Comparative studies of the antioxidant effects of a naturally occurring resveratrol analogue - Trans-3,3′,5,5′-tetrahydroxy-4′- methoxystilbene and resveratrol - Against oxidation and nitration of biomolecules in blood platelets

Cell Biology and Toxicology

Volumn 24, Issue 4, 2008, Pages 331-340

  Olas, Beata ^a   Wachowicz, Barbara ^a   Nowak, Pawel ^a   Stochmal, Anna ^b   Oleszek, Wieslaw ^b   Glowacki, Rafal ^a   Bald, Edward ^a  

^a UNIVERSITY OF LODZ   (Poland)

^b STATE RESEARCH INSTITUTE   (Poland)

Author keywords

3 ; 5 tetrahydroxy 4 methoxystilbene; Blood platelets; Oxidative stress; Peroxynitrite; Resveratrol; trans 3; Yucca schidigera

Indexed keywords

3,3',5,5' TETRAHYDROXY 4' METHOXYSTILBENE; 5,5' DITHIOBIS(2 NITROBENZOIC ACID); GLUTATHIONE; PEROXYNITRITE; PLANT EXTRACT; RESVERATROL; THIOBARBITURIC ACID REACTIVE SUBSTANCE;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; ENZYME LINKED IMMUNOSORBENT ASSAY; GRAPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIPID PEROXIDATION; NITRATION; NITRATIVE STRESS; OXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN CARBONYLATION; THROMBOCYTE; WINE; YUCCA;

ADULT; ANTIOXIDANTS; BLOOD PLATELETS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME-LINKED IMMUNOSORBENT ASSAY; GLUTATHIONE; HUMANS; LIPID PEROXIDATION; MALE; OXIDATION-REDUCTION; OXIDATIVE STRESS; PEROXYNITROUS ACID; PLANT BARK; PROTEIN CARBONYLATION; STILBENES; SULFHYDRYL COMPOUNDS; YUCCA;

VITACEAE; YUCCA SCHIDIGERA;

EID: 45849102090     PISSN: 07422091     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10565-007-9045-7     Document Type: Article

References (75)

1. Ando Y, Steiner M. Sulfhydryl and disulfide groups of platelet membranes: determination of disulfide groups. Biochim Biophys Acta. 1973a;311:26-37.
2. Ando Y, Steiner M. Sulfhydryl and disulfide groups of platelet membranes: determination of sulfhydryl groups. Biochim Biophys Acta. 1973b;311:38-44.
3. Arteel GE, Briviba K, Sies H. Protection against peroxynitrite. FEBS Lett. 1999;445:226-30.
4. Arts MJTJ, Haenen GRMM, Wilms LC, Beetstra SAJN, Heijnen CGM, Voss HP et al. Interactions between flavonoids and proteins: effect on the total antioxidant capacity. J Agric Food Chem. 2002;50:1184-7.
5. Bald E, Chwatko G, Glowacki R, Kusmierek K. Analysis of plasma thiols by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 2004;1032:109-15.
6. Balestrieri C, Felice F, Piacente S, Pizza C, Montoro P, Oleszek W et al. Relative effects of phenolics constituents from Yucca schidigera Roezl. Bark on kaposi's sarcoma cell proliferation, migration, and PAF synthesis. Biochem Pharmacol. 2006;71:1479-87.
7. Bartosz G. Peroxynitrite: mediator of the toxic action of nitric oxide. Acta Biochim Pol. 1996;43:645-59.
8. Bouaziz A, Romera-Castillo C, Salido S, Linares-Palomino PJ, Alterejos J, Bartegi A et al. Cinnamtannin B-1 from bay wood exhibits antiapoptotic effects in human platelets. Apoptosis. 2007;12:489-98.
9. Brito O, Almeida LM, Dinis TCP. The interaction of resveratrol with ferrylmyoglobin and peroxynitrite; protection against LDL oxidation. Free Radic Res. 2002;36:621-31.
10. Buss H, Chan TP, Sluis KB, Domigan NM, Winterbourn CC. Protein carbonyl measurement by a sensitive ELISA method. Free Radic Biol Med. 1997;23:361-6.
11. Calderón AA, Zapata JM, Munoz R, Pedreno MA, Ros Barceló A. Resveratrol production as a part of the hypersensitive-like response of grapevine cells to an elicitor from Trichoderma viride. New Phytol. 1993;124:455-63.
12. Chen T, Li J, Cao J, Xu Q, Komatsu K, Namba T. A new flavanone isolated from rhizoma smilacis glabrae and the structural requirements of its derivatives for preventing immunological hepatocyte damage. Planta Med. 1999;65:56-9.
13. Crane MS, Ollosson R, Moore KP, Rossi AG, Megson IL. Novel role for low molecular weight plasma thiols in nitric oxide-mediated control of platelet function. J Biol Chem. 2002;277:46858-63.
14. Daniel O, Meier MS, Schlatter J, Schlahter J, Frischhnecht P. Selected phenolic compounds in cultivated plants: ecologic functions, health implications, and modulation by pesticides. Environ Health Perspect. 1999;17:109-14.
15. Dong Z. Molecular mechanism of the chemopreventive effect of resveratrol. Mutat Res. 2003;523-524:145-50.
16. Ducrocq C, Blanchard B, Pignatelli B, Oshima H. Peroxynitrite: an endogenous oxidizing and nitrating agent. Cell Mol Life Sci. 1999;55:1068-77.
17. Fernandez MI, Pedro JR, Seoane E. Two polyhydroxystilbenes from stems of Phoenix dactylifera. Phytochemistry. 1983;22:2819-21.
18. Fiala ES, Sodum RS, Bhattacharaya M, Li H. (-)-Epigallocatechin gallate, a polyphenolic tea antioxidant, inhibits peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Experientia. 1996;52:922-6.
19. Fremont L, Belguendouz L, Delpal S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci. 1999;64:2511-21.
20. Giustarini D, Campocia G, Fanett G, Rossi R, Giannerini F, Lusini L, Di Simplicio P. Minor thiols cysteine and cysteinylglycine regulate the competition between glutathione and protein SH groups in human platelets subjected to oxidative stress. Arch Biochem Biophys. 2000;380:1-10.
21. Glowacki R, Wójcik K, Bald E. Facile and sensitive method for the determination of mesna in plasma by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 2001;914:29-35.
22. Hakimudin F, Paliyath G, Meckling K. Selective cytotoxicity of a red grape wine flavonoid fraction against MCF-7 cells. Breast Cancer Res Treat. 2004;85:65-79.
23. Hata K, Baba K, Kozawa M. Chemical studies on the heartwood of Cassia garrettina Craib II. Nonanthraquinonic constituents. Chem Pharm Bull. 1979;27:984-9.
24. Ischiropoulos H, Al-Mehdi AB. Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 1995;364:279-82.
25. Jayatilake GS, Jayasuriya H, Lee ES, Koonchanok NM, Geahlen RL, Ashendel CL et al. Kinase inhibitors from Polygonum cuspidatum. J Nat Prod. 1993;56:1805-10.
26. Jeandet PR, Bessis M, Sbaghi M, Meunier P. Production of the phytoalexin resveratrol by grapes as a response to Botrytis attack under natural conditions. J Phytopath. 1995;143:135-9.
27. Kato Y, Kawakishi S, Aoki T, Itakura K, Osawa T. Oxidative modification of tryptophan residues exposed to peroxynitrite. Biochim Biophys Res Commun. 1997;234:82-4.
28. Khan J, Brennan DM, Bradley N, Gao B, Brukdorfer R, Jacobs M. 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochem J. 1998;330:795-801.
29. Kim AR, Park MJ, Lee MK, Sung SH, Park EJ, Kim J et al. Flavonoids of Inula Britanica protect cultured cortical cells from cecrotic cell death induced by glutamate. Free Rad Biol Med. 2002;32:596-604.
30. Kimura Y, Okuda H, Kubo M. Effects of stilbenes isolated from medicinal plants on arachidonate metabolism and degranulation in human polymorphonuclear leukocytes. J Ethnopharmacol. 1995;45:131-9.
31. Klotz LO, Sies H. Defenses against peroxynitrite: selenocompounds and flavonoids. Toxicol Lett. 2003;140:125-32.
32. Kostyuk VA, Kraemer T, Sies H, Schewe T. Myeloperoxidase/nitrite-mediated lipid peroxidation of low-density lipoprotein as modulated by flavonoids. FEBS Lett. 2003;537:146-50.
33. Langcake P, Pryce RJ. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection and injury. Physiol Plant Pathol. 1976;9:77-86.
34. Lins AP, Ribeiro MN, Gottlieb OR, Gottlieb HE. Gnetins, resveratrol oligomers from Gnetum species. J Nat Prod. 1982;45:754-61.
35. Lufrano M, Balazy M. Interactions of peroxynitrite and other nitrating substances with human platelets: the role of glutathione and peroxynitrite permeability. Biochem Pharmacol. 2003;65:515-23.
36. Marzocco S, Piacente S, Pizza C, Oleszek W, Stochmal A, Pinto A et al. Inhibition of inducible nitric oxide synthase expression by yuccaol C from Yucca schidigers roezl. Life Sciences. 2004;75:1491-501.
37. Mayer B, Schrammel A, Klatt P, Koesling D, Schmidt K. Peroxynitrite-induced accumulation of cyclic GMP in endothelial cells and stimulated soluble guanylyl cyclase. Dependence on glutathione and possible role of S-nitrosylation. J Biol Chem. 1995;270:17355-60.
38. Messana I, Ferrari F, Cavalcanti MSB, Morace G. An anthraquinone and1 three naphthopyrone derivatives from Cassia pudibunda. Phytochemistry. 1991;30:708-10.
39. Mondoro TH, Shafer BC, Vostal JG. Peroxynitrite-induced tyrosine nitration and phosphorylation in human platelets. Free Rad Biol Med. 1997;22:1055-63.
40. Moro MA, Darley-Usmar VM, Goodwin DA, Read NG, Zamora-Pino R, Feelisch M et al. Paradoxical fate and biological action of peroxynitrite on human platelets. Proc Natl Acad Sci. 1994;91:6702-6.
41. Nowak P, Olas B, Bald E, Glowacki R, Wachowicz B. Peroxynitrite-induced changes of thiol groups in human blood platelets. Platelets. 2003;14:375-9.
42. Ogungbamila FO, Onawunmi GO, Ibewuike JC, Funmilayo KA. Antibacterial constituents of Ficus barteri fruits. Int J Pharmacogn. 1997;35:185-9.
43. Ohyama M, Tanaka T, Iinuma M, Goto K. Two novel resveratrol trimers, leachianols A and B, from Sophora leachiana. Chem Pharm Bull. 1994;42:2117-20.
44. Olas B, Wachowicz B. Resveratrol reduces oxidative stress induced by platinum compounds in blood platelets. Gen Physiol Biophys. 2004;23:1-12.
45. Olas B, Wachowicz B, Stochmal A, Oleszek W. Anti-platelet effects of different phenolic compounds from Yucca schidigera Roezl. Bark Platelets. 2002;13:167-73.
46. Olas B, Wachowicz B, Stochmal A, Oleszek W. Inhibition of oxidative stress in blood platelets by different phenolics from Yucca schidigera Roezl. Bark Nutrition. 2003;19:633-40.
47. Olas B, Wachowicz B, Bald E, Głowacki R. The protective effects of resveratrol against changes in blood platelet thiols induced by platinum compounds. J Physiol Pharmacol. 2004a;2:467-46.
48. Olas B, Nowak P, Kołodziejczyk J, Wachowicz B. The effects of antioxidants on peroxynitrite-induced changes in platelet proteins. Thromb Res. 2004b;113:399-406.
49. Olas B, Nowak P, Wachowicz B. Resveratrol protects against peroxynitrite-induced thiol oxidation in blood platelets. CMBL. 2004c;9:577-87.
50. Olas B, Wachowicz B, Majsterek I, Blasiak J. Resveratrol may reduce oxidative stress induced by platinum compounds in human plasma, blood platelets and lymphocytes. Anti-Cancer Drugs. 2005a;16:659-65.
51. Olas B, Wachowicz B, Stochmal A, Oleszek W. Inhibition of platelet adhesion and secretion by different phenolics from Yucca schidigera Roezl. Bark Nutr. 2005b;21:199-206.
52. Olas B, Nowak P, Kolodziejczyk J, Ponczek M, Wachowicz B. Protective effects of resveratrol against oxidative/nitrative modifications of plasma proteins and lipids exposed to peroxynitrite. J Nutr Biochem. 2006a;17:96-102.
53. Olas B, Nowak P, Ponczek M, Wachowicz B. Natural phenolic compound - resveratrol may reduce carbonylation of proteins induced by peroxynitrite in blood platelets. General Physiol Biophys. 2006b;25:215-22.
54. Olas B, Wachowicz B, Majsterek I, Blasiak J, Stochmal A, Oleszek W. Antioxidant properties of trans 3,3′,5,5′-tetrahydroxy-4- 4′methoxystilbene against modification of different biomolecules in human cells treated with platinum compounds. Nutrition. 2006c;22:1202-9.
55. Oleszek W, Sitek M, Stochmal A, Piacente S, Pizza C, Cheeke P. Resveratrol and other phenolics from the bark of Yucca schidigera Roezl. J Agri Food Chem. 2001;49:747-52.
56. Orsini F, Pelizzoni F, Verotta L, Aburjai T, Rogers CB. Isolation, synthesis and antiplatelet aggregation activity of resveratrol 3-O-β-d-glucopyranoside and related compounds. J Nat Prod. 1997;60:1082-7.
57. Pannala AS, Rice-Evans CA, Halliwell B, Singh S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem Biophys Res Commun. 1997;232:164-8.
58. Piacente S, Pizza C, Oleszek W. Saponins and phenolics of Yucca schidigera Roezl: Chemistry and bioactivity. Phytochemistry Rev. 2005;4:177-90.
59. Powell RG, Bajaj R, McLaughlin JL. Bioactive stilbenes of Scirpus maritimus. J Nat Prod. 1987;50:293-6.
60. Pryor WA, Squadrito GL. The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. Am J Physiol. 1995;268:L699-L722.
61. Robak J, Gryglewski RJ. Flavonoids are scavengers of superoxide anions. Biochem Pharmacol. 1988;37:837-41.
62. Rotondo S, Rotilio D, Cerletti CH, De Gaetano G. Red wine, aspirin and platelet function. Thromb Haemostas. 1996;76:813-21.
63. Sabetkar M, Low SY, Naseem KM, Bruckdorfer KR. The nitration of proteins in platelets: significance in platelet function. Free Rad Biol Med. 2002;33:728-36.
64. Savouret JF, Quesne M. Resveratrol and cancer: a review. Biomed Pharmacother. 2002;56:84-7.
65. Schroeder P, Zhang H, Klotz LO, Kalyanaraman B, Sies H. (-)-Epicatechin inhibits nitration and dimerization of tyrosine in hydrophilic as well as hydrophobic environments. Biochem Biophys Res Commun. 2001;289:1334-8.
66. Scorza G, Minetti M. One-electron oxidation pathway of thiols by peroxynitrite in biological fluids: bicarbonate and ascorbate promote the formation of albumin disulphide dimmers in human blood plasma. Biochem J. 1998;329:405-13.
67. Shin N-H, Ryu SY, Choi EJ, Kang SH, Chang IM, Min KR et al. Oxyresveratrol as the potent inhibitor of DOPA oxidase activity of mushroom tyrosinase. Biochem Biophys Res Commun. 1998;243:801-3.
68. Sies H. Ebselen, a selenoorganic compound as glutathione peroxidase mimic. Free Rad Biol Med. 1993;14:313-23.
69. Signorelli P, Ghidoni R. Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J Nutr Biochem. 2005;16:449-66.
70. Stojanovic S, Sprintz H, Brede O. Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Archiv Biochem Biophys. 2001;391:79-89.
71. van Acker SA, Tromp MN, Haenen GR, van der Vijgh WJ, Bast A. Flavonoids as scavengers of nitric oxide radical. Biochem Biophys Res Commun. 1995;214:755-9.
72. Wachowicz B. Adenine nucleotides in thrombocytes of birds. Cell Biochem Funct. 1984;2:167-70.
73. Walkowiak B, Michalak E, Koziołkiewicz W, Cierniewski CS. Rapid photometric method for estimation of platelet count in blood plasma or platelet suspension. Thromb Res. 1989;56:763-6.
74. Wippel R, Rehn M, Gorren ACF, Schmidt K, Mayer B. Interference of the polyphenol epicatechin with the biological chemistry of nitric oxide- and peroxynitrite-mediated reactions. Biochem Pharmacol. 2004;67:1285-95.
75. Zhao CY, Shi YM, Yao SD, Jia ZJ, Fan BT, Wang WF et al. Scavenging effects of natural phenols on oxidizing intermediates of peroxynitrite. Pharmazie. 2003;58:742-9.