Anti-inflammatory properties of clovamide and Theobroma cacao phenolic extracts in human monocytes: Evaluation of respiratory burst, cytokine release, NF-κB activation, and ppary modulation

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 10, 2011, Pages 5342-5350

  Zeng, HuaWu ^a,b   Locatelli, Monica ^a   Bardelli, Claudio ^a   Amoruso, Angela ^a   Coisson, Jean Daniel ^a   Travaglia, Fabiano ^a   Arlorio, Marco ^a   Brunelleschi, Sandra ^a  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Clovamide; Cocoa extracts; Cytokines; Human monocytes; NF B; PPAR ; Rosmarinic acid

Indexed keywords

ANTI-INFLAMMATORIES; ANTI-INFLAMMATORY ACTIVITY; ANTI-INFLAMMATORY EFFECTS; BELL-SHAPED CURVES; BIOACTIVE COMPOUNDS; CLOVAMIDE; COCOA BEANS; CYTOKINES; DARK CHOCOLATE; HUMAN CELLS; HUMAN MONOCYTES; PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR; PHENOLIC COMPOUNDS; PHORBOL 12 MYRISTATE 13 ACETATES; POTENT COMPOUNDS; POTENTIAL HEALTH; RESPIRATORY BURST; ROSMARINIC ACID; SUPEROXIDE ANIONS; THEOBROMA CACAO;

AMIDES; AMINO ACIDS; CALCINATION; COCOA; CYTOLOGY; OXYGEN; PHENOLS;

BODY FLUIDS;

ANTIINFLAMMATORY AGENT; CINNAMIC ACID DERIVATIVE; CLOVAMIDE; CYTOKINE; DEPSIDE; DRUG DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PHENOL DERIVATIVE; PHORBOL 13 ACETATE 12 MYRISTATE; PLANT EXTRACT; ROSMARINIC ACID; SUPEROXIDE; TYROSINE;

ARTICLE; CACAO; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; HEAT; HUMAN; METABOLISM; MONOCYTE; PHYSIOLOGY; PLANT SEED; RESPIRATORY BURST;

ANTI-INFLAMMATORY AGENTS; CACAO; CINNAMATES; CYTOKINES; DEPSIDES; HOT TEMPERATURE; HUMANS; MONOCYTES; NF-KAPPA B; PHENOLS; PLANT EXTRACTS; PPAR GAMMA; RESPIRATORY BURST; SEEDS; SUPEROXIDES; TETRADECANOYLPHORBOL ACETATE; TYROSINE;

THEOBROMA CACAO;

EID: 79957951006     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2005386     Document Type: Article

References (31)

1. Dillinger, T. L.; Barriga, P.; Escarcega, S.; Jimenez, M.; Salazar Lowe, D.; Grivetti, L. E. Food of the gods: Cure for humanity? A cultural history of the medicinal and ritual use of chocolate. J. Nutr. 2000, 130, 2057S-2072S. (Pubitemid 30619385)
2. Wollgast, J.; Anklam, E. Polyphenols in chocolate: is there a contribution to human health?. Food Res. Int. 2000, 33, 449-459. (Pubitemid 30427824)
3. Wollgast, J.; Anklam, E. Review on polyphenols in Theobroma cacao: Changes in composition during the manufacture of chocolate and methodology for identification and quantification. Food Res. Int. 2000, 33, 423-447. (Pubitemid 30427823)
4. Summa, C; Raposo, F. C; McCourt, J.; Lo Scalzo, R.; Wagner, K. H.; Elmadfa, I.; Anklam, E. Effect of roasting on the radical scavenging activity of cocoa beans. Eur. Food Res. Technol. 2006, 222, 368-375. (Pubitemid 43214129)
5. Baba, S.; Natsume, M.; Yasuda, A; Nakamura, Y.; Tamura, T.; Osakabe, N.; Kanegae, M.; Kondo, K. Plasma LDL and HDL cholesterol and oxidized LDL concentrations are altered in normo-and hypercholesterolemic humans after intake of different levels of cocoa powder. J. Nutr. 2007, 137, 1436-1441. (Pubitemid 46855482)
6. Hermann, F.; Spieker, L. E.; Ruschitzka, F.; Sudano, I.; Hermann, M.; Binggeli, C; Luscher, T. F.; Riesen, W.; Noll, G.; Corti, R. Dark chocolate improves endothelial and platelet function. Heart 2006, 92, 119-120. (Pubitemid 43021877)
7. Heiss, C; Kleinbongard, P.; Dejam, A.; Perre, S.; Schroeter, H.; Sies, H.; Kelm, M. Acute consumption of flavanol-rich cocoa on vascular function in humans. J. Am. Coll. Cardiol. 2005, 46, 1276-1283. (Pubitemid 41615549)
8. Murphy, K. J.; Chronopoulos, A K.; Singh, I.; Francio, M. A.; Moriarty, H; Pike, M. J.; Turner, A. H.; Mann, N. J.; Sinclair, A J. Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am. J. Clin. Nutr. 2003, 77, 1466-1473. (Pubitemid 39655281)
9. Taubert, D.; Roesen, R; Lehmann, C; Jung, N.; Schomig, E. Effects of low habitual cocoa intake on blood pressure and bioactive nitric oxide: A randomized controlled trial. J. Am. Med. Assoc. 2007, 298, 49-60. (Pubitemid 47026770)
10. Corti, R.; Flammer, A. J.; Hollenberg, N. K.; Luescher, T. F. Cocoa and cardiovascular health. Circulation 2009, 119, 1433-1441.
11. Selmi, C.; Mao, T. K.; Keen, C. L.; Schmitz, H. H.; Gershwin, M. E. The anti-inflammatory properties of cocoa flavanols. J. Cardiovasc. Pharmacol. 2006, 47, S163-S171. (Pubitemid 44620206)
12. Vinson, J. A.; Proch, J.; Bose, P.; Muchler, S.; Taffera, P.; Shuta, D.; Samman, N.; Agbor, G. A. Chocolate is a powerful ex vivo and in vivo antioxidant, an antiatherosclerotic agent in an animal model, and a significant contributor to antioxidants in the European and American diets. J. Agric. Food Chem. 2006, 54, 8071-8076. (Pubitemid 44785386)
13. Bayard, V.; Chamarro, F.; Motta, J.; Hollenberg, N. K. Does flavanol intake influence mortality from nitric oxide-dependent processes? Ischemic heart disease, stroke, diabetes mellitus, and cancer in Panama. Int. J. Med. Sci. 2007, 4, 53-58. (Pubitemid 46193047)
14. Yoshihara, T.; Yoshikawa, H.; Sakamura, S.; Sakuma, T. Clovamides: L-DOPA conjugated with trans-and cis-caffeic acids in red clover. Agric. Biol. Chem. 1974, 38, 1107-1109.
15. Sanbongi, C.; Osakabe, N.; Natsume, M.; Takizawa, T.; Gomi, S.; Osawa, T. Antioxidative polyphenols isolated from Theobroma cacao. J. Agric. Food Chem. 1998, 46, 454-457. (Pubitemid 128488407)
16. Arlorio, M.; Locatelli, M.; Travaglia, F.; Coisson, J. D.; Del Grosso, E.; Minassi, A.; Appendino., G; Martelli, A. Roasting impact on the contents of clovamide (N-caffeoyl-L-DOPA) and the antioxidant activity of cocoa beans (Theobroma cacao L.). Food Chem. 2008, 106, 967-975. (Pubitemid 47380050)
17. Stark, T.; Hofmann, T. Isolation, structure determination, synthesis, and sensory activity of N-phenylpropenoyl-L-amino acids from cocoa (Theobroma cacao). J. Agric. Food Chem. 2005, 53, 5419-5428. (Pubitemid 40994856)
18. Park, J. B. N-Coumaroyldopamine and N-caffeoyldopamine increase cAMP via beta 2-adreneceptors in myelocytic U937 cells. FASEB J. 2007, 19, 497-502. (Pubitemid 40471240)
19. Fallarini, S.; Miglio, G.; Paletti, T.; Minassi, A.; Amoruso, A.; Bardelli, C.; Brunelleschi, S.; Lombardi, G. Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death. Br. J. Pharmacol. 2009, 157, 1072-1084.
20. Amoruso, A.; Bardelli, C.; Gunella, G.; Fresu, L. G.; Ferrero, V.; Brunelleschi, S. Quantification of PPAR-gamma protein in monocyte/macrophages from healthy smokers and non-smokers: A possible direct effect of nicotine. Life Sci. 2007, 81, 906-915. (Pubitemid 47374210)
21. Jiang, C.; Ting, A. T.; Seed, B. PPARγ agonists inhibit production of monocyte inflammatory cytokines. Nature 1998, 391, 82-86. (Pubitemid 28079219)
22. Amoruso, A.; Bardelli, C.; Fresu, L. G.; Poletti, E.; Palma, A.; Federici Canova, D.; Zeng, H. W.; Brunelleschi, S. The nitric oxidedonating pravastatin, NCX6550, inhibits cytokine release and NF-κB activation while enhancing PPARγ expression in human monocyte/macrophages. Pharmacol. Res. 2010, 62, 391-399.
23. Amoruso, A.; Bardelli, C.; Fresu, L. G.; Palma, A.; Vidali, M.; Ferrero, V.; Ribichini, F.; Vassanelli, C.; Brunelleschi, S. Enhanced Peroxisome Proliferator-Activated Receptor-γ expression in monocyte/macrophages from coronary artery disease patients and possible gender differences. J. Pharmacol. Exp. Ther. 2009, 331, 531-538.
24. Caligiani, A.; Cirlini, M.; Palla, G.; Ravaglia, R.; Arlorio, M. GC-MS detection of chiral markers in cocoa beans of different quality and geographic origin. Chirality 2007, 19, 329-334. (Pubitemid 46659347)
25. Arlorio, M.; Bottini, C.; Travaglia, F.; Locatelli, M.; Bordiga, M.; Coïsson, J. D.; Martelli, A.; Tessitore, L. Protective activity of Theobroma cacao L. phenolic extract on AML12 and MPL29 liver cells by preventing apoptosis and inducing autophagy. J. Agric. Food Chem. 2009, 57, 10612-10618.
26. Qiao, S.; Li, W.; Tsubouchi, R.; Haneda, M.; Murakami, K.; Takeuchi, F.; Nisimoto, K.; Yoshino, M. Rosmarinic acid inhibits the formation of reactive oxygen and nitrogen species in RAW264.7 macrophages. Free Radical Res. 2005, 39, 995-1003. (Pubitemid 41227036)
27. Park, J. B.; Schoene, N. Clovamide-type phenylpropenoic acid amides, N-coumaroyldopamine and N-caffeoyldopamine, inhibit platelet-leukocyte interactions by suppressing P-selectin expression. J. Pharmacol. Exp. Ther. 2006, 317, 813-819.
28. Park, J. B. Caffedymine from cocoa has COX inhibitory activity suppressing the expression of a platelet activation marker, P-selectin. J. Agric. Food Chem. 2007, 55, 2171-2175. (Pubitemid 46556201)
29. Engler, M. B.; Engler, M. M.; Chen, C. Y.; Malloy, M. J.; Browne, A; Chiu, E. Y.; Kwak, H. K.; Milbury, P.; Paul, S. M.; Blumberg, J.; Mietus-Snyder, M. L. Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults. J. Am. Coll. Nutr. 2004, 23, 197-204. (Pubitemid 38746107)
30. Monagas, M.; Khan, N.; Andres-Lacueva, C; Casa, R; Urpí- Sardà, M.; Llorach, R; Lamuela-Raventos, R M.; Estruch, R. Effect of cocoa powder on the modulation of inflammatory biomarkers in patients at high risk of cardiovascular disease. Am. J. Clin. Nutr. 2009, 90, 1144-1150.
31. Park, J. B. Quantitation of clovamide-type phenylpropenoic amides in cells and plasma using high-performance liquid chromatography with a coulometric electrochemical detector. J. Agric. Food Chem. 2005, 53, 8135-8140. (Pubitemid 41564618)