d'Ischia M, Costantini C, Prota G
Department of Organic and Biological Chemistry, University of Naples Federico II, Italy.
Biochim Biophys Acta. 1996 Aug 13;1290(3):319-26. doi: 10.1016/0304-4165(96)00036-0.
Iron-promoted autoxidation of arachidonic acid in acetate buffer (pH 6.0) at 37 degrees C in the presence of glycine led to the formation after 24 h of a complex pattern of fluorescent products, one of which was identified as 1-carboxymethyl-4-methyl-1,4-dihydropyridine-3,5-dicarboxaldehyde (1), arising by reaction of glycine with malondialdehyde. When glutamic acid was used as the amine compound, the corresponding dihydropyridine 2 was detected in the oxidation mixture. Formation of adducts 1 and 2 was markedly decreased at pH 7.4, or in the presence of a large excess of the amino acid, and was suppressed by glutathione or ascorbic acid. In the presence of dopamine, norepinephrine or serotonin, autoxidation of arachidonic acid led likewise to complex patterns of fluorescent products, but no evidence of the dihydropyridine adducts 3-5, nor of their oxidation products 6-8 was obtained. No malondialdehyde-derived product could be detected when linoleic acid was used as the fatty acid. These and other results that are presented suggest that malondialdehyde is a possible contributor to, but not the primary determinant of fluorescent pigment formation by peroxidative degradation of polyunsaturated fatty acids in the presence of amine compounds.
在37摄氏度、pH值为6.0的醋酸盐缓冲液中，在甘氨酸存在的情况下，铁促进的花生四烯酸自氧化在24小时后导致形成了复杂的荧光产物模式，其中一种被鉴定为1 - 羧甲基 - 4 - 甲基 - 1,4 - 二氢吡啶 - 3,5 - 二甲醛（1），它是由甘氨酸与丙二醛反应产生的。当使用谷氨酸作为胺类化合物时，在氧化混合物中检测到了相应的二氢吡啶2。在pH值为7.4时，或在存在大量过量氨基酸的情况下，加合物1和2的形成显著减少，并且被谷胱甘肽或抗坏血酸抑制。在多巴胺、去甲肾上腺素或血清素存在的情况下，花生四烯酸的自氧化同样导致了复杂的荧光产物模式，但未获得二氢吡啶加合物3 - 5及其氧化产物6 - 8的证据。当使用亚油酸作为脂肪酸时，未检测到丙二醛衍生的产物。本文呈现的这些及其他结果表明，丙二醛可能是胺类化合物存在时多不饱和脂肪酸过氧化降解形成荧光色素的一个促成因素，但不是主要决定因素。
