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Vol. 52, Issue 4, 673-751, December 2000
,
Chebeague Island Institute of Natural Product Research, Chebeague
Island, Maryland (E.M., C.K.); and Department of Pharmacology and
Experimental Therapeutics, Tufts University School of Medicine, Boston,
Massachusetts (T.C.T.)
I. General Aspects
A. Introduction
B. Synthesis
C. Metabolism and Disposition
D. Adverse Reactions
II. Effects on Mammalian Enzyme Systems
A. Kinases
B. Phospholipase A2
C. ATPases
D. Lipoxygenases and Cyclooxygenases
E. Phospholipase C
F. Cyclic Nucleotide Phosphodiesterase
G. Adenylate Cyclase
H. Reverse Transcriptase
I. HIV-1 Proteinase
J. HIV-1 Integrase
K. Ornithine Decarboxylase
L. Topoisomerase
M. Glutathione S-Transferase
N. Epoxide Hydrolase
O. Glyoxalase
P. Xanthine Oxidase
Q. Aromatase
R. 11-
-Hydroxysteroid Dehydrogenase
S. Catechol-O-methyltransferase
T. Aldose Reductase
U. Monoamine Oxidase (FAD-Containing)
V. Aldo-Keto-Reductase Family of Enzymes
W. Hyaluronidase
X. Histidine Decarboxylase and DOPA Decarboxylase
Y. Malate Dehydrogenase
Z. Lactic Dehydrogenase and Pyruvate Kinase
AA. Aldehyde and Alcohol Dehydrogenases
BB. Amylase
CC. RNA and DNA Polymerases
DD. Human DNA Ligase I
EE. Ribonuclease
FF. Sialidase
GG. Cytochrome P450 Systems
HH. Elastase
II. Nitric-Oxide Synthase
III. Modulation of the Functions of Inflammatory Cells
A. T Lymphocytes
B. B Lymphocytes
C. Natural Killer Cells
D. Macrophages and Monocytes
E. Mast Cells and Basophils
F. Neutrophils
G. Eosinophils
H. Platelets
I. Adhesion Molecule Expression
IV. Effects of Flavonoids on Other Cells
A. Smooth Muscle and Cardiac Muscle Cells
B. Effects on Nerve Cells
C. Calcium Homeostasis
V. Endocrine and Metabolic Effects
VI. Antiviral Effects
VII. Antitoxic, Hepatoprotective, and Cytoprotective Effects
VIII. Antioxidant Activity
A. Influence of Flavonoids on Reactive Oxygen Species Production by
Phagocytic Cells
B. Effect of Flavonoids on Lipid Peroxidation and Oxyradical
Production
IX. Actions in Relation to Coronary Artery Disease and Vascular
Disorders
X. Flavonoid-Vitamin C Interactions
XI. Cancer-Related Properties
A. Microbial Mutagenicity Studies
B. Genetic Effects of Flavonoids in Mammalian Cells
C. Mutagenicity Studies in Vivo
D. Carcinogenicity of Flavonoids?
E. Anticarcinogenic Effects
F. Apoptosis and Cancer
G. Antiproliferative Activity
H. Differentiating Effects
I. Adhesion/Metastasis/Angiogenesis
J. Effect on Heat Shock Proteins
K. Effect on Multidrug Resistance
XII. Effects on Xenobiotic Metabolism
XIII. Concluding Remarks
Acknowlegments
References
Flavonoids are nearly ubiquitous in plants and are recognized as the pigments responsible for the colors of leaves, especially in autumn. They are rich in seeds, citrus fruits, olive oil, tea, and red wine. They are low molecular weight compounds composed of a three-ring structure with various substitutions. This basic structure is shared by tocopherols (vitamin E). Flavonoids can be subdivided according to the presence of an oxy group at position 4, a double bond between carbon atoms 2 and 3, or a hydroxyl group in position 3 of the C (middle) ring. These characteristics appear to also be required for best activity, especially antioxidant and antiproliferative, in the systems studied. The particular hydroxylation pattern of the B ring of the flavonoles increases their activities, especially in inhibition of mast cell secretion. Certain plants and spices containing flavonoids have been used for thousands of years in traditional Eastern medicine. In spite of the voluminous literature available, however, Western medicine has not yet used flavonoids therapeutically, even though their safety record is exceptional. Suggestions are made where such possibilities may be worth pursuing.
Deceased.
1
Address for correspondence: Theoharis C. Theoharides, Ph.D., M.D., Department of Pharmacology and Experimental
Therapeutics, Tufts University School of Medicine, 136 Harrison Avenue,
Boston, MA. E-mail: theoharis.theoharides{at}tufts.edu
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V. Stangl, M. Lorenz, A. Ludwig, N. Grimbo, C. Guether, W. Sanad, S. Ziemer, P. Martus, G. Baumann, and K. Stangl The Flavonoid Phloretin Suppresses Stimulated Expression of Endothelial Adhesion Molecules and Reduces Activation of Human Platelets J. Nutr., February 1, 2005; 135(2): 172 - 178. [Abstract] [Full Text] [PDF]
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H. Sies, T. Schewe, C. Heiss, and M. Kelm Cocoa polyphenols and inflammatory mediators Am. J. Clinical Nutrition, January 1, 2005; 81(1): 304S - 312S. [Abstract] [Full Text] [PDF]
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A. Gradolatto, J.-P. Basly, R. Berges, C. Teyssier, M.-C. Chagnon, M.-H. Siess, and M.-C. Canivenc-Lavier PHARMACOKINETICS AND METABOLISM OF APIGENIN IN FEMALE AND MALE RATS AFTER A SINGLE ORAL ADMINISTRATION Drug Metab. Dispos., January 1, 2005; 33(1): 49 - 54. [Abstract] [Full Text] [PDF]
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T. Walle, A. M. Browning, L. L. Steed, S. G. Reed, and U. K. Walle Flavonoid Glucosides Are Hydrolyzed and Thus Activated in the Oral Cavity in Humans J. Nutr., January 1, 2005; 135(1): 48 - 52. [Abstract] [Full Text] [PDF]
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 J. J.A. Hendriks, J. Alblas, S. M.A. van der Pol, E. A.F. van Tol, C. D. Dijkstra, and H. E. de Vries Flavonoids Influence Monocytic GTPase Activity and Are Protective in Experimental Allergic Encephalitis J. Exp. Med., December 20, 2004; 200(12): 1667 - 1672. [Abstract] [Full Text] [PDF]
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G.-S. Lee, K.-C. Choi, H.-J. Kim, and E.-B. Jeung Effect of Genistein As a Selective Estrogen Receptor Beta Agonist on the Expression of Calbindin-D9k in the Uterus of Immature Rats Toxicol. Sci., December 1, 2004; 82(2): 451 - 457. [Abstract] [Full Text] [PDF]
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M. Pinent, M. Blay, M. C. Blade, M. J. Salvado, L. Arola, and A. Ardevol Grape Seed-Derived Procyanidins Have an Antihyperglycemic Effect in Streptozotocin-Induced Diabetic Rats and Insulinomimetic Activity in Insulin-Sensitive Cell Lines Endocrinology, November 1, 2004; 145(11): 4985 - 4990. [Abstract] [Full Text] [PDF]
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 S. Y. Pan, A.-M. Ugnat, Y. Mao, S. W. Wen, K. C. Johnson, and The Canadian Cancer Registries Epidemiology Resear A Case-Control Study of Diet and the Risk of Ovarian Cancer Cancer Epidemiol. Biomarkers Prev., September 1, 2004; 13(9): 1521 - 1527. [Abstract] [Full Text] [PDF]
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C. Manach, A. Scalbert, C. Morand, C. Remesy, and L. Jimenez Polyphenols: food sources and bioavailability Am. J. Clinical Nutrition, May 1, 2004; 79(5): 727 - 747. [Abstract] [Full Text] [PDF]
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J.-S. Choi, Y.-J. Choi, S.-H. Park, J.-S. Kang, and Y.-H. Kang Flavones Mitigate Tumor Necrosis Factor-{alpha}-Induced Adhesion Molecule Upregulation in Cultured Human Endothelial Cells: Role of Nuclear Factor-{kappa}B J. Nutr., May 1, 2004; 134(5): 1013 - 1019. [Abstract] [Full Text] [PDF]
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 R. M. Harris, D. M. Wood, L. Bottomley, S. Blagg, K. Owen, P. J. Hughes, R. H. Waring, and C. J. Kirk Phytoestrogens Are Potent Inhibitors of Estrogen Sulfation: Implications for Breast Cancer Risk and Treatment J. Clin. Endocrinol. Metab., April 1, 2004; 89(4): 1779 - 1787. [Abstract] [Full Text] [PDF]
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G. Lopez-Lopez, L. Moreno, A. Cogolludo, M. Galisteo, M. Ibarra, J. Duarte, F. Lodi, J. Tamargo, and F. Perez-Vizcaino Nitric Oxide (NO) Scavenging and NO Protecting Effects of Quercetin and Their Biological Significance in Vascular Smooth Muscle Mol. Pharmacol., April 1, 2004; 65(4): 851 - 859. [Abstract] [Full Text]
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X. Gao, O. I. Bermudez, and K. L. Tucker Plasma C-Reactive Protein and Homocysteine Concentrations Are Related to Frequent Fruit and Vegetable Intake in Hispanic and Non-Hispanic White Elders J. Nutr., April 1, 2004; 134(4): 913 - 918. [Abstract] [Full Text] [PDF]
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H. Ralay Ranaivo, O. Rakotoarison, A. Tesse, C. Schott, A. Randriantsoa, A. Lobstein, and R. Andriantsitohaina Cedrelopsis grevei induced hypotension and improved endothelial vasodilatation through an increase of Cu/Zn SOD protein expression Am J Physiol Heart Circ Physiol, February 1, 2004; 286(2): H775 - H781. [Abstract] [Full Text] [PDF]
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A. Gradolatto, M.-C. Canivenc-Lavier, J.-P. Basly, M.-H. Siess, and C. Teyssier METABOLISM OF APIGENIN BY RAT LIVER PHASE I AND PHASE II ENZYMES AND BY ISOLATED PERFUSED RAT LIVER Drug Metab. Dispos., January 1, 2004; 32(1): 58 - 65. [Abstract] [Full Text] [PDF]
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B. H. Li and W. X. Tian Inhibitory Effects of Flavonoids on Animal Fatty Acid Synthase J. Biochem., January 1, 2004; 135(1): 85 - 91. [Abstract] [Full Text] [PDF]
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R. L Prior Fruits and vegetables in the prevention of cellular oxidative damage Am. J. Clinical Nutrition, September 1, 2003; 78(3): 570S - 578. [Abstract] [Full Text] [PDF]
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R. Cermak, S. Landgraf, and S. Wolffram The Bioavailability of Quercetin in Pigs Depends on the Glycoside Moiety and on Dietary Factors J. Nutr., September 1, 2003; 133(9): 2802 - 2807. [Abstract] [Full Text] [PDF]
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L. Favot, S. Martin, T. Keravis, R. Andriantsitohaina, and C. Lugnier Involvement of cyclin-dependent pathway in the inhibitory effect of delphinidin on angiogenesis Cardiovasc Res, August 1, 2003; 59(2): 479 - 487. [Abstract] [Full Text] [PDF]
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 D. O. McCarthy Rethinking Nutritional Support for Persons with Cancer Cachexia Biol Res Nurs, July 1, 2003; 5(1): 3 - 17. [Abstract] [PDF]
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S. E. McCann, J. L. Freudenheim, J. R. Marshall, and S. Graham Risk of Human Ovarian Cancer Is Related to Dietary Intake of Selected Nutrients, Phytochemicals and Food Groups J. Nutr., June 1, 2003; 133(6): 1937 - 1942. [Abstract] [Full Text] [PDF]
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J. S. Jeruss, N. X. Liu, Y. Chung, G. Magrane, F. Waldman, S. Edgerton, X. Yang, and A. D. Thor Characterization and chromosomal instability of novel derived cell lines from a wt-erbB-2 transgenic mouse model Carcinogenesis, April 1, 2003; 24(4): 659 - 664. [Abstract] [Full Text] [PDF]
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Y.-J. Choi, J.-S. Kang, J. H. Y. Park, Y.-J. Lee, J.-S. Choi, and Y.-H. Kang Polyphenolic Flavonoids Differ in Their Antiapoptotic Efficacy in Hydrogen Peroxide-Treated Human Vascular Endothelial Cells J. Nutr., April 1, 2003; 133(4): 985 - 991. [Abstract] [Full Text] [PDF]
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S. Zhang and M. E. Morris Effects of the Flavonoids Biochanin A, Morin, Phloretin, and Silymarin on P-Glycoprotein-Mediated Transport J. Pharmacol. Exp. Ther., March 1, 2003; 304(3): 1258 - 1267. [Abstract] [Full Text] [PDF]
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S. E Ebeler, C. A Brenneman, G.-S. Kim, W. T Jewell, M. R Webb, L. Chacon-Rodriguez, E. A MacDonald, A. C Cramer, A. Levi, J. D Ebeler, et al. Dietary catechin delays tumor onset in a transgenic mouse model Am. J. Clinical Nutrition, October 1, 2002; 76(4): 865 - 872. [Abstract] [Full Text] [PDF]
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P. Knekt, J. Kumpulainen, R. Jarvinen, H. Rissanen, M. Heliovaara, A. Reunanen, T. Hakulinen, and A. Aromaa Flavonoid intake and risk of chronic diseases Am. J. Clinical Nutrition, September 1, 2002; 76(3): 560 - 568. [Abstract] [Full Text] [PDF]
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F. Perez-Vizcaino, M. Ibarra, A. L. Cogolludo, J. Duarte, F. Zaragoza-Arnaez, L. Moreno, G. Lopez-Lopez, and J. Tamargo Endothelium-Independent Vasodilator Effects of the Flavonoid Quercetin and Its Methylated Metabolites in Rat Conductance and Resistance Arteries J. Pharmacol. Exp. Ther., July 1, 2002; 302(1): 66 - 72. [Abstract] [Full Text] [PDF]
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T. Schewe, H. Kuhn, and H. Sies Flavonoids of Cocoa Inhibit Recombinant Human 5-Lipoxygenase J. Nutr., July 1, 2002; 132(7): 1825 - 1829. [Abstract] [Full Text] [PDF]
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 R. Sevenier, I. M. van der Meer, R. Bino, and A. J. Koops Increased Production of Nutriments by Genetically Engineered Crops J. Am. Coll. Nutr., June 1, 2002; 21(90003): 199S - 204. [Abstract] [Full Text] [PDF]
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Q. Y. Zhu, R. R. Holt, S. A. Lazarus, T. J. Orozco, and C. L. Keen Inhibitory Effects of Cocoa Flavanols and Procyanidin Oligomers on Free Radical-Induced Erythrocyte Hemolysis Experimental Biology and Medicine, May 1, 2002; 227(5): 321 - 329. [Abstract] [Full Text] [PDF]
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S. Wolffram, M. Block, and P. Ader Quercetin-3-Glucoside Is Transported by the Glucose Carrier SGLT1 across the Brush Border Membrane of Rat Small Intestine J. Nutr., April 1, 2002; 132(4): 630 - 635. [Abstract] [Full Text] [PDF]
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N. Nair, S. Mahajan, R. Chawda, C. Kandaswami, T. C. Shanahan, and S. A. Schwartz Grape Seed Extract Activates Th1 Cells In Vitro Clin. Vaccine Immunol., March 1, 2002; 9(2): 470 - 476. [Abstract] [Full Text] [PDF]
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I. Bernatova, O. Pechanova, P. Babal, S. Kysela, S. Stvrtina, and R. Andriantsitohaina Wine polyphenols improve cardiovascular remodeling and vascular function in NO-deficient hypertension Am J Physiol Heart Circ Physiol, March 1, 2002; 282(3): H942 - H948. [Abstract] [Full Text] [PDF]
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T. Walle, U. K. Walle, and P. V. Halushka Carbon Dioxide Is the Major Metabolite of Quercetin in Humans J. Nutr., October 1, 2001; 131(10): 2648 - 2652. [Abstract] [Full Text] [PDF]
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 S. J. Duffy, J. A. Vita, M. Holbrook, P. L. Swerdloff, and J. F. Keaney Jr Effect of Acute and Chronic Tea Consumption on Platelet Aggregation in Patients With Coronary Artery Disease Arterioscler. Thromb. Vasc. Biol., June 1, 2001; 21(6): 1084 - 1089. [Abstract] [Full Text] [PDF]
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