Caffeic Acid Phenethyl Ester: A Review of Its Antioxidant Activity, Protective Effects against Ischemia-reperfusion Injury and Drug Adverse Reactions

Critical Reviews in Food Science and Nutrition

Volumn 56, Issue 13, 2016, Pages 2183-2190

  Tolba, Mai F ^a,b   Omar, Hany A ^c   Azab, Samar S ^a   Khalifa, Amani E ^a   Abdel Naim, Ashraf B ^a   Abdel Rahman, Sherif Z ^b  

^a Ain Shams University   (Egypt)

^b University of Texas Medical Branch School of Medicine   (United States)

^c Beni Suef University   (Egypt)

Author keywords

Antioxidant; caffeic acid phenethyl ester (CAPE); chemistry; ischemia reperfusion (I R)

Indexed keywords

ANTIBIOTICS; ANTIOXIDANTS; CHEMICAL COMPOUNDS; CHEMISTRY; CHEMOTHERAPY; ESTERS; IODINE; PHARMACODYNAMICS; PLATINUM COMPOUNDS; POLYPHENOLIC COMPOUNDS;

ADVERSE DRUG REACTION (ADRS); ANTI-OXIDANT ACTIVITIES; CAFFEIC ACID PHENETHYL ESTER; CHEMOTHERAPEUTIC AGENTS; CYTOPROTECTIVE ACTIVITIES; ISCHEMIA-REPERFUSION INJURY; ISCHEMIA/REPERFUSION; PHARMACOLOGICAL ACTIVITY;

BRAIN;

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTIOXIDANT; CAFFEIC ACID DERIVATIVE; CAFFEIC ACID PHENETHYL ESTER; PHENETHYL ALCOHOL; PROPOLIS;

ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; DRUG-RELATED SIDE EFFECTS AND ADVERSE REACTIONS; HUMAN; REPERFUSION INJURY;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CAFFEIC ACIDS; DRUG-RELATED SIDE EFFECTS AND ADVERSE REACTIONS; HUMANS; PHENYLETHYL ALCOHOL; PROPOLIS; REPERFUSION INJURY;

EID: 84982957860     PISSN: 10408398     EISSN: 15497852     Source Type: Journal    
DOI: 10.1080/10408398.2013.821967     Document Type: Article

References (60)

1. M.A.S.Abdel Haleem (2005). The Qur'an:A new translation by Abdel Haleem M.A.S., pp. 170. Oxford University Press Inc., New York
2. M.E.Altug, Y.Serarslan, R.Bal, T.Kontas, F.Ekici, I.M.Melek, H.Aslan, and T.Duman (2008). Caffeic acid phenethyl ester protects rabbit brains against permanent focal ischemia by antioxidant action:A biochemical and planimetric study. Brain Res. 1201:135–142.
3. A.R.Andrade-Silva, F.S.Ramalho, L.N.Ramalho, M.Saavedra-Lopes, A.A.Jordão, Jr, H.Vanucchi, C.E.Piccinato, and S.Zucoloto (2009). Effect of NFkappaB inhibition by CAPE on skeletal muscle ischemia-reperfusion injury. J. Surg. Res. 153:254–262.
4. A.Armagan, E.Uzar, E.Uz, H.R.Yilmaz, S.Kutluhan, H.R.Koyuncuoglu, S.Soyupek, H.Cam, and T.A.Serel, (2008). Caffeic acid phenethyl ester modulates methotrexate-induced oxidative stress in testes of rat. Hum. Exp. Toxicol. 27:547–552.
5. E.Atik, S.Gorur, and A.N.Kiper, (2006). The effect of caffeic acid phenethyl ester (CAPE) on histopathological changes in testicular ischemia-reperfusion injury. Pharmacol. Res. 54:293–297.
6. S.Bakir, M.Ozbay, R.Gun, E.Yorgancilar, V.Kinis, A.Keles, A.Abakay, O.Gokalp, and I.Topcu, (2013). The protective role of caffeic acid phenethyl ester against streptomycin ototoxicity. Am. J. Otolaryngol. 34:16–21.
7. V.Bankova, A.Dyulgerov, S.Popov, and N.Marekov, (1987). A GC/MS study of the propolis phenolic constituents. Z. Naturforsch. 42:147–151.
8. T.Cakir, E.Ozkan, E.Dulundu, U.Topaloglu, A.O.Sehirli, F.Ercan, E.Sener, and G.Sener, (2011). Caffeic acid phenethyl ester (CAPE) prevents methotrexate-induced hepatorenal oxidative injury in rats. J. Pharm. Pharmacol. 63:1566–1571.
9. Cayman (2011). Product information:Phenethyl caffeiate. vol. 70750. Cayman Chemical Company, p. 1.
10. N.Celli, L.K.Dragani, S.Murzilli, T.Pagliani, and A.Poggi, (2007). In vitro and in vivo stability of caffeic acid phenethyl ester, a bioactive compound of propolis. J. Agric. Food Chem. 55:3398–3407.
11. H.Chen, J.T.Tran, and R.E.erson, and M.N.Mandal, (2012). Caffeic acid phenethyl ester protects 661W cells from H2O2-mediated cell death and enhances electroretinography response in dim-reared albino rats. Mol. Vis. 18:1325–1338.
12. H.C.Chen, J.H.Chen, C.Chang, C.J.Shieh, (2011). Optimization of ultrasound accelerated synthesis of enzymatic caffeic acid phenethyl ester by response surface methodology. Ultrason. Sonochem. 18:455–459.
13. H.C.Chen, H.Y.Ju, Y.K.Twu, J.H.Chen, C.M.Chang, Y.C.Liu, C.Chang, and C.J.Shieh, (2010). Optimized enzymatic synthesis of caffeic acid phenethyl ester by RSM. N. Biotechnol. 27:89–93.
14. Y.J.Chen, A.C.Huang, H.H.Chang, H.F.Liao, C.M.Jiang, L.Y.Lai, J.T.Chan, Y.Y.Chen, and J.Chiang, (2009). Caffeic acid phenethyl ester, an antioxidant from propolis, protects peripheral blood mononuclear cells of competitive cyclists against hyperthermal stress. J. Food Sci. 74:H162–167.
15. S.Chlopcikova, J.Psotova, P.Miketova, J.Sousek, V.Lichnovsky, and V.Simanek, (2004). Chemoprotective effect of plant phenolics against anthracycline-induced toxicity on rat cardiomyocytes. Part II. caffeic, chlorogenic and rosmarinic acids. Phytother. Res. 18:408–413.
16. N.Cotelle, J.L.Bernier, J.P.Catteau, J.Pommery, J.C.Wallet, and E.M.Gaydou, (1996). Antioxidant properties of hydroxy-flavones. Free Radic. Biol. Med. 20:35–43.
17. M.Eşrefoğlu, M.Iraz, B.Ateş, and M.Gül, (2012). Not only melatonin but also caffeic acid phenethyl ester protects kidneys against aging-related oxidative damage in Sprague Dawley rats. Ultrastruct. Pathol. 36:244–251.
18. E.Fadillioglu, E.Oztas, H.Erdogan, M.Yagmurca, S.Sogut, M.Ucar, and M.K.Irmak, (2004). Protective effects of caffeic acid phenethyl ester on doxorubicin-induced cardiotoxicity in rats.J. Appl. Toxicol. 24:47–52.
19. Y.Feng, Y.W.Lu, P.H.Xu, Y.Long, W.M.Wu, W.Li, and R.Wang, (2008). Caffeic acid phenethyl ester and its related compounds limit the functional alterations of the isolated mouse brain and liver mitochondria submitted to in vitro anoxia-reoxygenation:Relationship to their antioxidant activities. Biochim. Biophys. Acta 1780:659–672.
20. H.Gocer, and I.Gulcin, (2011). Caffeic acid phenethyl ester (CAPE):Correlation of structure and antioxidant properties. Int. J. Food Sci. Nutr. 62:821–825.
21. M.Iraz, E.Ozerol, M.Gulec, S.Tasdemir, N.Idiz, E.Fadillioglu, M.Naziroglu, and O.Akyol, (2006). Protective effect of caffeic acid phenethyl ester (CAPE) administration on cisplatin-induced oxidative damage to liver in rat. Cell Biochem. Funct. 24:357–361
22. A.Kart, Y.Cigremis, H.Ozen, and O.Dogan, (2009). Caffeic acid phenethyl ester prevents ovary ischemia/reperfusion injury in rabbits. Food Chem. Toxicol. 47:1980–1984.
23. A.Kizilay, M.T.Kalcioglu, E.Ozerol, M.Iraz, M.Gulec, O.Akyol, and O.Ozturan, (2004). Caffeic acid phenethyl ester ameliorated ototoxicity induced by cisplatin in rats. J. Chemother. 16:381–387.
24. H.-P.Lin, C.-Y.Lin, C.Huo, L.-C.Su, and C.-P.Chuu, (2012). Anticancer effect of caffeic acid phenethyl ester. Pharmacologia 3:26–30.
25. Y.H.Lin, J.H.Chiu, W.S.Tseng, T.T.Wong, S.H.Chiou, and S.H.Yen, (2006). Antiproliferation and radiosensitization of caffeic acid phenethyl ester on human medulloblastoma cells. Cancer Chemother. Pharmacol. 57:525–532.
26. M.Loukas, Y.Saad, R.S.Tubbs, and M.M.Shoja,. (2010). The heart and cardiovascular system in the Qur'an and Hadeeth. Int. J. Cardiol. 140:19–23.
27. H.H.Mansour, and S.S.Tawfik, (2012). Early treatment of radiation-induced heart damage in rats by caffeic acid phenethyl ester. Eur. J. Pharmacol. 692:46–51.
28. H.Namazi, (2009). Decreasing the expression of LFA-1 and ICAM-1 as the major mechanism for the protective effect of caffeic acid phenethyl ester on ischemia-reperfusion injury. J. Plast. Reconstr. Aesthet. Surg. 62:550.
29. S.Ocak, S.Gorur, S.Hakverdi, S.Celik, and S.Erdogan, (2007). Protective effects of caffeic acid phenethyl ester, vitamin C, vitamin E and N-acetylcysteine on vancomycin-induced nephrotoxicity in rats. Basic Clin. Pharmacol. Toxicol. 100:328–333.
30. F.Oktem, F.Ozguner, O.Sulak, S.Olgar, O.Akturk, H.R.Yilmaz, and I.Altuntas, (2005). Lithium-induced renal toxicity in rats:Protection by a novel antioxidant caffeic acid phenethyl ester. Mol. Cell. Biochem. 277:109–115.
31. H.Okutan, N.Ozcelik, H.R.Yilmaz, and E.Uz, (2005). Effects of caffeic acid phenethyl ester on lipid peroxidation and antioxidant enzymes in diabetic rat heart. Clin. Biochem. 38:191–196.
32. S.Ozen, O.Akyol, M.Iraz, S.Sogut, F.Ozugurlu, H.Ozyurt, E.Odaci, and Z.Yildirim, (2004). Role of caffeic acid phenethyl ester, an active component of propolis, against cisplatin-induced nephrotoxicity in rats. J. Appl. Toxicol. 24:27–35.
33. M.Ozeren, N.Sucu, L.Tamer, B.Aytacoglu, O.Bayri, A.Dondas, L.Ayaz, and M.Dikmengil, (2005). Caffeic acid phenethyl ester (CAPE) supplemented St. Thomas’ hospital cardioplegic solution improves the antioxidant defense system of rat myocardium during ischemia-reperfusion injury. Pharmacol. Res. 52:258–263.
34. F.Ozguner, A.Armagan, A.Koyu, S.Caliskan, and H.Koylu, (2005). A novel antioxidant agent caffeic acid phenethyl ester prevents shock wave-induced renal tubular oxidative stress. Urol. Res. 33:239–243.
35. H.Ozyurt, B.Ozyurt, K.Koca, and S.Ozgocmen, (2007). Caffeic acid phenethyl ester (CAPE) protects rat skeletal muscle against ischemia-reperfusion-induced oxidative stress. Vascul. Pharmacol. 47:108–112
36. S.Reuter, S.C.Gupta, M.M.Chaturvedi, and B.B.Aggarwal,. (2010). Oxidative stress, inflammation and cancer:How are they linked? Free Radic. Biol. Med. 49:1603–1616.
37. A.Russo, R.Acquaviva, A.Campisi, V.Sorrenti, C.Di Giacomo, G.Virgata, M.L.Barcellona, and A.Vanella, (2000). Bioflavonoids as antiradicals, antioxidants and DNA cleavage protectors. Cell. Biol. Toxicol. 16:91–98.
38. A.Russo, R.Longo, and A.Vanella, (2002). Antioxidant activity of propolis:Role of caffeic acid phenethyl ester and galangin. Fitoterapia 73(Suppl 1):S21–29.
39. M.Saavedra-Lopes, F.S.Ramalho, L.N.Ramalho, A.Andrade-Silva, A.L.Martinelli, A.A.Jordão, Jr, O.Castro-e-Silva, and S.Zucoloto, (2008). The protective effect of CAPE on hepatic ischemia/reperfusion injury in rats. J. Surg. Res. 150:271–277.
40. A.Sahin, S.Kaya, G.Turkcu, A.K.Cingu, H.Yuksel, F.M.Turkcu, Y.Cinar, S.Ari, M.Sahin, I.Caca, and O.Gokalp, (2013a). The effects of caffeic acid phenethyl ester in acute methanol toxicity on rat retina and optic nerve. Cutan. Ocul. Toxicol. 32:263–267.
41. A.Sahin, A.Kursat Cingu, S.Kaya, G.Turkcu, S.Ari, O.Evliyaoglu, Y.Cinar, F.M.Turkcu, H.Yuksel, M.Murat, I.Caca, and O.Gokalp, (2013b). The protective effects of caffeic acid phenethyl ester in isoniazid and ethambutol-induced ocular toxicity of rats. Cutan. Ocul. Toxicol. 32:228–233.
42. Y.Shi, X.Wu, Y.Gong, Y.Qiu, H.Zhang, Z.Huang, and K.Su, (2010). Protective effects of caffeic acid phenethyl ester on retinal ischemia/reperfusion injury in rats. Curr. Eye. Res. 35:930–937.
43. Sigma-Aldrich (2012). Caffeic acid phenethyl ester. GENERIC EU MSDS. SIGMA-ALDRICH, p. 1–6.
44. G.M.Sulaiman, (2012). Role of caffeic acid phenethyl ester on mitomycin C induced clastogenesis:Analysis of chromosome aberrations, micronucleus, mitotic index and adenosine deaminase activity in vivo. J. Appl. Genet. 53:213–219.
45. Z.Teke, E.B.Bostanci, C.Yenisey, E.C.Kelten, M.Sacar, N.G.Simsek, S.E.Duzcan, and M.Akoglu, (2013). Caffeic Acid phenethyl ester prevents detrimental effects of remote ischemia-reperfusion injury on healing of colonic anastomoses. J. Invest. Surg. 26:16–29.
46. Z.Teke, E.B.Bostanci, C.Yenisey, M.Sacar, N.G.Simsek, and M.Akoglu, (2012). Caffeic acid phenethyl ester alleviates mesenteric ischemia/reperfusion injury. J. Invest. Surg. 25:354–365.
47. M.F.Tolba, S.S.Azab, A.E.Khalifa, S.Z.Abdel-Rahman, and A.B.Abdel-Naim,. (2013). Caffeic acid phenethyl ester, a promising component of propolis with a plethora of biological activities:A review on its anti-inflammatory, neuroprotective, hepatoprotective, and cardioprotective effects. IUBMB Life. 65:699–709.
48. T.Toyoda, T.Tsukamoto, S.Takasu, L.Shi, N.Hirano, H.Ban, T.Kumagai, and M.Tatematsu, (2009). Anti-inflammatory effects of caffeic acid phenethyl ester (CAPE), a nuclear factor-kappaB inhibitor, on Helicobacter pylori-induced gastritis in Mongolian gerbils. Int. J. Cancer J. Int Cancer 125:1786–1795.
49. E.Uz, F.Oktem, H.R.Yilmaz, E.Uzar, and F.Ozguner, (2005). The activities of purine-catabolizing enzymes and the level of nitric oxide in rat kidneys subjected to methotrexate:Protective effect of caffeic acid phenethyl ester. Mol. Cell. Biochem. 277:165–170.
50. E.Uzar, H.R.Koyuncuoglu, E.Uz, H.R.Yilmaz, S.Kutluhan, S.Kilbas, and F.Gultekin, (2006a). The activities of antioxidant enzymes and the level of malondialdehyde in cerebellum of rats subjected to methotrexate:Protective effect of caffeic acid phenethyl ester. Mol. Cell. Biochem. 291:63–68.
51. E.Uzar, O.Sahin, H.R.Koyuncuoglu, E.Uz, O.Bas, S.Kilbas, H.R.Yilmaz, V.A.Yurekli, H.Kucuker, and A.Songur, (2006b). The activity of adenosine deaminase and the level of nitric oxide in spinal cord of methotrexate administered rats:Protective effect of caffeic acid phenethyl ester. Toxicology 218:125–133.
52. S.A.van Acker, D.J.van den Berg, M.N.Tromp, D.H.Griffioen, W.P.van Bennekom, W.J.van der Vijgh, and A.Bast, (1996). Structural aspects of antioxidant activity of flavonoids. Free Radic. Biol. Med. 20:331–342.
53. M.Viuda-Martos, Y.Ruiz-Navajas, J.Fernandez-Lopez, and J.A.Perez-Alvarez, (2008). Functional properties of honey, propolis, and royal jelly. J. Food Sci. 73:R117–124.
54. T.Wang, L.Chen, W.Wu, Y.Long, and R.Wang, (2008). Potential cytoprotection:Antioxidant defence by caffeic acid phenethyl ester against free radical-induced damage of lipids, DNA, and proteins. Can. J. Physiol. Pharmacol. 86:279–287.
55. X.Wang, S.Stavchansky, S.M.Kerwin, and P.D.Bowman, (2010). Structure-activity relationships in the cytoprotective effect of caffeic acid phenethyl ester (CAPE) and fluorinated derivatives:Effects on hemeoxygenase-1 induction and antioxidant activities. Eur. J. Pharmacol. 635:16–22.
56. A.Widjaja, T.H.Yeh, and Y.H.Ju, (2008). Enzymatic synthesis of caffeic acid phenethyl ester. J. Chin. Inst. Chem. Eng. 39:413–418.
57. M.Yagmurca, H.Erdogan, M.Iraz, A.Songur, M.Ucar, and E.Fadillioglu, (2004). Caffeic acid phenethyl ester as a protective agent against doxorubicin nephrotoxicity in rats. Clin. Chim. Acta. 348:27–34.
58. H.R.Yilmaz, S.Sogut, B.Ozyurt, F.Ozugurlu, S.Sahin, B.Isik, E.Uz, and H.Ozyurt, (2005). The activities of liver adenosine deaminase, xanthine oxidase, catalase, superoxide dismutase enzymes and the levels of malondialdehyde and nitric oxide after cisplatin toxicity in rats:Protective effect of caffeic acid phenethyl ester. Toxicol. Ind. Health 21:67–73.
59. H.R.Yilmaz, E.Uz, A.Altunbasak, E.Sakalli, and N.Ozcelik, (2010). Anticlastogenic effect of caffeic acid phenethyl ester on cisplatin-induced chromosome aberrations in rat bone marrow cells. Toxicol. Ind. Health 26:33–37.
60. H.R.Yilmaz, E.Uz, N.Yucel, I.Altuntas, and N.Ozcelik, (2004). Protective effect of caffeic acid phenethyl ester (CAPE) on lipid peroxidation and antioxidant enzymes in diabetic rat liver. J. Biochem. Mol. Toxicol. 18:234–238.