Antioxidant Activities of Caffeic Acid and Its Related Hydroxycinnamic Acid Compounds

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 7, 1997, Pages 2374-2378

  Chen, Jiang Hong ^a   Ho, Chi Tang ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Antioxidants; Caffeic acid; Caffeic acid phenethyl ester; Free radical scavenging activity; Hydroxycinnamic acids

Indexed keywords

ZEA MAYS;

EID: 0001011682     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970055t     Document Type: Article

References (40)

1. Baltes, W. Precursors of color and aroma formation in coffee; Association Scientifique Internationale du Cafe (ASIC Symposium); Technical University of Berlin, 1976; pp 91-107.
2. Blois, M. S. Antioxidant determinations by the use of a stable free radical. Nature 1958, 181, 1199-1200.
3. Brand-Willams, W.; Cuvelier, M. E.; Berset, C. Use of free radical method to evaluate antioxidant activity. Food Sci. Technol. (London) 1995, 28, 25-30.
4. Chan, R. I.; San, R. H.; Stich, H. F. Mechanism of inhibition of N-methyl-N′-nitrosoguanidine-induced mutagenesis by phenolic compounds. Cancer Lett. 1986, 31, 27-34.
5. Chen, C. W.; Ho, C.-T. Antioxidant properties of polyphenols extracted from green and black teas. J. Food Lipids 1995, 2, 35-46.
6. Chen, H. M.; Muramoto, K.; Yamauchi, F.; Nokihara, K. Antioxidant activity of designed peptides based on the antioxidative peptide isolated from digests of a soybean protein. J. Agric. Food Chem. 1996, 44, 2619-2623.
7. Chen, J. H.; Shao, Y.; Huang, M.-T.; Chin, C. K.; Ho, C.-T. Inhibitory effect of caffeic acid phenethyl ester on human leukemia HL-60 cells. Cancer Lett. 1996, 108, 211-214.
8. Cuvelier, M. E.; Richard, H.; Berset, C. Comparison of the antioxidative activity of some acid-phenols: structure-activity relationship. Biosci., Biotechnol., Biochem. 1992, 56, 324-325.
9. Cuvelier, M. E.; Richard, H.; Berset, C. Antioxidative activity and phenolic composition of pilot-plant and commercial extracts of sage and rosemary. J. Am. Oil Chem. Soc. 1996, 73, 645-652.
10. Frankel, E. N.; Huang, S. W. Evaluation of antioxidant activity of rosemary extracts, carnosol and carnosic acid in bulk vegetable oils and fish oils and their emulsions. J. Sci. Food Agric. 1996, 72, 201-208.
11. Frankel, E. N.; Huang, S. W.; Kanner, J.; German, J. B. Interfacial phenomena in the evaluation of antioxidants: Bulk oils vs emulsions. J. Agric. Food Chem. 1994, 42, 1054-1059.
12. Frankel, E. N.; Huang, S. W.; Aeschbach, R.; Prior, E. Antioxidant activity of rosemary extract and its constituents, carnosic acid, carnosol, and rosemarinic acid, in bulk oils and oil-in-water emulsion. J. Agric. Food Chem. 1996, 44, 131-135.
13. Graf, E. Antioxidant potential of ferulic acid. Free Radical Biol. Med. 1992, 13, 435-448.
14. Grunberger, D.; Banerjee, R.; Eisinger, K.; Oltz, E. M.; Efros, L.; Caldwell, M.; Estevez, V.; Nakanishi, K. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis. Experientia 1988, 44, 230-232.
15. Guliiot, F. L.; Malnoee, A.; Stadler, R. H. Antioxidant properties of novel tetraoxygenated phenylindan isomers formed during thermal decomposition of caffeic acid. J. Agric. Food Chem. 1996, 44, 2503-2510.
16. Hayase, F.; Kato, H. Antioxidative components of sweet potatoes. J. Nutr. Sci. Vitaminol. 1984, 30, 37-46.
17. Herrmann, K. Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods. Crit. Rev. Food Sci. Nutr. 1989, 28, 315-347.
18. Herrmann, K. Contents of principle plant phenols in fruits. Fluess. Obst 1992, 59, 66-70.
19. Herrmann, K. Phenolcarboxylic acids in plant foods and their antioxidative activity. Gordian 1993, 93, 92-96.
20. Hopia, A. I.; Huang, S. W.; Schwarz, K.; German, J. B.; Frenkel, E. N. Effect of different lipid systems on antioxidant activity of rosemary constituents carnosol and carnosic acid with and without α-tocopherol. J. Agric. Food Chem. 1996, 44, 2030-2036.
21. Huang, M.-T.; Smart, R. C.; Wong, C. Q.; Conney, A. H. Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res. 1988 48, 5941-5946.
22. Huang, S. W.; Frankel, E. N.; Schwarz, K.; Aeschbach, R.; German, J. B. Effect of pH on antioxidant activity of α-tocopherol and trolox in oil-in-water emulsions. J. Agric. Food Chem. 1996a, 44, 2496-2502.
23. Huang, S. W.; Frankel, E. N.; Schwarz, K.; Aeschbach, R.; German, J. B. Antioxidant activity of carnosic acid and methyl carnosate in bulk oils and oil-in-water emulsions. J. Agric. Food Chem. 1996b, 44, 2951-2956.
24. Jackson, G. M. The effects of endogenous phenolic acids on the rheology of wheat flour doughs. Diss. Abstr. Int., B 1983, 44, 1439.
25. 2-dependent low density lipoprotein lipid peroxidation by naturally occurring phenolic acids. Biochem. Pharmacol. 1996, 51, 395-402.
26. Leung, J.; Fenton, T. W.; Clandinin, D. R. Phenolic components of sunflower flour. J. Food Sci. 1981, 46, 1386-1388, 1393.
27. Maillard, M. N.; Berset, C. Evolution of antioxidant activity during kilning: role of insoluble bound phenolic acids of barley and malt. J. Agric. Food Chem. 1995, 43, 1789-1793.
28. Marinova, E. M.; Yanishlieva, N. V. Effect of temperature on the antioxidative action of inhibitors in lipid antioxidation. J. Sci. Food Agric. 1992, 60, 313-318.
29. Mieth, G.; Pohl, J.; Kozlowska, H.; Rotkiewicz, D. A. Phenolic constituents of sunflower seed II. Effect of phenolic acids on solubility characteristics of plant proteins Nahrung 1992, 26, K11-K13.
30. Nardini, M.; D'Aquino, M.; Tomassi, G.; Gentili, V.; Di Felice, M.; Scaccini, C. Inhibition of human low-density-lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radical Biol. Med. 1995, 19, 541-552.
31. Ohnishi, M.; Morishita, H.; Iwahashi, H.; Toda, S.; Shiratati, Y.; Kimura, M.; Kido, R. Inhibitory effects of chlorogenic acid on linoleic acid peroxidation and haemlysis. Phytochemistry 1994, 36, 579-583.
32. Peleg, H.; Naim, M.; Zehavi, U.; Rouseff, R. L.; Nagy, S. Pathways of 4-vinylguaiacol formation from ferulic acid in model solutions of orange juice. J. Agric. Food Chem. 1992, 40, 764-767.
33. Rao, C. V.; Desai, D.; Rivenson, A.; Simi, B.; Amin, S.; Reddy, B. S. Chemoprevention of colon carcinogenesis by phenyl-ethyl-3-methylcaffeate. Cancer Res. 1995, 55, 2310-2315.
34. Rodriguez de Sotillo, D.; Hadley, M.; Holm, E. T. Phenolics in aqueous potato peel extract: extraction, identification and degradation. J. Food Sci. 1994, 59, 649-651.
35. Rybka, K.; Sitarski, J.; Raczyaaka-Bojanowska, K. Ferulic acid in rye and wheat grain and grain dietary fiber. Cereal Chem. 1993, 71, 55-59.
36. Schwarz, K.; Frankel, E. N.; German, J. B. Partition behavior of antioxidative phenolic compounds in heterophasic systems. Fett/Lipid 1996, 98, 115-121.
37. Smith, A. W. Introduction. In Coffee; Clarke, R. J., Macrae, R., Eds.; Elsevier Applied Science Publication: New York 1985; Vol. 1, p 33.
38. Stadler, R. H.; Welti, D. H.; Staempfli, A. A.; Fay, L. B. Thermal decomposition of caffeic acid in model systems: Identification of novel tetraoxygenated phenylindan isomers and their stability in aqueous solution. J. Agric. Food Chem. 1996, 44, 898-905.
39. Sud'ina, G. F.; Mirzoeva, O. K.; Pushkaraeva, M. A.; Korshunova, G. A.; Shubatyan, N. V.; Varfolomeev, S. D. Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties. FEBS Lett. 1993, 329, 21-24.
40. Terao, J.; Karasawa, H.; Arai, H.; Nagao, A.; Suzuki, T.; Takawa, K. Peroxyl radical scavenging activity of caffeic acid and its related phenolic compounds in solution. Biosci., Biotechnol., Biochem. 1993, 57, 1204-1205.