Antioxidative activity of heterocyclic compounds found in coffee volatiles produced by Maillard reaction.
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 microg/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 microg/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.
Yanagimoto
Kenichi
K
Japan Institute for the Control of Aging, 723-1 Haruoka, Fukuroi-shi, Shizuoka-ken, 437-01 Japan.
Lee
Kwang-Geun
KG
Ochi
Hirotomo
H
Shibamoto
Takayuki
T
D000447:Aldehydes / Q000737:chemistry; D000975:Antioxidants / Q000494:pharmacology*; D003069:Coffee / Q000737:chemistry*; D005663:Furans / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000032:analysis* / Q000494:pharmacology*; D015416:Maillard Reaction; D011719:Pyrazines / Q000494:pharmacology; D011758:Pyrroles / Q000494:pharmacology; D013844:Thiazoles / Q000494:pharmacology; D013876:Thiophenes / Q000494:pharmacology; D014835:Volatilization
D000447:Aldehydes; D000975:Antioxidants; D003069:Coffee; D005663:Furans; D006571:Heterocyclic Compounds; D011719:Pyrazines; D011758:Pyrroles; D013844:Thiazoles; D013876:Thiophenes; C010463:n-hexanal