B.; Muller, L.; Bartak, P.; Stavek, J.;Pavlousek, P.; Lemr, K. Utilization of capillaryelectrophoresis/mass spectrometry (CE/MS) for the study ofanthocyanin dyes. J. Sep. Sci., 2005, 28, 1291-1299.
109. Yang, F.Q.; Zhao, J.; Li, S.P. CEC of phytochemical bioactivecompounds. Electrophoresis, 2010, 31, 260-277.
110. Baldi, A.; Romani, A.; Mulinnaci, N.; Vincieri, F.F.; Casetta, B. HPLC/MS application to anthocyanins of Vitis vinifera, L. J. Agric. Food Chem., 1995, 43, 2104-2109.
111. Kamangerpour, A.; Ashraf-Khorassani, M.; Taylor, L.T. McNair, H.M.; Chorida, L. Supercritical fluid chromatography ofpolyphenolic compounds in grape seed extract. Chromatographia, 2002, 55, 417-421.
112. da Costa, C.T.; Hortonb, D.; Margolis, S.A. Analysis ofanthocyanins in foods by liquid chromatography, liquidchromatography-mass spectrometry and capillary electrophoresis. J. Chromatogr. A, 2000, 881, 403-410.
113. Molnar-Perl, I.; Zs. Füzfai, Zs. Chromatographic, capillaryelectrophoretic and capillary electrochromatographic techniques inthe analysis of flavonoids. J. Chromatogr. A, 1073, 2005, 201-227
114. Gattuso, G.; Barreca, D.; Gargiulli, C.; Leuzzi, U.; Caristi, C. Flavonoid composition of Citrus juices. Molecules, 2007, 12, 1641-1673.
115. Stalikas, C.D. Extraction, separation, and detection methods forphenolic acids and flavonoids. J. Sep. Sci., 2007, 30, 3268-3295.
116. Marston, A.; Hostettmann, K. Natural product analysis over the lastdecades. Planta Med., 2009, 75: 672-682.
117. Valls, J.; Millána, S.; Martía, M.P.; Borràsa, E.; Arola, L. Advanced separation methods of food anthocyanins, isoflavonesand flavanols. J. Chromatogr. A, 2009, 1216, 7143-7172.
118. Ignat, I.; Volf, I.; Popa, V.I. A critical review of methods forcharacterisation of polyphenolic compounds in fruits andvegetables. Food Chem., 2011, 126, 1821-1835.
119. Harnly, J.M.; Bhagwat, S.; Lin, L.Z. Profiling methods for thedetermination of phenolic compounds in foods and dietarysupplements. Anal. Bioanal. Chem., 2007, 389, 47-61.
120. Kostiainen, R.; Kotiaho, T.; Kuuranne, T.; Auriola, S. Liquidchromatography/atmospheric pressure ionization-massspectrometry in drug metabolism studies. J. Mass Spectrom., 2003, 38, 357-372.
121. Justino, G.C.; Borges, C.M.; Florêncio, M.H. Electrosprayionization tandem mass spectrometry fragmentation of protonatedflavone and flavonol aglycones: a reexamination. Rapid Commun. Mass Spectrom., 2009, 23, 237-248.
122. 14C]-quercetin-4'-glucoside in rats. J. Agric. Food Chem., 2008, 56, 12127-12137.
123. Nakagawa, K.; Miyazawa, T. Chemiluminescence-highperformance liquid chromatographic determination of tea catechin,(-)-epigallocatechin-3-gallate, at picomole levels in rat and humanplasma. Anal. Biochem., 1997, 248, 41-49.
124. Wang, X.J.; Sun, W.; Sun, H.; Lv, H.; Wu, Z.; Wang, P.; Liu, L. Cao, H. Analysis of the constituents in the rat plasma after oraladministration of Yin Chen Hao Tang by UPLC/Q-TOF-MS/MS. J. Pharmaceut. Biomed. Anal., 2008, 46, 477-490.
125. Wang, Y.; Yao, Y.; An, R.; You, L.; Wang, X. Simultaneousdetermination of puerarin, daidzein, baicalin, wogonoside andliquiritin of GegenQinlian decoction in rat plasma by ultraperformanceliquid chromatography-mass spectrometry. J. Chromatogr. B, 2009, 877, 1820-1826
126. Serra, A.; Macia, A.; Romero, M.P.; Salvadó, M.J.; Bustos, M.;Fernández-Larrea, J.; Motilva, M.J. Determination of procyanidinsand their metabolites in plasma samples by improved liquidchromatography-tandem mass spectrometry. J. Chromatogr. B, 2009, 877, 1169-1176.
127. Suárez, M.; Romero, M.P.; Macia, A.; Valls, R.M.; Fernández, S.;Solà, R.; Motilva, M.J. Improved method for identifying andquantifying olive oil phenolic compounds and their metabolites inhuman plasma by microelution solid-phase extraction plate andliquid chromatography-tandem mass spectrometry. J. Chromatogr. B, 2009, 877, 4097-4106.
128. Marti, M.P.; Pantaleon, A.; Rozek, A.; Soler, A.; Valls, J.; Macià, A.; Romero, M.P.; Motilva, M.J. Rapid analysis of procyanidinsand anthocyanins in plasma by microelution SPE and ultra-HPLC. J. Sep. Sci., 2010, 33, 2841-2853.
129. Su, S.; Guo, J.; Duan, J.; Wang, T.; Qian, D.; Shang, E.; Tang, Y. Ultra-performance liquid chromatography-tandem massspectrometry analysis of the bioactive components and theirmetabolites of Shaofu Zhuyu decoction active extract in rat plasma. J. Chromatogr. B, 2010, 878, 355-362.
130. Zhang, W.; Xu, M.; Yu, C.; Zhang, G.; Tang, X. Simultaneousdetermination of vitexin-4'-O-glucoside, vitexin-2'-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma byUPLC-ESI-MS/MS. J. Chromatogr. B, 2010, 878, 1837-1844.
131. Pérez-Jiménez, J.; Hubert, J.; Hooper, L.; Cassidy, A.; Manach, C.;Williamson, G.; Scalbert, A. Urinary metabolites as biomarkers ofpolyphenol intake in humans: a systematic review. Am. J. Clin. Nutr., 2010, 92, 801-809.
132. Roura, E.; Andres-Lacueva, C.; Estruch, R.; Lamuela-Raventos, R.M. Total polyphenol intake estimated by a modified Folin-Ciocalteu assay of urine. Clin. Chem., 2006, 52, 749-752.
133. Medina-Remon, A.; Barrionuevo-González, A.; Zamora-Ros, R., Andres-Lacueva, C.; Estruch, R.; Martínez-González, M.A.; Diez-Espino, J.; Lamuela-Raventos, R.M. Rapid Folin-Ciocalteu methodusing microtiter 96-well plate cartridges for solid phase extractionto assess urinary total phenolic compounds, as a biomarker of totalpolyphenols intake. Anal. Chim. Acta., 2009, 634, 54-60.
134. Andersen, Ø.; Markham, K. Flavonoids: Chemistry, Biochemistryand Applications; CRC Press: Boca Raton, 2006.
135. Beecher, G.R. Flavonoids in food. In: Antioxidant FoodSupplements in Human Health, Packer, L.; Hiramatsu, M. andYoshikawa, T., Eds.; Academic Press: San Diego, 1999, pp269-281.
136. Kyle, J.A.M.; Duthie, G.G. In: Flavonoids: Chemistry, Biochemistry and Applications, Andersen, O.; Markham, K.R., Eds.; CRC Press: Boca Raton, 2006, pp219-262.
137. Crozier, A.; Jaganath, I.B.; Clifford, M.N. Dietary phenolics:chemistry, bioavailability and effects on health. Nat. Prod. Rep., 2009, 26, 1001-1043.
138. Manach, C.; Scalbert, A.; Morand, C.; Rémésy, C.; Jiménez, L. Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr., 2004, 79, 727-747.
139. Price, S.F.; Breen, P.J.; Valladao, M.; Watson, B.T. Cluster sunexposure and quercetin in Pinot noir grapes and wine. Am. J. Enol. Vitic., 1995, 46, 187-94.
140. Stewart, A.; Bozonnet, S.; Mullen, W.; Jenkins, G.I.; Lean, M.E.J.;Crozier, A. Occurrence of flavonols in tomato and tomato-basedproducts. J. Agric. Food Chem., 2000, 48, 2663-2669.
141. Hollman, P.C.H.; Arts, I.C.W. Flavonols, flavones and flavanols-nature, occurrence and dietary burden. J. Sci. Food Agric., 2000, 80, 1081-1093.
142. Erdman, J.W. Jr; Balentine, D.; Arab, L.; Beecher, G.; Dwyer, J.T.;Folts, J.; Harnly, J.; Hollman, P.; Keen, C.L.; Mazza, G.; Messina, M.; Scalbert, A.; Vita, J.; Williamson, G.; Burrowes, J. Flavonoidsand heart health: proceedings of the ILSI North America flavonoidsworkshop, May 31-June 1, 2005, Washington, DC. J. Nutr., 2007, 137, 718S-737S.
143. Erlund, I. Review of the flavonoids quercetin, hesperetin, andnaringenin. Dietary sources, bioactivities, bioavailability, andepidemiology. Nutr. Res., 2004, 24, 851-874.
144. Hertog, M.G.; Kromhout, D.; Aravanis, C.; Blackburn, H.; Buzina, R.; Fidanza, F.; Giampaoli, S.; Jansen, A.; Menotti, A.;Nedeljkovic, S.; Pekkarinen, M.; Simic, B.S.; Toshima, H.;Feskens, E.J.M.; Hollman, P.C.H.; Katan, M.B. Flavonoid intakeand longterm risk of coronary heart disease and cancer in the SevenCountries Study. Arch. Intern. Med., 1995; 155, 381-386.
145. Sampson, L.; Rimm, E.; Hollman, P.C.; de Vries, J.H.; Katan, M.B. Flavonol and flavone intakes in US health professionals. J. Am. Diet. Assoc., 2002, 102, 1414-1420.
146. Tomás-Barberán, F.A.; Clifford, M.N. Flavanones, chalcones anddihydrochalcones-nature, occurrence and dietary burden. J. Sci. Food Agric., 2000, 80, 1073-1080.
147. Kumpulainen, J.T.; Lehtonen, M.; Mattila, P. In: NaturalAntioxidants in Nutrition, Health and Disease, Kumpulainen JT, Salonen JT, Eds.; Cambridge: The Royal Society of Chemistry;1999; pp. 141-150.
148. Vacek, J.; Klejdus, B.; Lojkov, L.; Kubán, V. Current trends inisolation, separation, determination and identification ofisoflavones: A review. J. Sep. Sci., 2008, 31, 2054-2067.
149. Cassidy, A.; Hansley, B.; Lamuela-Raventos, R.M. Isoflavones, lignans and stilbenes-origins, metabolism and potentialimportance to human health. J. Sci. Food Agric., 2000, 80, 1044-62.
150. Coward, L.; Smith, M.; Kirk, M.; Barnes, S. Chemical modificationof isoflavones in soyfoods during cooking and processing. Am. J. Clin. Nutr., 1998, 68, 1486S-1491S.
151. Liggins, J.; Bluck, L.J.; Runswick, S.; Atkinson, C.; Coward, W.A.; Bingham, S.A. Daidzein and genistein contents ofvegetables, Br. J. Nutr., 2000, 84, 717-725.
152. Mortensen, A.; Kulling, S.E.; Schwartz, H.; Rowland, I.; Ruefer, C.E.; Rimbach, G.; Cassidy, A.; Magee, P.; Millar, J.; Hall, W.L.;Birkved, F.K.; Sorensen, I.K.; Sontag, G. Analytical andcompositional aspects of isoflavones in food and their biologicaleffects. Mol. Nutr. Food Res., 2009, 53, S266-S309.
153. Han, X.; Shen, T.; Lou, H. Dietary polyphenols and their biologicalsignificance. Int. J. Mol. Sci., 2007, 8, 950-988.
154. de Pascual-Teresa, S.; Moreno, D.A.; García-Viguera, C. Flavanolsand anthocyanins in cardiovascular health: a review of currentevidence. Int. J. Mol. Sci., 2010, 11, 1679-1703.
155. Arts, I.C.W.; van de Putte, B.; Hollman, P.C.H. Catechin contentsof foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods. J. Agric. FoodChem., 2000, 48, 1746-51.
156. Hooper, L.; Cassidy, A. A review of the health care potential ofbioactive compounds. J. Sci. Food Agric., 2006, 86, 1805-1813.
157. Spanos, G.A.; Wrolstad, R.E.; Heatherbell, D.A. Influence ofprocessing and storage on the phenolic composition of apple juice. J. Agric. Food Chem., 1990, 38, 1572-1579.
158. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.;Haytowitz, D.; Gebhardt, S.; Prior, R. Concentrations ofproanthocyanidins in common foods and estimations of normalconsumption. J. Nutr., 2004, 134, 613-617.
159. de Pascual-Teresa, S.; Rivas-Gonzalo, J.C.; Santos-Buelga, C. Catechins intake in the Spanish diet. In COST 916-BioactiveCompounds in Plant Foods. Health Effects and Perspectives for theFood Industry, Amadò, R., Abt, B., Bravo, L., Goñi, I., Saura-Calixto, F., Eds.; Office for Official Publications of the EuropeanCommunities: Tenerife, 2002; pp. 317-318.
160. Arts, I.C.; Hollman, P.C.; Feskens, E.J.; Bueno de Mesquita, H.B.;Kromhout, D. Catechin intake and associated dietary and lifestylefactors in a representative sample of Dutch men and women. Eur.J. Clin. Nutr., 2001, 55, 76-81.
161. Clifford, M.N. Anthocyanins-nature, occurrence and dietaryburden. J. Sci. Food Agric., 2000, 80, 1063-1072.
162. Wu, X.L.; Beecher, G.R.; Holden, J.M.; Haytowitz, D.B.;Gebhardt, S.E.; Prior, R.L. Concentrations of anthocyanins incommon foods in the United States and estimation of normalconsumption. J. Agric. Food Chem., 2006, 54, 4069-4075.
163. Elmadfa, I.; Meyer, A.L. Importance of food composition data tonutrition and public health. Eur. J. Clin. Nutr., 2010, 64, S4-S7.
164. Neveu, V.; Perez-Jiménez, J.; Vos, F.; Crespy, V.; du Chaffaut, L.;Mennen, L.; Knox, C.; Eisner, R.; Cruz, J.; Wishart, D.; Scalbert, A. Phenol-Explorer: an online comprehensive database onpolyphenol contents in foods. Database, 2010, Article ID bap024, doi:10.1093/database/bap024.
165. Harnly, J.M.; Doherty, R.F.; Beecher, G.R.; Holden; J.M.;Haytowitz, D.B.; Bhagwat, S.; Gebhardt, S. Flavonoid content of U.S. fruits, vegetables, and nuts. J. Agric. Food Chem., 2006, 54, 9966-9977.
166. Holden, J. M.; Bhagwat, S. A.; Haytowitz, D. B.; Gebhardt, S. E.;Dwyer, J. T.; Peterson, J.; Beechera, G.R.; Eldridgec, A.L.;Balentine, D. Development of a database of critically evaluatedflavonoids data: application of USDA's data quality evaluationsystem. J. Food Compos. Anal., 2005, 18, 829-844.
167. USDA Database for the Flavonoid Content of Selected Foods, Release 2.1 (2007). http://www.ars.usda.gov/services/docs.htm?docid=6231.
168. Gry, J.; Black, L.; Eriksen, F.D.; Pilegaard, K.; Plumb, J.; Rhodes, M.; Sheehan, D.; Kiely, M.; Kroon, P. A. EuroFIR BASISDatabase. Trends Food Sci. Technol., 2007, 18, 434-444.
169. Pérez-Jiménez, J.; Neveu, V.; Fvos, F.; Scalbert, A. Identificationof the 100 richest dietary sources of polyphenols: an application ofthe Phenol-Explorer database. Eur. J. Clin. Nutr., 2010, 64, S112-S120.
170. Pérez-Jiménez, J.; Neveu, V.; Vos, F.; Scalbert, A. Systematicanalysis of the content of 502 polyphenols in 452 foods andbeverages: an application of the phenol-explorer database. J. Agric. Food Chem., 2010, 58, 4959-4969.
171. Schwartz, H.; Sontag, G.; Plumb, J. Inventory of phytoestrogendatabases. Food Chem., 2009, 113, 736-747.
172. Scalbert, A.; Andres-Lacueva, C.; Arita, M.; Kroon, P.; Manach, C.; Urpi-Sarda, M.; Wishart. D. Databases on food phytochemicalsand their health-promoting effects. J. Agric. Food Chem., 2011, 59, 4331-4348.