3,4,4′-Trihydroxy-trans-stilbene, an analogue of resveratrol, is a potent antioxidant and cytotoxic agent

Free Radical Research

Volumn 45, Issue 11-12, 2011, Pages 1379-1387

  Cai, Wenqing ^a,b   Zhang, Liangwei ^a   Song, Yanlin ^a   Zhang, Baoxin ^a   Cui, Xuemei ^a   Hu, Guanming ^a   Fang, Jianguo ^a  

^a LANZHOU UNIVERSITY   (China)

^b BURNHAM INSTITUTE   (United States)

Author keywords

Antioxidant; DNA oxidation; Free radicals; Lipid peroxidation; Resveratrol

Indexed keywords

3,4,4 TRIHYDROXY TRANS STILBENE; ANTIOXIDANT; CYTOTOXIC AGENT; FREE RADICAL; RESVERATROL; RIBONUCLEOTIDE REDUCTASE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HL 60; CYTOTOXICITY; DRUG ACTIVITY; DRUG DEVELOPMENT; ERYTHROCYTE; GROWTH INHIBITION; HEMOLYSIS; HUMAN; LEUKEMIA CELL; LIPID PEROXIDATION;

ANISOLES; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CELL PROLIFERATION; DNA DAMAGE; FREE RADICALS; HEMOLYSIS; HL-60 CELLS; HUMANS; KINETICS; LINOLEIC ACID; LIPID PEROXIDATION; MOLECULAR STRUCTURE; OXIDATIVE STRESS; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80555127458     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2011.629199     Document Type: Article

References (51)

1. Halliwell B, Gutteridge J. Free Radicals in Biology and Medicine. 4th ed. USA: Oxford University Press; 2007.
2. Coyle JT, Puttfarcken P. Oxidative stress, glutamate, and neurodegenerative disorders. Science 1993;262(5134):689-695. (Pubitemid 23350687)
3. Lin MT, Beal MF. Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases. Nature 2006;443(7113): 787-795. (Pubitemid 44622683)
4. Rice ME. Ascorbate regulation and its neuroprotective role in the brain. Trends Neurosci 2000;23(5):209-216. (Pubitemid 30236180)
5. Martin HD, Kock S, Scherrers R, Lutter K, Wagener T, Hundsdorfer C, et al. 3,3-Dihydroxyisorenieratene, a natural carotenoid with superior antioxidant and photoprotective properties. Angew Chem Int Ed Engl 2009;48(2):400-403.
6. Balsano C, Alisi A. Antioxidant effects of natural bioactive compounds. Curr Pharm Des 2009;15(26):3063-3073.
7. Aggarwal BB, Shishodia S. Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol 2006;71(10):1397-1421.
8. Konishi T. "From herb to kitchen and bedside: food factors are pharmacological molecules with antioxidant activity". Free Radic Res 2011;45(8):863.
9. Nam TG, Rector CL, Kim HY, Sonnen AF, Meyer R, Nau WM, et al. Tetrahydro-1,8-naphthyridinol analogues of alpha-tocopherol as antioxidants in lipid membranes and low-density lipoproteins. J Am Chem Soc 2007;129(33): 10211-10219. (Pubitemid 47312964)
10. Muller A, Cadenas E, Graf P, Sies H. A novel biologically active seleno-organic compound-I. Glutathione peroxidaselike activity in vitro and antioxidant capacity of PZ 51 (Ebselen). Biochem Pharmacol 1984;33(20):3235- 3239. (Pubitemid 14023257)
11. Ghosh N, Ghosh R, Mandal SC. Antioxidant protection: A promising therapeutic intervention in neurodegenerative disease. Free Radic Res 2011;45(8):888-905.
12. Velioglu-Ogunc A, Sehirli O, Toklu HZ, Ozyurt H, Mayadagli A, Eksioglu-Demiralp E, et al. Resveratrol protects against irradiation-induced hepatic and ileal damage via its antioxidative activity. Free Radic Res 2009;43(11):1060-1071.
13. Somoza V. MAGIC-OL Resveratrol. Mol Nutr Food Res 2005;49(5):373. (Pubitemid 40780386)
14. Milne JC, Lambert PD, Schenk S, Carney DP, Smith JJ, Gagne DJ, et al. Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes. Nature 2007; 450(7170):712-716. (Pubitemid 350207685)
15. Baur JA, Pearson KJ, Price NL, Jamieson HA, Lerin C, Kalra A, et al. Resveratrol improves health and survival of mice on a high-calorie diet. Nature 2006;444(7117):337-342. (Pubitemid 44764104)
16. C onstant J. Alcohol, ischemic heart disease, and the French paradox. Coron Artery Dis 1997;8(10):645-649. (Pubitemid 28029590)
17. Kopp P. Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the ' French paradox ' ? Eur J Endocrinol 1998;138(6):619-620. (Pubitemid 28313808)
18. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997;275(5297): 218-220. (Pubitemid 127696281)
19. Pervaiz S, Holme AL. Resveratrol: its biologic targets and functional activity. Antioxid Redox Signal 2009;11(11): 2851-2897.
20. Danz ED, Skramsted J, Henry N, Bennett JA, Keller RS. Resveratrol prevents doxorubicin cardiotoxicity through mitochondrial stabilization and the Sirt1 pathway. Free Radic Biol Med 2009;46(12):1589-1597.
21. Fang JG, Lu M, Chen ZH, Zhu HH, Li Y, Yang L, et al. Antioxidant effects of resveratrol and its analogues against the free-radical-induced peroxidation of linoleic acid in micelles. Chemistry 2002;8(18):4191-4198.
22. Holthoff JH, Woodling KA, Doerge DR, Burns ST, Hinson JA, Mayeux PR. Resveratrol, a dietary polyphenolic phytoalexin, is a functional scavenger of peroxynitrite. Biochem Pharmacol 2010;80(8):1260-1265.
23. Kang SS, Cuendet M, Endringer DC, Croy VL, Pezzuto JM, Lipton MA. Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappaB. Bioorg Med Chem 2009;17(3): 1044-1054.
24. Fang JG, Zhou B. Structure-activity relationship and mechanism of the tocopherol-regenerating activity of resveratrol and its analogues. J Agric Food Chem 2008;56(23): 11458-11463.
25. Heynekamp JJ, Weber WM, Hunsaker LA, Gonzales AM, Orlando RA, Deck LM, et al. Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor kappaB. J Med Chem 2006;49(24):7182-7189. (Pubitemid 44886003)
26. Cai YJ, Wei QY, Fang JG, Yang L, Liu ZL, Wyche JH, et al. The 3,4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities. Anticancer Res 2004;24(2B):999-1002. (Pubitemid 38625050)
27. Shang YJ, Qian Y, Liu XD, Dai F, Shang XL, Jia WQ, et al. Radical-scavenging activity and mechanism of resveratroloriented analogues: infl uence of the solvent, radical, and substitution. J Org Chem 2009;74(14):5025-5031.
28. Roberti M, Pizzirani D, Simoni D, Rondanin R, Baruchello R, Bonora C, et al. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J Med Chem 2003;46(16):3546-3554. (Pubitemid 36909831)
29. Mazue F, Colin D, Gobbo J, Wegner M, Rescifi na A, Spatafora C, et al. Structural determinants of resveratrol for cell proliferation inhibition potency: experimental and docking studies of new analogs. Eur J Med Chem 2010;45(7):2972-2980.
30. de Lima DP, Rotta R, Beatriz A, Marques MR, Montenegro RC, Vasconcellos MC, et al. Synthesis and biological evaluation of cytotoxic properties of stilbene-based resveratrol analogs. Eur J Med Chem 2009;44(2):701-707.
31. Yamamoto Y, Niki E, Kamiya Y, Miki M, Tamai H, Mino M. Free radical chain oxidation and hemolysis of erythrocytes by molecular oxygen and their inhibition by vitamin E. J Nutr Sci Vitaminol (Tokyo) 1986;32(5):475-479. (Pubitemid 17222401)
32. Fang JG, Lu M, Ma LP, Yang L, Wu LM, Liu ZL. Protective effects of resveratrol and its analogues against free radicalinduced oxidative hemolysis of red blood cells. Chinese Journal of Chemistry 2002;20(11):1313-1318.
33. Epe B, Pfl aum M, Boiteux S. DNA damage induced by photosensitizers in cellular and cell-free systems. Mutat Res 1993;299(3-4):135-145. (Pubitemid 23115153)
34. Kumar SS, Ghosh A, Devasagayam TP, Chauhan PS. Effect of vanillin on methylene blue plus light-induced single-strand breaks in plasmid pBR322 DNA. Mutat Res 2000;469(2):207-214. (Pubitemid 30662445)
35. Porter NA, Caldwell SE, Mills KA. Mechanisms of free radical oxidation of unsaturated lipids. Lipids 1995;30(4):277-290.
36. Goupy P, Vulcain E, Caris-Veyrat C, Dangles O. Dietary antioxidants as inhibitors of the heme-induced peroxidation of linoleic acid: mechanism of action and synergism. Free Radic Biol Med 2007;43(6):933-946. (Pubitemid 47241207)
37. Chao CC, Ma YS, Stadtman ER. Modifi cation of protein surface hydrophobicity and methionine oxidation by oxidative systems. Proc Natl Acad Sci USA 1997;94(7):2969-2974. (Pubitemid 27157248)
38. Rubbo H, Radi R, Anselmi D, Kirk M, Barnes S, Butler J, et al. Nitric oxide reaction with lipid peroxyl radicals spares alpha-tocopherol during lipid peroxidation. Greater oxidant protection from the pair nitric oxide/alpha-tocopherol than alpha-tocopherol/ascorbate. J Biol Chem 2000;275(15): 10812-10818. (Pubitemid 30212711)
39. Yang Y, Song ZG, Liu ZQ. Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals. Free Radic Res 2011;45(4):445-453.
40. Piette J. Biological consequences associated with DNA oxidation mediated by singlet oxygen. J Photochem Photobiol B 1991;11(3-4):241-260.
41. Iglesias J, Pazos M, Andersen ML, Skibsted LH, Medina I. Caffeic acid as antioxidant in fi sh muscle: mechanism of synergism with endogenous ascorbic acid and alpha-tocopherol. J Agric Food Chem 2009;57(2):675-681.
42. Niki E. Interaction of ascorbate and alpha-tocopherol. Ann N Y Acad Sci 1987;498:186-199.
43. Frombaum M, Therond P, Djelidi R, Beaudeux JL, Bonnefont-Rousselot D, Borderie D. Piceatannol is more effective than resveratrol in restoring endothelial cell dimethylarginine dimethylaminohydrolase expression and activity after high-glucose oxidative stress. Free Radic Res 2011;45 (3):293-302.
44. Hung LM, Chen JK, Lee RS, Liang HC, Su MJ. Benefi cial effects of astringinin, a resveratrol analogue, on the ischemia and reperfusion damage in rat heart. Free Radic Biol Med 2001;30(8):877-883.
45. Di Mascio P, Kaiser S, Sies H. Lycopene as the most effi cient biological carotenoid singlet oxygen quencher. Arch Biochem Biophys 1989;274(2):532-538. (Pubitemid 19261144)
46. Foote CS, Denny RW. Chemistry of singlet oxygen. VII. Quenching by beta-carotene. J Am Chem Soc 1968; 90(22):6233-6235.
47. Celaje JA, Zhang D, Guerrero AM, Selke M. Chemistry of trans-Resveratrol with Singlet Oxygen: [2+2] Addition, [4+2] Addition, and Formation of the Phytoalexin Moracin M. Org Lett 2011;13(18):4846-4849.
48. Fontecave M, Lepoivre M, Elleingand E, Gerez C, Guittet O. Resveratrol, a remarkable inhibitor of ribonucleotide reductase. FEBS Lett 1998;421(3):277-279. (Pubitemid 28045770)
49. Holmgren A, Sengupta R. The use of thiols by ribonucleotide reductase. Free Radic Biol Med 2010;49(11):1617-1628.
50. F ritzer-Szekeres M, Savinc I, Horvath Z, Saiko P, Pemberger M, Graser G, et al. Biochemical effects of piceatannol in human HL-60 promyelocytic leukemia cells-synergism with Ara-C. Int J Oncol 2008;33(4):887-892.
51. Saiko P, Pemberger M, Horvath Z, Savinc I, Grusch M, Handler N, et al. Novel resveratrol analogs induce apoptosis and cause cell cycle arrest in HT29 human colon cancer cells: inhibition of ribonucleotide reductase activity. Oncol Rep 2008;19(6):1621-1626.