Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets

Journal of Medicinal Chemistry

Volumn 50, Issue 16, 2007, Pages 3937-3944

  Amor, Nidhal Ben ^a   Bouaziz, Aicha ^a   Romera Castillo, Cristina ^b   Salido, Sofia ^b   Linares Palomino, Pablo J ^b   Bartegi, Aghleb ^a   Salido, Ginés M ^c   Rosado, Juan A ^c  

^a UNIVERSITY OF MONASTIR   (Tunisia)

^b UNIVERSITY OF JAÉN   (Spain)

^c UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ALPHA TOCOPHEROL; ANTHOCYANIN; ANTIOXIDANT; ASCORBIC ACID; BRUTON TYROSINE KINASE; CATALASE; CINNAMTANNIN B 1; COLCHICINE; HYDROXYTYROSOL; PROTEIN KINASE P60; ROSMARINIC ACID; SCAVENGER; TANNIN DERIVATIVE; THROMBIN; TROLOX C; TUBULIN; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; ENZYME ACTIVATION; ENZYME INHIBITION; HUMAN; HUMAN CELL; LAURUS; LAURUS NOBILIS; MICROTUBULE; NORMAL HUMAN; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION INHIBITION; THROMBOSIS;

ANTHOCYANINS; CALCIUM; CELL SURVIVAL; ENZYME ACTIVATION; FREE RADICAL SCAVENGERS; HUMANS; LAURUS; MICROTUBULES; PHOSPHORYLATION; PLATELET AGGREGATION INHIBITORS; PROTEIN-TYROSINE KINASES; PROTO-ONCOGENE PROTEINS PP60(C-SRC); THROMBIN; TYROSINE;

EID: 34548076147     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070508d     Document Type: Article

References (56)

1. Ariga, T. The antioxidative function, preventive action on disease and utilization of proanthocyanidins. Biofactors 2004, 21, 197-201.
2. Yamakoshi, J.; Kataoka, S.; Koga, T.; Ariga, T. Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis 1999, 142, 139-149.
3. Bagchi, D.; Sen, C. K.; Ray, S. D.; Das, D. K.; Bagchi, M.; Preuss, H. G.; Vinson, J. A. Molecular mechanisms of cardioprotection by a novel grape seed proanthocyanidin extract. Mutat. Res. 2003, 523, 87-97.
4. Romera, C.; Salido, S.; Linares-Palomino, P.; Nogueras, M.; Sánchez, A.; Altarejos, J. Radical scavenging constituents from Laurus nobilis wood. In Abstract Book, IVth Spanish-Portuguese-Japanese Organic Chemistry Symposium, Santiago de Compostela, Spain, September 8-11, 2006; University of Santiago de Compostela: Santiago de Compostela, Spain, 2006; p 140.
5. Jayaprakasha, G. K.; Ohnishi-Kameyama, M.; Ono, H.; Yoshida, M.; Jaganmohan, RL. Phenolic constituents in the fruits of Cinnamomum zeylanicum and their antioxidant activity. J. Agric. Food Chem. 2006, 54, 1672-1679.
6. 2+ homeostasis and platelet hyperaggregability in type 2 diabetes mellitus patients. Arch. Biochem. Biophys. 2007, 457, 235-242.
7. Bouaziz, A.; Romera-Castillo, C.; Salido, S.; Linares-Palomino, P. J.; Altarejos, J.; Bartegi, A.; Rosado, J. A.; Salido, G. M. Cinnamtannin B-1 from bay wood exhibits antiapoptotic effects in human platelets. Apoptosis 2007, 12, 489-498.
8. White, J. G.; Krumwiede, M.; Burris, S. M.; Heagan, B. Isolation of microtubule coils from platelets after exposure to aggregating agents. Am. J. Pathol. 1986, 125, 319-326.
9. Canizares, C.; Vivar, N.; Herdoiza, M. Role of the microtubular system in platelet aggregation. Braz. J. Med. Biol. Res. 1994, 27, 1533-1551.
10. Salari, H.; Duronio, V.; Howard, S. L.; Demos, M.; Jones, K.; Reany, A.; Hudson, A. T.; Pelech, S. L. Erbstatin blocks platelet activating factor-induced protein-tyrosine phosphorylation, polyphosphoinositide hydrolysis, protein kinase C activation, serotonin secretion and aggregation of rabbit platelets. FEBS Lett. 1990, 263, 104-108.
11. Asahi, M.; Yanagi, S.; Ohta, S.; Inazu, T.; Sakai, K.; Takeuchi, F.; Taniguchi, T.; Yamamura, H. Thrombin-induced human platelet aggregation is inhibited by protein-tyrosine kinase inhibitors, ST638 and genistein. FEBS Lett. 1992, 31, 10-14.
12. Tibbles, H. E.; Vassilev, A.; Wendorf, H.; Schonhoff, D.; Zhu, D.; Lorenz, D.; Waurzyniak, B.; Liu, X. P.; Uckun, F. M. Role of a JAK3-dependent biochemical signaling pathway in platelet activation and aggregation. J. Biol. Chem. 2001, 276, 17815-17822.
13. Pani, G.; Colavitti, R.; Borrello, S.; Galeotti, T. Endogenous oxygen radicals modulate protein tyrosine phosphorylation and JNK-1 activation in lectin-stimulated thymocytes. Biochem. J. 2000, 347, 173-181.
14. Meurer, S.; Pioch, S.; Gross, S.; Muller-Esterl, W. Reactive oxygen species induce tyrosine phosphorylation of and Src kinase recruitment to NO-sensitive guanylyl cyclase. J. Biol Chem. 2005, 280, 33149-33156.
15. 2+ entry in human platelets. Cell. Signal. 2005, 17, 1011-1021.
16. Landino, L. M.; Robinson, S. H.; Skreslet, T. E.; Cabral, D. M. Redox modulation of tau and microtubule-associated protein-2 by the glutathione/glutaredoxin reductase system. Biochem. Biophys. Res. Commun. 2004, 323, 112-117.
17. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. Technol. 1995, 28, 25-30.
18. 2+ mobilization and aggregation in platelets from type 2 diabetic patients. Biochem. Biophys. Res. Commun. 2005, 333, 794-802.
19. 2+ entry in human platelets: evidence for involvement of small GTP-binding proteins and actin cytoskeleton. Biochem. J. 2000, 347, 183-192.
20. Rosado, J. A.; Porras, T.; Conde, M.; Sage, S. O. Cyclic nucleotides modulate store-mediated calcium entry through the activation of protein-tyrosine phosphatases and altered actin polymerization in human platelets. J. Biol. Chem. 2001, 276, 15666-15675.
21. Redondo, P. C.; Salido, G. M.; Pariente, J. A.; Rosado, J. A. Dual effect of hydrogen peroxide on store-mediated calcium entry in human platelets. Biochem. Pharmacol. 2004, 67, 1065-1076.
22. Kolodziej, H.; Ferreira, D.; Lemière, G.; De Bruyne, T.; Pieters, L.; Vlietinck, A. On the nomenclature of oligoflavonoids with an A-type unit. J. Nat. Prod. 1993, 56, 1199-1200.
23. Kamiya, K.; Watanabe, C.; Endang, H.; Umar, M.; Satake, T. Studies on the constituents of bark of Parameria laevigata Moldenke. Chem. Pharm. Bull. 2001, 49, 551-557.
24. src activation in human platelets: evidence for the involvement of this pathway in store-mediated calcium entry. J. Biol. Chem. 2004, 279, 1665-1675.
25. Diaz, J. F.; Strobe, R.; Engelborghs, Y.; Souto, A. A.; Andreu, J. M. Molecular recognition of taxol by microtubules. Kinetics and thermodynamics of binding of fluorescent taxol derivatives to an exposed site. J. Biol. Chem. 2000, 275, 26265-26276.
26. Vepa, S.; Scribner, W. M.; Natarajan, V. Activation of protein phosphorylation by oxidants in vascular endothelial cells: identification of tyrosine phosphorylation of caveolin. Free Radic. Biol. Med. 1997, 22, 25-35.
27. 2+ entry in human platelets. FEBS Lett. 1993, 315, 242-246.
28. 2+ mobilisation in human platelets through sulphydryl oxidation dependent and independent mechanisms. Biochem. Pharmacol. 2004, 67, 491-502.
29. Qin, S.; Stadtman, E. R.; Chock, P. B. Regulation of oxidative stress-induced calcium release by phosphatidylinositol 3-kinase and Bruton's tyrosine kinase in B cells. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 7118-7123.
30. Mahajan, S.; Ghosh, S.; Sudbeck, E. A.; Zheng, Y.; Downs, S.; Hupke, M.; Uckun, F. M. Rational design and synthesis of a novel anti-leukemic agent targeting Bruton's tyrosine kinase (BTK), LFM-A13 [alpha-cyano-beta-hydroxy- beta-methyl-N-(2,5-dibromophenyl)-propenamide]. J. Biol. Chem. 1999, 274, 9587-9599.
31. Rawlings, D. J.; Scharenberg, A. M.; Park, H.; Wahl, M. I.; Lin, S.; Kato, R. M.; Fluckiger, A. C.; Witte, O. N.; Kinet, J. P. Activation of BTK by a phosphorylation mechanism initiated by SRC family kinases. Science 1996, 271, 822-825.
32. c-src. Biochem. J. 1994, 299, 613-621.
33. c-src to the cytoskeleton during platelet aggregation. EMBO J. 1992, 11, 855-861.
34. Rosado, J. A.; Meijer, E. M.; Hamulyak, K.; Novakova, I.; Heemskerk, J. W.; Sage, S. O. Fibrinogen binding to the integrin alpha(IIb)beta(3) modulates store-mediated calcium entry in human platelets. Blood 2001, 97, 2648-2656.
35. Liu, Y.; Bishop, A.; Witucki, L.; Kraybill, B.; Shimizu, E.; Tsien, J.; Ubersax, J.; Blethrow, J.; Morgan, D. O.; Shokat, K. M. Structural basis for selective inhibition of Src family kinases by PP1. Chem. Biol. 1999, 6, 671-678.
36. Huang, Y. T.; Hwang, J. J.; Lee, P. P.; Ke, F. C.; Huang, J. H.; Huang, C. J.; Kandaswami, C.; Middleton, E., Jr.; Lee, M. T. Effects of luteolin and quercetin, inhibitors of tyrosine kinase, on growth and metastasis-associated properties in A431 cells overexpressing epidermal growth factor receptor. Br. J. Pharmacol. 1999, 128, 999-1010.
37. Hertog, M. G. L.; Hollom, P. C. H.; Katan, M. B.; Kromhout, D. Intake of potential anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr. Cancer 1995, 20, 21-29.
38. Middleton, E., Jr.; Kandaswami, C.; Theoharidis, T. C. The impact of plant flavonoids on mammalian biology: implications for inflammations. Pharmacol. Rev. 2000, 52, 673-751.
39. Sieg, D. J.; Hauck, C. R.; Ilic, D.; Klingbeil, C. K.; Schaefer, E.; Damsky, C. H.; Schlaepfer, D. D. FAK integrates growth-factor and integrin signals to promote cell migration. Nature Cell Biol. 2000, 2, 249-256.
40. Kappagoda, C. T.; Karim, M.; McCormic, K.; Kandaswami, C. Unraveling the French paradox. Chem. Innov. 2000, 30, 26-31.
41. Sato, F.; Matsukawa, Y.; Matsumoto, K.; Nishino, H.; Sakai, T. Apegenin induces morphological differentiation and G2/M arrest in rat neuronal cells. Biochem. Biophys. Res. Commun. 1994, 204, 578-584.
42. Wei, Y. Q.; Zhao, X.; Kariya, Y.; Fukata, H.; Teshigawara, K.; Uchida, A. Induction of apoptosis by quercetin: involvement of heat shock protein. Cancer Res. 1994, 54, 4952-4957.
43. Pignatelli, P.; Di Santo, S.; Buchetti, B.; Sanguigni, V.; Brunelli, A.; Violi, F. Polyphenols enhance platelet nitric oxide by inhibiting protein kinase C-dependent NADPH oxidase activation: effect on platelet recruitment. FASEB J. 2006, 20, 1082-1089.
44. Guzik, T. J.; Olszanecki, R.; Sadowski, J.; Kapelak, B.; Rudzinski, P.; Jopek, A.; Kawczynska, A.; Ryszawa, N.; Loster, J.; Jawien, J.; Czesnikiewicz-Guzik, M.; Channon, K. M.; Korbut, R. Superoxide dismutase activity and expression in human venous and arterial bypass graft vessels. J. Physiol. Pharmacol. 2005, 56, 313-323.
45. Suzuki-Inoue, K.; Wilde, J. I.; Andrews, R. K.; Auger, J. M.; Siraganian, R. P.; Sekiya, F.; Rhee, S. G.; Watson, S. P. Glycoproteins VI and Ib-IX-V stimulate tyrosine phosphorylation of tyrosine kinase Syk and phospholipase Cgamma2 at distinct sites. Biochem. J. 2004, 378, 1023-1029.
46. Bouaziz, A.; Ben Amor, N.; Woodard, G. E.; Zibidi, H.; López, J. J.; Bartegi, A.; Salido, G. M.; Rosado, J. A. Tyrosine phosphorylation/ dephosphorylation balance is involved in thrombin-evoked microtubular reorganisation in human platelets. Thromb. Haemost. 2007, in press.
47. Uckun, F. M.; Vassilev, A.; Bartell, S.; Zheng, Y.; Mahajan, S.; Tibbies, H. E. The anti-leukemic Bruton's tyrosine kinase inhibitor alpha-cyano-beta- hydroxy-beta-methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13) prevents fatal thromboembolism. Leuk. Lymphoma 2003, 44, 1569-1577.
48. Mukhopadhyay, S.; Ramars, A. S.; Dash, D. Bruton's tyrosine kinase associates with the actin-based cytoskeleton in activated platelets. J. Cell Biochem. 2001, 81, 659-665.
49. Soriani, A.; Moran, B.; de Virgilio, M.; Kawakami, T.; Altman, A.; Lowell, C.; Eto, K.; Shattil, S. J. A role for PKCtheta in outside-in alpha(IIb)beta3 signaling. J. Thromb. Haemost. 2006, 4, 648-655.
50. Redondo, P. C.; Harper, M. T.; Rosado, J. A.; Sage, S. O. A role for cofilin in the activation of store-operated calcium entry by de novo conformational coupling in human platelets. Blood 2006, 107, 973-979.
51. 2+ release from two different intracellular stores in human platelets. Biochem. J. 2007, 401, 167-174.
52. Csiszar, A.; Smith, K.; Labinskyy, N.; Orosz, Z.; Rivera, A.; Ungvari, Z. Resveratrol attenuates TNF-alpha-induced activation of coronary arterial endothelial cells: role of NF-kappaB inhibition. Am. J. Physiol. Heart Circ. Physiol. 2006, 291, H1694-H1699.
53. Luceri, C.; Giannini, L.; Lodovici, M.; Antonucci, E.; Abbate, R.; Masini, E.; Dolara, P. p-Coumaric acid, a common dietary phenol, inhibits platelet activity in vitro and in vivo. Br. J. Nutr. 2007, 97, 458-463.
54. Singh, I.; Mok, M.; Christensen, A. M.; Turner, A. H.; Hawley, J. A. The effects of polyphenols in olive leaves on platelet function. Nutr. Metab. Cardiovasc. Dis. 2007, in press.
55. Pignatelli, P.; Di Santo, S.; Buchetti, B.; Sanguigni, V.; Brunelli, A.; Violi, F. Polyphenols enhance platelet nitric oxide by inhibiting protein kinase C-dependent NADPH oxidase activation: effect on platelet recruitment. FASEB J. 2006, 20, 1082-1089.
56. Nomura, S.; Shouzu, A.; Omoto, S.; Nishikawa, M.; Fukuhara, S.; Iwasaka, T. Losartan and simvastatin inhibit platelet activation in hypertensive patients. J. Thromb. Thrombolysis 2004, 18, 177-185.