Derivatives of resveratrol: Potential agents in prevention and treatment of cardiovascular disease

Current Medicinal Chemistry

Volumn 19, Issue 24, 2012, Pages 4175-4183

  Ruan, Ban Feng ^a   Lu, Xiao Qin ^a   Song, Jie ^a   Zhu, Hai Liang ^b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Akt; AMPK; Apoptosis; Cardiovascular disease; Derivatives of resveratrol; Reactive oxygen species; SIRT1; Structure activity relationship

Indexed keywords

2,6 DIBROMO 4 (3,5 DIBROMOSTYRYL)PHENOL; 3,4,3',4' TETRAHYDROXY STILBENE; 3,4,5 TRIHYDROXYBENZOHYDROXAMIDOXIME; 3,5 DIHYDROXY 4' THIOMETHYL STILBENE; 4,4' DIHYDROXY STILBENE; 5 [4 (OCTYLOXY)STYRYL]BENZENE 1,3 DIOL; 5 HYDROXY 2 (4 HYDROXYSTYRYL) 4H PYRAN 4 ONE; BENZOHYDROXAMIC ACID; DIHYDROXYSTILBENE; FUNCTIONAL GROUP; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE KINASE; PICEATANNOL; PROTEIN KINASE B; PTEROSTILBENE; REACTIVE OXYGEN METABOLITE; RESVERATROL; SIRTUIN 1; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CARDIOVASCULAR DISEASE; CHEMOPROPHYLAXIS; DRUG SYNTHESIS; FOOD; HEART VENTRICLE HYPERTROPHY; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMP-ACTIVATED PROTEIN KINASES; APOPTOSIS; CARDIOVASCULAR AGENTS; CARDIOVASCULAR DISEASES; HUMANS; HYDROXAMIC ACIDS; PROTO-ONCOGENE PROTEINS C-AKT; REACTIVE OXYGEN SPECIES; SIRTUIN 1; STILBENES;

EID: 84866659260     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712802430054     Document Type: Article

References (110)

1. Das, M.; Das, D.K. Resvertrol and cardiovascular health. Mol. Aspects. Med., 2010, 31, 503-512.
2. Murray, C.J.; Lopez, A.D. Global mortality, disability and the contribution of risk factor: global burden of disease study. Lancet, 1998, 349, 1436-1442.
3. Castelli, W.P. The new pathophysiology of coronary artery disease. Am. J. Cardiol., 1988, 82, 60-65.
4. Abeywardena, M.Y. Dietary fats, carbohydrates and vascular disease: Sri Lankan perspectives. Atherosclerosis, 2003, 171, 157-161.
5. Zalba, G.; Fortuno, A.; San Jose, G.; Moreno, M.U.; Beloqui, O.; Diez, J. Oxidative stress, endothelial dysfunction and cerebrovascular disease. Cerebrovasc. Dis., 2007, 24, 24-29.
6. de Lorimier, A.A. Alcohol, wine, and health. Am. J. Surg., 2000, 180, 357-361.
7. Gronbaek, M. Alcohol, type of alcohol, and all-cause and coronary heart disease mortality. Ann. N. Y. Acad. Sci., 2002, 957, 16-20.
8. Richard, J.L. Les facteurs de risque coronarien: Le paradoxe français. Arch. Mal. Coeur. Vaiss., 1987, 80, 17-21.
9. Hao, H.D.; He, L.R. Mechanisms of cardiovascular protection by resveratrol. J. Med. Food, 2004, 7, 290-298.
10. Pace-Asciak, C.R.; Hahn, S.; Diamandis, E.P.; Soleas, G.; Goldberg, D.M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin. Chim. Acta, 1995, 235, 207-219.
11. Fernández-Mar, M.I.; Mateos, R.; García-Parrilla, M.C.; Puertas, B.; Cantos-Villar, E. Bioactive compounds in wine: Resveratrol, hydroxytyrosol and melatonin: A review. Food Chem., 2012, 130, 797-813.
12. Pettit, G.R.; Singh, S.B.; Boyd, M.R.; Hamel, E.; Pettit, R.K.; Schmidt, J.M.; Hogan, F. Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. J. Med. Chem., 1995, 38, 1666-1672.
13. Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A.K.; Lin, C.M.; Hamel, E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J. Med. Chem., 1991, 34, 2579-2588.
14. Hata, K.; Baba, K.; Kozawa, M. Chemical studies on the heartwood of Cassia garrettiana Craib. II. Nonanthraquinonic constituents. Chem. Pharm. Bull., 1979, 27, 984-989.
15. Subramanian, M.; Shadakshari, U.; Chattopadhyay, S. A mechanistic study on the nuclease activities of some hydroxystilbenes. Bioorg. Med. Chem., 2004, 12, 1231-1237.
16. Vishal, v.k.; Subhash, P.; Navindra, P.S. Sources and chemistry of resveratrol. Resveratrol in Health and Disease, 2005, 17-32.
17. Bhat, K.P.L.; Kosmeder, J.W.; Pezzuto, J.M. Biological effects of resveratrol. Antioxid. Redox Signaling, 2001, 3, 1041-1064.
18. Baur, J.A.; Sinclair, D.A. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov., 2006, 5, 493-506.
19. Langcake, P.; Pryce, R.J. A new class of phytoalexins from grapevines. Experientia, 1977, 33, 151-152.
20. Dixon, R.A. Natural products and plant disease resistance. Nature, 2001, 411, 843-847.
21. Lamuela-Raventos, R.M.; Romero-Perez, A.I.; Waterhouse, A.L.; Torre-Boronat, M.C. Direct HPLC analysis of cis-and trans-resveratrol and piceid isomers in spanish red vitis vinifera wines. J.Agric. Food Chem., 1995, 43, 281-283.
22. Pan, M.H.; Gao, J.H.; Lai, C.S.; Wang, Y.J.; Chen, W.M.; Lo, C.Y.; Wang, M.F.; Dushenkov, S.; Ho, C.T. Antitumor activity of 3,5,4-trimethoxystilbene in COLO 205 cells and xenografts in SCID mice. Mol. Carcinog., 2008, 47, 184-196.
23. Locatelli, G.A.; Savio, M.; Forti, L.; Shevelev, I.; Ramadan, K.; Stivala, L.A.; Vannini, V.; Hübscher, U.; Spadari, S.; Maga, G. Inhibition of mammalian DNA polymerases by resveratrol: mechanism and structural determinants. Biochem. Soc., 2005, 389, 259-268.
24. Coppa, T.; Lazzè, M.C.; Cazzalini, O.; Perucca, P.; Pizzala, R.; Bianchi, L.; Stivala, L.; Forti, L.; Maccario, C.; Vannini, V.; Savio, M. Structure-activity relationship of resveratrol and its analogue, 4,4-dihydroxy-trans-stilbene, toward the endothelin axis in human endothelial cells. J. Med. Food, 2011, 14, 1175-1179.
25. Das, J.; Pany, S.; Majhi, A. Chemical modifications of resveratrol for improved protein kinase C alpha activity. Bioorg. Med. Chem., 2011, 19, 5321-5333.
26. Rimando, A.M.; Cuendet, M.; Desmarchelier, C.; Mehta, R.G.; Pezzuto, J.M.; Duke, S.O. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. J. Agric. Food Chem., 2002, 50, 3453-3457.
27. Ferrer, P.; Asensi, M.; Segarra, R.; Ortega, A.; Benlloch, M.; Obrador, E.; Varea, M.T.; Asensio, G.; Jordá, L.; Estrela, J.M. Association between pterostilbene and quercetin inhibits metastatic activity of B16 melanoma. Neoplasia, 2005, 7, 37-47.
28. Russo, G.L.; Russo, M. Ins and outs of apoptosis in cardiovascular diseases. Nutr. Metab. Cardiovasc. Dis., 2003, 13, 191-300.
29. Elizabeth, G.; Nabel, M.D. Cardiovascular disease. N. Engl. J. Med., 2003, 349, 60-72.
30. Ndeye, C.N.; Mohsen, A.N.; Said. E.S.; Maria, G.S.; Sophie, V.S. Cardiovascular diseases and genome-wide association studies. Clin. Chim. Acta, 2011, 412, 1697-1701.
31. Ravussin, E.; Smith, S.R. Increased fat intake, impaired fat oxidation, and failure of fat cell proliferation result in ectopic fat storage, insulin resistance, and type 2 diabetes mellitus. Ann. N. Y. Acad. Sci., 2002, 967, 363-378.
32. Roger, V.L.; Go, A.S.; Lloyd-Jones, D.M.; Adams, R.J.; Berry, J.D.; Brown, T.M.; Carnethon, M.R.; Dai, S.; de Simone, G.; Ford, E.S.; Fox, C.S.; Fullerton, H.J.; Gillespie, C.; Greenlund, K.J.; Hailpern, S.M.; Heit, J.A.; Ho, P.M.; Howard, V.J.; Kissela, B.M.; Kittner, S.J.; Lackland, D.T.; Lichtman, J.H.; Lisabeth, L.D.; Makuc, D.M.; Marcus, G.M.; Marelli, A.; Matchar, D.B.; McDermott, M.M.; Meigs, J.B.; Moy, C.S.; Mozaffarian, D.; Mussolino, M.E.; Nichol, G.; Paynter, N.P.; Rosamond, W.D.; Sorlie, P.D.; Stafford, R.S.; Turan, T.N.; Turner, M.B.; Wong, N.D.; Wylie-Rosett, J. Heart disease and stroke statistics-2011 update: a report from the American Heart Association. Circulation, 2011,123, e18-e209.
33. Finkel, T. Signal transduction by reactive oxygen species in non-phagocytic cells. J. Leukoc. Biol., 1999, 65, 337-340.
34. Suzuki, Y.J.; Ford, G.D. Redox regulation of signal transduction in cardiac and smooth muscle. J. Mol. Cell Cardiol., 1999, 31, 345-353.
35. Mike, S.; Yee, H.L.; Ajay, M.S. Oxidative stress and redox signalling in cardiac hypertrophy and heart failure. Heart, 2007, 93, 903-907.
36. Josephson, R.A.; Silverman, H.S.; Lakatta, E.G.; Stern, M.D.; Zweier, J.L. Study of the mechanisms of hydrogen peroxide and hydroxyl free radicalinduced cellular injury and calcium overload in cardiac myocytes. J. Biol. Chem., 1991, 266, 2354-2361.
37. Li, J.M.; Shah, A.M. Endothelial cell superoxide generation: regulation and relevance for cardiovascular pathophysiology. Am. J. Physiol., 2004, 287, 1014-1030.
38. Dhalla, N.S.; Temsah, R.M.; Netticadan, T. Role of oxidative stress in cardiovascular diseases. J. Hypertens., 2000, 18, 655-673.
39. Chien, K.R. Stress pathways and heart failure. Cell, 1999, 98, 555-558.
40. Sugden, P.H.; Clerk, A. Cellular mechanisms of cardiac hypertrophy. J. Mol. Med., 1998, 76, 725-746.
41. Ide, T.; Tsutsui, H.; Hayshidani, S.J.; Kang, D.C.; Suematsu, N.B.; Nakamura, K.I.; Utsumi, H.; Hamasaki, N.; Takeshita, A. Mitochondrial DNA damage and dysfunction Associated with oxidative stress in failing hearts after myocardial infarction. Circ. Res., 2001, 88, 529-535.
42. Cristine, E.B.; Joshua, M.H. Xanthine oxidoreductase and cardiovascular disease: molecular mechanisms and pathophysiological implications. J. Physiol., 2004, 555, 589-606.
43. Verhaar, M.C.; Westerweel, P.E.; van Zonneveld, A.J.; Rabelink, T.J. Free radical production by dysfunctional eNOS. Heart, 2004, 90, 494-495.
44. Shah, A.M.; MacCarthy, P.A. Paracrine and autocrine effects of nitric oxide on myocardial function. Pharmacol. Ther., 2000, 86, 49-86.
45. Griendling, K.K.; Sorescu, D.; Ushio-Fukai, M. NAD(P)H oxidase: role in cardiovascular biology and disease. Circ. Res., 2000, 86, 494-501.
46. Bayraktutan, U.; Blayney, L.; Shah, A.M. Molecular characterization and localization of the NAD(P)H oxidase components gp91-phox and p22-phox in endothelial cells. Arterioscl. Thromb. Vasc. Biol., 2000, 20, 1903-1911.
47. Gorlach, A.; Brandes, R.P.; Nguyen, K.; Amidi, M.; Dehghani, F.; Busse, R. A gp-91-phox containing NADPH oxidase selectively expressed in endothelial cells is a major source of oxygen radical generation in the arterial wall. Circ. Res., 2000, 87, 26-32.
48. Pagano, P.J.; Clark, J.K.; Cifuentes-Pagano, M.E.; Clark, S.M.; Callis, G.M.; Quinn, M.T. Localization of a constitutively active, phagocyte-like NADPH oxidase in rabbit aortic adventitia: enhancement by angiotensin II. Proc. Natl. Acad. Sci. U S A., 1997, 94, 14483-14488.
49. Lambeth, J.D. NOX enzymes and the biology of reactive oxygen. Nat. Rev. Immunol., 2004, 4, 181-189.
50. Li, J.M.; Gall, N.P.; Grieve, D.J.; Chen. M.; Shah, A.M. Activation of NADPH oxidase during progression of cardiac hypertrophy to failure. Hypertension, 2002, 40, 477-484.
51. Heymes, C.; Bendall, J.K.; Ratajczak, P.; Cave, A.C.; Samuel, J.L.; Hasenfuss, G.; Shah, A.M. Increased myocardial NADPH oxidase activity in human heart failure. J. Am. Coll. Cardiol., 2003, 41, 2164-2171.
52. Maack, C.; Kartes, T.; Kilter, H.; Schafers, H.J.; Nickenig, G.; Bohm, M.; Laufs, U. Oxygen free radical release in human failing myocardium is associated with increased activity of Rac1-GTPase and represents a target for statin treatment. Circulation, 2003, 108, 1567-1574.
53. Knaapen, M.W.; Davies, M.J.; De, B.M.; Haven, A.J.; Martinet, W.; Kockx, M.M. Apoptotic versus autophagic cell death in heart failure. Cardiovasc. Res., 2001, 51, 304-312.
54. Kang, P.M. Apoptosis and heart failure: a critical review of the literature. Circ. Res., 2000, 86, 1107-1113.
55. Gottlieb, R.A.; Burleson, K.O.; Kloner, R.A.; Babior, B.M.; Engler, R.L. Reperfusion injury induces apoptosis in rabbit cardiomyocytes. J. Clin. Invest., 1994, 94, 1621-1628.
56. Li, P.; Nijhawan, D.; Budihardjo, I.; Srinivasula, S.M.; Ahmad, M.; Alnemri, E.S.; Wang, X. Cytochrome c and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade. Cell, 1997, 91, 479-489.
57. Peter M.K.; Seigo, L. Apoptosis in heart: basic mechanisms and implications in cardiovascular diseases. Trends Mol. Med., 2003, 9, 177-182.
58. Dryden, S.C.; Nahhas, F.A.; Nowak, J.E.; Goustin, A.S.; Tainsky, M.A. Role for human SIRT2 NAD-dependent deacetylase activity in control of mitotic exit in the cell cycle. Mol. Cell Biol., 2003, 23, 3173-3185.
59. Tissenbaum, H.A.; Guarente, L. Increased dosage of a sir-2 gene extends lifespan in Caenorhabditis elegans. Nature, 2001, 410, 227-230.
60. Ilwola, M.; Cuk-Seong, K.; Asma, N.; Tohru, Y.; Timothy, A. H.; Saet-Byel, J.; Jeremy, D.; Kenji, K.; Kaikobad, I. SIRT1 promotes endotheliumdependent vascular relaxation by activating endothelial nitric oxide synthase. Proc. Natl. Acad. Sci. U S A., 2007, 104, 14855-14860.
61. Corton, J.M.; Gillespie, J.G.; Hardie, D.G. Role of the AMP-activated protein kinase in the cellular stress response. Curr. Biol., 1994, 4, 315-324.
62. Ian, S.; Jakub, W.C.; Simon, A.H.; Alan, P.; Angela, W.; David, C.; D.Grahame, H. AMP-activated protein kinase: greater AMP dependence, and preferential nuclear localization, of complexes containing the-2 isoform. Biochem. J., 1998, 334, 177-187.
63. Chan, A.Y.; Soltys, C.L.; Young, M.E.; Proud, C.G.; Dyck, J.R. Activation of AMP-activated protein kinase inhibits protein synthesis associated with hypertophy in the cardiac myocyte. J. Biol. Chem., 2004, 279, 32771-32779.
64. Noga, A.A.; Soltys, C.L.; Barr, A.J.; Kovacic, S.; Lopaschuk, G.D.; Dyck, J.R. Expression of an active LKB1 complex in cardiac myocytes results in decreased protein synthesis associated with phenylephrine-induced hypertrophy. Am. J. Physiol. Heart Circ. Physiol., 2007, 292, 1460-1469.
65. Anita, Y.M.C.; Vernon, W.D.; Carrie-Lynn, M.S.; Benoit, V.; Shairaz, B.; Peter, E.L.; Jason, R.B.D. Resveratrol Inhibits Cardiac Hypertrophy via AMP-activated Protein Kinase and Akt. J. Bio. Chem., 2008, 283, 24194-24201.
66. Chen, Z.P.; Mitchelhill, K.I.; Michell, B.J.; Stapleton, D.; Rodriguez-Crespo, I.; Witters, L.A.; Power, D.A.; Ortiz de Montellano, P.R.; Kemp, B.E. AMPactivated protein kinase phosphorylation of endothelial NO synthase. FEBS Lett., 1999, 443, 285-289.
67. Robich, M.P.; Osipov, R.M.; Nezafat, R.; Feng, J.; Clements, R.T.; Bianchi, C.; Boodhwani, M.; Coady, M.A.; Laham, R.J.; Sellke, F.W. Resveratrol improves myocardial perfusion in a swine model of hypercholesterolemia and chronic myocardial ischemia. Circulation, 2011, 122, S142-S149.
68. Wang, L.; Wang, X.; Proud, C.G. Activation of Mrna translation in rat cardiac myocytes by insulin involves multiple rapamycin-sensitive steps. Am. J. Physiol. Heart Circ. Physiol., 2000, 278, H1056-H1068.
69. Cross, D.A.; Alessi, D.R.; Cohen, P.; Andjelkovich, M.; Hemmings, B.A. Inhibition of glycogen synthase kinase-3 by insulin mediated by protein kinase B. Nature, 1995, 378, 785-789.
70. Kovacic, S.; Soltys, C.L. Barr, A.J.; Shiojima, I.; Walsh, K.; Dyck, J.R. Akt activity negatively regulates phosphorylation of AMP-activated protein kinase in the heart. J. Biol. Chem., 2003, 278, 39422-39427.
71. Horman, S.; Vertommen, D.; Heath, R.; Neumann, D.; Mouton, V.; Woods, A.; Schlattner, U.; Wallimann, T.; Carling, D.; Hue, L.; Rider, M.H. Insulin antagonizes ischemia-induced Thr172 phosphorylation of AMP-activated protein kinase alpha-subunits in heart via hierarchical phosphorylation of Ser485/491. J. Biol. Chem., 2006, 281, 5335-5340.
72. Soltys, C.L.; Kovacic, S.; Dyck, J.R. Activation of cardiac AMP-activated protein kinase by LKB1 expression or chemical hypoxia is blunted by increased Akt activity. Am. J. Physiol. Heart Circ. Physiol., 2006, 290, H2472-H2479.
73. Matsumura, Y.; Tsukahara, Y.; Kojima, T.; Murata, S.; Murakami, A.; Takada, K.; Takaoka, M.; Morimoto, S. Effects of phosphoramidon on endothelin-1 and big endothelin-1 production in human aortic endothelial cells. Biol. Pharm. Bull., 1995, 18, 401-406.
74. Schweigert, N.; Hunziker, R.; Escher, B.J.; Eggen, R.I.L. The acute toxicity of (chloro-) catechol and (chloro-)catechol/copper combinations in Escherichia coil corresponds to the membrane toxicity of these compounds. Environ. Toxicol. Chem., 2001, 20, 239-247.
75. Hider, B.C.; Liu, Z.D.; Khodr, H.H. Metal chelation of polyphenols. Methods Enzymol., 2001, 335, 190-203.
76. Foti, M.; Ruberto, G. Kinetic solvent effects on phenolic antioxidant determined by spectrophotometric measurements. J. Agric. Food Chem., 2001, 49, 342-348.
77. Patel, K.B.; Wilson, R.L. Semiquinone free radicals and oxygen. Pulse radiolysis study of one electron transfer equilibria. J. Chem. Soc., 1973, 69, 814-825.
78. Fukuhara, K.; Nagakawa, M.; Nakanishi, I.; Ohkubo, K.; Imai, K.; Urano, S.; Fukuzumi, S.; Ozawa, T.; Ikota, N.; Mochizuki, M.; Miyata, N.; Okuda, H. Structural basis for DNA-cleaving activity of resveratrol in the presence of Cu(II). Bioorg. Med. Chem., 2006, 14, 1437-1443.
79. Zheng, L.F.; Wei, Q.Y.; Cai, Y.J.; Fang, J.G.; Zhou, B.; Yang, L.; Liu, Z.L. DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu (II) ions: Mechanism and structure-activity relationship. Free Radical Biol. Med., 2006, 41, 1807-1816.
80. Cheng, J.C.; Fang, J.G.; Chen, W.F.; Zhou, B.; Yang, L.; Liu, Z.L. Structureactivity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation. Bioorg. Chem., 2006, 34, 142-157.
81. Bernini, R.; Barontini, M.; Spatafora, C. New lipophilic piceatannol derivatives exhibiting antioxidant activity prepared by aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). Mol., 2009, 14, 4669-4681.
82. Murias, M.; Jäger, W.; Handler, N.; Erker, T.; Horvath, Z.; Szekeres, T.; Nohl, H.; Gille, L. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem. Pharmacol., 2006, 69, 903-912.
83. Murias, M.; Handler, N.; Erker, T.; Pleban, K.; Ecker, G.; Saiko, P.; Szekeres, T.; Jäger, W. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem., 2004, 12, 5571-5578.
84. Wang, M.F.; Jin, Y.; Ho, C.T. Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2-diphenyl-1-picryhydrazyl radical. J. Agric. Food Chem., 1999, 47, 3974-3977.
85. Chen, C.W.; Ho, C.T. Antioxidant properties of polyphenols extracted from green and black tea. J. Food Lipids, 1995, 2, 35-46.
86. Fulda, S. Resveratrol and derivatives for the prevention and treatment of cancer. Drug Discovery Today, 2010, 15, 1-9.
87. Lee, S.K.; Nam, K.A.; Hoe, Y.H.; Min, H.Y.; Kim, E.Y.; Ko, H.; Song, S.; Lee, T.; Kim, S. Synthesis and evaluation of cytotoxicity of stilbene analogues. Arch. Pharm. Res., 2003, 26, 253-257.
88. Chao, J.F.; Li, H.T.; Cheng, K.W.; Yu, M.S.; Chang, R.C.C.; Wang, M.F. Protective effects of pinostilbene, a resveratrol methylated derivative, against 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells. J. Nutr. Biochem., 2010, 21, 482-489.
89. Rimando, A.M.; Suh, N. Biological/chemopreventive activity of stilbenes and their effect on colon cancer. Planta Med., 2008, 74, 1635-1643.
90. Rimando, A.M.; Nagmani, R.; Feller, D.R.; Yokoyama, W. Pterostilbene, a new agonist for the peroxisome proliferatoractivated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J. Agric. Food Chem., 2005, 53, 3403-3407.
91. Remsberg, C.M.; Yáñez, J.A.; Ohgami, Y.; Vega-Villa, K.R.; Rimando, A.M.; Davies, N.M. Pharmacometrics of pterostilbene: preclinical, pharmacokinetics and metabolism, anticancer, antiinflammatory, antioxidant and analgesic activity. Phytother. Res., 2008, 22, 169-179.
92. Yan, Y.; Yan, J.Y.; Chen, G.L.; Mou, Y.H.; Zhao, Y.N.; Pan, L.Y.; Ma, C.H.; Liu, X.W.; Wu, C.F. Protection of resveratrol and its analogues against ethanol-induced oxidative DNA damage in human peripheral lymphocytes. Mutat. Res., 2011, 721, 171-177.
93. Meng, X.L.; Yang, J.Y.; Chen, G.L.; Wang, L.H.; Zhang, L.J.; Wang, S.; Li, J.; Wu, C.F. Effects of resveratrol and its derivatives on lipopolysaccharideinduced microglial activation and their structure-activity relationships. Chem. Biol. Interact, 2008, 174, 51-59.
94. Cho, D.I.; Koo, N.Y.; Chung, W.J.; Kim, T.S.; Ryu, S.Y.; Im, S.Y.; Kim, K.M. Effects of resveratrol-related hydroxystilbenes on the nitric oxide production in macrophage cells: structural requirements and mechanism of action. Life Sci., 2002, 71, 2071-2082.
95. Goldberg, D.M.; Ng, E.; Karumanchiri, A.; Yan, J.; Diamandis, E.P.; Soleas, G.J. Assay of resveratrol glucosides and isomers in wine by directinjection highperformance liquid chromatography. J. Chromatogr., 1995, 708, 984-989.
96. Coimbra, M.; Isacchi, B.; Bloois, L.V.; Torano, J.S.; Ket, A.; Wu, X.J.; Broere, F.; Metselaar, J.M.; Rijcken, C.J.F.; Storma, G.; Bilia, R.; Schiffelers, R.M. Improving solubility and chemical stability of natural compounds for medicinal use by incorporation into liposomes. Int. J. Pharm., 2011, 416, 433-442.
97. Belleri, M.; Ribatti, D.; Nicoli, S.; Cotelli, F.; Forti, L.; Vannini, V.; Stivala, L.A.; Presta, M. Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3,5,4- trimethoxystilbene. Mol. Pharmacol., 2005, 67, 1451-1459.
98. Kim, M.H.; Shin, J.S.; Lee, K.T.; Lee, Y.S. Synthesis of pyronyl derivatives as resveratrol analogues and their inhibitory effects on nitric oxide and PGE2 Productions. Bull. Korean Chem. Soc., 2011, 32, 299-301.
99. Oberyszyn, T.M. Inflammation and wound healing. Front Biosci., 2007, 12, 2993-2999.
100. Szekeres, T.; Fritzer-Szekeres, M.; Saiko, P.; Jäger, W. Resveratrol and resveratrol analogues-structure-activity relationship. Pharm. Res., 2010, 27, 1042-1048.
101. Szekeres, T.; Gharehbaghi, K.; Fritzer, M.; Woody, M.; Srivastava, A.; van't Riet, B.; Jayaram, H.N.; Elford, H.L. Biochemical and antitumor activity of trimidox, a new inhibitor of ribonucleotide reductase. Cancer Chemother. Pharmacol., 1994, 34, 63-66.
102. Battaini, F.; Mochly-Rosen, D. Happy birthday protein kinase C: past, present and future of a superfamily. Pharmacol. Res., 2007, 55, 461-466.
103. Koivunen, J.; Aaltonen, V.; Peltonen, J. Protein kinase C (PKC) family in cancer progression. Cancer Lett., 2006, 235, 1-10.
104. Van Duuren, B.L.; Baneriee, S.; Witz, G. Fluorescence studies on the interaction of the tumor promoter phorbol myristate acetate and related compounds with rat liver plasma membranes. Chem. Biol. Interact, 1976, 15, 233-246.
105. Van Duuren, B.L.; Tseng, S.S.; Segal, A.; Smith, A.C.; Melchionne, S.; Seidman, I. Effects of structural changes on the tumor-promoting activity of phorbol myristate acetate on mouse skin. Cancer Res., 1979, 39, 2644-2646.
106. Hongo, M.; Kono, J.; Yamada, H.; Misawa, T.; Tanaka, M.; Nakatsuka, T.; Kinoshita, O.; Okubo, S.; Sekiguchi, M. Doppler echocardiographic assessments of left ventricular diastolic filling in patients with amyloid heart disease. J. Cardiol., 1991, 21, 391-401.
107. Bourgault, S.; Choi, S.; Buxbaum, J.N.; Kelly, J.W.; Price, J.L.; Reixach, N. Mechanisms of transthyretin cardiomyocyte toxicity inhibition by resveratrol analogs. Biochem. Biophys. Res. Commun., 2011, 410, 707-713.
108. Yang, H.; Baur, J.A.; Chen, A.; Miller, C.; Sinclair, D.A. Design and synthesis of compounds that extend yeast replicative lifespan. Aging Cell, 2007, 6, 35-43.
109. Torres, P.; Poveda, A.; Jimenez-Barbero, J.; Ballesteros, A.; Plou, F.J. Regioselective lipase-catalyzed synthesis of 3-O-acyl-derivatives of resveratrol and study of their antioxidant properties. J. Agric. Food Chem., 2010, 58, 807-813.
110. Lee, H.J.; Seo, J.W.; Lee, B.H.; Chung, K.H.; Chi, D.Y. Syntheses and radical scavenging activities of resveratrol derivatives. Bioorg. Med. Chem. Lett., 2004, 14, 463-466.