Journal Article

Formation of the mutagenic/carcinogenic imidazoquinoxaline-type heterocyclic amines through the unstable free radical Maillard intermediates and its inhibition by phenolic antioxidants

Tetsuta Kato, Takehiro Harashima, Natsumi Moriya, Kiyomi Kikugawa and Kazuyuki Hiramoto

in Carcinogenesis

Volume 17, issue 11, pages 2469-2476
Published in print November 1996 | ISSN: 0143-3334
Published online November 1996 | e-ISSN: 1460-2180 | DOI: http://dx.doi.org/10.1093/carcin/17.11.2469
Formation of the mutagenic/carcinogenic
                    imidazoquinoxaline-type heterocyclic amines through the unstable free radical
                    Maillard intermediates and its inhibition by phenolic
                    antioxidants

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Generation of the imidazoquinoxaline-type heterocyclic amines in the heated model system composed of glucose/ glycine/creatinine in aqueous diethylene glycol was effectively prevented by phenolic antioxidants, butylated hydro-xyanisole (BHA), propyl gallate (PG), sesamol, esculetin and epigallocatechin gallate (EGCG) in a dose-dependent manner. Generation of the mutagens in heated-and-dried bonito meat was effectively prevented on pretreatment with EGCG or green tea extract. Electron spin resonance (ESR) studies showed that the heated model mixture of glucose/ glycine generated the unstable pyrazine cation radical, and its formation was inhibited by BHA, sesamol and EGCG. ESR-spin trapping studies using 5, 5-dimethyl-l-pyrroline N-oxide (DMPO) and N-tert-butyl-α-phenylnitrone (PBN) showed that the heated model mixture of glucose/glycine or glucose/glycine/creatinine generated unstable carbon-centred radical(s), and their formation was effectively inhibited by BHA, sesamol and EGCG. It is likely that the unstable free radical Maillard intermediates played an important role in the formation of the imidazoquinoxaline-type heterocyclic amines, and the phenolic antioxidants effectively scavenged the radical species to prevent the mutagen formation.

Journal Article.  0 words. 

Subjects: Clinical Cytogenetics and Molecular Genetics

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