Yanagimoto Kenichi, Lee Kwang-Geun, Ochi Hirotomo, Shibamoto Takayuki
Japan Institute for the Control of Aging, 723-1 Haruoka, Fukuroi-shi, Shizuoka-ken, 437-01 Japan.
J Agric Food Chem. 2002 Sep 11;50(19):5480-4. doi: 10.1021/jf025616h.
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.
对美拉德反应产物中发现的各种带有不同官能团取代的典型杂环化合物进行了抗氧化活性检测。在所有测试的杂环化合物中，吡咯表现出最大的抗氧化活性。所有吡咯在浓度为50微克/毫升时，40天内对己醛氧化的抑制率几乎达到100%。在吡咯环上添加甲酰基和乙酰基可显著增强抗氧化活性。吡咯-2-甲醛、2-乙酰基吡咯、1-甲基-2-吡咯甲醛和2-乙酰基-1-甲基吡咯在10微克/毫升时对己醛氧化的抑制率>80%。在测试的呋喃中，未取代的呋喃表现出最大的抗氧化活性。本研究中使用的所有官能团添加到呋喃上都会降低抗氧化活性。噻吩的抗氧化活性随着甲基和乙基的添加而增加，但在噻吩上添加甲酰基或乙酰基会降低抗氧化活性。在所有测试浓度下，噻唑和吡嗪均为无效抗氧化剂。所有杂环化合物与过氧化氢反应都会生成各种氧化产物。
