Antioxidant Properties of Novel Tetraoxygenated Phenylindan Isomers Formed during Thermal Decomposition of Caffeic Acid

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 9, 1996, Pages 2503-2510

  Guillot, François L ^a   Malnoë, Armand ^a   Stadler, Richard H ^a  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Antioxidants, prooxidants; Caffeic acid; Lipid peroxidation; Phenylindan isomers; Polyphenols

Indexed keywords

EID: 0001176052     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9508155     Document Type: Article

References (52)

1. Aeschbach, R.; Aeschbacher H. U.; Philippossian G. H. Procédé d'obtention d'acide carnosique et son utilisation pour ses propriétés anticarcinogènes et antivirales. Eur. Pat. No. 90119218.7, 1990.
2. Aeschbach, R.; Löliger, J.; Scott, B. C.; Murcia, A.; Butler, J.; Halliwell, B.; Aruoma, O. I. Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol. Food Chem. Toxicol. 1994, 32, 31-36.
3. Ames, B. N.; Gold, L. S. Endogenous mutagens and the causes of aging and cancer. Mutat. Res. 1991, 250, 3-16.
4. Ames, B. N.; Shigenaga, M. K.; Hagen, T. M. Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7915-7922.
5. Ames, B. N.; Gold, L. S.; Willett, W. C. Review. The causes and prevention of cancer. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 5258-5265.
6. Aruoma, O. I. Prooxidant properties: an important consideration for food additives and /or nutrient components? In Free Radicals and Food Additives; Aruoma, O. I., Halliwell, B., Eds.; Taylor & Francis: London, 1991; pp 173-195.
7. Aruoma, O. I. Nutrition and health aspects of free radicals and antioxidants. Food Chem. Toxicol. 1994, 32, 671-683.
8. Aruoma, O. I.; Evans, P. J.; Kaur, H.; Sutcliffe, L.; Halliwell, B. An evaluation of the antioxidant and potential prooxidant properties of food additives and of trolox c, vitamin E and probucol. Free Radical Res. Commun. 1990, 10, 143-147.
9. Buege, J. A.; Aust, S. D. Microsomal lipid peroxidation. Methods Enzymol. 1978, 12, 302-310.
10. Clifford, M. N. Chlorogenic acids. In Coffee, Vol. 1: Chemistry; Clarke, R. J., Macrae, R., Eds.; Elsevier Applied Science: London, 1985; pp 153-202.
11. 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.
12. Eriksson, C. E.; Na, A. Antioxidant agents in raw materials and processed foods. In Free Radicals and Antioxidants in Nutrition; Corongiu, F., Banni, S., Dessi, M. A., Rice-Evans, C., Eds.; Richelieu Press: London, 1993; pp 205-225.
13. Fischer-Nielsen, A.; Poulsen, H. E.; Loft, S. 8-Hydroxydeoxyguanosine in vitro: effects of glutathione, ascorbate, and 5-aminosalicylic acid. Free Radicals Biol. Med. 1992, 13, 121-126.
14. Graf, E. Antioxidant potential of ferulic acid. Free Radicals Biol. Med. 1992, 13, 435-448.
15. Gutteridge, J. M. C.; Xaio-Chang, F. Enhancement of bleomycin-iron free radical damage to DNA by antioxidants and their inhibition of lipid peroxidation. FEBS Lett. 1981, 123, 71-74.
16. Halliwell, B. How to characterise a biological antioxidant. Free Radical Res. Commun. 1990, 9, 1-32.
17. Halliwell, B. Vitamin C: the key to health or a slow-acting carcinogen? Redox Rep. 1994, 1, 5-9.
18. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 2nd ed,; Clarendon Press: Oxford, 1989.
19. Halliwell, B.; Aeschbach, R.; Löliger, J.; Aruoma, O. I. The characterization of antioxidants. Food Chem. Toxicol. 1995, 33, 601-617.
20. Hanham, A. F.; Dunn, B. P.; Stich, H. F. Clastogenic activity of caffeic acid and its relationship to hydrogen peroxide generated during autooxidation. Mutat. Res. 1983, 116, 333-339.
21. Harman, D. The aging process. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 7124-7128.
22. Inoue, S.; Ito, K.; Yamamoto, K.; Kawanishi, S. Caffeic acid causes metal-dependent damage to cellular and isolated DNA through hydrogen peroxide formation. Carcinogenesis 1992, 13, 1497-1502.
23. Kasai, H.; Nishimura, S. Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 1984, 12, 2137-2145.
24. Kasai, H.; Nishimura, S. Hydroxylation of guanine in nucleosides and DNA at the C-8 position by heated glucose and oxygen radical forming agents. Environ. Health Perspect. 1986, 67, 111-116.
25. King, D. L.; Hahm, T. S.; Min, D. B. Chemistry of antioxidants in relation to shelf life of foods. In Shelf Life Studies of Foods and Beverages; Charalambous, G., Ed.; Elsevier: Amsterdam, 1993; pp 629-650.
26. Kitahara, K.; Matsumoto, Y.; Ueda, H.; Ueoka, R. A remarkable antioxidation effect of natural phenol derivatives on the autoxidation of gamma-irradiated methyl linoleate. Chem. Pharm. Bull. 1992, 40, 2208-2209.
27. Kitta, K.; Hagiwara, Y.; Shibamoto, T. Antioxidative activity of an isoflavanoid, 2″-O-glycosylisovitexin isolated from green barley leaves. J. Agric. Food Chem. 1992, 40, 1843-1845.
28. Kroyer, G. Th.; Kretschmer, L.; Washütti, J. Antioxidant properties of tea and coffee extracts. Agric. Food Chem. Consum., Proc. Ear. Conf. Food Chem. 1989, 5, 433-437.
29. Laranjinha, J.; Almeida, L.; Madeira, V. Reduction of ferrylmyoglobin by dietary phenolic acid derivatives of cinnamic acid. Free Radicals Biol. Med. 1995, 19, 329-337.
30. Lin, T. S.; Cheng, J.-C.; Ishiguro, K.; Sartorelli, A. C. 8-Substituted guanosine and 2′-deoxyguanosine derivatives as potential inducers of Friend erythroleukemia cells. J. Med. Chem. 1985, 28, 1194-1198.
31. Löliger, J.; Wille, H. J. Natural antioxidants. Oils Fats Int. 1993, 9, 18-22.
32. Macku, C. T.; Shibamoto, T. Volatile antioxidants isolated from brewed coffee. 14th ASIC, San Fransisco, CA, 1991; pp 146-155.
33. Mahoney, J. R.; Graf, E. Role of alpha-tocopherol, ascorbic acid, citric acid and EDTA as oxidants in model systems. J. Food Sci. 1986, 51, 1293-1296.
34. Maiorino, M. A.; Zamburlini, A.; Roveri, A.; Ursini, F. Prooxidant role of vitamin E in copper induced lipid peroxidation. FEBS Lett. 1993, 330, 174-176.
35. Marklund, S.; Marklund, G. Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur. J. Biochem. 1974, 47, 469-474.
36. Matsuzaki, T.; Hara, M. Antioxidative activity of tea leaf catechins. Nippon Nogeikegatu Kai Shi 1985, 59, 129-134.
37. Namiki, M. Antioxidants/Antimutagens in food. Crit. Rev. Food. Sci. Nutr. 1990, 29, 4, 273-300.
38. Namiki, M. The chemistry and physiological functions of sesame. Food Rev. Int. 1995, 11, 281-329.
39. Okuda, T. Natural polyphenols as antioxidants and their potential use in cancer prevention. In Polyphenolic Phenomena; Scalbert, A., Ed.; INRA: Paris, 1993; pp 221-235.
40. Osawa, T.; Katsuzaki, H.; Hagiwara, Y.; Hagiwara, H.; Shibamoto, T. A novel antioxidant isolated from young green barley leaves. J. Agric. Food Chem. 1992, 40, 1135-1138.
41. Pratt, D. E. Natural antioxidants from plant material. In Phenolic Compounds in Food and Their Effects on Health; Huang, M.-T., Ho, C.-T., Lee, C. Y., Eds.; ACS Symposium Series; Washington DC, 1992; Vol. II, pp 55-71.
42. Scott, B. C.; Butler, J.; Halliwell, B.; Aruoma, O. I. Evaluation of the antioxidant actions of ferulic acid and catechins. Free Radical Res. Commun. 1993, 19, 241-253.
43. Sharma, O. P. Antioxidant activity of curcumin and related compounds. Biochem. Pharmacol. 1976, 25, 1811-1812.
44. Stadler, R. H. Phenylindans, their preparation and utilization. Eur. Pat. No. 94109355.1, 1994.
45. Stadler, R. H.; Turesky, R. J.; Müller, O.; Markovic, J.; Leong-Morgenthaler, P.-M. The inhibitory effects of coffee on radical-mediated oxidation and mutagenicity. Mutat. Res. 1994, 308, 177-190.
46. Stadler, R. H.; Welti, D. H.; Stämpfli, 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.
47. 2 oxidation system. J. Agric. Food Chem. 1991, 39, 439-442.
48. Tatum, V. L.; Changchit, C.; Chow, C. K. Measurement of malondialdehyde by HPLC with fluorescence detection. Lipids 1990, 25, 226-229.
49. Taylor, A. R.; Keen, G. W.; Eisenbraun, E. J. Cyclodimerization of styrene. J. Org. Chem. 1977, 42, 3477-3480.
50. Toda, S.; Miyase, T.; Arichi, H.; Tanizawa, H.; Takino, Y. Natural antioxidants III. Antioxidative components isolated from rhizome of Curcuma longa L. Chem. Pharm. Bull. 1985, 53, 1725-1728.
51. Tyson, C. A.; Martell, A. E. Kinetics and mechanism of the metal chelate catalysed oxidation of pyrocatechols. J. Am. Chem. Soc. 1972, 94, 939-945.
52. Uchiyama, M.; Mihara, M. Determination of malonaldehyde precursor in tissues by thiobarbituric acid test. Anal. Biochem. 1977, 86, 271-278.