Pentameric Procyanidins Isolated from Theobroma cacao Seeds Selectively Downregulate ErbB2 in Human Aortic Endothelial Cells

Experimental Biology and Medicine

Volumn 229, Issue 3, 2004, Pages 255-263

  Kenny, Thomas P ^a   Keen, Carl L ^a   Jones, Paul ^b   Kung, Hsing Jien ^c   Schmitz, Harold H ^b   Gershwin, M Eric ^a,d  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MARS INC   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

ErbB2; Flavonoids; Oxidative defense; Procyanidin; Vascular endothelial growth factor

Indexed keywords

ASCORBIC ACID; CAROTENOID; EPIDERMAL GROWTH FACTOR RECEPTOR 2; FLAVONOID; MITOGEN ACTIVATED PROTEIN KINASE P38; PROCYANIDIN DERIVATIVE; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; TOCOPHEROL DERIVATIVE; VASCULOTROPIN; VASCULOTROPIN RECEPTOR 2;

ANGIOGENESIS; ANTIANGIOGENIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CACAO; CARDIOVASCULAR RISK; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; ENDOTHELIUM CELL; GENE EXPRESSION REGULATION; GENE OVEREXPRESSION; GENE SEQUENCE; GENETIC CONSERVATION; HUMAN; HUMAN CELL; MOLECULAR WEIGHT; RECEPTOR DOWN REGULATION;

ANIMALIA; THEOBROMA; THEOBROMA CACAO;

EID: 1442324344     PISSN: 15353702     EISSN: None     Source Type: Journal    
DOI: 10.1177/153537020422900306     Document Type: Article

References (48)

1. Dillinger TL, Barriga P, Escarcega S, Jimenez M. Salazar Lowe D. Grivetti LE. Food of the gods: cure for humanity? A cultural history of the medicinal and ritual use of chocolate. J Nutr 130:2057S-2072S, 2000.
2. Adamson GE, Lazarus SA, Mitchell AE, Prior RL, Cao G, Jacobs PH, Kremers BG, Hammerstone JF, Rucker RB, Ritter KA, Schmitz HH. HPLC method for the quantification of procyanidins in cocoa and chocolate samples and correlation to total antioxidant capacity. J Agric Food Chem 47:4184-4188, 1999.
3. Kris-Etherton PM, Derr J, Mitchell DC, Mustad VA, Russell ME, McDonnell ET, Salabsky D, Pearson TA. The role of fatty acid saturation on plasma lipids, lipoproteins, and apolipoproteins: 1. Effects of whole food diets high in cocoa butter, olive oil, soybean oil, dairy butter, and milk chocolate on the plasma lipids of young men. Metabolism 42:121-129, 1993.
4. Kozikowski AP, Tuckmantel W, Bottcher G, Romanczyk LJ Jr. Studies in polyphenol chemistry and bioactivity. 4.(1) Synthesis of trimeric, tetrameric, pentameric, and higher oligomeric epicatechin-derived procyanidins having all-4beta,8-interflavan connectivity and their inhibition of cancer cell growth through cell cycle arrest. J Org Chem 68:1641-1658, 2003.
5. Karim M, McCormick K, Kappagoda CT. Effects of cocoa extracts on endothelium-dependent relaxation. J Nutr 130:2105S-2108S, 2000.
6. Schewe T, Sadik C, Klotz LO, Yoshimoto T, Kuhn H, Sies H. Polyphenols of cocoa: inhibition of mammalian 15-lipoxygenase. Biol Chem 382:1687-1696, 2001.
7. Pearson DA, Schmitz HH, Lazarus SA, Keen CL. Inhibition of in vitro low-density lipoprotein oxidation by oligomeric procyanidins present in chocolate and cocoas. Methods Enzymol 335:350-360, 2001.
8. Heiss C, Dejam A, Kleinbongard P, Schewe T, Sies H, Kelm M. Vascular effects of cocoa rich in flavan-3-ols. JAMA 290:1030-1031, 2003.
9. Taubert D, Berkels R, Roesen R, Klaus W. Chocolate and blood pressure in elderly individuals with isolated systolic hypertension. JAMA 290:1029-1030, 2003.
10. Mackenzie GG, Carrasquedo F, Delfino JM, Keen CL, Fraga CG, Oteiza PI. Epicatechin, catechin, and dimeric procyanidins inhibit PMA-induced NF-kappaB activation at multiple steps in Jurkat T cells. FASEB J, 12 Nov, 2003 (E-publication).
11. Kondo K, Hirano R, Matsumoto A, Igarashi O, Itakura H. Inhibition of LDL oxidation by cocoa. Lancet 348:1514,1996.
12. Kris-Etherton PM, Keen CL. Evidence that the antioxidant flavonoids in tea and cocoa are beneficial for cardiovascular health. Curr Opin Lipidol 13:41-49, 2002.
13. Pearson DA, Paglieroni TG, Rein D, Wun T, Schramm DD, Wang JF, Holt RR, Gosselin R, Schmitz HH, Keen CL. The effects of flavonolrich cocoa and aspirin on ex vivo platelet function. Thromb Res 106:191-197, 2002.
14. Folts JD. Potential health benefits from the flavonoids in grape products on vascular disease. Adv Exp Med Biol 505:95-111, 2002.
15. Rein D, Paglieroni TG, Wun T, Pearson DA, Schmitz HH, Gosselin R, Keen CL. Cocoa inhibits platelet activation and function. Am J Clin Nutr 72:30-35, 2000.
16. Murphy KJ, Chronopoulos AK, Singh 1, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ. Dietary flavonols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am J Clin Nutr 77:1466-1473, 2003.
17. Holt RR, Schramm DD, Keen CL, Lazarus SA, Schmitz HH. Chocolate consumption and platelet function. JAMA 287:2212-2213, 2002.
18. Schroeder P, Klotz LO, Sies H. Amphiphilic properties of (-)-epicatechin and their significance for protection of cells against peroxynitrite. Biochem Biophys Res Commun 307:69-73, 2003.
19. Verstraeten SV, Keen CL, Schmitz HH, Fraga CG, Oteiza PI. Flavan-3-ols and procyanidins protect liposomes against lipid oxidation and disruption of the bilayer structure. Free Radic Biol Med 34:84-92, 2003.
20. Lotito SB, Actis-Goretta L, Renart ML, Caligiuri M, Rein D, Schmitz HH, Steinberg FM, Keen CL, Fraga CG. Influence of oligomer chain length on the antioxidant activity of procyanidins. Biochem Biophys Res Commun 276:945-951, 2000.
21. Ottaviani JI, Carrasquedo F, Keen CL, Lazarus SA, Schmitz HH, Fraga CG. Influence of flavan-3-ols and procyanidins on UVC-mediated formation of 8-oxo-7,8-dihydro-2′-deoxyguanosine in isolated DNA. Arch Biochem Biophys 406:203-208, 2002.
22. Mao TK, Powell JJ, Van de Water J, Keen CL, Schmitz HH, Hammerstone JF, Gershwin ME. The effect of cocoa procyanidins on the transcription and secretion of interleukin 1β in peripheral blood mononuclear cells. Life Sci 66:1377-1386, 2000.
23. Mao TK, Van De Water J, Keen CL, Schmitz HH, Gershwin ME. Cocoa flavonols and procyanidins promote transforming growth factor-beta1 homeostasis in peripheral blood mononuclear cells. Exp Biol Med (Maywood) 228:93-99, 2003.
24. Sanbongi C, Suzuki N, Sakane T. Polyphenols in chocolate, which have antioxidant activity, modulate immune function in humans in vitro. Cell Immunol 177:129-136, 1997.
25. Hertog MGL, Feskens EJM, Hollman PCH, Katan MB, Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet 342:1007-1011, 1993.
26. Keli SO, Hertog MG, Feskens EJ, Kromhout D. Dietary flavonoids, antioxidant vitamins, and incidence of stroke: the Zutphen study. Arch Intern Med 156:637-642, 1996.
27. Steinmetz KA, Potter JD. Vegetables, fruit, and cancer. 1. Epidemiology. Cancer Causes Control 2:325-357, 1991.
28. Steinberg FM, Bearden MM, Keen CL. Cocoa and chocolate flavonoids: implications for cardiovascular health. J Am Diet Assoc 103:215-223, 2003.
29. Arts IC, Jacobs DR Jr., Gross M, Hamack LJ, Folsom AR. Dietary catechins and cancer incidence among postmenopausal women: the Iowa Women's Health Study (United States). Cancer Causes Control 13:373-382, 2002.
30. Robinson D, He F, Pretlow T, Kung HJ. A tyrosine kinase profile of prostate carcinoma. Proc Natl Acad Sci U S A 93:5958-5962, 1996.
31. Kung HJ, Chen HC, Robinson D. Molecular profiling of tyrosine kinases in normal and cancer cells. J Biomed Sci 5:74-78, 1998.
32. Ferrara N, Clapp C, Weiner R. The 16K fragment of prolactin specifically inhibits basal or fibroblast growth factor stimulated growth of capillary endothelial cells. Endocrinology 129:896-900, 1991.
33. Carnesecchi S, Schneider Y, Lazarus SA, Coehlo D, Gosse F, Raul F. Flavonols and procyanidins of cocoa and chocolate inhibit growth and polyamine biosynthesis of human colonic cancer cells. Cancer Lett 175:147-155, 2002.
34. Yamagishi M, Natsume M, Osakabe N, Okazaki K, Furukawa F, Imazawa T, Nishikawa A, Hirose M. Chemoprevention of lung carcinogenesis by cacao liquor proanthocyanidins in a male rat multiorgan carcinogenesis model. Cancer Lett 191:49-57, 2003.
35. Pianetti S, Guo S, Kavanagh KT, Sonenshein GE. Green tea polyphenol epigallocatechin-3 gallate inhibits Her-2/neu signaling, proliferation, and transformed phenotype of breast cancer cells. Cancer Res 62:652-655, 2002.
36. Lamy PJ, Pujol P, Thezenas S, Kramar A, Rouanet P, Guilleux F, Grenier J. Progesterone receptor quantification as a strong prognostic determinant in postmenopausal breast cancer women under tamoxifen therapy. Breast Cancer Res Treat 76:65-71, 2002.
37. Arts IC, Hollman PC, Kromhout D. Chocolate as a source of tea flavonoids. Lancet 354:488,1999.
38. Borchers A, Keen C, Hannum S, Gershwin M. Cocoa and chocolate: composition, bioavailability, and health implications. J Medicinal Food 3:77-105, 2000.
39. Klotz LO, Sies H. Defenses against peroxynitrite: selenocompounds and flavonoids. Toxicol Lett 140-141:125-132, 2003.
40. Benhar M, Engelberg D, Levitzki A. ROS, stress-activated kinases and stress signaling in cancer. EMBO Rep 3:420-425, 2002.
41. Lamy S, Gingras D, Beliveau R. Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation. Cancer Res 62:381-385, 2002.
42. Manni A. Polyamine involvement in breast cancer phenotype. In Vivo 16:493-500, 2002.
43. Hudson LG, Thompson KL, Xu J, Gill GN. Identification and characterization of a regulated promoter element in the epidermal growth factor receptor gene. Proc Natl Acad Sci U S A 87:7536-7540, 1990.
44. Yen L, You XL, Al Moustafa AE, Batist G, Hynes NE, Mader S, Meloche S, Alaoui-Jamali MA. Heregulin selectively upregulates vascular endothelial growth factor secretion in cancer cells and stimulates angiogenesis. Oncogene 19:3460-3469, 2000.
45. Baba S, Osakabe N, Natsume M, Terao J. Absorption and urinary excretion of procyanidin B2 [epicatechin-(4beta-8)-epicatechin] in rats. Free Radic Biol Med 33:142-148, 2002.
46. Natsume M. Osakabe N. Oyama M, Sasaki M, Baba S, Nakamura Y, Osawa T, Terao J. Structures of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin: differences between human and rat. Free Radic Biol Med 34:840-849, 2003.
47. Zhu QY, Holt RR, Lazarus SA, Orozco TJ, Keen CL. Inhibitory effects of cocoa flavonols and procyanidin oligomers on free radical-induced erythrocyte hemolysis. Exp Biol Med (Maywood) 227:321-329, 2002.
48. Rios LY, Bennett RN, Lazarus SA, Remesy C, Scalbert A, Williamson G. Cocoa procyanidins are stable during gastric transit in humans. Am J Clin Nutr 76:1106-1110, 2002.