Chemical versus pharmacological actions of nutraceutical phytochemicals: Antioxidant and anti inflammatory modalities

Current Topics in Nutraceutical Research

Volumn 2, Issue 1, 2004, Pages 13-26

  Hensley, Kenneth ^a   Mou, Shenyun ^a   Pye, Quentin N ^a   Dixon, Richard A ^b   Summner, Lloyd W ^b   Floyd, Robert A ^a  

^a OKLAHOMA MEDICAL RESEARCH FOUNDATION   (United States)

^b PLANT BIOLOGY DIVISION   (United States)

Author keywords

Antioxidant; Curcumin; Cyclooxygenase; Flavone; Inflammation; Isoflavone; Lipoxygenase; NDGA; Nitric oxide; Redox signaling; Tyrosine kinase

Indexed keywords

2 (2 AMINO 3 METHOXYPHENYL)CHROMONE; ACETYLCYSTEINE; ALPHA TOCOPHEROL; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; BIOCHEMICAL MARKER; BIOFLAVONOID; CATECHIN; CATECHOL DERIVATIVE; CURCUMIN; ENZYME INHIBITOR; EPICATECHIN; FLAVONE DERIVATIVE; FOOD ADDITIVE; GENISTEIN; HYDROGEN PEROXIDE; ISOFLAVONE DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE; NITRIC OXIDE; NORDIHYDROGUAIARETIC ACID; PICEATANNOL; PLANT EXTRACT; POLYPHENOL; QUERCETIN; REACTIVE OXYGEN METABOLITE; RESVERATROL; SCAVENGER; SILYMARIN; STILBENE DERIVATIVE; UNINDEXED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; CANCER; CARDIOVASCULAR DISEASE; CHRONIC INFLAMMATION; DEGENERATIVE DISEASE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG POTENCY; DRUG SPECIFICITY; DRUG STRUCTURE; ENZYME INHIBITION; FOOD INDUSTRY; INFLAMMATION; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PHARMACOPHORE; REVIEW; SCAVENGING SYSTEM; SIGNAL TRANSDUCTION; SYNTHESIS;

ANIMALIA;

EID: 2442681925     PISSN: 15407535     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (75)

1. Allred, C.D., Ju, Y.H., Allred, K.F., Chang, J., Helferich, W.G. (2001) Dietary genistin stimulates growth of estrogendependent breast cancer tumors similar to those observed with genistein. Carcinogenesis 22, 1667-1673.
2. Akiyama, T., Ishida, J., Nakagawa, S., Ogawara, H., Watanabe, S., Itoh, N., Shibuya, M., Fukami, Y. (1987) Genistein, a specific inhibitor of tyrosine-specific protein kinases. Journal of Biological Chemistry 262, 5592-5595.
3. Anderson, J.W., Diwadkar, V.A., Bridges, S.R. (1998) Selective effects of different antioxidants on oxidation of lipoproteins from rats. Proceedings of the Society for Experimental Biology & Medicine 21,376-381.
4. Anthony, M.S., Clarkson, T.B., Williams, J.K. (1998) Effects of soy isoflavones on atherosclerosis: Potential mechanisms. American Journal of Clinical Nutrition 68 (6 Suppl): 1390S-1393S.
5. Arora, A., Nair, M.G., Strasburg, G.M. (1998) Antioxidant activities of isoflavones and their biological metabolites in a liposomal system. Archives of Biochemistry and Biophysics 356, 133-141.
6. Barrett, W.C., DeGnore, J.P., Konig, S., Fales, H.M., Keng, Y.F., Zhang, Z.Y., Yim, M.B., Chock, P.B. (1999) Regulation of PTP1B via glutathiolynation of the active site cysteine 215. Biochemistry 38, 6699-6705.
7. Bavaresco, L., Fregoni, C., Cantu, E., Trevisan, M. (1999) Stilbene compounds: from the grapevine to wine. Drugs Under Experimental and Clinical Research (Geneva) 25: 57-63.
8. Blum, G., Gavit, A., Levitski, A. (2000) Substrate competitive inhibitors of IGF-I receptor kinase. Biochemistry 39, 15705-15712.
9. Boveris, A., Chance, B. (1973) The mitochondrial generation of hydrogen peroxide. General properties and effect of hyperbaric oxygen. Biochemical Journal 134, 707-716.
10. Brown, G., Stewart, M.Q., Liu, H., Ha, V.L., Yaffe, M.B. (2003) A novel assay system implicates Ptdlns(3,4)P(2), Ptdlns(3)P, and PKC delta in intracellular production of reactive oxygen species by the NADPH oxidase. Molecular Cell 11, 35-47.
11. Buetner, G.R. The pecking order of free radicals and antioxidants: Lipid peroxidation, α-tocopherol, and ascorbate. Archives of Biochemistry and Biophysics 300, 535-543.
12. Colton, C.A., Snell, J., Chernyshev, O., Gilbert, D.L. (1994) Induction of superoxide anion and nitric oxide production in cultured microglia. Annals of the New York Academy of Sciences 738, 54-63.
13. Dang, P.M., Cross, A.R., Quinn, M.T., Babior, B.M. (2002) Assembly of the neutrophil respiratory burst oxidase: A direct interaction between p67PHOX and cytochrome b558 II. Proceedings of the National Academy of Sciences of the USA 99, 4262-4265.
14. Das, D.K., Sato, M., Ray, P.S., Maulik, G., Engelman, R.M., Bertelli, A.A., Bertelli, A. (1999) Cardioprotection of red wine: role of polyphenolic antioxidants. Drugs Under Experimental and Clinical Research (Geneva) 25:115-120.
15. Davis, J.N., Kucuk, O., Djuric, Z., Sarkar, F.H. (2001) Soy isoflavone supplementation in healthy men prevents NFΚB activation by TNFα in blood lymphocytes. Free Radicals in Biology and Medicine 30, 1293-1302.
16. DeLeo, F.R., Allen, L.A., Apicella, M., Nauseef, W.M. (1999) NADPH oxidase activation and assembly during phagocytosis. Journal of Immunology 163, 6732-6740.
17. Delledonne, M., Xia, Y., Dixon, R.A., Lamb, C. (1998) Nitric oxide functions as a signal in plant disease resistance. Nature 394, 585-588.
18. Denu, J.M., Tanner, K.G. (1998) Specific and reversible inactivation of protein tyrosine phosphatases by hydrogen peroxide: Evidence for a sulfenic acid intermediate and implications for redox regulation. Biochemistry 37, 5633-5642.
19. Dixon, R.A. (2001) Natural products and disease resistance. Nature 411,843-847.
20. Dixon, R.A., Ferreira, D. (2002) Genistein. Phytochemistry 50, 205-211.
21. Dorai, T., Gehani, N., Katz, A. (2000) Therapeutic potential of curcumin in human prostate cancer II. Curcumin inhibits tyrosine kinase activity of epidermal growth factor receptor and depletes the protein. Molecular Urology 4, 1-6.
22. Esterbauer H., Schaur R.J, Zollner H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malondaldehyde and related aldehydes. Free Radicals in Biology and Medicine 11, 81-128.
23. Flynn, D.L., Rafferty, M.F., Boctor, A.M. (1986) Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally-occurring diarylheptanoids: Inhibitory activities of curcuminoids and yakuchinones. Prostaglandins and Leukotriene Medicine 22, 357-360.
24. Frautschy, S.A., Hu, W., Kim, P., Miller, S.A., Chu, T., Harris-White, M.E., Cole, G.M. (2001) Phenolic anti-inflammatory antioxidant reversal ofAβ-induced cognitive defecits and neuropathology. Neurobiology of Aging 22, 993-1005.
25. Frey, R.S., Rahman, A., Kefer, J.C., Minshall, R.D., Malic, A.B. (2002) PKC-ζ regulates TNFα-induced activation of NADPH oxidase in endothelial cells. Circulation Research 90, 1012-1019.
26. Funk, C.D. (2001) Prostaglandins and leukotrienes: Advances in eicosanoid biology. Science 294, 1871-1875.
27. Gabbita, S.P., Robinson, K.A., Stewart, C.A., Floyd, R.A., Hensley, K. (2000) Redox regulatory mechanisms of cellular signal transduction. Archives of Biochemistry and Biophysics 376, 1-13.
28. Garg, A.K., Aggarwall, B.B. (2002) Reactive oxygen intermediates in TNF signaling. Molecular Immunology 39, 509-517.
29. Geahlen, R.L., Koonchanok, N.M., McLaughlin, J.L., Pratt, D.E. (1989) Inhibition of protein-tyrosine kinase activity by flavonoids and related compounds. Journal of Natural Products-Lloydia 52, 982-986.
30. Gusman J, Malonne H, Atassi G. (2001) A reappraisal of the potential chemopreventive and chemotherapeutic properties of resveratrol. Carcinogenesis 22:1111-1177.
31. Halliwell, B., Gutteridge, J.M.C. (1989) Free Radicals in Biology and Medicine, 2nd Ed. Clarendon Press, Oxford.
32. Hensley, K.; Hall, N.; Subramaniam, R.; Cole, P.; Harris, M.; Aksenov, M.; Aksenova, M.; Gabbita, S.P.; Wu, J.F.; Carney, J.M.; Lovell, M.; Markesbery, W.R.; Butterfield, D.A. (1995) Brain regional correspondence between Alzheimer's disease histopathology and biomarkers of protein oxidation. Journal of Neurochemistry 65:2146-2156.
33. Hensley, K., Pye, Q.N., Maidt, M.L., Stewart, C.A., Robinson, K.A., Jaffrey, F., Floyd, R.A. (1998) Interaction of α-phenyl-N-tert-butyl nitrone and alternative electron acceptors with complex I indicates a substrate reduction site upstream from the rotenone binding site. Journal of Neurochemistry 71,549-2557.
34. 2 generation in liver mitochondria. Carcinogenesis 21,983-989.
35. Hensley, K., Floyd, R.A. (2002) Reactive oxygen species and protein oxidation in aging: A look back, a look ahead. Archives of Biochemistry and Biophysics 397, 377-383.
36. Huang, R.Q., Dillon, G.H. (2000) Direct inhibition of glycine receptors by genistein, a tyrosine kinase inhibitor. Neuropharmacology 39, 2195-2204.
37. Iles, K.E., Forman, H.J. (2002) Macrophage signaling and respiratory burst. Immunology Research 26, 95-105.
38. Irani, K.; Goldschmidt-Clermont, P.J. (1998) Ras, superoxide and signal transduction. Biochemical Pharmacology 55, 1339-1346.
39. Joneson, T.; Bar-Sagi, D. (1998) A Racl effector site controlling mitogenesis through superoxide production. Journal of Biological Chemistry 273, 17991-17994.
40. Kemal, C.; Louis-Flamberg, P.; Krupinski-Olsen, R.; Shorter, A, (1987) Reductive inactivation of soybean lipoxygenase-1 by catechols. Biochemistry 26, 7064-7072.
41. Kim, H., Peterson, T.G., Barnes, S. (1998) Mechanisms of action of the soy isoflavone genistein: Emerging role for its effects via transforming growth factor beta signaling pathways. American Journal of Clinical Nutrition 68 (6 Suppl): 1418S-1425S.
42. Korutla, L., Kumar, R. (1994) Inhibitory effect of curcumin on epidermal growth factor receptor tyrosine kinase activity in A431 cells. Biochimica et Biophysica Acta 1224, 597-600.
43. Kwon, H., Park, S., Lee, S., Lee, D.K., Yang, C.H. (2001) Determination of binding constant of transcription factor AP-1 and DNA. Application of inhibitors. European Journal of Biochemistry 268, 565-572.
44. Lamb, C., Dixon, R.A. (1997) The oxidative burst in plant disease resistance. Annual Review of Plant Physiology-Plant Molecular Biology 48, 251-275.
45. Lee, S.R., Kwon, K.S., Kim, S.R., Rhee, S.G. (1998) Reversible inactivation of protein-tyrosine phosphatase 1B in A431 cells stimulated with epidermal growth factor. Journal of Biological Chemistry 273, 15366-15372.
46. Lehman, A.J., Fitzhugh, O.G., Nelson, A.A., Woodard, G. (1951) The pharmacological evaluation of antioxidants. Advances in Food Research 3, 197.
47. Li, S., Whorton R.A. (2003) Regulation of protein tyrosine phosphatase 1B in intact cells by S-nitrosothiols. Archives of Biochemistry and Biophysics 410, 269-279.
48. Lichtenstein, A.H. (1998) Soy protein, isoflavones and cardiovascular disease risk. Journal of Nutrition 128, 1589-1592.
49. Lim, G.P.; Chu, T.; Yang, F.; Beech, W.; Frautschy, S.A.; Cole, G.M. (2001) The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse. Journal of Neuroscience 21, 8370-8377.
50. Natarajan, C., Bright, J.J. (2002) Curcumin inhibits experimental allergic encephalomyelitis by blocking IL-12 signaling through Janus kinase-STAT pathway in T lymphocytes. Journal of Immunology 168, 6506-6513.
51. Oliver, J.M., Burg, D.L., Wilson, B.S., McLaughlin, J.L., Geahlen, R.L. (1994) Inhibition of mast cell Fc epsilon R1-mediated signaling and effector function by the Syk-selective inhibitor, piceatannol. Journal of Biological Chemistry 269: 29697-29703.
52. Pang, L., Sawada, T., Decker, S.J., Saltiel, A.R. (1995) Inhibition of MAP kinase kinase blocks the differentiation of PC-12 cells induced by nerve growth factor. Journal of Biological Chemistry 270, 13585-13588.
53. Patel, R.P., Boersma, B.J., Crawford, J.H., Hogg, N., Kirk, M., Kalyanaraman, B., Parkes D.A., Barnes S., Darley-Usmar V. (2001) Antioxidant mechanisms of isoflavones in lipid systems: Paradoxical effects of peroxyl radical scavenging. Free Radicals in Biology and Medicine 31, 1570-1581.
54. Robinson, K., Stewart, C.A., Pye, Q.N., Nguyen, X., Kenney, L., Salsman, S., Floyd, R.A., Hensley, K. (1999) Redox-sensitive protein phosphatase activity regulates the phosphorylation state of p38 protein kinase in primary astrocyte culture. Journal of Neuroscience Research 55, 724-732.
55. Salari, H.; Braquet, P.; Borgeat, P, (1984) Comparative effects of indomethacin, acetylenic acids, 15-HETE, nordihydroguaiaretic acid, and BW755C on the metabolism of arachidonic acid in human leukocytes and platelets. Prostaglandins. Leukotriene Medicine 13, 53-60.
56. Sarkar, F.H., Li, Y. (2002) Mechanisms of cancer chemoprevention by soy isoflavone genistein. Cancer Metastasis Review 21,265-280.
57. Shishido, Y.; Furushiro, M.; Hashimoto, S.; Yokokura, T. (2001) Effect of nordihydroguaiaretic acid on behavioral impairment and neuronal cell death after forebrain ischemia. Pharmacology, Biochemistry and Behavior 69, 469-474.
58. Sirtori, C.R., Lovati, M.R. (2001) Soy proteins and cardiovascular disease. Current Atherosclerosis Report 3, 47-53.
59. Skrzypczak-Jankun, E.; McCabe, N.P.; Selman, S.H.; Jankun, J. (2000) Curcumin inhibits lipoxygenase by binding to its central cavity: Theoretical and X-ray evidence. International Journal of Molecular Medicine 6, 521-526.
60. Steinberg, F.M., Guthrie, N.L., Villablanca, A.C., Kumar, K., Murray, M.J. (2003) Soy protein with isoflavones has favorable effects on endothelial function that are independent of lipid and antioxidant effects in healthy postmenopausal women. American Journal of Clinical Nutrition 78:123-130.
61. 2 for platelet-derived growth factor signal transduction. Science 270, 296-299.
62. Takakura, K., Beckman, J.S., MacMillan-Crow, L.A., Crow, J.P. (1999) Rapid and irreversible inactivation of protein tyrosine phosphatases PTP1B, CD45, and LAR by peroxynitrite. Archives of Biochemistry and Biophysics 369, 197-207.
63. Toda, S., Shirataki, Y. (2001) Inhibitory effects of licoisoflavones A and B and sophoraisoflavone A of Sophra mooracroftiana Beth ex Baker on copper-ion -induced protein oxidative modification of mouse brain homogenate, in vitro. Biological Trace Element Research. 81, 169-175.
64. Torres, M. (2003) Mitogen-activated protein kinase pathways in redox signaling. Frontiers of Biosciences 8, D369-D391.
65. Traxler, P., Green, J., Mett, H., Sequink, U., Furet, P. (1999) Use of a pharmacophore model for the design of EGFR tyrosine kinase inhibitors: Isoflavones and 3-phenyl-4(1H)-quinolones. Journal of Medicinal Chemistry 42, 1018-1026.
66. Trieu, V.N., Uckun, F.M. (1999) Genistein is neuroprotective in murine models of familial amyotrophic lateral sclerosis. Biochemical and Biophysical Research Communications 258, 685-688.
67. Vlahos, C.J., Matter, W.F., Hui, K.Y., Brown, R.F. (1994) A specific inhibitor of phosphatidylinositol 3-kinase, 2-(4-morpholinyl)-8-phenyl-4H- 1-benzopyran-4-one (LY294002). Journal of Biological Chemistry 269, 5241-5248.
68. Wang, M-L, Lin, W-W., Chen, H-L., Chang, Y-H., Ou, H-C., Kuo, J-S., Hong, J-S., Jeng, K-C. G. (2002) Silymarin protects dopaminergic neurons against lipopolysaccharide-induced neurotoxicity by inhibiting microglial activation. European Journal of Neuroscience 16, 2103-2112.
69. Watanabe, S., Haba, R., Terashima, K., Arai, Y., Miura, T., Chiba, H., Takamatsu, K. (2000) Antioxidant activity of soya hypocotyls tea in humans. Biofactors 12, 227-232.
70. Wei, H., Cai, Q., Rahn, R.O. (1996) Inhibition of UV light-and Fenton reaction-induced oxidative DNA damage by the soy isoflavone genistein. Carcinogenesis 17, 73-77.
71. Whitman, S.; Gezginci, M.; Timmermann, B.N.; Holman, T.R. (2002) Structure-activity relationship studies of nordihydroguaiaretic acid inhibitors toward soybean 12-human and 15-human lipoxygenase. Journal of Medicinal Chemistry 45, 2659-2666.
72. Wiseman, H., O'Reilly, J.D., Adlercreutz, H., Mallet, A.I., Bowey, E.A., Rowlan, I.R., Sanders, T.A. (2000) Isoflavone phytoestrogens consumed in soy decrease F(2)-isoprostane concentrations and increase resistance of low-density lipoprotein to oxidation in humans. American Journal of Clinical Nutrition 72, 395-400.
73. Woo C-H, Eom Y-W, Yoo M-H, You H-J, Han H-J, Song W-K, Yoo Y-J, Chun J-S, Kim J-H (2000) Tumor necrosis factor alpha generates reactive oxygen species via a cytosolic phospholipase A2-linked cascade Journal of Biological Chemistry 275, 32357-32362.
74. Wu, J.M., Wang, Z.R., Hsieh, T.C., Bruder, J.L., Zou, J.G., Huang, Y.Z. (2001) Mechanism of cardioprotection by resveratrol, a phenolic antioxidant present in red wine. International Journal of Molecular Medicine 8:13-17.
75. Yang, S., Hardaway, M., Sun, G., Ries, W.L., Key, L.L. Jr. Superoxide generation and tyrosine kinase. Biochemistry & Cell Biology 78, 11-17.