Antioxidative activity of heterocyclic compounds formed in Maillard reaction products

Kenichi Yanagimoto; Kwang Geun Lee; Hirotomo Ochi; Takayuki Shibamoto

doi:10.1016/S0531-5131(02)01007-5

Antioxidative activity of heterocyclic compounds formed in Maillard reaction products

Kenichi Yanagimoto, Kwang Geun Lee, Hirotomo Ochi, Takayuki Shibamoto

Department of Food Science & Biotechnology

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

Typical heterocyclic compounds substituted with various functional groups found in Maillard reaction 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 a formyl group to the pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde inhibited hexanal oxidation by about 90% at 5 μg/ml. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups tested to the furan decreased antioxidative activity. Antioxidant activity of thiophene was increased by the addition of methyl groups, but addition of formyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested.

Original language	English
Pages (from-to)	335-340
Number of pages	6
Journal	International Congress Series
Volume	1245
Issue number	C
DOIs	https://doi.org/10.1016/S0531-5131(02)01007-5
State	Published - 1 Nov 2002

Keywords

Antioxidants
Heterocyclic compounds
Maillard reaction

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10.1016/S0531-5131(02)01007-5

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title = "Antioxidative activity of heterocyclic compounds formed in Maillard reaction products",

abstract = "Typical heterocyclic compounds substituted with various functional groups found in Maillard reaction 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 a formyl group to the pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde inhibited hexanal oxidation by about 90% at 5 μg/ml. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups tested to the furan decreased antioxidative activity. Antioxidant activity of thiophene was increased by the addition of methyl groups, but addition of formyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested.",

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T1 - Antioxidative activity of heterocyclic compounds formed in Maillard reaction products

AU - Yanagimoto, Kenichi

AU - Lee, Kwang Geun

AU - Ochi, Hirotomo

AU - Shibamoto, Takayuki

PY - 2002/11/1

Y1 - 2002/11/1

N2 - Typical heterocyclic compounds substituted with various functional groups found in Maillard reaction 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 a formyl group to the pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde inhibited hexanal oxidation by about 90% at 5 μg/ml. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups tested to the furan decreased antioxidative activity. Antioxidant activity of thiophene was increased by the addition of methyl groups, but addition of formyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested.

AB - Typical heterocyclic compounds substituted with various functional groups found in Maillard reaction 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 a formyl group to the pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde inhibited hexanal oxidation by about 90% at 5 μg/ml. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups tested to the furan decreased antioxidative activity. Antioxidant activity of thiophene was increased by the addition of methyl groups, but addition of formyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested.

KW - Antioxidants

KW - Heterocyclic compounds

KW - Maillard reaction

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Antioxidative activity of heterocyclic compounds formed in Maillard reaction products

Abstract

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