Tenorio LFA, del Valle ML, Pastelín HG

Idioma: Español
Referencias bibliográficas: 107
Paginas: 33-45
Archivo PDF: 155.65 Kb.

RESUMEN

Se ha sugerido que el consumo de flavonoides en la dieta puede reducir el riesgo de desarrollar una enfermedad cardiovascular. Por otra parte, los estudios realizados in vitro e in vivo indican que los flavonoides presentan un gran abanico de actividades biológicas. Esta revisión tiene por objeto evidenciar el efecto de los flavonoides sobre varios sistemas enzimáticos que pudiesen ser un blanco terapéutico potencial. Basados en los reportes que diversos grupos de investigación líderes en el campo de los productos naturales han aportado a lo largo de los años, y con el objeto de conjuntar estos resultados con los hallazgos aportados por algunos estudios epidemiológicos, se podría fundamentar, a futuro, la introducción de estos compuestos en la práctica clínica.

REFERENCIAS (EN ESTE ARTÍCULO)

1. Hertog MGL, Feskens EJM, Hollman PCH, Katan MB, Kromhout D: Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr Cancer 1993; 20: 21-29.

2. Kühnau J: The flavonoids: a class of semi-essential food components: their role in human nutrition. World Rev Nutr Diet 1976; 24: 117-120.

3. Manach C, Regerat F, Texier O, Argullo G, Demigne C, Remesy C: Bioavailability, metabolism and physiological impact of 4-oxo-flavonoids. Nutr Res 1996; 16: 517-544.

4. Middleton E, Kandaswami C, Theoharides TC: The Effects of Plant Flavonoids on Mammalian Cells: Implications for Inflammation, Heart Disease, and Cancer. Pharmacol Rev 2000; 52: 673-751.

5. Bilyk A, Sapers GM: Distribution of quercetin and kaempferol in lettuce, kale, chive, garlic chive, leek, horseradish, red radish, and red cabbage tissues. J Agric Food Chem 1985; 33: 226-228.

6. 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: 2379-2383.

7. Timberlake CF, Henry BS: Plant pigments as natural food colours. Endeavour 1986; 10: 31-36.

8. Smith DA, Banks SW: Formation and biological properties of isoflavonoid phytoalexins. En: Cody V, Middleton E, Harborne JB. Eds. Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships. New York. Alan R. Liss., 1986: 113-124.

9. Firmin JL, Wilson KE, Rossen L, Johnston AWB: Flavonoid activation of nodulation genes in Rhizobium reversed by other compounds present in plants. Nature 1986; 324: 90-92.

10. Peters NK, Frost JW, Long SR: A plant isoflavone, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science 1986; 233: 978-980.

11. Djordjevic MA, Redmond JW, Batley M, Rolfe BG: Clovers secrete specific phenolic compounds which either stimulate or repress nod gene expression in Rhizobium trifolii. EMBO J 1987; 6: 1173-1179.

12. Zaat SAJ, Wijffelman CA, Spaink HP, VanBrussel AAM, Okker RJH, Lugtenberg BJJ: Induction of the nodA promoter of Rhizobium leguminosarum symplasmid pRLIJI by plant flavanones and flavonoids. J Bacteriol 1987; 169: 198-204.

13. Gabor M: Anti-inflammatory substances of plant origin. En: Vane JR, Ferreira JH. Eds. Handbook of Experimental Pharmacology: Anti-Inflammatory Drugs. New York. Springer-Verlag., 1979: 698-739.

14. Havsteen B: Flavonoids: A class of natural products of high pharmacological potency. Biochem Pharmacol 1984; 32: 1141-1148.

15. Selway JWT: Antiviral activity of flavones and flavans. En: Cody V, Middleton E, Harborne JB. Eds. Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships. New York. Alan R. Liss., 1986: 521-536.

16. Welton AR, Hurley I, Will P: Flavonoids and arachidonic acid metabolism. En: Cody V, Middleton E, Harborne JB. Eds. Plant Flavonoids in Biology and Medicine II: Biochemical, Cellular and Medicinal Properties. New York. Alan R. Liss., 1988: 301-312.

17. Das DK: Naturally occurring flavonoids: Structure, chemistry, and high performance liquid chromatography methods for separation and characterization. Methods Enzymol 1994; 234: 410-420.

18. Carroll KK, Guthrie N, So FV, Chambers AS: Anticancer properties of flavonoids, with emphasis on citrus flavonoids. En: Rice-Evans CA, Packer L. Eds. Flavonoids in Health and Disease. New York. Marcel-Dekker., 1998: 437-446.

19. Hughes RE, Wilson HK: Flavonoids: Some physiological and nutritional consideration. Prog Med Chem 1977; 14: 285-301.

20. Torel J, Cillard J, Cillard P: Antioxidant activity of flavonoids and reactivity of with peroxy radical. Phytochemistry 1986; 25: 383-385.

21. Clemetson CAB: Biflavonoids. En: Clemetson CAB. Ed. Vitamin C. Boca Raton. CRC Press., 1989: 101-128.

22. Kandaswami C, Middleton E: Free radical scavenging and antioxidant activity of plant flavonoids. En: Armstrong D. Ed. Free Radicals in Diagnostic Medicine. New York. Plenum Press., 1994: 351-376.

23. Kandaswami C, Middleton E: Flavonoids as antioxidants. En: Shahidi F. Ed. Natural Antioxidants: Chemistry, Health Effects and Applications. Champaign, IL. AOCS Press., 1995: 174-203.

24. Hertog MGL, Hollman PCH, Katan MB, Kromhout D: Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 1993; 342: 1007-1011.

25. Hertog MGL, Kromhout D, Aravanis C, Blackburn H, Buzina R, Fidaza F, et al: Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch Intern Med 1995; 155: 381-386.

26. Hertog MG, Feskens EJ, Kromhout D: Antioxidant flavonols and coronary heart disease risk. Lancet 1997; 349: 699.

27. Hertog MGL: Epidemiological evidence on potential health properties of flavonoids. Proc Nutr Soc 1996; 55: 385-397.

28. Knekt P, Järvinen R, Reunanen A, Maatela J: Flavonoid intake and coronary mortality in Finland: a cohort study. Br J Med 1996; 312: 478-481.

29. Rimm ER, Katan MB, Ascherio A, Stampfer M, Willet W: Relation between intake of flavonoids and risk of coronary heart disease in male health professionals. Ann Intern Med 1996; 125: 384-389.

30. Yochum L, Kushi LH, Meyer K, Folsom AR: Dietary flavonoid intake and risk of cardiovascular disease in postmenopausal women. Am J Epidemiol 1999; 149: 943-949.

31. Hirvonen T, Pietinen P, Virtanen M, Ovaskainen ML, Hakkinen S, Albanes D, Virtamo J: Intake of flavonols and flavones and risk of coronary heart disease in male smokers. Epidemiology 2001; 12: 62-67.

32. Ko FN, Huan TF, Teng CM: Vasodilatory action mechanisms of apigenin isolated from Apium graveolens in rat thoracic aorta. Biochim Biophys Acta 1991; 1115: 69-74.

33. Duarte J, Pérez-Vizcaíno F, Jimenez F, Tamargo J, Zarzuelo A: Vasodilatory effects of flavonoids in rat aortic smooth muscle. Structure-activity relationships. Gen Pharmacol 1993; 24: 857-862.

34. Duarte J, Pérez-Vizcaíno F, Zarzuelo A, Jimenez J, Tamargo J: Vasodilator effects of quercetin on isolated rat vascular smooth muscle. Eur J Pharmacol 1993; 239: 1-7.

35. Duarte J, Pérez-Vizcaíno F, Zarzuelo A, Jimenez J, Tamargo J: Inhibitory effects of quercetin and staurosporine on phasic contractions in rat vascular smooth muscle. Eur J Pharmacol 1994; 262: 149-156.

36. Duarte J, Pérez-Vizcaíno F, Jiménez J, Tamargo J, Zarzuelo A: Flavonoids and cardiovascular diseases. En: Atta-Ur-Rahman. Ed. Studies in Natural Products Chemistry. Vol 25, part F. Amsterdam. Elsevier., 2001: 565-605.

37. Duarte J, Galisteo M, Ocete MA, Pérez-Vizcaíno F, Zarzuelo A, Tamargo J: Effects of chronic quercetin treatment on hepatic oxidative status of spontaneously hypertensive rats. Mol Cell Biochem 2001; 221: 155-160.

38. Duarte J, Pérez-Palencia R, Vargas F, Pérez-Vizcaíno F, Zarzuelo A, Tamargo J: Antihypertensive effects of the flavonoid quercetin in spontaneously hypertensive rats. Br J Pharmacol 2001; 133: 117-124.

39. Pérez-Vizcaíno F, Ibarra M, Cogolludo AL, Duarte J, Zaragoza-Arnáez F, Moreno L, et al: Endothelium-Independent Vasodilator Effects of the Flavonoid Quercetin and Its Methylated Metabolites in Rat Conductance and Resistance Arteries. J Pharmacol Exp Ther 2002; 302(1): 66-72.

40. Haji-Faraji M, Haji-Tarkhani AH: The effect of sour tea (Hibiscus sabdariffa) on essential hypertension. J Ethnopharmacol 1999; 65: 231-236.

41. Herrera-Arellano A, Flores-Romero S, Chavez-Soto MA, Tortoriello J: Effectiveness and tolerability of a standardized extract from Hibiscus sabdariffa in patients with mild to moderate hypertension: a controlled and randomized clinical trial. Phytomedicine 2004; 11(5): 375-382.

42. Most MM: Estimated phytochemical content of the dietary approaches to stop hypertension (DASH) diet is higher than in the Control Study Diet. J Am Diet Assoc 2004; 104(11): 1725-1727.

43. Javorkova V, Pechanova O, Andriantsitohaina R, Vrbjar N: Effect of polyphenolic compounds on the renal Na+,K(+)-ATPase during development and persistence of hypertension in rats. Exp Physiol 2004; 89(1): 73-81.

44. Aoi W, Niisato N, Miyazaki H, Marunaka Y: Flavonoid-induced reduction of EnaC expression in the kidney of Dahl salt-sensitive hypertensive rat. Biochem Biophys Res Commun 2004; 315(4): 892-896.

45. Park YK, Kim JS, Kang MH: Concord grape juice supplementation reduces blood pressure in Korean hypertensive men: double-blind, placebo controlled intervention trial. Biofactors 2004; 22(1-4): 145-147.

46. Liu X, Wei J, Tan F, Zhou S, Wurthwein G, Rohdewald P: Pycnogenol, french maritime pine bark extract, improves endothelial function in hypertensive patients. Life Sci 2004; 74(7): 855-862.

47. Keen CL, Holt RR, Oteiza PI, Fraga CG, Schmitz HH: Cocoa antioxidants and cardiovascular health. Am J Clin Nutr 2005; 81(1): 298S-303S.

48. Hellner W, Forkmann G: Biosynthesis. En: Harborne JB. Ed. The Flavonoids. Advances in Research since 1986. London. Chapman and Hall., 1993: 499-535.

49. Wagner H, Farkas L: Synthesis of flavonoids. En: Harborne JB, Mabry TJ, Mabry H. Eds. The Flavonoids. Part I. New York. Academic Press., 1975, p 127-213.

50. Atoui AK, Mansouri A, Boskou G, Kefalas P: Tea and herbal infusions: their antioxidant activity and phenolic profile. Food Chem 2005; 89: 27-36.

51. Ames BN, Shigenaga MK, Hagen TM: Oxidants, antioxidants, and the degenerative diseases of aging. Proc Natl Acad Sci 1990; 90: 7915-7922.

52. Negishi H, Xu JW, Ikeda K, Njelekela M, Nara Y, Yamori Y: Black and green tea polyphenols attenuate blood pressure increases in stroke-prone spontaneously hypertensive rats. J Nutr 2004; 134(1): 38-42.

53. Ubando-Rivera J, Navarro-Ocaña A, Valdivia-López MA: Mexican lime peel: comparative study on contents of dietary fibre and associated antioxidant activity. Food Chem 2005; 89: 57-61.

54. Moskaug JO, Carlsen H, Myhrstad MC, Blomhoff R: Polyphenols and glutathione synthesis regulation. Am J Clin Nutr 2005; 81(1): 277S-283S.

55. Nishizuka Y: Studies and perspective of protein kinase C. Science 1986; 233: 305-312.

56. Nishizuka Y: The molecular heterogeneity of protein kinase C and its implications for cellular regulation. Nature 1988; 334: 661-665.

57. Nishizuka Y: Protein kinase and lipid signaling for sustained cellular responses. FASEB J 1995; 9: 484-496.

58. Graziani Y, Chayoth R, Karny N, Feldman B, Levy J: Regulation of protein kinase activity by quercetin in Ehrlich Ascites tumor cells. Biochim Biophys Acta 1981; 28: 415-421.

59. Gschwendt M, Horn F, Kittstein W, Marks F: Inhibition of the calcium- and phospholipid- dependent protein kinase activity from mouse brain cytosol by quercetin. Biochem Biophys Res Comm 1983; 117: 444-447.

60. End DW, Look RA, Shaffer NL, Balles EA, Persico FJ: Non-selective inhibition of mammalian protein kinases by flavonoids in vitro. Res Commun Chem Pathol Pharm 1987; 56: 75-86.

61. Hagiwara M, Inoue S, Tanaka T, Nunoki K, Ito M, Hidaka H: Differential effects of flavonoids as inhibitors of tyrosine protein kinase and serine/threonine protein kinases. Biochem Pharmacol 1988; 37: 2987-2999.

62. Ferriola PC, Cody V, Middleton E: Protein kinase C inhibition by plant flavonoids, kinetic mechanism and structure-activity relationships. Biochem Pharmacol 1989; 38: 1617-1624.

63. Picq M, Dubois M, Munari-Silem Y, Prigent AF, Pacheco H: Flavonoid modulation of protein kinase C activation. Life Sci 1989; 44: 1563-1571.

64. Graziani Y, Erikson E, Erikson RL: The effect of quercetin on the phosphorilation activity of the Rous sarcoma virus transforming gene producti in vitro and in vivo. Eur J Pharmacol 1983; 135: 583-589.

65. Alexandrakis M, Singh L, Boucher W, Letourneau R, Theoflopoulos P, Theoharides TC: Differential effects of flavonoids on inhibition of secretion and on accumulation of secretory granules in rat basophile leukemia cells. Int J Immunopharmacol 1999; 21: 379-390.

66. Bird TA, Schule HD, Delaney PB, Sims JE, Thoma B, Dower SK: Evidence that MAP (mitogen-activated protein) kinase activation may be a necessary but not sufficient signal for a restricted subset of responses in IL-1 treated epidermoid cells. Cytokine 1992; 4: 429-440.

67. Rogers JC, Williams DL: Kaempferol inhibits myosin light chain kinase. Biochem Biophys Res Comm 1989; 164: 419-425.

68. Jinsart W, Ternal B, Polya GM: Inhibition of rat liver cyclic AMP-dependent protein kinase by flavonoids. Biol Chem Hoppe-Seyler 1992; 373: 205-211.

69. Rodney G, Swanson AL, Wheeler LM, Smith GN, Worrel CS: The effect of a series of flavonoids of hyaluronidase and some other related enzymes. J Biol Chem 1950; 183: 739-747.

70. Carpenedo F, Bortignon C, Bruni A, Santi R: Effect of quercetin on membrane-linked activities. Biochem Pharmacol 1969; 18: 1495-1500.

71. Lang DR, Racker E: Effects of quercetin on F1 inhibitor or mitochondrial ATPase and energy-linked reactions in submitochondrial particles. Biochim Biophys Acta 1974; 333: 180-186.

72. Deters DW, Racker E, Nelson N, Nelson H: Partial resolution of the enzymes catalyzing photophosphorylation. J Biol Chem 1975; 250: 1041-1047.

73. Cantley LC, Hammes GG: Investigation of quercetin binding sites on chloroplast coupling factor. Biochemistry 1976; 15: 1-8.

74. Long GD, DeChatelet LR, O’Flaherty JT, McCall CE, Blass DA, Shirley PS, Parce JW: Effects of quercetin on magnesium-dependent adenosine triphosphatase and the metabolism of human polymorphonuclear leukocytes. Blood 1981; 57: 561-566.

75. Fewtrell CMS, Gomperts BD: Effect of flavone inhibitors of transport ATPases on histamine secretion from rat mast cells. Nature 1977; 265: 635-636.

76. Zyma VL, Miroshnichenko NS, Danilova VM, En-Grin E: Interaction of flavonoid compounds with contractile proteins of skeletal muscle. Gen Physiol Biophys 1988; 7: 165-175.

77. Hirano T, Oka K, Akiba M: Effects of synthetic and natural flavonoids on Na+, K+-ATPase: Aspects of the structure-activity relationship and action mechanism. Life Sci 1989; 45: 1111-1117.

78. Pruzanki W, Vadas P: Phospholipase A2 – A mediator between proximal and distal effectors of inflammation. Immunol Today 1991; 12: 143-144.

79. Lee TP, Matteliano ML, Middleton E: Effect of quercetin on human polymorphonuclear leukocyte lysosomal enzyme release and phospholipid metabolism. Life Sci 1982; 31: 2765-2774.

80. Lanni C, Becker EL: Inhibition of neutrophil phospholipase A2 by p-bromophenylacyl bromide, nordihydroguaiaretic acid, 5,8,11,14-eicotetrayenoic acid and quercetin. Int Arch Allergy Appl Immunol 1985; 76: 214-217.

81. Gil B, Sanz MJ, Terencio M, Ferrandiz ML, Bustos G, Paya M, et al: Effects of flavonoids on Naja naja and human recombinant synovial phospholipase A2 and inflammatory responses in mice. Life Sci 1994; 54: PL333-PL338.

82. Lewis RA, Austen KF: The biologically active leukotrienes: Biosynthesis, metabolism, receptors, functions and pharmacology. J Clin Invest 1984; 73: 889-897.

83. Yamamoto S, Yoshimoto T, Furukawa M, Horie T, Watanabe-Kohno S: Arachinodate S-lipoxygenase and its new inhibitors. J Allergy Clin Immunol 1984; 74: 349-352.

84. Yoshimoto T, Furukawa M, Yamamoto S, Hone T, Watanabe-Kohno S: Flavonoids: Potent inhibitors of arachinodate 5-lipoxygenase. Biochem Biophys Res Comm 1983; 116: 612-618.

85. Laughton MJ, Evans PJ, Moroney MA, Hoult JR, Halliwell B: Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolic dietary additives. Relationship to antioxidant activity and to iron ion-reducing ability. Biochem Pharmacol 1991; 42: 1673-1681.

86. Hoult JRS, Maroney MA, Paya M: Actions of flavonoids and coumarins on lipoxygenase and cyclooxygenase. Methods Enzimol 1994; 234: 443-454.

87. Cockcroft S: Phosphatidylinositol metabolism in mast cells and neutrophils. Cell Calcium 1982; 3: 337-349.

88. Ruckstuhl M, Landry Y: Inhibition of lung cyclic AMP- and GMP- phosphodiesterases by flavonoids and other chromone-like compounds. Biochem Pharmacol 1981; 30: 697-702.

89. Beretz A, Anton R, Cazenave JP: The effects of flavonoids on cyclic nucleotide phosphodiesterases. En: Cody V, Middleton E, Harborne JB. Eds. Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-Activity Relationships. New York. Alan R. Liss., 1986, p 281-296.

90. Beretz A, Joly M, Stoclet JC, Anton R: Inhibition of 3’,5’-AMP phosphodiesterase by flavonoids and xanthones. Planta Med 1979; 36: 193-195.

91. Ferrell JE, Chang-Sing PDG, Loew G, King R, Mansour JM, Mansour TE: Structure/activity studies of flavonoids as inhibitors of cyclic AMP phosphodiesterase and relationship to quantum chemical indices. Mol Pharmacol 1979; 16: 556-568.

92. Landolfi R, Nower RL, Steiner M: Modification of platelet function and arachidonic acid metabolism by bioflavonoids. Structure-activity relationships. Biochem Pharmacol 1984; 36: 907-914.

93. Nagai T, Miyaichi Y, Tomimori T, Yamada H: Inhibition of mouse liver sialidase by plant flavonoids. Biochem Biophys Res Comm 1989; 163: 25-31.

94. Nagai T, Miyaichi Y, Tomimori T, Suzuki Y, Yamada H: Inhibition of influenza virus sialidase and anti-influenza virus activity by plant flavonoids. Chem Pharm Bull 1990; 38: 1329-1332.

95. Nagai T, Miyaichi, Tomimori T, Suzuki Y, Yamada H: In vivo anti-influenza virus activity of plant flavonoids possessing inhibitory activity for influenza virus sialidase. Antiviral Res 1992; 19: 207-217.

96. Murad F: Discovery of some biological effects of nitric oxide and its role in cell signaling (Nobel Lecture). Agewandte Chemie International Edition 1999; 38: 1856-1868.

97. Ignarro LJ: Nitric oxide: a unique endogenous signaling molecule in vascular biology (Nobel Lecture). Angewandte Chemie International Edition 1999; 38: 1882-1892.

98. Wandehenne D, Pugin A, Klessig DF, Durner J: Nitric oxide: comparative synthesis and signaling in animal and plant cells. TRENDS in Plant Science 2001; 6(4): 177-182.

99. Feinstein DL, Galea E, Reis DJ: Supression of glial iNOS expression by tyrosine kinase inhibitors. Ann NY Acad Sci 1994; 738: 325-328.

100. Soliman KF, Mazzio EA: In vitro attenuation of nitric oxide production in C6 astrocyte cell culture by various dietary compounds. Proc Exp Biol Med 1998; 218: 390-397.

101. Chiesi M, Schwaller R: Inhibition of constitutive endothelial NO-synthase activity by tannin and quercetin. Biochem Pharmacol 1995; 14: 495-501.

102. Li H, Xia N, Brausch I, Yao Y, Förstermann U: Flavonoids from Artichoke (Cynara scolymus L.) Up-Regulate Endothelial-Type Nitric-Oxide Synthase Gene Expression in Human Endothelial Cells. J Pharmacol Exp Ther 2004; 310(3): 926-932.

103. Huang Y, Chan NW, Lau CW, Yao XQ, Chan FL, Chen ZY: Involvement of endothelium/nitric oxide in vasorelaxation induced by purified green tea (-)epicatechin. Biochim Biophys Acta 1999; 1427(2): 322-328.

104. Wessler LM, Follmann E, Michaelis W, Dusterhoft T, Baumann G, Stangl K, Stangl V: A constituent of green tea, epigallocatechin-3-gallate, activates endothelial nitric oxide synthase by a phosphatidylinositol-3-OH-kinase-, cAMP-dependent protein kinase-, and Akt-dependent pathway and leads to endothelial-dependent vasorelaxation. J Biol Chem 2004; 279(7): 6190-6195.

105. Duarte J, Jimenez R, Villar IC, Perez-Vizcaino F, Jimenez J, Tamargo J: Vasorelaxant effects of the bioflavonoid chrysin in isolated rat aorta. Planta Med 2001; 67(6): 567-569.

106. Gugler R, Leschik M, Dengler HJ: Disposition of quercetin after single oral and intravenous doses. Eur J Clin Pharmacol 1975; 9: 229-234.

107. Manach C, Morand C, Crespy V, Demigne C, Texier O, Regerat F, Remesy C: Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett 1998; 24: 331-336.