Anti-inflammatory effects of a bioavailable compound, Artepillin C, in Brazilian propolis

European Journal of Pharmacology

Volumn 587, Issue 1-3, 2008, Pages 296-301

  Paulino, Niraldo ^a,b   Abreu, Sheila Rago Lemos ^a,b   Uto, Yoshihiro ^c   Koyama, Daisuke ^c   Nagasawa, Hideko ^c   Hori, Hitoshi ^c   Dirsch, Verena M ^d   Vollmar, Angelika M ^d   Scremin, Amarilis ^e   Bretz, Walter A ^f  

^a Universidade Bandeirante de Sao Paulo   (Brazil)

^b Centro Universitário Barriga Verde   (Brazil)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

^d UNIVERSITY OF MUNICH   (Germany)

^e FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^f NEW YORK UNIVERSITY   (United States)

Author keywords

Artepillin C; Inflammation; NF B; Nitric oxide; Propolis; Prostaglandin E2

Indexed keywords

ANTIINFLAMMATORY AGENT; ARTEPILLIN C; BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL; CARRAGEENAN; DEXAMETHASONE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDOMETACIN; NITRIC OXIDE; PLANT EXTRACT; PROSTAGLANDIN E2;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFECT; EMBRYO; GAS CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NEUTROPHIL COUNT; NONHUMAN; PAW EDEMA; PERITONITIS; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS INHIBITION; SINGLE DRUG DOSE; SWISS WEBSTER MOUSE;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BIOLOGICAL AVAILABILITY; CARRAGEENAN; CELL SURVIVAL; CELLS, CULTURED; DINOPROSTONE; EDEMA; INDICATORS AND REAGENTS; INDOMETHACIN; INTESTINAL ABSORPTION; LEUPEPTINS; MALE; MICE; NF-KAPPA B; NITRIC OXIDE; NITRITES; PHENYLPROPIONATES; PROPOLIS; TRANS-ACTIVATION (GENETICS);

EID: 44149099992     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2008.02.067     Document Type: Article

References (45)

1. Ahn M.-R., Kunimasa K., Ohta T., Kumazawa S., Kamihira M., Kaji K., Uto Y., Hori H., Nagasawa H., and Nakayama T. Suppression of tumor-induced angiogenesis by Brazilian propolis: major component artepillin C inhibits in vitro tube formation and endothelial cell proliferation. Cancer Lett. 252 (2007) 235-243
2. Akao Y., Maruyama H., Matsumoto K., Ohguchi K., Nishizawa K., Sakamoto T., Araki Y., Mishima S., and Nozawa Y. Cell growth inhibitory effect of cinnamic acid derivatives from propolis on human tumor cell lines. Biol. Pharm. Bull. 26 (2003) 1057-1059
3. Banerjee T., Vandervliet A., and Ziboh Va. Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line. Prostaglandins Leuk. Essent. Fatty. 66 (2002) 485-492
4. Bankova V., Krasteva G.B., Sforcin J.M., Frete X., Kajjumgiev A., Rodella R.M., and Popov S. Phytochemical evidence for the plant origin of Brazilian propolis from São Paulo State. Z. Naturforsch. 54 (1999) 401-405
5. Calixto J.B., Zanini Jr. J.C., Cruz A.B., Yunes R.A., and Medeiros Y.S. Extract and compounds obtained from Mandevilla velutina inhibit arachidonic acid-induced ear oedema in mice, but not rat stomach contraction. Prostaglandins 41 (1991) 515-526
6. Calixto J.B., Otuki M.F., and Santos A.R. Anti-inflammatory compounds of plant origin. Part I. Action on arachidonic acid pathway, nitric oxide and nuclear factor kappa (NF-κB). Planta Med. 69 (2004) 973-983
7. Carlsson O., and Rippe B. Peritoneal lymphatic absorption and solute exchange during zymosan-induced peritonitis in the rat. Am. J. Physiol. 277 (1999) (Heart Circ. Physiol. 46, H1107-H1112
8. Carvalho J.C., Sertie J.A., Barbosa M.V., Patricio K.C., Caputo L.R., Sarti S.J., Ferreira L.P., and Bastos J.K. Anti-inflammatory activity of the crude extract from the fruits of Pterodon emarginatus Vog. J. Ethnopharmacol. 64 (1999) 127-133
9. Dallegri F., and Ottonello L. Tissue injury in neutrophilic inflammation. Inflamm. Res. 46 (1997) 382-391
10. Dirsch V.M., Keiss H.P., and Vollmar A.M. Garlic metabolites fail to inhibit the activation of the transcription factor NF-kappaB and subsequent expression of the adhesion molecule E-selectin in human endothelial cells. Eur. J. Nutr. 43 (2004) 55-59
11. Gekker G., Hu S., Spivak M., Lokensgard J.R., and Peterson P.K. Anti-HIV-1 activity of propolis in CD4(+) lymphocyte and microglial cell cultures. J. Ethnopharmacol. 102 (2005) 158-163
12. 15N] nitrate in biological fluids. Anal. Biochem. 126 (1984) 131-138
13. Hayashi K., Komura S., Isaji N., Ohishi N., and Yagi K. Isolation of antioxidative compounds from Brazilian propolis: 3,4-Dihydroxy-5-prenylcinnamic acid, a novel potent antioxidant. Chem. Pharm. Bull. 47 (1999) 1521-1524
14. Kasai H. Chemistry-based studies on oxidative DNA damage: formation, repair, and mutagenesis. Free Radic. Biol. Med. 33 (2002) 450-456
15. Kimoto T., Arai S., Aga M., Hanaya T., Kohguchi M., Nomura Y., and Kurimoto M. Cell cycle and apoptosis in cancer induced by the artepillin C extracted from Brazilian propolis. Gan-To-Kagaku-Ryoho 23 (1996) 1855-1859
16. Kimoto, T., Chaen, H., Kurimoto, M., 1998. Apoptosis-controlling agent. United State Patent n°US5830914.
17. Kimoto T., Koya S., Hino K., Yamamoto Y., Nomura Y., Micallef M.J., Hanaya T., Arai S., Ikeda M., and Kurimoto M. Renal carcinogenesis induced by ferric nitrilotriacetate in mice, and protection from it by Brazilian propolis and artepillin C. Pathol. Int. 50 (2000) 679-689
18. Kimoto T., Aga M., Hino K., Koya-Miyata S., Yamamoto Y., Micallef M.J., Hanaya T., Arai S., Ikeda M., and Kurimoto M. Apoptosis of human leukemia cells induced by Artepillin C, an active ingredient of Brazilian propolis. Anticancer Res. 21 (2001) 221-228
19. Kimoto T., Koya-Miyata S., Hino K., Micallef M.J., Hanaya T., Arai S., Ikeda M., and Kurimoto M. Pulmonary carcinogenesis induced by ferric nitrilotriacetate in mice and protection from it by Brazilian propolis and artepillin C. Virchows Arch. 438 (2001) 259-270
20. Krzek J., Kaleta J., Hubicka U., and Niedzwiedz A. Reversed-phase high-performance liquid chromatography determination of selected phenolic acids in propolis concentrates in terms of standardization for drug manufacturing purposes. J. AOAC Int. 89 (2006) 352-358
21. Konishi Y., Hitomi Y., Yoshida M., and Yoshioka E. Absorption and bioavailability of artepillin C in rats after oral administration. J. Agric. Food. Chem. 53 (2005) 9928-9933
22. Krediet R.T., Zuyderhoudt F.M.J., Boeschoten E.W., and Arisz L. Alterations in the peritoneal transport of water and solutes during peritonitis in continuous ambulatory peritoneal dialysis. Eur. J. Clin. Investig. 17 (1987) 43-52
23. Marcucci M.C., Ferreres F., Garcia-Viguera C., Bankova V.S., De Castro S.L., Dantas A.P., and Paulino N. Phenolic compounds from Brazilian propolis with pharmacological activities. J. Ethnopharmacol. 74 (2001) 105-112
24. Matsuno T., Jung S.K., Matsumoto Y., Saito M., and Morikawa J. Preferential cytotoxicity to tumor cells of 3,5-diprenyl-4-hydroxycinnamic acid (artepillin C) isolated from propolis. Anticancer Res. 17 (1997) 3565-3568
25. Morris B. The effect of diaphragmatic movement on the absorption of protein and red cells from the peritoneal cavity. Aust. J. Exp. Biol. Med. Sci. 31 (1953) 239-246
26. Nakanishi I., Uto Y., Ohkubo K., Miyazaki K., Yakumaru H., Urano S., Okuda H., Ueda J., Ozawa T., Fukuhara K., Fukuzumi S., Nagasawa H., Hori H., and Ikota N. Efficient radical scavenging ability of artepillin C, a major component of Brazilian propolis, and the mechanism. Org. Biomol. Chem. 1 (2003) 1452-1454
27. Olszanecki R., Gebska A., Kozlovski V.I., and Gryglewski R.J. Flavonoids and nitric oxide synthase. J. Physiol. Pharmacol. 53 (2002) 571-584
28. Orsolic N., Saranovic A.B., and Basic I. Direct and indirect mechanism(s) of antitumour activity of propolis and its polyphenolic compounds. Planta Med. 72 (2006) 20-27
29. Pan N., and Hori H. The interaction of acteoside with mitochondrial lipid peroxidation as an ischemia/reperfusion injury model. Adv. Exp. Med. Biol. 361 (1994) 319-325
30. Park Y.K., Paredes-Guzman J.F., Aguiar C.L., Alencar S.M., and Fujiwara F.Y. Chemical constituents in Baccharis dracunculifolia as the main botanical origin of Southeastern Brazilian propolis. J. Agric. Food Chem. 52 (2004) 1100-1103
31. Paulino N., Dantas A.P., Bankova V.S., Longhi D.T., Scremin A., De Castro S.L., and Calixto J.B. Bulgarian propolis induces analgesic and anti-inflammatory effects in mice and inhibits in vitro contraction of airway smooth muscle. J. Pharmacol. Sci. 93 (2003) 307-313
32. Pisco L., Kordian M., Peseke K., Feist H., Michalik D., Estrada E., Carvalho J., Hamilton G., Rando D., and Quincoces J. Synthesis of compounds with antiproliferative activity as analogues of prenylated natural products existing in Brazilian propolis. Eur. J. Med. Chem. 41 (2006) 401-407
33. Rosenkranz H.S., and Thampatty B.P. SAR: flavonoids and COX-2 inhibition. Oncol. Res. 13 (2003) 529-535
34. Salomão K., Dantas A.P., Borba C.M., Campos L.C., Machado D.G., Aquino Neto F.R., and de Castro S.L. Chemical composition and microbicidal activity of extracts from Brazilian and Bulgarian propolis. Lett. Applied Microbiol. 38 (2004) 87-92
35. Shimizu K., Ashida H., Matsuura Y., and Kanazawa K. Antioxidative bioavailability of artepillin C in Brazilian propolis. Arch. Biochem. Biophys. 424 (2004) 181-188
36. Shimizu K., Das S.K., Hashimoto T., Sowa Y., Yoshida T., Sakai T., Matsuura Y., and Kanazawa K. Artepillin C in Brazilian propolis induces G(0)/G(1) arrest via stimulation of Cip1/p21 expression in human colon cancer cells. Mol. Carcinog. 44 (2005) 293-299
37. Simões L.M., Gregorio L.E., Da Silva Filho A.A., De Souza M.L., Azzolini A.E., Bastos J.K., and Lucisano-Valim Y.M. Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils. J. Ethnopharmacol. 94 (2004) 59-65
38. Song Y.S., Park E.H., Hur G.M., Ryu Y.S., Kim Y.M., and Jin C. Ethanol extract of propolis inhibits nitric oxide synthase gene expression and enzyme activity. J. Ethnopharmacol. 80 (2002) 155-161
39. Sugimoto Y., Iba Y., Kayasuga R., Kirino Y., Nishiga M., Alejandra Hossen M., Okihara K., Sugimoto H., Yamada H., and Kamei C. Inhibitory effects of propolis granular A P C on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice. Cancer Lett. 193 (2003) 155-159
40. Tan-No K., Nakajima T., Shoji T., Nakagawasai O., Niijima F., Ishikawa M., Endo Y., Sato T., Satoh S., and Tadano T. Anti-inflammatory effect of propolis through inhibition of nitric oxide production on carrageenin-induced mouse paw edema. Biol. Pharm. Bull. 29 (2006) 96-99
41. Uto, Y., Ae, S., Koyama, D., Sakakibara, M., Otomo, N., Otsuki, M., Nagasawa, H., Kirk, K.L., Hori, H., in press. Artepillin C isoprenomics: design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity. Bioorg. Med. Chem.
42. Uto Y., Hirata A., Fujita T., Takubo S., Nagasawa H., and Hori H. First total synthesis of artepillin C established by o,o′-diprenylation of p-halophenols in water. J. Org. Chem. 67 (2002) 2355-2357
43. Woo S.K., Roszkowski P., Waterbury L.D., and Garay G.L. Gastric mucosal binding studies with enprostil: a potent anti-ulcer prostaglandin. Prostaglandins 32 (1986) 243-257
44. Ying N.L., Chao R.C., Hsin L.Y., Chu C.L., and Chieh M.J.C. Isolation and purification of 3,5-diprenyl-4-hydroxycinnamic acid (artepillin C) in Brazilian propolis by supercritical fluid extractions. Sep. Purif. Tech. 54 (2007) 130-138
45. Zimmermann M. Ethical guidelines for investigations of experimental pain in conscious animals. Pain 6 (1983) 109-110