Synthesis and antiradical/antioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analogues

Molecules

Volumn 17, Issue 12, 2012, Pages 14637-14650

  LeBlanc, Luc M ^a   Paré, Aurélie F ^a   Jean Francois, Jacques ^a   Hébert, Martin J G ^a   Surette, Marc E ^a   Touaibia, Mohamed ^a  

^a UNIVERSITÉ DE MONCTON   (Canada)

Author keywords

2 (3,4 Dihydroxyphenyl) acetic acid esters; 3,4 Dihydroxybenzoic acid esters; 3 (3,4 Dihydroxyphenyl) propanoic acid esters; Antioxidant; Caffeic acid; CAPE

Indexed keywords

ACETIC ACID; ANTIOXIDANT; BENZOIC ACID; CAFFEIC ACID DERIVATIVE; CAFFEIC ACID PHENETHYL ESTER; CARBON; DRUG DERIVATIVE; PHENETHYL ALCOHOL; PROPIONIC ACID; PROPIONIC ACID DERIVATIVE; PROPOLIS;

ARTICLE; CHEMISTRY; LIPID PEROXIDATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ACETIC ACID; ANTIOXIDANTS; BENZOIC ACID; CAFFEIC ACIDS; CARBON; LIPID PEROXIDATION; OXIDATION-REDUCTION; PHENYLETHYL ALCOHOL; PROPIONATES; PROPOLIS;

EID: 84871547129     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171214637     Document Type: Article

References (31)

1. Newman, D.J. Natural Products as Sources of New Drugs over the Period 1981-2002. J. Nat. Prod. 2003, 66, 1022-1037.
2. Deshpande, S.S.; Sathe, S.K.; Salunkhe, D.K. Chemistry and safety of plant polyphenols. Adv. Exp. Med. Biol. 1984, 177, 457-495.
3. Harris, P.J.; Hartley, R.D. Detection of bound ferulic acid in cell walls of the gramineae by ultraviolet fluorescent microscopy. Nature 1976, 259, 508-510.
4. Hartley, R.D.; Morrison, W.H.; Himmelsbach, D.S.; Borneman, N.S. Cross-linking of cell wall phenolics to arabinoxylans in graminaceous plants. Phytochemistry 1990, 29, 3701-3709.
5. Cuvelier, M.E.; Richard, H.; Berset, C. Comparison of the antioxidant activity of some acid phenols:structure-activity relationship. Biosci. Biotechnol. Biochem. 1992, 56, 324-325.
6. Maillard, M.N.; Soum, M.H.; Boivia, P.; Berset, C. Antioxidant activity of barley and malt: Relationship with phenolic content. Lebensm.-Wiss.-Technol. 1996, 3, 238-244.
7. Friedman, M. Chemistry, biochemistry and dietary role of potato polyphenols: A review. J. Agric. Food Chem. 1997, 45, 1523-1540.
8. Michaluart, P.; Masferrer, J.L.; Carothers, A.M.; Subbaramaiah, K.; Zweifel, B.S.; Koboldt, C.; Mestre, J.R.; Grunberger, D.; Sacks, P.G.; Tanabe, T.; et al. Inhibitory Effects of Caffeic Acid Phenethyl Ester on the Activity and Expression of Cyclooxygenase-2 in Human Oral Epithelial Cells and in a Rat Model of Inflammation. Cancer Res. 1999, 59, 2347-2352.
9. Liao, H.F.; Chen, Y.Y.; Liu, J.J.; Hsu, M.L.; Shieh, H.J.; Liao, H.J.; Shieh, C.J.; Shiao, M.S.; Chen, Y.J. Inhibitory effect of caffeic acid phenethyl ester on angiogenesis, tumor invasion and metastasis. J. Agric. Food Chem. 2003, 51, 7907-7912.
10. Baranowski, J.D.; Davidson, P.M.; Nagel, C.W.; Brannen, R.L. Inhibition of Saccharomyces cerevisiae by naturally occurring hydroxy cinnamates. J. Food Sci. 1980, 45, 592-594.
11. Natarajan, K.; Singh, S.; Burke, T.R., Jr.; Grunberger, D.; Aggarwal, B.B. Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kB. Proc. Natl. Acad. Sci. USA 1996, 93, 9090-9095.
12. Sugiura, M.; Naito, Y.; Yamaura, Y.; Fukaya, C.; Yokohama, K. Inhibitory activities and inhibition specificities of caffeic acid derivatives and related compounds toward 5-lipoxygenase. Chem. Pharm. Bull. 1989, 37, 1039-1043.
13. Toyoda, T.; Tsukamoto, T.; Takasu, S.; Shi, L.; Hirano, N.; Ban, H.; Kumagai, T.; Tatematsu, M. 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 2009, 125, 1786-1795.
14. Son, S.; Lewis, B.A. Free radical scavenging and antioxydative activity of caffeic acid amide and ester analogues: Structure-activity relationship. J. Food Agric. Chem. 2002, 50, 468-472.
15. Göçer, H.; Gülçin, I. Caffeic acid phenethyl ester (CAPE): Correlation of structure and antioxidant properties. Int. J. Food Sci. Nutr. 2011, 62, 821-825.
16. Jayaprakasam, B.; Vanisree, M.; Zhang, Y.; Dewitt, D.L.; Nair, M.G. Impact of alkyl esters of caffeic acid and ferulic acids on tumor cell proliferation, cyclooxygenase enzyme and lipid peroxidation. J. Agric. Food Chem. 2006, 54, 5375-5381.
17. Silva, F.A.M.; Borges, F.; Guimaraes, C.; Lima, J.L.F.C.; Matos, C.; Reis, S. Phenolic acids and derivatives: Studies on the relationship among structure, radical scavenging activity and physicochemical properties. J. Agric. Food Chem. 2000, 48, 2122-2126.
18. Zhang, Z.; Xiao, B.; Chen, Q.; Lian, X.Y. Synthesis and biological evaluation of caffeic acid 3,4-dihydroxyphenethyl ester. J. Nat. Prod. 2010, 73, 252-254.
19. Tazaki, H.; Taguchi, D.; Hayashida, T.; Nabeta, K. Stable isotope-labeling studies on the oxidative coupling of caffeic acid via o-quinone. Biosci. Biotechnol. Biochem. 2001, 65, 2613-2621.
20. Saito, S.; Kurakane, S.; Seki, M.; Takai, E.; Kasai, T.; Kawabata, J. Radical scavenging activity of dicaffeoyloxycyclohexanes: Contribution of an intramolecular interaction of two caffeoyl residues. Bioorg. Med. Chem. 2005, 13, 4191-4199.
21. Prior, R.L.; Wu, X.L.; Schaich, K. Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J. Agric. Food Chem. 2005, 53, 4290-4302.
22. Huang, D.; Ou, B.; Prior, R.L. The chemistry behind antioxidant capacity assays. J. Agric. Food Chem. 2005, 53, 1841-1856.
23. Akita, H.; Nozawa, M.; Mitsuda, A.; Ohsawa, H. A convenient synthesis of (+)-albicanol based on enzymatic function: Total syntheses of (+)-albicanyl acetate, (-)-albicanyl 3,4-dihydroxycinnamate, (-)-drimenol, (-)-drimenin and (-)-ambrox. Tetrahedron: Asymmetry 2000, 11, 1375-1388.
24. Touaibia, M.; Guay, M. Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), A Potent 5-Lipoxygenase Inhibitor from Honeybee Hives. J. Chem. Educ. 2011, 88, 473-475.
25. Bruckner, R. Advanced Organic Chemistry: Reaction Mechanisms; Harcourt/Academic Press: San Diego, CA, USA, 2002; pp. 238-240.
26. Magalhaes, L.M.; Segundo, M.A.; Reis, S.; Lima, J.F.L.C. Methodological aspects about in vitro evaluation of antioxidant properties. Anal. Chim. Acta 2008, 613, 1-19.
27. Gülçin, I. Antioxydant activity of food constituents. Arch. Toxicol. 2012, 86, 345-391.
28. Boudreau, L.H.; Maillet, J.; LeBlanc, L.M.; Jean-François, J.; Touaibia, M.; Flamand, N.; Surette, M.E. Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes. PLoS One 2012, 7, e31833.
29. Lee, Y.; Shin, D.; Kim, J.H.; Hong, S.; Choi, D.; Kim, Y.J.; Kwak, M.K.; Jung, Y. Caffeic acid phenethyl ester-mediated Nfr-2 activation and IκB kinase inhibition are involved in NFκB inhibitory effect: Structural analysis of NFκB inhibition. Eur. J. Pharmacol. 2010, 643, 21-28.
30. Liégeois, C.; Lermusieau, G.; Collin, C. Measuring antioxidant efficiency of wort, malt and hop against 2, 2'-azobis(2-amidopropane)- dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid. J. Agric. Food Chem. 2000, 48, 1129-1134.
31. Lin, C.F.; Chang, T.C.; Chiang, C.C.; Tsai, H.J.; Hsu, L.Y. Synthesis of selenium containing polyphenolic acid esters an evaluation of their effects on antioxydation and 5-lipoxygenase inhibition. Chem. Pharm. Bull. 2005, 53, 1402-1407.