Uses and Properties of Citrus Flavonoids

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 12, 1997, Pages

  Benavente García, Obdulio ^a   Castillo, Julián ^a   Marin, Francisco R ^a   Ortuño, Ana ^a   Del Río, José A ^a  

^a Ulniversidad de Murcia   (Spain)

Author keywords

Analgesic; Antiallergic; Anticarcinogenic; Antiinflammatory; Antimicrobial; Antioxidant; Food additives; Free radicals; Platelet aggregation

Indexed keywords

CITRUS; LETHRINIDAE;

EID: 0642363623     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970373s     Document Type: Review

References (99)

1. Afanas'ev, I. B.; Dorozhko, A. I.; Brodskii, A. V.; Kostyuk, V. A.; Potapovitch, A. I. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation. Biochem. Pharmacol. 1989, 38, 1763-1769.
2. Attaway, J. A. Medical benefits of juice flavonoids. In The Citrus Processing and Technology Conference, Lake Alfred, FL, 1992; pp 207-219.
3. Aust, S. D.; Svingen, B. A. The role of iron in enzymic lipid peroxidation. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1982; Vol. 5, pp 1-28.
4. Belt, J. A.; Thomas, J. A.; Buchsbaum, R. N.; Racker, E. Inhibition of lactate transport and glycolysis in Ehrlich ascites tumor cells by bioflavonoids. Biochemistry 1979, 18, 3506-3511.
5. Benavente-García, O.; Castillo, J.; Del Rio, J. A. Changes in neodiosmin levels during the development of Citrus aurantium leaves and fruits. Postulation of a neodiosmin biosynthetic pathway. J. Agric. Food Chem. 1993, 41, 1916-1919.
6. Benavente-García, O.; Castillo, J.; Sabater, F.; Del Rio, J. A. Characterisation of S-adenosyl-L-methionine:eriodictyol 4′-O-methyltransferase from Citrus aurantium. Plant Physiol. Biochem. 1995, 33, 263-271.
7. Beret, A.; Cazenave, J. P. The effect of flavonoids on bloodvessel wall interactions. In Plant Flavonoids in Biology and Medicine II: Biochemical, Cellular, and Medicinal Properties; Cody, V., Middleton, E., Harborne, J. B., Beretz, A., Eds.; Progress in Clinical and Biological Research 280; Alan R. Liss Inc.: New York, 1988; pp 187-200.
8. Beret, A.; Anton, A.; Cazenave, J. P. The effects of flavonoids on cyclic nucleotide phosphodiesterase. In Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships; Cody, V., Middleton, E., Harborne, J. B., Beretz, A., Eds.; Progress in Clinical and Biological Research 213; Alan R. Liss Inc.: New York, 1986; pp 281-296.
9. Bombardelli, E.; Morazzoni, P. The flavonoids: New perspectives in biological activities and therapeutics. Chim. Oggi 1993, July-August, 25-28.
10. Boozer, C. E.; Hammond, G. S.; Hamilton, C. E.; Sen, J. N. Air oxidation of hydrocarbons. II. The stoichometry and fate of inhibitions in benzene and chlorobenzene. J. Am. Chem. Soc. 1955, 77, 3233-3237.
11. Bors, W.; Saran, M. Radical scavenging by flavonoid antioxidants. Free Radical Res. Commun. 1987, 2, 289-294.
12. Bors, W.; Hellers, W.; Michel, C.; Saran, M. Radical chemistry of flavonoids antioxidant. In Antioxidants in therapy and preventive medicine; Emerit, Ed.; Plenum Press: New York, 1990a; Vol. 1, pp 165-170.
13. Bors, W.; Hellers, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. In Methods in enzymology; Packer, L., Glazer, A. N., Eds.; Academic Press: San Diego, CA, 1990b; Vol. 186, pp 343-355.
14. Bracke, M. E.; Vyncke, B.; Opdenakker, J. M.; Foidart, G.; De Pestel, G. H.; Mareel, M. Effect of catechins and citrus flavonoids on invasion in vitro. Clin. Exp. Metastasis 1991, 9, 13-25.
15. Bracke, M. E.; Vyncke, B.; Van Larebeke, N. A.; Bruyneel, E. A.; De Bruyne, G. K.; De Pestel, G. H.; De Coster, W. J.; Espeel, M. F.; Mareel, M. The flavonoid tangeretin inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro. Clin. Exp. Metastasis 1989, 7, 283-300.
16. Bradbury, R. B.; White, D. E. Chemistry of subterranean clover. II. Synthesis and reduction of isoflavones related to genistein and formononetin. J. Chem. Soc. 1953, 12, 207-233.
17. Castillo, J.; Benavente-García, O.; Del Rio, J. A. Naringin and neohesperidin levels during development of leaves, flower buds, and fruits of Citrus aurantium. Plant Physiol. 1992, 99, 67-73.
18. Castillo, J.; Benavente-García, O.; Del Rio, J. A. Hesperetin 7-O-glucoside and prunin in Citrus species (C. aurantium and C. paradisi). A study of their quantitative distribution in immature fruits and as immediate precursors of neohesperidin and naringin in Citrus aurantium. J. Agric. Food Chem. 1993, 11, 1920-1924.
19. Cillard, J.; Cillard, P. Composés phénoliques et radicaux libres. S. T. P. Pharma 1988, 4, 592-596.
20. Critchfield, J. W.; Welsh, C. J.; Phang, J. M.; Yeh, G. C. Modulation of adriamycin accumulation and efflux by flavonoids in HCT-15 colon cells. Activation of P-glycoprotein as a putative mechanism. Biochem. Pharmacol. 1994, 48, 1437-1445.
21. Darmon, N.; Ferrandiz, V.; Canal, M. T.; Mitjavilla, S. Activite antiradicallaire de flavonoides vis-à-vis de l'anion Superoxide et du radical hydroxyle. Liaison-Grupe Polyphenols Bull. 1990, 15, 158-162.
22. Das, N. P.; Pereira, T. A. Effects of flavonoids on thermal autoxidation of palm oil: Structure-activity relationships. J. Am. Oil Chem. Soc. 1990, 4, 255-258.
23. De Boer, G.; Hanson, F. E. Feeding responses to solanaceous allelochemicals by larvae of the tobacco hornworm Munduca sexta. Entomol. Exp. Appl. 1987, 45, 123-131.
24. Deschner, E. E.; Ruperto, J.; Wong, G.; Newmark, H. L. The effect of dietary quercetin and rutin on AOM-induced acute colonic epithelial abnormalities in mice fed a high-fat diet. Nutr. Cancer 1993, 20, 199-204.
25. Dreyer, D. L.; Jones, K. C. Feeding deterrency of flavonoids and related phenolics toward Schizophis graminum and Myzuz persice: Aphid feeding deterrents in wheat. Phytochemistry 1981, 20, 2489-2493.
26. Duarte, J.; Perez-Vizcaino, F.; Utrilla, P.; Jimenez, J.; Tamargo, J.; Zarzuelo, A. Gen. Pharmacol. 1993, 24, 857-862.
27. Duffey, S. S.; Isman, M. B. Inhibition of insect larval growth by phenolics in glandular trichomes of tomato leaves. Experientia 1981, 37, 574-576.
28. Elangovan, V.; Sekar, N.; Govindasamy, S. Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis. Cancer Lett. 1994, 87, 107-113.
29. Elliger, C. A.; Chan, B. C.; Waiss, A. C. Flavonoids as larval growth inhibitors. Structural factors governing toxicity. Naturwissenchafften 1980, 67, 358-360.
30. Erben-Russ, M.; Bors, W.; Saran, M. Reactions with phenolic antioxidants: A pulse radiolysis study. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 1987, 52, 393-412.
31. Foote, C. S. Photosensitized oxidation and singlet oxygen: Consequences in biological systems. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1976; Vol. 2, pp 85-133.
32. Fraga, C. G.; Martino, V. S.; Ferraro, G. E.; Coussio, J. D.; Boveris, A. Flavonoids as antioxidants evaluated by in vitro and in situ liver chemiluminescence. Biochem. Pharmacol. 1987, 36, 717-720.
33. Gabor, M. Anti-inflammatory and anti-allergic properties of flavonoids. In Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships; Cody, V., Middleton, E., Harborne, J. B., Beretz, A., Eds.; Progress in Clinical and Biological Research 213; Alan R. Liss Inc.: New York, 1986; pp 471-480.
34. Galati, E. M.; Monforte, M. T.; Kirjavainen, S.; Forestieri, A. M.; Trovato, A.; Tripodo, M. M. Biological effects of hesperidin, a citrus flavonoid (Note I): Antimflammatory and analgesic activity. Farmaco 1994, 40, 709-712.
35. Geroulakos, G.; Nicolaides, A. N. Controlled studies of Daflon 500 mg in chronic venous insufficiency. Angiology 1994, 45, 549-553.
36. Guadagni, D. G.; Maier, V. P.; Turnbaugh, J. G. Effect of neodiosmin on threshold and bitterness of limonin in water and orange juice. J. Food Sci. 1976, 41, 681-684.
37. Havsteen, B. Biochemical effects of flavonoids. Biochem. Pharmacol. 1983, 32, 1141-1148.
38. Heo, H. Y.; Lee, S. J.; Kwon, C. H.; Kin, S. W.; Sohn, D. H.; Au, W. W. Anticlastogenic effects of galangin against bleomycin-induced chromosomal aberrations in mouse spleen lymphocytes. Mutat. Res. 1994, 311, 225-229.
39. Hertog, M. G. L.; Feskeens, E. J. M.; Hollman, C. H.; Katan, M. B.; Kromhout, D. Dietary antioxidant flavonoids and risk of coronary heart disease: de Zutphen elderly study. Lancet 1993, 342, 1007-1011.
40. Hirano, T.; Gotoh, M.; Oka, K. Natural flavonoids and lignans are potent cytostatic agents against human leukemia HL-60 cells. Life Sci 1994, 55, 1061-1069.
41. +-ATPase: aspects of structure-activity relationship and action mechanisms. Life Sci. 1989, 45, 1111-1117.
42. Horowitz, R.; Gentili, B. Dihydrochalcones derivatives and their use as sweetening agents. U.S. Patent 3,087,821,1963.
43. Horowitz, R.; Gentili, B. Taste and structure in phenolic glycosides. J. Agric. Food Chem. 1969, 17, 696-700.
44. Horowitz, R.; Gentili, B. Flavonoids constituents of Citrus. In Citrus Science and Technology; Nagy, S., Shaw, P. E., Vedhuis, M. K., Eds.; AVI Publishing: Westport, CT, 1977; pp 397-426.
45. Huet, R. Constituents of Citrus fruits with pharmacodynamic effect:Citroflavonoids. Fruits 1982, 37, 267-271.
46. Jean, T.; Bodinier, M. C. Mediators involved in inflammation: Effects of Daflon 500 mg on their release. Angiology 1994, 45, 554-559.
47. Kandaswami, C.; Perkins, E.; Soloniuk, D. S.; Drzewiecki, G.; Middleton, E. Antitproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro. Cancer Lett. 1991, 56, 147-152.
48. Kaul, T. N.; Middleton, E.; Ogra, P. L. Antiviral effects of flavonoids on human viruses. J. Med. Virol. 1985, 15, 71-79.
49. Khan, A. U. Singlet molecular oxygen spectroscopy: Chemical and photosensitized. In Singlet oxygen, Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 1, pp 39-79.
50. Kooststra, M. Protection from UV-B induced DNA damage by flavonoids. Plant Mol. Biol. 1994, 26, 771-774.
51. Kupchan, S. M.; Sigel, C. W.; Knox, J. R.; Udayamurthy, M. D. Tumor inhibitors. 36. Eupatin and eupatoretin, two cytotoxic flavonols from Eupatorium semiserratum. J. Org. Chem. 1969, 34, 1460-1463.
52. Labrid, C. Pharmacologic properties of Daflon 500 mg. Angiology 1994, 45, 524-530.
53. Larocca, L. M.; Piantelli, M.; Leone, G.; Sica, S.; Teofili, L.; Benedetti-Panici, P.; Scambia, G.; Mancuso, S.; Capelli, A.; Ranelletti, F. O. Type II oestrogen binding sites in acute lymphoid and myeliod leukaemias: Growth inhibitory effect of oestrogen and flavonoids. Br. J. Hematol. 1990, 75, 489-495.
54. Lewinsohn, E.; Berman, E.; Mazur, Y.; Gressel, J. (7)Glucosylation and (1-6)rhamnosylation of exogenous flavanones by undifferentiated Citrus cell cultures. Plant Sci. 1989, 61, 23-28.
55. Liota, L. A.; Wewer, U.; Rao, N. C.; Schiffmann, E.; Stracke, M.; Guirguis, R.; Thorgeirson, U.; Muschel, R.; Sobel, M. Biochemical mechanims of tumor invasion and metastasis. In Cancer Metastasis: Biological and Biochemical Mechanisms and Clinical Aspects; Prodi, G., Liotta, L. A., Lollini, P. L., Garbisa, S., Gorini, S.; Hellmann, K, Eds.;. Plenum Press: New York, 1988; pp 161-169.
56. Lonchampt, M.; Guardiola, B.; Sicot, N.; Bertrand, M.; Perdrix, L.; Duhault, J. Protective effect of a purified flavonoid fraction against reactive oxigen radicals. In vivo and in vitro study. Arzneim. Forsch. Drug Res. 1989, 39, 882-885.
57. Manach, C.; Regerat, F.; Texier, O.; Agullo, G.; Demigne, C.; Remesy, C. Bioavailability, metabolism and physiological impact of 4-oxo-flavonoids. Nutr. Res. 1996, 16, 517-544.
58. Manson, R. P. Free radical intermediates in the metabolism of toxic chemicals. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1982; Vol. 5, pp 161-222.
59. Matsuda, H. Pharmacological study on citrus fruits. II. Antiallergic effects of fruit of Citrus unshiu Markovich (2) on flavonoid components. Yakugaku Zasshi 1991, 111, 193-198.
60. Matsuura, T.; Matsushima, H.; Nakashima, R. Photoinduced reactions. 36. Photosensitized oxygenation of 3-hydroxyflavones as a nonenzymatic model for quercetinase. Tetrahedron 1970, 26, 435-443.
61. Mead, J. F. Free radical mechanisms of lipid damage and consequences for cellular membranes. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1976; Vol. 5, pp 51-68.
62. Middleton, E. Effect of flavonoids on basophil histamine release and other secretory systems. In Plant Flavonoids in Biology and Medicine II: Biochemical, Pharmacological, and Structure-Activity Relationships; Cody, V., Middleton, E., Harborne, J. B. , Beretz, A., Eds.; Progress in Clinical and Biological Research 213; Alan R. Liss Inc.: New York, 1986; pp 493-506.
63. Middleton, E.; Drzewiwcki, G. Effects of flavonoids and transitional metal cations on antigen-induced histamine release from human basophils. Biochem. Pharmacol. 1982, 31, 1449-1453.
64. Middleton, E.; Drzewiwcki, G.; Krishnarao, D. Quercetin: An inhibitor of antigen-induced human basophil histamine. J. Immunol. 1981, 127, 546-550.
65. Monforte, M. T.; Trovato, A.; Kirjarainen, S.; Forestieri, A. M.; Galati, E. M.; Lo Curto, R. B. Biological effects of hesperidin, a Citrus flavonoid. (Note II): Hypolipidemic activity on experimental hypercholesterolemia in rat. Farmaco 1995, 9, 595-599.
66. Morel, I.; Lescoat, G.; Cogrel, P.; Sergent, O.; Pasdecoup, N.; Brissot, P.; Cillard, P.; Cillard, J. Antioxidant and ironchelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem. Pharmacol. 1993, 1, 13-19.
67. 2+ mobilization in human platelets by affecting polyphosphoinositide turnover. Biochem. Pharmacol. 1993, 46, 395-403.
68. Peterson, G.; Barnes, S. Genistein and biochain A inhibit the growth of human prostate cancer cells but not epidermal growth factor receptor tyrosine autophosphorylation. Prostate 1993, 22, 335-345.
69. Pincemail, J.; Deby, C.; Lion, Y.; Braguet, P.; Hans, P.; Drien, K.; Goutier, R. Role of flavonoids in lipoperoxidation and radicalar reactions. In Flavonoids and Bioflavonoids, Proceedings of the 7th Hungarian Bioflavonoid Symposium, Szeged, Hungary, 1985; Farkas, L., Gabor, M., Kallay, F., Eds.; Elsevier Science Publishers: New York, 1986; pp 423-436.
70. Pryor, W. A.; Lightsey, J. W.; Prier, D. G. The production of free radicals in vivo from the action of xenobiotics: The initiation of autoxidation of polynsaturated fatty acids by nitrogen dioxide and ozone. In Lipid Peroxides in Biology and Medicine; Kunio, Y., Ed.; Academic Press: New York, 1982; pp 1-22.
71. Pryor, W. A. The role of free radical reactions in biological systems. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1976; Vol. 1, pp 1-49.
72. Ratty, A. K.; Das, N. P. Effects of flavonoids on nonenzymatic lipid peroxidation: Structure-activity relationship. Biochem. Med. Metabolic Biol. 1988, 39, 69-79.
73. Robbins, R. C. Action of flavonoids on blood cells: Trimodal action of flavonoids elucidates their inconsistent physiologic effects. Int. J. Vit. Nutr. Res. 1974, 44, 203-216.
74. Robbins, R. C. Regulatory action of phenylbenzo-γ-pyrone (PBP) derivatives on blood constituents affecting rheology in patients with coronary heart disease (CHD). Int. J. Vit. Nutr. Res. 1976, 46, 338-347.
75. Saez Tormo, G.; Oliva, M. R.; Muñiz, P.; Valls, V.; Iradi, A.; Ramos, M.; Climent, J. Oxidative stress and genetic damage. In Health and Orange; Fundación Valenciana de Estudios Avanzados: Valencia, Spain, 1994; pp 51-60.
76. Salah, N.; Miller, N. J.; Paganga, G.; Tijburg, L.; Bolwell, G. P.; Rice-Evans, C. Polyphenolic flavonols as scavenger of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 1995, 2, 339-346.
77. Saran, M.; Vetter, G.; Erben-Russ, M.; Winter, R.; Kruse, A.; Michel, C.; Bors, W. Pulse radiolysis equipment: A setup for simultaneous multiwavelength kinetic spectroscopy. Rev. Sci. Instrum. 1987, 58, 363-367.
78. Scambia, G.; Ranelletti, F. O.; Benedetti-Panici, P.; De Vincenzo, R.; Bonanno, G.; Ferrandina, G.; Piantelli, M.; Bussa, S.; Rumi, C.; Cianfriglia, M. Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line: P-glycoprotein as a possible target. Cancer Chemother. Pharmacol. 1994, 34, 459-464.
79. Scambia, G.; Ranelletti, F. O.; Benedetti-Panici, P.; Piantelli, M.; Bonanno, G.; De Vincenzo, R.; Ferrandina, G.; Rumi, C.; Larocca, L. M.; Mancuso, S. Inhibitory effect of quercetin on OVCA 433 cells and presence of type II oestrogen binding sites in primary ovariun tumors and cultured cells. Br. J. Cancer 1990, 62, 942-946.
80. Sher, E.; Codignola, A.; Biancardi, E.; Cova, D.; Clementi, F. Amine uptake inhibition by diosmin and diosmetin in human neuronal and neuroendocrine cell lines. Pharmacol. Res. 1992, 26, 395-402.
81. Shimoi, K.; Masuda, S.; Furogori, M.; Esaki, S.; Kinae, N. Radioprotective affect of antioxidative flavonoids in γ-ray irradiated mice. Carcinogenesis 1994, 15, 2669-2672.
82. 2+)-ATPase of sarcoplasmic reticulum. J. Biol. Chem. 1981, 256, 887-892.
83. •-. Free Radical Biol. Med. 1991, 11, 1-8.
84. Sorata, Y.; Takahama, U.; Kimura, M. Protective effect of quercetin and rutin on photosensittized lysis of human erythrocytes in the presence of hematoporphyrin. Biochim. Biophys. Acta 1984, 799, 313-317.
85. Stapleton A. E.; Walbot, V. Flavonoids can protect maize DNA from the induction of ultraviolet radiation damage. Plant Physiol. 1994, 105, 881-889.
86. Stout, M. G.; Reich, M.; Huffman, M. N. 4′,5,6,7-Oxygenated flavones and flavanones. Cancer Chemother. Rep. 1964, 36, 23-24.
87. Suolinna, E. M.; Buchsbaum, R. N.; Racker, E. The effect of flavonoids on aerobic glycolysis and growth of tumor cells. Cancer Res. 1975, 35, 1865-1872.
88. Szent-Gyorgyi, A. Methoden zur Herstellung von Citrin. Physiol. Chem. 1938, 255, 126-131.
89. Takahama, U.; Youngman, R. J.; Elsnert, E. F. Transformation of quercetin by singlet oxygen generated by a photosensitized reaction. Photobiochem. Photobiophys. 1974, 7, 175-181.
90. Tordera, M.; Ferrandiz, M. L.; Alcaraz, M. J. Influence of antiinflamatory flavonoids on granulation and arachidonic acid release in rat neutrophils. Z. Naturforsch. C 1994, 49, 235-240.
91. Torel, J.; Cillard, J.; Cillard, P. Antioxidant activity of flavonoids and reactivity with peroxy radical. Phytochemistry 1986, 2, 383-385.
92. 1Δg) quenching. J. Photochem. Photobiol. B. 1993, 19, 205-215.
93. Tsuchiya, J.; Niki, E.; Kamiya, Y. Oxidation of lipids. IV. Formation and reaction of chromanoxyl radicals as studied by electron spin resonance. Bull. Chem. Soc. Jpn. 1983, 56, 229.
94. Tzeng, S. H.; Ko, W. C.; Ko, F. N.; Teng, C. M. Inhibition of platelet aggregation by some flavonoids. Thromb. Res. 1991, 64, 91-100.
95. Waldworth, A. N.; Faulds, D. Hydroxyethylrutosides: A review of its pharmacology and therapeutic efficacy in venous insufficiency and related disorders. Drugs 1992, 44, 1013-1032.
96. Wang, P. F.; Zheng, R. L. Inhibitions of the autoxidation of linoleic acids flavonoids in micelles. Chem. Phys. Lipids 1992, 63, 37-40.
97. Winterle, J.; Dulin, D.; Mill, T. Products of stoichiometry of reaction of vitamin E with alkylperoxy radicals. J. Org. Chem. 1984, 49, 491.
98. Yoshida, M.; Sakai, T.; Hosokawa, N.; Marui, N.; Matsumoto, K.; Nishino, H.; Aoike, A. The effect of quercetin on cell-cycle progression and growth of human gastric cancer cells. FEBS Lett. 1990, 260, 10-13.
99. Yuting, C.; Rongliang, Z.; Zhongjian, J.; Yong, J. Flavonoids as Superoxide scavengers and antioxidants. Free Radical Biol. Med. 1990, 9, 19-21.