Flavonoids: Chemical properties and analytical methodologies of identification and quantitation in foods and plants

Natural Product Research

Volumn 25, Issue 5, 2011, Pages 469-495

  Corradini, Eleonora ^a   Foglia, Patrizia ^a   Giansanti, Piero ^a   Gubbiotti, Riccardo ^a   Samperi, Roberto ^a   Laganà, Aldo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

analytical determination; flavonoids; mass spectrometry

Indexed keywords

AFZELECHIN; ANTHOCYANIN; CATECHIN; CYANIDIN 3 GLUCOSIDE; DAIDZEIN; DELPHINIDIN; EPICATECHIN; EPIFISETINIDOL; EPIGALLOCATECHIN; FISETINIDOL; FLAVAN 3 OL DERIVATIVE; FLAVANONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; GALLOCATECHIN; GENISTEIN; GLYCITEIN; ISOFLAVONOID; ISORHAMNETIN; KAEMPFEROL; MALVIDIN CHLORIDE; MYRICETIN; PELARGONIDIN; PEONIDIN; PETUNIDIN CHLORIDE; PHYTOALEXIN; PROANTHOCYANIDIN DERIVATIVE; QUERCETIN; ROBINETINDOL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANTIOXIDANT ACTIVITY; BIOLOGICAL ACTIVITY; DRUG CLASSIFICATION; DRUG DETERMINATION; DRUG STRUCTURE; ELECTROSPRAY; FLOWERING; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; LIQUID LIQUID EXTRACTION; NONHUMAN; REVIEW; SOLID PHASE EXTRACTION; SOLVENT EXTRACTION; TANDEM MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY; VEGETABLE;

ANIMALS; ANTIOXIDANTS; CHROMATOGRAPHY, LIQUID; FLAVONOIDS; FOOD ANALYSIS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PHENOLS; PLANTS; SOLID PHASE EXTRACTION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 79952635473     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2010.482054     Document Type: Review

References (158)

1. Adlercreutz, H., Goldin, B.R., Gorbach, S.L., Haockerstedt, K.A.V., Watanabe, S., Haamaalaainen, E.K., et al. (1995). Soybean phytoestrogen intake and cancer risk. Journal of Nutrition, 125, 757S-770S.
2. Andrade, P.B., Leitão, R., Seabra, R.M., Oliveira, M.B., & Ferreira, M.A. (1997). Development of an HPLC/diode-array detector method for simultaneous determination of seven hydroxycinnamic acids in green coffee. Journal of Liquid Chromatography and Related Technologies, 20, 2023-2030, doi:10.1080/10826079708005561. (Pubitemid 27313804)
3. Andreasen, M.F., Christensen, L.P., Meyer, A.S., & Hansen, A. (2000). Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties. Journal of Agricultural and Food Chemistry, 48, 2837-2842, doi:10.1021/jf991266w. (Pubitemid 30490499)
4. Aron, P.M., & Kennedy, J.A. (2008). Flavan-3-ols: nature, occurrence and biological activity. Molecular Nutrition and Food Research, 52, 79-104, doi:10.1002/mnfr.200700137. (Pubitemid 351211804)
5. Bakker, J., Bridle, P., & Koopman, A. (1992). Strawberry juice colour: the effect of some processing variables on the stability of anthocyanins. Journal of Science and Food Agriculture, 60, 471-476.
6. Barnes, S., Kirk, M., & Coward, L. (1994). Isoflavones and their conjugates in soy foods - extraction conditions and analysis by HPLC mass spectrometry. Journal Agricultural and Food Chemistry, 42, 2466-2474, doi:10.1021/jf00047a019.
7. Bassam, B.J., Djordjevic, M.A., Redmond, J.W., Batley, M., & Rolfe, B.G. (1988). Identification of a nodD-dependent locus in the rhizobium strain NGR234 activated by phenolic factors secreted by soybean and other legumes. Molecular Plant-Microbe Interactions, 1, 161-168, doi:10.1094/MPMI-1-161.
8. Bate-Smith, E.C. (1973). Tannins of herbaceous Leguminosae. Phytochemistry, 12, 1809-1812, doi:10.1016/0031-9422(73)80409-1.
9. Beara, I.N., Lesjak, M.M., Jovin, E., & Balo, K.J. (2009). Plantain (Plantago L.) species as novel sources of flavonoid antioxidants. Journal of Agricultural and Food Chemistry, 57, 9268-9273, doi:10.1021/jf902205m.
10. Bogdanov, S. (1989). Determination of pinocembrin in honey using HPLC. Journal Apicultural Research, 28, 55-57.
11. Bolling, B.W., Dolnikovski, G., Blumberg, J.B., & Chen, C.Y.O. (2009). Quantification of almond skin polyphenols by liquid chromatography-mass spectrometry. Journal of Food Science, 74(4), C326-C332, doi:10.1111/j.1750- 3841.2009.01133.x.
12. Boúe, S.M., Carter-Wientjes, C.H., Shih, B.Y., & Cleveland, T.E. (2003). Identification of flavone aglycones and glycosides in soybean pods by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A, 991, 61-68, doi:10.1016/S0021-9673(03)00209-7. (Pubitemid 36287626)
13. Boyles, M.J., & Wrolstad, R.E. (1993). Anthocyanin composition of red raspberry juice: Influences of cultivar, processing, and environmental factors. Journal of Food Science, 58, 1135-1141.
14. Bridle, P., & Garciá-Viguera, C. (1997). Analysis of anthocyanins in strawberries and elderberries. A comparison of capillary zone electrophoresis and HPLC. Food Chemistry, 59, 299-304, doi:10.1016/S0308- 8146(96)00176-8.
15. Brolis, M., Gabetta, B., Fuzzati, N., Pace, R., Panzeri, F., & Peterlongo, F. (1998). Identification by high-performance liquid chromatographysdiode array detectionsmass spectrometry and quantification by high-performance liquid chromatographys UV absorbance detection of active constituents of Hypericum perforatum. Journal of Chromatography A, 825, 9-16, doi:10.1016/S0021-9673(98)00697-9. (Pubitemid 28486952)
16. Bronner, W.E., & Beecher, G.R. (1995). Extraction and measurement of prominent flavonoids in orange and grapefruit juice concentrates. Journal of Chromatography A, 705, 247-256, doi:10.1016/0021-9673(95)00304-6.
17. Bronner, W.E., & Beecher, G.R. (1998). Method for determining the content of catechins in tea infusions by high-performance liquid chromatography. Journal of Chromatography A, 805, 137-142, doi:10.1016/S0021-9673(98)00040-5. (Pubitemid 28231195)
18. Buiarelli, F., Coccioli, F., Jasionowska, R., Merolle, M., & Terracciano, A. (2007). Analysis of some stilbenes in Italian wines by liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 21, 2955-2964, doi:10.1002/rcm.3174. (Pubitemid 47401432)
19. Careri, M., Elviri, L., Mangia, A., & Musci, M. (2000). Spectrophotometric and coulometric detection in the high-performance liquid chromatography of flavonoids and optimization of sample treatment for the determination of quercetin in orange juice. Journal of Chromatography A, 881, 449-460, doi:10.1016/S0021-9673(00)00256-9. (Pubitemid 30332227)
20. Castillo, M.N., Gómez, A.S., García Romero, E., & Hermosín Gutiérrez, I. (2007). Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines. Journal of Agricultural and Food Chemistry, 55, 992-1002.
21. Cavaliere, C., Cucci, F., Foglia, P., Guarino, C., Samperi, R., & Laganà, A. (2007). Flavonoid profile in soybeans by high-performance liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 21, 2177-2187, doi: 10.1002/rcm.3049. (Pubitemid 47121148)
22. Cavaliere, C., Foglia, P., Gubbiotti, R., Sacchetti, P., Samperi, R., & Laganà, A. (2008). Rapid-resolution liquid chromatography/mass spectrometry for determination and quantitation of polyphenols in grape berries. Rapid Communications in Mass Spectrometry, 22, 3089-3099, doi:10.1002/rcm.3705.
23. Cavaliere, C., Foglia, P., Pastorini, E., Samperi, R., & Laganà, A. (2005). Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high-performance liquid chromatography with tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 19, 3143-3158, doi:10.1002/rcm.2185. (Pubitemid 41540744)
24. Chen, H., Zuo, Y.G., & Deng, Y.W. (2001). Separation and determination of flavonoids and other phenolic compounds in cranberry juice by high-performance liquid chromatography. Journal of Chromatography A, 913, 387-395, doi:10.1016/S0021-9673(00)01030-X. (Pubitemid 32261005)
25. Cos, P., Calomme, M., Sindambiwe, J.B., De Bruyne, T., Cimanga, K., Pieters, L., et al. (2001). Cytotoxicity and lipid peroxidation-inhibiting activity of flavonoids. Planta Medica, 67, 515-519, doi:10.1055/s-2001-16472. (Pubitemid 32800415)
26. Cos, P., Ying, L., Calomme, M., Hu, J.P., Cimanga, K., Van Poel, B., et al. (1998). Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. Journal of Natural Products, 61, 71-76, doi:10.1021/np970237h. (Pubitemid 28086977)
27. Crozier, A., Lean, M.E.J., McDonald, M.S., & Black, C. (1997). Quantitative analysis of the flavonoid content of commercial tomatoes, onions, lettuce, and celery. Journal of Agricultural and Food Chemistry, 45, 590-595. (Pubitemid 127483672)
28. Cuyckens, F., & Claeys, M.J. (2004). Mass spectrometry in the structural analysis of flavonoids. Journal of Mass Spectrometry, 39, 1-15, doi:10.1002/jms.585. (Pubitemid 38213098)
29. Cuyckens, F., Shahat, A.A., Van den Heuvel, H., Abdel- Shafeek, K.A., El-Messiry, M.M., Seif-El Nasr, M.M., et al. (2003). The application of liquid chromatography-electrospray ionization mass spectrometry and collision-induced dissociation in the structural characterization of acylated flavonol O-glycosides from the seeds of Carrichtera annua. European journal of mass spectrometry, 9, 409-420. (Pubitemid 37163451)
30. Dalluge, J.J., Nelson, B.C., Brown Thomas, J., & Sander, L.C. (1998). Selection of column and gradient elution system for the separation of catechins in green tea using high-performance liquid chromatography. Journal of Chromatography A, 793, 265-274, doi:10.1016/S0021-9673(97)00906-0. (Pubitemid 28044252)
31. De Cooman, L., Everaert, E., & De Keukeleire, D. (1998). Quantitative analysis of hop acids, essential oils and flavonoids as a clue to the identification of hop varieties. Phytochemical Analysis, 9, 145-150, doi:10.1002/(SICI)1099-1565 (199805/06)9:〈145::AID-PCA393〉33.0.CO;2-K.
32. de Rijke, E., Joshi, H.C., Sanderse, H.R., Ariese, F., Th. Brinkman, U.A., & Gooijer, C. (2002). Natively fluorescent isoflavones exhibiting anomalous stokes' shifts. Analitica Chimica Acta, 468, 3-11, doi:10.1016/S0003-2670(02)00630-x. (Pubitemid 35223113)
33. de Rijke, E., Out, P., Niessen, W.M.A., Ariese, F., Gooijer, C., & Brinkman, U.A.Th. (2006). Analytical separation and detection methods for flavonoids. Journal of Chromatography A, 1112, 31-63, doi:10.1016/j.chroma.2006. 01.019.
34. de Rijke, E., Zappey, H., Ariese, F., Gooijer, C., & Brinkman, U.A. (2003). LC with APCI and ESI-MS of flavonoids with triple-quadrupole and ion trap instruments. Journal of Chromatography A, 984, 45-48, doi:10.1016/S0021- 9673(02)01868-X.
35. Del Monte, P., Perry, J., & Rader, J.I. (2006). Determination of isoflavones in dietary supplements containing soy, red clover and kudzu: extraction followed by basic or acid hydrolysis. Journal of Chromatography A, 1107, 59-69, doi:10.1016/j.chroma.2005.11.060. (Pubitemid 43184207)
36. Di Carlo, G., Autore, G., Izzo, A.A., Maiolino, P., Mascolo, N., Viola, P., et al. (1993). Inhibition of, intestinal motility and secretion by flavonoids in mice and rats; structure activity relationships. Journal of Pharmacy and Pharmcology, 45, 1045-1059.
37. Domon, B., & Costello, C.E. (1988). A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate Journal, 5, 397-490.
38. Donner, H., Gao, L., & Mazza, G. (1997). Separation and characterization of simple and malonylated anthocyanins in red onions, Allium cepa L. Food Research International, 30, 637-643, doi:10.1016/S0963-9969(98) 00011-8.
39. Edelmann, A., Diewok, J., Schuster, K.C., & Lendl, B. (2001). Rapid method for the discrimination of red wine cultivars based on mid-infrared spectroscopy of phenolic wine extracts. Journal of Agricultural and Food Chemistry, 49, 1139-1145, doi:10.1021/jf001196p. (Pubitemid 32884923)
40. Escarpa, A., & Gonzalez, M.C. (2000). Optimization strategy and validation of one chromatographic method as approach to determine the phenolic compounds from different sources. Journal of Chromatography A, 897, 161-170, doi:10.1016/S0021-9673(00)00817-7.
41. Ewald, C., Fjelkner-Modig, S., Johansson, K., Sjóholm, I., & Akesson, B. (1999). Effect of processing on major flavonoids in processed onions, green beans, and peas. Food Chemistry, 64, 231-235, doi:10.1016/s0308- 8146(98)00136-8. (Pubitemid 28552679)
42. Fahey, J.W., & Stephenson, K.K. (2002). Pinostrobin from honey and thai ginger (Boesenbergia pandurata): A potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes. Journal of Agricultural and Food Chemistry, 50, 7472-7476, doi:10.1021/jf025692k. (Pubitemid 35424920)
43. Ferrali, M., Signorini, C., Caciotti, B., Sugherini, L., Ciccoli, L., Giachetti, D., et al. (1997). Protection against oxidative damage of erythrocyte membrane by the flavonoid quercetin and its relation to iron chelating activity. FEBS Letters, 416, 123-129, doi:10.1016/S0014-5793(97)01182-4. (Pubitemid 27462770)
44. Ferrer, I., Thurman, E.M., & Zwelgenbaum, J.A. (2007). Screening and confermation of 100 pesticides in food samples by liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 21, 3869-3882, doi:10.1002/rcm. 3870 I. (Pubitemid 350220695)
45. Firmin, J.L., Wilson, K.E., Rossen, L., & Johnston, A.W.B. (1986). Flavonoid activation of nodulation genes in rhizobium reversed by other compounds present in plants. Nature, 324, 90-92, doi:10.1038/324090a0. (Pubitemid 16008425)
46. Friedman, M., & Jurgens, H.S. (2000). Effect of pH on the stability of plant phenolic compounds. Journal of Agricultural and Food Chemistry, 48, 2101-2110, doi:10.1021/jf990489j. (Pubitemid 30431196)
47. Galensa, R., & Herrmann, K. (1980a). Analysis of flavonoids by HPLC. Journal of Chromatography, 189, 217-224.
48. Galensa, R., & Herrmann, K. (1980b). Hochdruckflü ssigkeitschromatographische bestimmung von hesperidin in orangensäften. Deutsche Lebensmittel-Rundschau, 76, 270-273.
49. Garrett, S.D., Lee, H.A., Friar, P.M.K., & Morgan, M.R.A. (1999). Validation of a novel estrogen receptor-based microtitration plate assay for the determination of 488 E. Corradini et al. phytoestrogens in soy-based foods. Journal of Agricultural and Food Chemistry, 47, 4106-4111, doi:10.1021/ jf9905790. (Pubitemid 29506208)
50. Gel-Moreto, N., Streich, R., & Galensa, R. (2001). Chiral separation of six diastereomeric flavanone-7-O-glycosides by capillary electrophoresis and analysis of lemon juice. Journal of Chromatography A, 925, 279-289, doi:10.1016/S0021-9673(01)01038-X. (Pubitemid 32680985)
51. Gil-Izquierdo, A., & Mellenthin, A. (2001). Identification and quantitation of flavonols in rowanberry (Sorbus aucuparia L.) juice. European Food Research and Technology, 213, 12-17, doi:10.1007/s002170100328. (Pubitemid 33808413)
52. Goiffon, J.P., Brun, M., & Bourrier, M.J. (1991). High performance liquid chromatography of red fruit anthocyanins. Journal of Chromatography A, 537, 101-121, doi:10.1016/S0021(01)88890-7.
53. González-SanJosé, M.L., & Diez, C. (1992). Relationship between anthocyanins and sugars during the ripening of grape berries. Food Chemistry, 43, 193-197, doi:10.1016/0308-8146(92)90172-X.
54. Graham, T.L. (1991). Flavonoid and isoflavonoid distribution in developing soybean seedling tissues and in seed and root exudates. Plant Physiology, 95, 594-603.
55. Griffith, A.P., & Collison, M.W. (2001). Improved methods for the extraction and analysis of isoflavones from soy-containing foods and nutritional supplements by reversed-phase high-performance liquid chromatography and liquid chromatographymass spectrometry. Journal of Chromatography A, 913, 397-413, doi:10.1016/S0021-9673(00)01077. (Pubitemid 32261006)
56. Gryglewski, R.J., Korbut, R., Robak, J., & Swips, J. (1987). On the mechanism of antithrombotic action of flavonoids. Biochemical Pharmacology, 36, 317-322, doi:10.1016/0006-2952(87)90288-7. (Pubitemid 17003331)
57. Gu, L., & Gu, W. (2001). Characterisation of soy isoflavones and screening for novel malonyl glycosides using high-performance liquid chromatography-electrospray ionisation-mass spectrometry. Phytochemical Analysis, 12, 377-382, doi:10.1002/pca.603. (Pubitemid 33130740)
58. Guedon, D.J., & Pasquier, B.P. (1994). Analysis and distribution of flavonoid glycosides and rosmarinic acid in 40 Mentha piperita clones. Journal of Agricultural and Food Chemistry, 42, 679-684, doi:10.1021/jf00039a015.
59. 3+. Spectrochimica Acta Part A, 58, 83-89, doi:10.1016/S1386-1425(01)00515-7.
60. Harborne, J.B., & Boardley, M. (1984). Use of high-performance liquid chromatography in the separation of flavonol glycosides and flavonol sulphates. Journal of Chromatography, 299, 377-385.
61. Harborne, J.B., & Williams, C.A. (1998). Anthocyanins and other flavonoids. Natural Product Reports, 15, 631-652, doi:10.1039/a815631y. (Pubitemid 29025681)
62. Hedin, P.A., Jenkins, J.N., Collum, D.H., White, W.H., & Parrott, W.L. (1983). Multiple factors in cotton contributing to resistance to the tobacco budworm. In P.A. Hedin (Ed.), Plant resistance to insects (pp. 347-365). Washington, D.C: American Chemical Society.
63. Heinonen, I.M., Lehtonen, P.J., & Hopia, A.I. (1998). Antioxidant activity of berry and fruit wines and liquors. Journal of Agricultural and Food Chemistry, 46, 25-31, doi:10.1021/jf970489o. (Pubitemid 128488016)
64. Hellström, J., Sinkkonen, J., Karonen, M., & Mattila, P. (2007). Isolation and structure elucidation of procyanidin oligomers from saskatoon berries (Amelanchier alnifolia). Journal of Agricultural and Food Chemistry, 55, 157-164, doi:10.1021/jf062441t. (Pubitemid 46059134)
65. Hollman, P.C.H., Van Trijp, J.M.P., & Buysman, M.N.C.P. (1996). Fluorescence detection of flavonols in HPLC by postcolumn chelation with aluminium. Analytical Chemistry, 68, 3511-3515, doi:0014-5793(97)01367-7.
66. Hong, V., & Wrolstad, R.E. (1990). Characterization of anthocyanin-containing colorants and fruit juices by HPLC/photodiode array detection. Journal of Agricultural and Food Chemistry, 38, 698-708, doi:10.1021/jf00093a025.
67. Huck, C.W., & Bonn, G.K. (2001). Evaluation of detection methods for the reversed-phase HPLC determination of 3′,4′,5′- trimethoxyflavone in different phytopharmaceutical products and in human serum. Phytochemical Analysis, 12, 104-109, doi:10.1002/pca547.
68. Hughes, R.J., Croley, T.R., Metcalfe, C.D., & March, R.E. (2001). A tandem mass spectrometric study of selected characteristic flavonoids. International Journal of Mass Spectrometry, 210/211, 371-385, doi:10.1016/S1387-3806(01)00451-1. (Pubitemid 32947110)
69. Iwashina, T. (2000). The structure and distribution of the flavonoids in plants. Journal of Plant Research, 113, 287-299, doi:10.1007/PL00013940.
70. Iwashina, T. (2003). Flavonoid function and activity to plants and other organisms. Biological Sciences in Space, 17, 24-44, doi:10.2187/bss.17.24.
71. Izzo, A.A., Dicarlo, G., Mascolo, N., Capasso, F., & Autore, G. (1991). Antiulcer effects of flavonoids. Role of endogenous PAF. Phytotherapy Research, 8, 179-181.
72. Justesen, U., Knuthsen, P., & Leth, T. (1998). Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. Journal of Chromatography A, 799, 101-110, doi:10.1016/S0021-9673(97)01061-3. (Pubitemid 28161212)
73. Kanes, K., Tisserat, B., Berhow, M., & Vandercook, C. (1993). Phenolic composition of various tissues of Rutaceae species. Phytochemistry, 32, 967-974, doi:10.1016/0031-9422(93)85237-L.
74. Kanner, J., Frankel, E., Granit, R., German, B., & Kinsella, J.E. (1994). Natural antioxidants in grapes and wines. Journal of Agricultural and Food Chemistry, 42, 64-69, doi:10.1021/jf00037a010.
75. Kapiotis, S., Hermann, M., Held, I., Seelos, C., Ehringer, H., & Gmeiner, B.M.K. (1997). Genistein, the dietary-derived angiogenesis inhibitor, prevents LDL oxidation and protects endothelial cells from damage by atherogenic LDL. Arteriosclerosis, Thrombosis and Vascular Biology, 17, 2868-2874. (Pubitemid 28016034)
76. Khokhar, S., Venema, D., Hollman, P.C.H., Dekker, M., & Jongen, W. (1997). A RP-HPLC method for the determination of tea catechins. Cancer Letters, 114, 171-172, doi:10.1016/S0304-3835(97)04653-3. (Pubitemid 27140103)
77. Kim, H.P., Mani, I., Iversen, L., & Ziboh, V.A. (1998). Effects of naturally occurring flavonoids and bioflavonoids on epidermal cycloxygenase and lipoxygenase from guinea pigs. Prostaglandins, Leukotrienes Essential Fatty Acids, 58, 17-24, doi:10.1016/S0952-3278(98)90125-9.
78. Kinoshita, E., Ozawa, Y., & Aishima, T. (1997). Novel tartaric acid isoflavone derivatives that play key roles in differentiating Japanese soy sauces. Journal of Agricultural and Food Chemistry, 45, 3753-3759, doi:10.1021/jf9702095. (Pubitemid 127485666)
79. Kinoshita, E., Sugimoto, T., Ozawa, Y., & Aishima, T. (1998). Differentiation of soy sauce produced from whole soybeans and defatted soybeans by pattern recognition analysis of HPLC profiles. Journal of Agricultural and Food Chemistry, 46, 877-883. (Pubitemid 128488084)
80. Kong, J.M., Chia, L.S., Goh, N.K., Chia, T.F., & Brouillard, R. (2003). Analysis and biological activities of anthocyanins. Phytochemistry, 64, 923-933, doi:10.1016/S0031-9422(03)00438-2.
81. Kontruck, S.J., Radecki, T., & Brozozowski, T. (1986). Anti-ulcer and gastroprotective effects of solon, a synthetic flavonoid derivative of sophorandin. Role of endogenous prostaglandins. British Journal of Pharmacology, 125, 185-192. (Pubitemid 16075429)
82. Krause, M., & Galensa, R. (1991). High-performance liquid chromatography of diastereomeric flavanone glycosides in citrus on a β-cyclodextrin-bonded stationary phase (cyclobond I). Journal of chromatography, 588, 41-45.
83. Kumamoto, M., & Sonda, T. (1998). Evaluation of the antioxidative activity of tea by an oxygen electrode method. Bioscience Biotechnology and Biochemistry, 62, 175-177.
84. Kurzer, M.S. (2000). Hormonal effects of soy isoflavones: Studies in premenopausal and postmenopausal women. Journal of Nutrition, 130, 660S-661S.
85. Le Marchand, L. (2002). Cancer preventive effects of flavonoids: a review. Biomedicine and Pharmacotherapy, 56, 296-301, doi:10.1016/S0753-3322(02) 00186-5.
86. Li, Q.M., & Claeys, M. (1994). Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biological Mass Spectrometry, 23, 406-416, doi:10.1002/bms. 1200230705.
87. Loewenstein, W.R. (1979). Junctional intercellular communication and the control of growth. Biochimica et Biophysica Acta, 560, 1-65.
88. Lorenz, W., Kusche, J., Barth, H., & Mathias, C.H. (1994). Action of several flavonoids on enzyme of histidine metabolism in vivo. In C.Z. Maslinski (Ed.), Histamine (pp. 265-269). Pennsylvania: Hutchinson and Ross.
89. Lou, F.Q., Zhang, M.F., Zhang, X.G., Liu, J.M., & Yuan, W.L. (1989). A study on tea-pigment in prevention of antherosclerosis. Chinese Medical Journal (Engl), 102, 579-583.
90. Ma, Y.L., Li, Q.M., van den Heuvel, H., & Claeys, M. (1997). Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Communication in Mass Spectrometry, 11, 1357-1364, doi:10.1002/(SICI)1097-0231(199708)11. (Pubitemid 27358300)
91. Mabry, T.J., Markham, K.R., & Thomas, M. (Eds.). (1970). The systematic identification of flavonoids. New York: Springer-Verlag.
92. Manthey, J., & Guthrie, N. (2002). Antiproliferative activities of citrus flavonoids against six human cancer cell lines. Journal of Agricultural Food Chemistry, 50, 5837-5843, doi:10.1021/jf020121d. (Pubitemid 35155302)
93. Mataix, E., & de Castro, M.D.L. (2001). Determination of anthocyanins in wine based on flow-injection, liquid-solid extraction, continuous evaporation and high-performance liquid chromatography-photometric detection. Journal of Chromatography A, 910, 255-263, doi:10.1016/S0021-9673(00)01227-9. (Pubitemid 32126293)
94. Mattila, P., Astola, J., & Kumpulainen, J. (2000). Determination of flavonoids in plant material by HPLC with diode-array and electro-array detections. Journal of Agricultural and Food Chemistry, 48, 5834-5841, doi:10.1021/jf000661f. (Pubitemid 32056815)
95. Mazza, G., & Velioglu, Y.S. (1992). Anthocyanins and other phenolic compounds in fruits of red-flesh apple. Food Chemistry, 43, 113-117, doi:10.16/0308-8146(92)90223-0.
96. Merken, H.M., & Beecher, G.R. (2000). Liquid chromatographic method for the separation and quantification of prominent flavonoid aglycones. Journal of Chromatography A, 897, 177-184, doi:10.1016/S0021-9673(00)00826-8.
97. Merken, H.M., Merken, C.D., & Beecher, G.R. (2001). Kinetics method for the quantitation of anthocyanidins, flavonols, and flavones in foods. Journal of Agricultural and Food Chemistry, 49, 2727-2732, doi:10.1021/ jf001266s. (Pubitemid 32826060)
98. Miksicek, R.J. (1993). Commonly occurring plant flavonoids have estrogenic activity. Molecular Pharmacology, 44, 37-43.
99. Milligan, S.R., Kalita, J.C., Heyerick, A., Rong, H., De Cooman, L., & De Keukeleire, D. (1999). Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. Journal of Clinical Endocrinology and Metabolism, 84, 2249-2252. (Pubitemid 30647064)
100. Monici, M., Baglioni, P., Mulinacci, N., Baldi, A., & Vincieri, F.F. (1994). A research model on flavonoids as photoprotectors: studies on the photochemistry of kaempferol and pelargonidin. Acta Horticulturae, 381, 340-347.
101. Murakami, S., Muramatsu, M., & Otomo, S. (1992). Gastric H+/K+ ATPase inhibition by catechins. Journal of Pharmacy and Pharmacology, 44, 926-928.
102. Nicolas, J.J., Richard-Forget, F.C., Goupy, P.M., Amiot, M.J., & Aubert, S.Y. (1994). Enzymatic browning reaction in apple and apple products. Critical Reviews in Food Science and Nutrition, 34, 109-157, doi:10.1080/10408399409527653.
103. Nicolas, J.J., Richard-Forget, F.C., Goupy, P.M., Amiot, M.J., Murray, N.J., Williamson, M.P., et al. (1994). Study of the interaction between salivary proline-rich proteins and polyphenol by 1H-NMR spectroscopy. European Journal of Biochemistry, 219, 923-935. (Pubitemid 24050962)
104. Nijveldt, R.J., van Nood, E., van Hoorn, D.E.C., Boelens, P.G, van Norren, K., & van Leeuwen, P.A.M. (2001). Flavonoids: a review of probable mechanisms of actions and potential applications. American Journal of Clinical Nutrition, 74, 418-425. (Pubitemid 32880250)
105. Nogata, Y., Ohta, H., Yoza, K.I., Berhow, M., & Hasegawa, S. (1994). High-performance liquid chromatographic determination of naturally occurring flavonoids in citrus with a photodiode-array detector. Journal of Chromatography A, 667, 59-66, doi:10.1016/0021-9673(94)89051-X. (Pubitemid 24142502)
106. Ooghe, W.C., Ooghe, S.J., Detavernier, C.M., & Huyghebaert, A. (1994). Characterization of orange juice (Citrus sinensis) by polymethoxylated flavones. Journal of Agricultural and Food Chemistry, 42, 2191-2195, doi:10.1021/jf00046a021.
107. Osman, H.E., Maalej, N., Shanmuganayagam, D., & Folts, J.D. (1998). Grape juice but not orange or grapefruit juice inhibits platelet activity in dogs and monkeys (Macaca fasciularis). The Journal of Nutrition, 128, 2307-2312. (Pubitemid 29012976)
108. Park, G.L., Avery, S.M., Byers, J.L., & Nelson, D.B. (1983). Identification of bioflavonoids from citrus. Food Technology, 37, 98-105.
109. Park, G.L., Byers, J.L., Pritz, C.M., Nelson, D.B., Navarro, J.L., Smolensky, D.C., et al. (1983). Characteristics of California navel orange juice and pulpwasn. Journal of Food Science, 48, 627-632, doi:10.1111/j.1365-2621. 1983.tb10805.x.
110. Peleg, H., Naim, M., Rouseff, R.L., & Zehavi, U. (1991). Distribution of bound and free phenolic acids in oranges (Citrus sinensis) and grapefruits (Citrus paradisi). Journal of the Science of Food and Agriculture, 57, 417-426, doi:10.1002/jsfa.2740570312.
111. Pietta, P.G. (2000). Flavonoids as antioxidants. Journal of Natural Products, 63, 1035-1042, doi:10.1021/np9904509.
112. Porter, L.J. (1994). Flavans and proanthocyanidins. In J.B. Harborne (Ed.), The flavonoids: Advances in research since 1986 (pp. 27-56). London, UK: Chapman and Hall.
113. Rauha, J.P., Vuorela, H., & Kostiainen, R. (2001). Effect of eluent on the ionization efficiency of flavonoids by ion spray, atmospheric pressure chemical ionization, and atmospheric pressure photoionization mass spectrometry. Journal of Mass Spectrometry, 36, 1269-1280, doi:10.1002/jms.231. (Pubitemid 34048518)
114. Ricardo da Silva, J.M., Cheynier, V., Souquet, J.M., Moutounet, M., Cabanis, J.C., & Bourzeix, M. (1991). Interaction of grape seeds procyanidins with various proteins in relation to wine fining. Journal of the Science of Food and Agriculture, 57, 111-125, doi:10.1002/jsfa.2740570113.
115. Robards, K. (2003). Strategies for the determination of bioactive phenols in plants, fruit and vegetables. Journal of Chromatography A, 1000, 657-691, doi:10.1016/S0021-9673(03)00058-X.
116. Robards, K., & Antolovich, M. (1997). Analytical chemistry of fruits bioflavonoids. Analyst, 122, 11R-34R, doi:10.1039/a606499j.
117. Robards, K., Li, X., Antolovich, M., & Boyd, S. (1997). Characterisation of citrus by chromatographic analysis of flavonoids. Journal of the Science of Food and Agriculture, 75, 87-101, doi:10.1002/(SICI)1097- 0010(199709)75:13.0.CO;2-B. (Pubitemid 27389676)
118. Robbins, R. (2003). Phenolic acids in foods: an overview of analytical methodology. Journal of Agricultural and Food Chemistry, 51, 2866-2887, doi:10.1021/jf026182t.
119. Rouseff, R.L. (1978). Determination of citrus phenolics using HPLC with fluorescence detection - a preliminary report. Trends in Fluorescence, 1, 10-13.
120. Rouseff, R.L., Martin, S.F., & Youtsey, C.O. (1987). Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus. Journal of Agricultural and Food Chemistry, 35, 1027-1030, doi:10.1021/jf00078a040.
121. Rouseff, R.L., & Ting, S.V. (1979). Quantification of polymethoxylated flavones in orange juices by high-performance liquid chromatography. Journal of Chromatography, 176, 75-87, doi:10.1016/S0021- 9673(00)92088-0.
122. Saini, K.S., & Ghosal, S. (1984). Naturally occurring flavans unsubstituted in the heterocyclic ring. Phytochemistry, 23, 2415-2421, doi:10.1016/S0031-9422(00)84067-4.
123. Scalbert, A. (1991). Antimicrobial properties of tannins. Phytochemistry, 30, 3875-3883, doi:10.1016/0031-9422(91)83426-L.
124. Schieber, A., Keller, P., Streker, P., Klaiber, I., & Carle, R. (2002). Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. 'Brettacher') by HPLC-PDA and HPLC-APCI-MS/MS. Phytochemical Analysis, 13, 87-94, doi:10.1002/pca.630. (Pubitemid 34285521)
125. Schmidtlein, H., & Herrmann, K. (1976). Quantitative analysis of flavanones and 3-hydroxyflavanones by thin-layer chromatography. Journal of Chromatography A, 123, 385-390, doi:10.1016/S0021-9673(00)82207-4.
126. Schneider, V. (1995). Evaluation of small amounts of flavonoid phenols in white wines by colorimetric assays. American Journal of Enology and Viticulture, 46, 274-277.
127. Schuster, R. (1980). Separation and positive identification of compounds in complex sample mixtures using on-line, LC-UV/VIS and LC-MS, direct coupling techniques. Chromatographia, 13, 379-385, doi:10.1007/BF02261517.
128. Selway, J.W.T. (1986). Antiviral activity of flavones, flavans. In V. Cody, E. Middleton, & J.B. Harborne (Eds.), Plant flavonoids in biology and medicine: Biochemical, pharmacological and structure-activity relationships (pp. 521-536). New York: Alan R. Liss.
129. Sendra, J.M., Navarro, J.L., & Izquierdo, L. (1988). C18 solid-phase isolation and high-performance liquid chromatography/ultraviolet diode array determination of fully methoxylated flavones in citrus juices. Journal of Chromatographic Science, 26, 443-448.
130. Sengupta, P.K., & Kasha, M. (1979). Excited state proton-transfer spectroscopy of 3-hytdroxyflavone and quercetin. Chemical Physics Letters, 68, 382-385, doi:10.1016/0009-2614(79)87221-8.
131. Shahrzad, S., & Bitsch, I. (1996). Determination of some pharmacologically active phenolic acids in juices by high-performance liquid chromatography. Journal of Chromatography A, 741, 223-231, doi:10.1016/0021- 9673(96)00169-0. (Pubitemid 26276222)
132. Soleas, G.J., Diamandis, E.P., Karumanchiri, A., & Goldberg, D.M. (1997). A multiresidue derivatization gas chromatographic assay for fifteen phenolic constituents with mass selective detection. Analytical Chemistry, 69, 4405-4409, doi:10.1021/ac961320x.
133. Spanos, G.A., & Wrolstad, R.E. (1990). Influence of processing and storage on the phenolic composition of Thompson seedless grape juice. Journal of Agricultural and Food Chemistry, 38, 1565-1571, doi:10.1021/jf00097a030.
134. Stach, D., & Schmitz, O.J. (2001). Decrease in concentration of free catechins in tea over time determined by micellar electrokinetic chromatography. Journal of Chromatography A, 924, 519-522, doi:10.1016/S0021-9673(01)00903-7. (Pubitemid 32721887)
135. Stobiecki, M. (2000). Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry, 54, 237-256, doi:10.1016/S0031-9422(00)00091-1.
136. Stobiecki, M., Malosse, C., Kerhoas, L., Wojlaszek, P., & Einhorn, J. (1999). Detection of isoflavonoids and their glycosides by liquid chromatography/electrospray ionization mass spectrometry in root extracts of lupin (Lupinus albus). Phytochemical Analysis, 10, 198-207, doi:10.1002/(SICI) 1099-1565(199907/08)10:43.0.CO;2-C.
137. Stoggl, W.M., Huck, C.W., & Bonn, G.K. (2004). Structural elucidation of catechin and epicatechin in sorrel leaf extract using liquid-chromatography coupled to diode array-,fluorescence-, and mass spectrometric detection. Journal of Separation Science, 27, 524-528, doi:10.1002/jssc.200301694. (Pubitemid 38735638)
138. Strack, D., & Wray, V. (1994). The anthocyanins. In J.B. Harborne (Ed.), The flavonoids: Advances in research since 1986 (pp. 27-56). London, UK: Chapman and Hall.
139. Swatsitang, P., Tucker, G., Robards, K., & Jardine, D. (2000). Isolation and identification of phenolic compounds in Citrus sinensis. Analytica Chimica Acta, 417, 231-240, doi:10.1016/S0003-2670(00)00937-5. (Pubitemid 30412083)
140. Tahara, S., & Ibrahim, R.K. (1995). Prenylated isoflavonoids-an update. Phytochemistry, 38, 1073-1094, doi:10.1016/0031-9422(94)00788-U.
141. Takeda, K., Harborne, J.B., & Self, R. (1986). Identification and distribution of malonated anthocyanins in plants of the compositae. Phytochemistry, 25, 1337-1342, doi:10.1016/S0031-9422(00)81285-6.
142. Takeda, K., Tochika, Y., Fukazawa, R., & Mori, T. (1994). Flavonoids as UV-protectant. Acta Horticulturae, 381, 348-354.
143. Thomas, P.R.S., Nash, G.B., & Dormandly, J.A. (1988). White cells accumulation in dependent legs of patients with venous hypertension: a possible mechanism for trophic changes in the skin. British Medical Journal, 296, 1673-1695.
144. Tomas-Barberan, F.A., & Clifford, M.N. (2000). Flavanones, chalcones
145. Tura, D., & Robards, K. (2002). Sample handling strategies for the determination of biophenols in food and plants. Journal of Chromatography A, 975, 71-93, doi:10.1016/S0021-9673(02)00879-8. (Pubitemid 35232362)
146. van Acker, S.A.B.E., Tromp, M.N.J.L., Haenen, G.R.M.M., van der Vijgh, W.J.F., & Bast, A. (1995). Flavonoids as scavengers of nitric oxide radical. Biochemical and Biophysical Research Communications, 214, 755-759, doi:10.1006/bbrc.1995.2350.
147. van Rensburg, E., & Engelbrecht, A.H.P. (1986). Effect of calcium salts on susceptibility to browning of avocado fruit. Journal of Food Science, 51, 1067-1068, doi:10.1111/ j.1365-2621.1986.tb11235.x.
148. Vande Casteele, K., Geiger, H., de Loose, R., & Van Sumere, C.F. (1983). Separation of some anthocyanidins, anthocyanins, proanthocyanidins and related substances by reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 259, 291-300.
149. Wang, W., & Goodman, M.T. (1999). Antioxidant property of dietary phenolic agents in a human LDL-oxidation ex vivo model: interaction of protein binding activity. Nutrition Research, 19, 191-202, doi:10.1016/S0271-5317(98) 00183-3. (Pubitemid 29131645)
150. Wang, H., & Murphy, P.A. (1994). Isoflavone content in commercial soybean foods. Journal of Agricultural and Food Chemistry, 42, 1666-1673, doi:10.1021/jf00044a016.
151. Wang, J., & Sporns, P. (1999). Analysis of anthocyanins in red wine and fruit juice using MALDI-MS. Journal of Agricultural and Food Chemistry, 47, 2009-2015, doi:10.1021/jf981008j. (Pubitemid 29438752)
152. Winkel-Shirley, B. (1999). Evidence for enzyme complexes in the phenylpropanoid and flavonoid pathways. Physiologia Plantarum, 107, 142-149, doi:10.1034/j.1399-3054.1999.100119.x.
153. Wulf, L.W., & Nagel, C.W. (1976). Analysis of phenolic acids and flavonoids by high-performance liquid chromatography. Journal of Chromatography, 116, 271-279.
154. Xian, G.H. (2000). On-line identification of phytochemical constituents in botanical extracts by combined high-performance liquid chromatographic-diode array detection-mass spectrometric techniques. Journal of Chromatography A, 880, 203-232, doi:10.1016/S0021-9673(00)00059-5.
155. Xu, L., & Diosady, L.L. (1997). Rapid method for total phenolic acid determination in rapeseed/canola meals. Food Research International, 30, 571-574, doi:10.1016/S0963-9969(98)00022-2. (Pubitemid 28362188)
156. Yanagida, A., Kanda, T., Takahashi, T., Kamimura, A., Hamazono, T., & Honda, S. (2000). Fractionation of apple procyanidins according to their degree of polymerization by normal-phase high-performance liquid chromatography. Journal of Chromatography A, 890, 251-259, doi:10.1016/S0021-9673(00)00614-2. (Pubitemid 30621565)
157. Zaat, S.A.J., Schripsema, J., Wijffelman, C.A., van Brussel, A.A.N., & Lugtenberg, B.J.J. (1989). Analysis of the major inducers of the rhizobium nodA promoter from Vicia sativa root exudate and their activity with different nodD genes. Plant Molecular Biology, 13, 175-188, doi:10.1007/BF00016136.
158. Zgorka, G., & Glowniak, K. (1999). Simultaneous determination of phenolic acids and linear furanocoumarins in fruits of Libanotis dolichostyla by solid-phase extraction and high performance liquid chromatography. Phytochemical Analysis, 10, 268-271. (Pubitemid 29450353)