From resveratrol to its derivatives: New sources of natural antioxidant

Current Medicinal Chemistry

Volumn 20, Issue 8, 2013, Pages 1005-1017

  He, Shan ^a   Yan, Xiaojun ^a  

^a NINGBO UNIVERSITY   (China)

Author keywords

Antioxidant; Biological Activity; Chemical Diversity; Derivative; Resveratrol; Structure Activity Relationship

Indexed keywords

AMPELOPSIN B; AMPELOPSIN G; AMURENSIN B; ASTRINGIN; CHUNGANENOL; CYPHOSTEMMIN B; DIVINIFERIN B; GNEMONOL B; GNETOL; HEYNEANOL A; HOPEAPHENOL; ISORHAPONTIGENIN; MIYABENOL C; OXYRESVERATROL; PALLIDOL; PARTHENOCISSIN A; PARTHENOSTILBENIN A; PARTHENOSTILBENIN B; PHENOL DERIVATIVE; PICEATANNOL; PICEATANOL; PICEID; PINOSYLVIN; RESVERATROL; RHAPONTIGENIN; RHAPONTIN; SCIRPUSIN A; STILBENE DERIVATIVE; TRICUSPIDATOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BRAIN DISEASE; CARDIOVASCULAR DISEASE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 84877968112     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/0929867311320080004     Document Type: Article

References (91)

1. Miller, D.M.; Buettner, G.R.; Aust, S.D. Transition metals as catalysts of "autoxidation" reactions. Free Radic. Biol. Med., 1990, 8, 95-108.
2. Moro, M. A.; Almeida, A.; Bolanos, J. P.; Lizasoain, I. Mitochondrial respiratory chain and free radical generation in stroke. Free Radic. Biol. Med., 2005, 39, 1291-1304. (Pubitemid 41540085)
3. Valko, M.; Leibfritz, D.; Moncol, J.; Cronin, M.T.D.; Mazur, M.; Telser, J. Free radicals and antioxidants in normal physiological functions and human disease. Int. J. Biochem. Cell Biol., 2007, 39, 44-84. (Pubitemid 44566469)
4. Crack, P.J.; Taylor, J.M. Reactive oxygen species and the modulation of stroke. Free Radic. Biol. Med., 2005, 38, 1433-1444. (Pubitemid 40693828)
5. Ma, Z.; Zhao, B.; Yuan, Z. Application of electrochemical and spin trapping techniques in the investigation of hydroxyl radicals. Anal. Chim. Acta, 1999, 389, 213-218. (Pubitemid 29236111)
6. Marnett, L.J. Oxyradicals and DNA damage. Carcinogenesis, 2000, 21, 361-370. (Pubitemid 30137921)
7. Fang, Y.Z.; Yang, S.; Wu, G. Free radicals, antioxidants, and nutrition. Nutrition, 2002, 18, 872-879. (Pubitemid 35292261)
8. Foyer, C.H.; Noctor, G. Redox homeostasis and antioxidant signaling: a metabolic interface between stress perception and physiological responses. Plant Cell, 2005, 17, 1866-1875.
9. Takaoka, M.J. Of the phenolic substances of white hellebore (Veratrum grandiflorum Loe. fil.). J. Faculty Sci. Hokkaido Imperial University, 1940, 3, 1-16.
10. Nonomura, S.; Kanagawa, H.; Makimoto, A. Chemical constituents of polygonaceous plants. I. Studies on the components of Ko-jo-kon (Polygonum cuspidatum Sieb. et Zucc.). Yakugaku Zasshi, 1963, 83, 988-990.
11. Langcake, P.; Pryce, R. J. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol. Plant Pathol., 1976, 9, 77-86.
12. Renaud, S.; de Lorgeril, M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet, 1992, 339, 1523-1526
13. Siemann, E.H.; Creasy, L.L. Concentration of the phytoalexin resveratrol in wine. Am. J. Eno. Vitic., 1992, 43, 49-52.
14. Jang, M.; Cai, L.; Udeani, G.O.; Slowing, K.V.; Thomas, C.F.; Beecher, C.W.; Fong, H.H.; Farnsworth, N.R.; Kinghorn, A.D.; Mehta, R.G.; Moon, R.C.; Pezzuto, J.M. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science, 1997, 275, 218-220. (Pubitemid 127696281)
15. Burkitt, M.J.; Duncan, J. Effects of trans-resveratrol on copper-dependent hydroxyl-radical formation and DNA damage: evidence for hydroxyl-radical scavenging and a novel, glutathione-sparing mechanism of action. Arch. Biochem. Biophys., 2000, 381, 253-263. (Pubitemid 32260312)
16. Sinha, K.; Chaudhary, G.; Gupta, Y.K. Protective effect of resveratrol against oxidative stress in middle cerebral artery occlusion model of stroke in rats. Life Sci., 2002, 71, 655-665. (Pubitemid 34628827)
17. Howitz, K.T.; Bitterman, K.J.; Cohen, H.Y.; Lamming, D.W.; Lavu, S.; Wood, J.G.; Zipkin, R. E.; Chung, P.; Kisielewski, A.; Zhang, L.L.; Scherer, B.; Sinclair, D.A. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature, 2003, 425, 191-196.
18. Leonard, S.S.; Xia, C.; Jiang, B.H.; Stinefelt, B.; Klandorf, H.; Harris, G.K.; Shi, X. Resveratrol scavenges reactive oxygen species and effects radical-induced cellular responses. Biochem. Biophys. Res. Commun., 2003, 309, 1017-1026. (Pubitemid 37122632)
19. Bradamante, S.; Barenghi, L.; Villa, A. Cardiovascular protective effects of resveratrol. Cardiovasc. Drug Rev., 2004, 22, 169-188.
20. Valenzano, D.R.; Terzibasi, E.; Genade, T.; Cattaneo, A.; Domenici, L.; Cellerino, A. Resveratrol prolongs lifespan and retards the onset of age-related markers in a short-lived vertebrate. Curr. Biol., 2006, 16, 296-300. (Pubitemid 43190229)
21. Fremont, L. Biological effects of resveratrol. Life Sci., 2000, 66, 663-673.
22. Bhat, K.P. L.; Kosmeder, J. W., 2nd; Pezzuto, J. M. Biological effects of resveratrol. Antioxid. Redox Signal., 2001, 3, 1041-1064.
23. Baur, J. A.; Sinclair, D. A. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov., 2006, 5, 493-506. (Pubitemid 44136961)
24. Mikulski, D.; Molski, M. Quantitative structure-Antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: Trans-piceid, cispiceid, trans-Astringin and trans-resveratrol-4-O-D-glucopyranoside. Eur. J. Med. Chem., 2010, 45, 2366-2380.
25. Stivala, L.A.; Savio, M.; Carafoli, F.; Perucca, P.; Bianchi, L.; Maga, G.; Forti, L.; Pagnoni, U. M.; Albini, A.; Prosperi, E.; Vannini, V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem., 2001, 276, 22586-22594.
26. Lee, S.K.; Mbwambo, Z.H.; Chung, H.; Luyengi, L.; Gamez, E. J.; Mehta, R. G.; Kinghorn, A.D.; Pezzuto, J.M. Evaluation of the antioxidant potential of natural products. Comb. Chem. High. Throughput Screen., 1998, 1, 35-46. (Pubitemid 128541767)
27. Wang, M.; 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. (Pubitemid 29506186)
28. Fauconneau, B.; Waffo-Teguo, P.; Huguet, F.; Barrier, L.; Decendit, A.; Merillon, J.M. Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests. Life Sci., 1997, 61, 2103-2110. (Pubitemid 27478837)
29. Ito, T.; Tanaka, T.; Iinuma, M.; Iliya, I.; Nakaya, K.-i.; Ali, Z.; Takahashi, Y.; Sawa, R.; Shirataki, Y.; Murata, J.; Darnaedi, D. New resveratrol oligomers in the stem bark of Vatica pauciflora. Tetrahedron, 2003, 59, 5347-5363. (Pubitemid 36929760)
30. Chong, J.; Poutaraud, A.; Hugueney, P. Metabolism and roles of stilbenes in plants. Plant Sci., 2009, 177, 143-155.
31. Hall, D.; De Luca, V. Mesocarp localization of a bi-functional resveratrol/hydroxycinnamic acid glucosyltransferase of Concord grape (Vitis labrusca). Plant J., 2007, 49, 579-591. (Pubitemid 46233078)
32. Schmidlin, L.; Poutaraud, A.; Claudel, P.; Mestre, P.; Prado, E.; Santos-Rosa, M.; Wiedemann-Merdinoglu, S.; Karst, F.; Merdinoglu, D.; Hugueney, P. A stress-inducible resveratrol O-methyltransferase involved in the biosynthesis of pterostilbene in grapevine. Plant Physiol., 2008, 148, 1630-1639. (Pubitemid 352847496)
33. Jeandet, P.; Douillet-Breuil, A.C.; Bessis, R.; Debord, S.; Sbaghi, M.; Adrian, M. Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J. Agric. Food Chem., 2002, 50, 2731-2741. (Pubitemid 34493577)
34. Yu, C.K.; Lam, C.N.; Springob, K.; Schmidt, J.; Chu, I.K.; Lo, C. Constitutive accumulation of cis-piceid in transgenic Arabidopsis overexpressing a sorghum stilbene synthase gene. Plant Cell. Physiol., 2006, 47, 1017-1021. (Pubitemid 44286339)
35. Sobolev, V.S.; Potter, T.L.; Horn, B.W. Prenylated stilbenes from peanut root mucilage. Phytochem. Anal., 2006, 17, 312-322. (Pubitemid 44404614)
36. Cichewicz, R.H.; Kouzi, S.A. Resveratrol oligomers: Structure, chemistry, and biological activity. In Stud. Nat. Prod. Chem., Atta-ur-Rahman, Ed. Elsevier B.V.: Amsterdam, 2002; Vol. 26, pp 507-579.
37. Lin, M.; Yao, C.S. Natural oligostilbenes. In Stud. Nat. Prod. Chem., Atta-ur-Rahman, Ed.; Elsevier B.V.; Amsterdam, 2006; Vol. 33, pp 601-644
38. Xiao, K.; Zhang, H.J.; Xuan, L.J.; Zhang, J.; Xu, Y.M.; Bai, D.L. Stilbenoids: Chemistry and bioactivities. In Stud. Nat. Prod. Chem., Atta ur, R., Ed. Elsevier: 2008; Vol. Volume 34, pp 453-646.
39. Shen, T.; Wang, X.N.; Lou, H.X. Natural stilbenes: an overview. Nat. Prod. Rep., 2009, 26, 916-935.
40. Tanaka, T.; Ito, T.; Nakaya, K.-i.; Iinuma, M.; Takahashi, Y.; Naganawa, H.; Matsuura, N.; Ubukata, M. Vaticanol D, a novel resveratrol hexamer isolated from Vatica rassak. Tetrahedron Lett., 2000, 41, 7929-7932.
41. Ito, T.; Tanaka, T.; Nakaya, K.-i.; Iinuma, M.; Takahashi, Y.; Naganawa, H.; Ohyama, M.; Nakanishi, Y.; Bastow, K.F.; Lee, K.-H. A novel bridged stilbenoid trimer and four highly condensed stilbenoid oligomers in Vatica rassak. Tetrahedron, 2001, 57, 7309-7321. (Pubitemid 32770047)
42. Ito, T.; Tanaka, T.; Nakaya, K.-i.; Iinuma, M.; Takahashi, Y.; Naganawa, H.; Ohyama, M.; Nakanishi, Y.; Bastow, K.F.; Lee, K.-H. A new resveratrol octamer, vateriaphenol A, in Vateria indica. Tetrahedron Lett., 2001, 42, 5909-5912. (Pubitemid 32781642)
43. He, S.; Jiang, L.; Wu, B.; Li, C.; Pan, Y. Chunganenol: an unusual antioxidative resveratrol hexamer from Vitis chunganensis. J. Org. Chem., 2009, 74, 7966-7969.
44. Langcake, P.; Pryce, R.J. Oxidative dimerisation of 4-hydroxystilbenes in vitro: production of a grapevine phytoalexin mimic. J. Chem. Soc. Chem. Commun., 1977, 208-210.
45. Takaya, Y.; Terashima, K.; Ito, J.; He, Y.H.; Tateoka, M.; Yamaguchi, N.; Niwa, M. Biomimic transformation of resveratrol. Tetrahedron, 2005, 61, 10285-10290. (Pubitemid 41345728)
46. Ferré-Filmon, K.; Delaude, L.; Demonceau, A.; Noels, A.F. Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins. Coord. Chem. Rev., 2004, 248, 2323-2336.
47. Nicolaou, K.; Kang, Q.; Wu, T.R.; Lim, C.S.; Chen, D.Y.K. Total Synthesis and Biological Evaluation of the Resveratrol-Derived Polyphenol Natural Products Hopeanol and Hopeahainol A. J. Am. Chem. Soc., 2010, 132, 7540-7548.
48. Snyder, S. A.; Gollner, A.; Chiriac, M.I. Regioselective reactions for programmable resveratrol oligomer synthesis. Nature, 2011, 474, 461-466.
49. Choi, Y.L.; Kim, B.T.; Heo, J.-N. Total Synthesis of Laetevirenol A. J. Org. Chem., 2012, 77, 8762-8767.
50. Kolak, U.; Öztürk, M.; Özgökçe, F.; Ulubelen, A. Norditerpene alkaloids from Delphinium linearilobum and antioxidant activity. Phytochemistry, 2006, 67, 2170-2175. (Pubitemid 44344754)
51. Luo, X.D.; Basile, M.J.; Kennelly, E.J. Polyphenolic antioxidants from the fruits of Chrysophyllum cainito L.(star apple). J. Agric. Food. Chem., 2002, 50, 1379-1382. (Pubitemid 34233195)
52. Schlesier, K.; Harwat, M.; Böhm, V.; Bitsch, R. Assessment of antioxidant activity by using different in vitro methods. Free Radical Res., 2002, 36, 177-187.
53. He, S.; Wu, B.; Pan, Y.; Jiang, L. Stilbene oligomers from Parthenocissus laetevirens: isolation, biomimetic synthesis, absolute configuration, and implication of antioxidative defense system in the plant. J. Org. Chem., 2008, 73, 5233-5241.
54. He, S.; Jiang, L.; Wu, B.; Li, C.; Pan, Y. Chunganenol: an unusual antioxidative resveratrol hexamer from Vitis chunganensis. J. Org. Chem., 2009, 74, 7966-7969.
55. The average IC50 values of different DPs are 100-M (monomer), 102-M (dimer), 166-M (trimer), and 126-M (tetramer). Since these data are from different investigations, the result is not conclusive.
56. Zidorn, C.; Grass, S.; Ellmerer, E.P.; Ongania, K.H.; Stuppner, H. Stilbenoids from Tragopogon orientalis. Phytochemistry, 2006, 67, 2182-2188. (Pubitemid 44363092)
57. Kim, H.J.; Saleem, M.; Seo, S.H.; Jin, C.; Lee, Y.S. Two new antioxidant stilbene dimers, parthenostilbenins A and B from Parthenocissus tricuspidata. Planta Med., 2005, 71, 973-976. (Pubitemid 41658580)
58. He, S.; Lu, Y.; Jiang, L.; Wu, B.; Zhang, F.; Pan, Y. Preparative isolation and purification of antioxidative stilbene oligomers from Vitis chunganensis using high-speed counter-current chromatography in stepwise elution mode. J. Sep. Sci., 2009, 32, 2339-2345.
59. Jiang, L.; He, S.; Sun, C.; Pan, Y. Selective 1O2 quenchers, oligostilbenes, from Vitis wilsonae: Structural identification and biogenetic relationship. Phytochemistry, 2012, 77, 294-303.
60. Pastor, N.; Weinstein, H.; Jamison, E.; Brenowitz, M. A detailed interpretation of OH radical footprints in a TBP-DNA complex reveals the role of dynamics in the mechanism of sequence-specific binding. J. Mol. Biol., 2000, 304, 55-68.
61. Jiang, L.Y.; He, S.; Jiang, K.Z.; Sun, C.R.; Pan, Y.J. Resveratrol and Its Oligomers from Wine Grapes Are Selective 1O2 Quenchers: Mechanistic Implication by High-Performance Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry and Theoretical Calculation. J. Agric. Food. Chem., 2010, 58, 9020-9027.
62. Valko, M.; Morris, H.; Cronin, M. Metals, toxicity and oxidative stress. Curr. Med. Chem., 2005, 12, 1161-1208.
63. Kovacic, P.; Pozos, R.S.; Somanathan, R.; Shangari, N.; O'Brien, P.J. Mechanism of mitochondrial uncouplers, inhibitors, and toxins: focus on electron transfer, free radicals, and structure-Activity relationships. Curr. Med. Chem., 2005, 12, 2601-2623. (Pubitemid 41460268)
64. Valko, M.; Izakovic, M.; Mazur, M.; Rhodes, C.J.; Telser, J. Role of oxygen radicals in DNA damage and cancer incidence. Mol. Cell. Biochem., 2004, 266, 37-56. (Pubitemid 39562306)
65. Privat, C.; Telo, J.P.; Bernardes-Genisson, V.; Vieira, A.; Souchard, J.P.; Nepveu, F. Antioxidant properties of trans-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media. J. Agric. Food. Chem., 2002, 50, 1213-1217. (Pubitemid 34194082)
66. Iliya, I.; Ali, Z.; Tanaka, T.; Iinuma, M.; Furusawa, M.; Nakaya, K.; Murata, J.; Darnaedi, D.; Matsuura, N.; Ubukata, M. Stilbene derivatives from Gnetum gnemon Linn. Phytochemistry, 2003, 62, 601-606. (Pubitemid 36216080)
67. Aikens, J.; Dix, T. Perhydroxyl radical (HOO.) initiated lipid peroxidation. The role of fatty acid hydroperoxides. J. Biol. Chem., 1991, 266, 15091-15098. (Pubitemid 21907623)
68. Aikens, J.; Dix, T. Hydrodioxyl (perhydroxyl), peroxyl, and hydroxyl radical-initiated lipid peroxidation of large unilamellar vesicles (liposomes): comparative and mechanistic studies. Arch. Biochem. Biophys., 1993, 305, 516-525. (Pubitemid 23282940)
69. Dix, T.A.; Aikens, J. Mechanisms and biological relevance of lipid peroxidation initiation. Chem. Res. Toxicol., 1993, 6, 2-18. (Pubitemid 23040365)
70. He, S.; Lu, Y.; Wu, B.; Pan, Y. Isolation and purification of antioxidative isomeric polyphenols from the roots of Parthenocissus laetevirens by counter-current chromatography. J. Chromatogr. A, 2007, 1151, 175-179. (Pubitemid 46679010)
71. Redmond, R.W.; Gamlin, J.N. A compilation of singlet oxygen yields from biologically relevant molecules. Photochem. Photobiol., 1999, 70, 391-475. (Pubitemid 129555813)
72. Wright, A.; Bubb, W.A.; Hawkins, C.L.; Davies, M.J. Singlet Oxygen-mediated Protein Oxidation: Evidence for the Formation of Reactive Side Chain Peroxides on Tyrosine Residues. Photochem. Photobiol., 2002, 76, 35-46.
73. Wilkinson, F.; Helman, W.P.; Ross, A.B. Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data, 1995, 24, 663-1021.
74. Gracanin, M.; Hawkins, C.L.; Pattison, D.I.; Davies, M.J. Singlet-oxygenmediated amino acid and protein oxidation: Formation of tryptophan peroxides and decomposition products. Free Radic. Biol. Med., 2009, 47, 92-102.
75. Davies, M.J. Singlet oxygen-mediated damage to proteins and its consequences. Biochem. Biophys. Res. Commun., 2003, 305, 761-770. (Pubitemid 36579294)
76. Tyrrell, R.M. Role for singlet oxygen in biological effects of ultraviolet a radiation. Methods Enzymol., 2000, 319, 290-296. (Pubitemid 30448051)
77. Davies, M.J.; Truscott, R.J. W. Photo-oxidation of proteins and its role in cataractogenesis. J. Photochem. Photobiol. B: Biol., 2001, 63, 114-125. (Pubitemid 33040729)
78. He, S.; Jiang, L.; Wu, B.; Pan, Y.; Sun, C. Pallidol, a resveratrol dimer from red wine, is a selective singlet oxygen quencher. Biochem. Biophys. Res. Commun., 2009, 379, 283-287.
79. He, S.; Jiang, L.; Wu, B.; Zhou, J.; Pan, Y.J. Two novel antioxidative stilbene tetramers from Parthenocissus laetevirens. Helv. Chim. Acta, 2009, 92, 1260-1267.
80. Jung, M.Y.; Choi, D.S. Electron Spin Resonance and Luminescence Spectroscopic Observation and Kinetic Study of Chemical and Physical Singlet Oxygen Quenching by Resveratrol in Methanol. J. Agric. Food. Chem., 2010, 58, 11888-11895.
81. Hung, L.M.; Chen, J.K.; Lee, R.S.; Liang, H.C.; Su, M.J. Beneficial effects of astringinin, a resveratrol analogue, on the ischemia and reperfusion damage in rat heart. Free Radic. Biol. Med., 2001, 30, 877-883.
82. Andrabi, S.A.; Spina, M.G.; Lorenz, P.; Ebmeyer, U.; Wolf, G.; Horn, T.F.W. Oxyresveratrol (trans-2, 3-, 4, 5-Tetrahydroxystilbene) is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. Brain Res., 2004, 1017, 98-107. (Pubitemid 38917149)
83. Li, H.L.; Wang, A.B.; Huang, Y.; Liu, D.P.; Wei, C.; Williams, G.M.; Zhang, C.N.; Liu, G.; Liu, Y.Q.; Hao, D.L.; Hui, R.T.; Lin, M.; Liang, C.C. Isorhapontigenin, a new resveratrol analog, attenuates cardiac hypertrophy via blocking signaling transduction pathways. Free Radic. Biol. Med., 2005, 38, 243-257. (Pubitemid 39656135)
84. He, S.; Yang, J.; Wu, B.; Pan, Y.; Wan, H.; Wang, Y.; Du, Y.; Wang, S. Neuroprotective effect of parthenocissin A, a natural antioxidant and free radical scavenger, in focal cerebral ischemia of rats. Phytother. Res., 2010, 24, S63-S70.
85. Stojanovi, S.; Sprinz, H.; Brede, O. Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Arch. Biochem. Biophys., 2001, 391, 79-89. (Pubitemid 32612575)
86. Caruso, F.; Tanski, J.; Villegas-Estrada, A.; Rossi, M. Structural basis for antioxidant activity of trans-resveratrol: ab initio calculations and crystal and molecular structure. J. Agric. Food. Chem., 2004, 52, 7279-7285.
87. Foti, M.; Ruberto, G. Kinetic Solvent Effects on Phenolic Antioxidants Determined by Spectrophotometric Measurements. J. Agric. Food. Chem., 2000, 49, 342-348. (Pubitemid 32104532)
88. Wright, J.S.; Johnson, E.R.; DiLabio, G.A. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants. J. Am. Chem. Soc., 2001, 123, 1173-1183. (Pubitemid 32148182)
89. Fang, J.G.; Lu, M.; Chen, Z.H.; Zhu, H.H.; Li, Y.; Yang, L.; Wu, L.M.; Liu, Z.L. Antioxidant Effects of Resveratrol and its Analogues against the Free-Radical-Induced Peroxidation of Linoleic Acid in Micelles. Chem. Eur. J., 2002, 8, 4191-4198.
90. Cai, Y.J.; Fang, J.G.; Ma, L.P.; Yang, L.; Liu, Z.L. Inhibition of free radicalinduced peroxidation of rat liver microsomes by resveratrol and its analogues. Biochim. Biophys. Acta, 2003, 1637, 31-38. (Pubitemid 36071593)
91. 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., 2005, 69, 903-912. (Pubitemid 40312708)