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Antioxidative Activity of Heterocyclic Compounds Found in Coffee Volatiles Produced by Maillard Reaction

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Japan Institute for the Control of Aging, 723-1 Haruoka, Fukuroi-shi, Shizuoka-ken, 437-01 Japan, and Department of Environmental Toxicology, University of California, Davis, California 95616
Cite this: J. Agric. Food Chem. 2002, 50, 19, 5480–5484
Publication Date (Web):August 6, 2002
https://doi.org/10.1021/jf025616h
Copyright © 2002 American Chemical Society

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    Abstract

    Typical heterocyclic compounds substituted with various functional groups found in Maillard reaction products were examined for antioxidant activity. Pyrroles exhibited the greatest antioxidant activity among all heterocyclic compounds tested. All pyrroles inhibited hexanal oxidation by almost 100% at a concentration of 50 μg/mL over 40 days. Addition of formyl and acetyl groups to a pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde, 2-acetylpyrrole, 1-methyl-2-pyrrolecarboxaldehyde, and 2-acetyl-1-methylpyrrole inhibited hexanal oxidation by >80% at 10 μg/mL. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups used in this study to furan decreased antioxidative activity. The antioxidant activity of thiophene increased with the addition of methyl and ethyl groups, but the addition of formyl or acetyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested. Reaction of all heterocyclic compounds with hydrogen peroxide resulted in the formation of various oxidized products.

    Keywords: Antioxidants; heterocyclic compounds; pyrroles; furans; thiophenes

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     Japan Institute for the Control of Aging.

     University of California.

    *

     Author to whom correspondence should be addressed [telephone (530) 752-4523; fax (530) 752-3394; e-mail [email protected]].

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