Flavonoids: Dietary occurrence and biochemical activity

Nutrition Research

Volumn 18, Issue 12, 1998, Pages 1995-2018

  Peterson, Julia ^a   Dwyer, Johanna ^a  

^a TUFTS UNIVERSITY   (United States)

Author keywords

Antioxidant; Diet; Flavanones; Flavones; Flavonoids; Flavonols

Indexed keywords

ANTHOCYANIN; ANTIOXIDANT; CATECHIN; FLAVAN DERIVATIVE; FLAVANONE; FLAVONE; FLAVONOID; FLAVONOL; ISOFLAVONOID; PROPOLIS; TROXERUTIN;

ANTIOXIDANT ACTIVITY; CANCER PREVENTION; COMMON COLD; CONTACT DERMATITIS; DIETARY INTAKE; FOOD PROCESSING; HUMAN; ISCHEMIC HEART DISEASE; NONHUMAN; PHYTOCHEMISTRY; PRIORITY JOURNAL; RASH; REVIEW; TOXICITY TESTING;

EID: 0032400815     PISSN: 02715317     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0271-5317(98)00169-9     Document Type: Review

References (88)

1. 1. Harborne Jeffrey B. Flavonoids in the environment: structure-activity relationships. Prog Clin Biol Res 1988;280:17-27
2. 2. Ranganna S, Govindarajan VS, Ramana KVR. Citrus fruits. Part II. Chemistry, technology, and quality evaluation. B. Technology. CRC Crit Rev 1983;19:1-98
3. 3. Kuhnau J. The flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev Nutr Diet 1976;24:117-91
4. 4. Horowitz RM. Taste effects of flavonoids. Prog Clin Biol Res. 1986;213:163-175
5. 5. Herrman, K. Flavonols and flavones in food plants: a review. J Food Technol 1976;11:433-48
6. 6. Franke AA, Custer LJ, Cerna CM, Narala KK. Quantitation of phytoestrogens in legumes by HPLC. J Agric Food Chem 1994;42:1905-13
7. 7. Mazur W, Fotsis T, Wähala K et al. Isotope dilution gas chromatographic - Mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Anal Biochem 1996;233:169-180
8. 8. Pierpoint WS. Flavonoids in the human diet. Prog Clin Biol Res. 1986;213:125-140
9. 9. Timberlake CF, Henry BS. Anthocyanins as natural food colorants. Prog Clin Biol Res. 1988;280:107-21
10. 10. Hertog MGL, Hollman PCH, Katan MB. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J Agric Food Chem 1992;40:2379-83
11. 11. Harborne, Jeffrey B. Nature, distribution and function of plant flavonoids. Prog Clin Biol Res 1986;213:15-24
12. 12. Brouillard R, Cheminat A. Flavonoids and plant color. Prog Clin Biol Res 1988;280:93-106
13. 13. Hutchins AM, Lampe JW, Martini MC, et al. Vegetables, fruits, and legumes: Effect on urinary isoflavonoid phytoestrogen and lignan excretion. J Am Diet Assoc 1995;95:769-74
14. 14. Tomás-Lorente F, Garcia-Viguera C, Ferreres F, Tomás-Barberán FA. Phenolic compounds analysis in the determination of fruit jam genuineness. J Agric Food Chem 1992;40:1800-4
15. 15. Hertog MGL, Hollman PCH, Katan MB, Kromhout D. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutr Cancer 1993;20:21-9
16. 16. Bronner WE, Beecher GR. Extraction and measurement of prominent flavonoids in orange and grapefruit juice concentrates. Journal of Chromatography 1995;705:247-256
17. 17. Hirono I. Carcinogenicity of plant constituents: Pyrrolizidine alkaloids, flavonoids, bracken fer:n. Genetic Toxicology of the Diet. 1986;45-53
18. 18. Nagao M, Wakabayashi K, Fujita Y et al. Genetic Toxicology of the Diet 1986;55-62.
19. 19. MacGregor JT. Genetic toxicology of dietary flavonoids. Genetic Toxicology of the Diet 1986;33-43
20. 20. Jaeger A, Wälti M, Neftel K. Side effects of flavonoids in medical practice. Plant Flavonoids in Biology and Medicin II: Biochemical, cellular, and medicinal properties. 1988;379-394
21. 21. Anton R. Flavonoids and traditional medicine. Plant Flavonoids in Biology and Medicin II: Biochemical, cellular, and medicinal properties. 1988;423-39
22. 22. Wollenweber E. Occurrence of flavonoid aglycones in medicinal plants. Plant Flavonoids in Biology and Medicin II: Biochemical, cellular, and medicinal properties. 1988;45-55
23. 23. Clemetson CAB, Andersen L. Plant polyphenols as antioxidants for ascorbic acid. Ann NY Acad Sci 1966;136:339-78
24. 24. Yuting C, Rongliang Z, Zhonghan J, Yong J. Flavonoids as superoxide scavengers and antioxidants. Free Rad Biol Med 1990;9:19-21
25. 25. Robak J, Gryglewski RJ. Flavonoids are scavengers of superoxide anions. Biochem Pharmacol 1988;37:837-41
26. 26. Ramanathan R, Das NP, Tan CH. Effects of △-linolenic acid, flavonoids, and vitamins on cytotoxicity and lipid peroxidation. Free Rad Biol Med 1994;16:43-8
27. 27. Fraga CG, Martino VS, Ferraro GE et al. Flavonoids as antioxidants evaluated by in vitro and in situ liver chemiluminescence. Biochem Pharmacol 1987;36:717-720
28. 28. Mora A, Payá M, Ríos JL, Alcaraz MJ. Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of non-enzymatic lipid peroxidation. Biochem Pharmacol 1990;40:793-97
29. 4-induced microsomal lipid peroxidation. Experient 1991;47:195-199
30. 30. Laughton MJ, Evans PJ, Moroney MA, et al. Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolic and dietary additives. Biochem Pharmacol 1991;42:1673-81
31. 31. Wang P-F, Zheng R-L. Inhibitions of the autoxidation of linoleic acid by flavonoids in micelles. Chem Phys Lipids 1992;63:37-40
32. 2°. Free Rad Biol Med 1991;11:1-8
33. 33. Laughton MJ, Halliwell B, Evans PJ, Hoult JRS. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochem Pharmacol 1989;38:2859-65
34. 34. Sahu SC, Gray GC. Kaempferol-induced nuclear DNA damage and lipid peroxidation. Cancer Lett 1994;85:159-64
35. 1 metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Res 1981;41:67-72
36. 1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogen 1990;11:2275-79
37. 37. Friedman FK, Wesr D, Sugimura T, Gelboin HV. Flavone modulators of rat hepatic aryl hydrocarbon hydroxylase. Pharmacol 1985;31:203-7
38. 38. Scambia G, Ranelletti FO, Panici PB et al. Type-II estrogen binding sites in a lymphoblastoid cell line and growth inhibitory effect of estrogen, anti-estrogen and bioflavonoids. In J Cancer 1990;46:1112-1116
39. 39. Nakadate T, Yamamoto S, Aizu E, Kato R. Effects of flavonoids and antioxidants on 12-O-tetradecanoyl-phorbol-13-acetate-caused epidermal orhithine decarboxylase induction and tumor promotion in relation to lipoxygenase inhibition by these compounds. Gann 1984;75:214-22
40. 40. Markaverich BM, Roberts RR, Alejandro MA et al. Bioflavonoid interaction with rat uterine type II binding sites and cell growth inhibition. J Steroid Biochem 1988;30:1-6
41. 41. Larocca LM, Piantelli M, Leone G et al. Type II oestrogen binding sites in acute lymphoid and myeloid leukaemias: growth inhibitory effect of oestrogen and flavonoids. Br J Hema 1990;75:489-95
42. 42. Shimoi K, Masuda S, Furugori et al. Radioprotective effect of antioxidative flavonoids in △-ray irradiated mice. carcinogen 1994;15:2669-72
43. 43. Shah GM, Bhattacharya RK. Modulation by plant flavonoids and related phenolics of microsome catalyzed adduct formation between benzo(a)pyrene and DNA. Chem Biol Interact 1986;59:1-15
44. 44. Popp R, Schimmer O. induction of sister-chromatid exchanges (SCE), polyploidy, and micronuclei by plant flavonoids in human lymphocyte cultures. A comparative study of 19 flavonoids. Mutation Res 1991;246:205-213
45. 45. Brown JP. A review of the genetic effects of naturally occuring flavonoids, anthraquinones and related compounds. Mutation Res 1980;75:243-77
46. 46. Kellis JTJr, Vickery LE. Inhibition of human estrogen synthetase (aromatase) by flavones. Science 1984;225:1032-34
47. 47. Miniscalco A, Lundahl J, Regàrdh CG et al. Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmaol Exp Thera 1992;261:1195-99
48. 48. Hsieh RJ, German JB, Kinsella JE. Relative inhibitory potencies of flavonoids on 12-lipoxygenase of fish gill. Lipids 1988;23:322-26
49. 49. deWahlley CV, Rankin SM, Hoult JRS et al. Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages. Biochem Pharmacol 1990;39:1743-50
50. 50. Moroney M-A, Alcaraz MJ, Forder RA et al. Selectivity of neutrophil 5-lipoxygenase and cyclo-oxygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids. J Pharm Pharmacol 1988;40:787-92
51. 51. Middleton EJr, Drzewiecki G. Flavonoid inhibition of human basophil histamine release stimulated by various agents. Biochem Pharmacol 1984;33:3333-38
52. 52. Busse WW, Kopp DE, Middleton EJr. Flavonoid modulation of human neutrophil function. J Allergy Clin Immunol 1984;73:801-9
53. 53. Vernet A, Siess MH. Comparison of the effects of various flavonoids on ethoxy coumarin deethylase activity of rat intestinal and hepatic microsomes. Fd Chem Tox 1986;24:857-61
54. 54. Kuppusamy UR, Khoo HE, Das NP. Structure-activity studies of flavonoids as inhibitors of hyaluronidase. Biochem Pharmacol 1990;40:397-401
55. 55. Katengwa S, Polla BS. Flavonoids, but not protein kinase C inhibitors, prevent stress protein synthesis during erythophagocytosis. Biochem Biophys Res Commun 1991;180:308-314
56. 56. Emim JADS, Oliveira AB, Lapa AJ. Pharmacological evaluation of the anti-inflammatory activity of a citrus bioflavonoid, hesperidin, and the isoflavonoids, duartin and claussequinone, in rats and mice. J Pharrn Pharmacol 1994;46:118-22
57. 57. Nègre-Salvayre A, Salvayre R. Quercetin prevents the cytotoxicity of oxidized LDL on lymphoid cell lines. Free Rad Biol Med 1992;12:101-06
58. 2+-loaded brain neurons. Brain Res 1994;635:125-29
59. 59. Nakayama T. Suppresion of hydroperoxide-induced cytotoxicy by polyphenols. Cancer res 1994;54:1991-93S
60. 60. Grinberg LN, Rachmilewitz EA, Newmark H. Protective effects of rutin against hemoglobin oxidation. Biochem Pharmacol 1994;48:643-9
61. 61. Bindoli A, Valente M, Cavalini L. Inhibitory action of quercetin on xanthine oxidase and xanthine dehydrogenase activity. Pharmacol Res Commun1985;17:831-39
62. 62. Sanhueza J, Valdes J, Campos R et al. Changes in the xanthine dehydrogenase/xanthine oxidase ratio in the rat kidney subjected to ischemia-reperfusion stress: preventive effect of some flavonoids. Res Commun Chem Pathol Pharmacol 1992;78:211-218
63. 63. Morel I, Lescoat G, Cogrel P et al. Antioxidant and iron-chelating activities of he flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem Pharmacol 1993;45:13-19
64. 64. Elliott AJ, Scheiber SA, Thomas C, Pardini RS. Inhibition of glutathione reductse by flavonoids a structure-activity study. Biochem Pharmacol 1992;44:1603-08
65. 65. Thiyagarajah P, kuttan SC, Lim SC et al. Effect of myricetin and other flavonoids on the liver plasma membrane Ca2+ pump kinetics and structure-function relationships. Biochem Pharmacol 1991;41:669-75
66. 66. Gordon PB, Holen I, Seglen PO. Protection by naringin and some other flavonoids of hepatocytic autophagy and endocytosis against inhibition by okadaic acid. J Biol Chem 1995;270:5830-38
67. 84 cells. j Nutr 1993;123:259-268
68. 68. Clayton EM Jr, Feldhous WD, Phythyon JM. Effect of citrus bioflavonoid, carbazochrome salicylate, and ascorbic acid on the transplancental passage of fetal erythrocytes. Obst Gyn 1967;29:382-5
69. 69. Robbins RC. Effect of methoxylated flavones on erythocyte aggregation and sedimentation in blood of normal subjects: evidence os a dietary role for flavonoids. Int J Vit Nutr Res 1973;43:494-503
70. 70. Robbins RC. Action of flavonoids on blood cells: trimodal action of flavonoids elucidates their inconsistent physiologic effects. Int J Vit Nutr Res 1974;44:203-16
71. 71. Baird IM, Hughes RE, et al. The effects of ascorbic acid and flavonoids on the occurrence of symptoms normally associated with the common cold. Am J Clin Nutr 1979;32:1686-90
72. 72. Franz WL, Sands GW, Heyl HL. Blood ascorbic acid level in bioflavonoid and ascorbic acid therapy of common cold. JAMA1956;162:1224
73. 73. Tebrock HE, Arming JJ, Ossining NY, Johnston JH. Usefulness of bioflavonoids and ascorbic acid in treatment of common cold. JAMA 1956;162:1227
74. 74. Vinson JA, Bose P. Comparative bioavailability to humans of ascorbic acid alone or in citrus extract. Am J Clin Nutr 1988;48:601-4
75. 75. Hertog MG, Feskens EJ, Hollman PC, Katan MB, Kromhout D.. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly study. Lancet 1993;342:1007-11
76. 76. Hertog MGL, Kromhout D, Aravanis C, Blackburn H, Buzina R, Fidanza F, Giampaoli S, Jansen A, Menotti A, Nedeljkovic S, Pekkarinen M, Simic BS, Toshima H, Feskens EJM, Hollman PCH, Katan MB. Flavonoid intake and long term risk of coronary heart disease and cancer in the seven countries study. Arch Intern Med 1995;155:381-6
77. 77. Hacket, Andrew M. The metabolism of flavonoid compounds in mammals. Prog Clin Biol Res 1986;213:177-194
78. 78. Cova D, DeAngelis L, Giavarini F, et al. Pharmacokinetics and metabolism of oral diosmin in healthy volunteers. Int J Clin Pharmacol Ther Tox 1992;30:29-33
79. 79. Hollman Peter C.H, de Vries Jeanne H.M., van Leeuwen Sonja D. et al. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am J Clin Nutr 1995;62:1276-82
80. 3H-diosmine. Arznei Forsch 1977;27:1688-91
81. 81. Sawai Y, Kohsaka Y, Nishiyama Y, Ando K. Serum concentrations of rutoside metabolism after oral administration of a rutoside formualtion to humans. Arzneim Forsch 1987;37:729-32
82. 82. .Baba S, Furuta T, Horie M, Nakagawa H. Studies on drug metabolism by use of isotopes XXVI: determination of urinary metabolites of rutin in humans. J Pharmaceut Sci 1981;70:780-82
83. 83. Boutin JA, Meunier F, Lambert P-H et al. In vivo and in vitro glucuronidation of the flavonoid diosmetin in rats. Drug Metab Disp 1993;21:1157-66
84. 84. Adlercreutz H, Fotsis T, Lampe J, et al. Quantitation of phytoestrogens in legumes by HPLC. J Agric Food Chem 1994;42:1905-13
85. 85. Lee, M-J, Wang Z-Y, Li H, et al. Analysis of plasma and urinary tea polyphenols in human subjects. Cancer Epid Biomark Prev 1995;4:393-9
86. 86. Kandaswami C, Perkins E, Soloniuk DS et al. Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro. Cancer Lett 1991;56:147-152
87. 87. Beretz A, Anton R, Stoclet JC. Flavonoid compound are potent inhibitors of cyclic AMP phosphodiesterase. Experientia 1978;34:1054-55
88. 88. Ferrell JE, Jr, Sing PDGC, Loew G et al. Structure/activity studies of flavonoids as inhibitors of cyclic AMP phosphodiesterase and relationship to Quantum chemical indices. Mol Pharmacol 1979;16:556-68