Mlakar A, Spiteller G
Lehrstuhl fr Organische Chemie I, Universitt Bayreuth, Germany.
Chem Phys Lipids. 1996 Jan 25;79(1):47-53. doi: 10.1016/0009-3084(95)02506-5.
Arachidonic acid was oxidized by iron ascorbate. Samples were withdrawn in time intervals. The aldehydic oxidation products were trapped by preparation of pentafluorbenzyloximes. Their trimethylsilylated derivatives were subjected to analysis by GC/MS. The main aldehydic lipid peroxidation product was found to be the well-known 4-hydroxy-2-nonenal (HNE), but 2-hydroxy heptanal (HH) -- a previously unknown lipid peroxidation product of arachidonic acid -- was detected to be nearly equally abundant. Malondialdehyde (MDA), glyoxal and 2-hydroxy-4-decenal (HDE) were detected to be produced in up to 100 times lower amounts compared to HNE. The amounts of aldehydes increased steadily with time. In addition, n-l-hydroxy-n-oxo acids were detected. Similar aldehydes were obtained by iron ascorbate-induced oxidation of hydroxy acids derived by NaBH4-reduction of 13-hydroperoxy-9-cis-11-trans-octadecadienoic acid. Since this and analogous hydroxy acids (LOHs) are the main biological degradation products of hydroperoxides of unsaturated acids (LOOHs) their further peroxidation seems to be a main source of toxic aldehydes.
花生四烯酸被抗坏血酸铁氧化。每隔一定时间间隔采集样品。醛类氧化产物通过制备五氟苄基肟进行捕获。它们的三甲基硅烷化衍生物通过气相色谱/质谱联用仪进行分析。主要的醛类脂质过氧化产物被发现是著名的4-羟基-2-壬烯醛（HNE），但2-羟基庚醛（HH）——一种花生四烯酸先前未知的脂质过氧化产物——被检测到含量几乎与HNE相当。丙二醛（MDA）、乙二醛和2-羟基-4-癸烯醛（HDE）被检测到的生成量比HNE低多达100倍。醛类的量随时间稳步增加。此外，还检测到了n-1-羟基-n-氧代酸。通过抗坏血酸铁诱导13-氢过氧-9-顺式-11-反式-十八碳二烯酸经硼氢化钠还原得到的羟基酸氧化，获得了类似的醛类。由于这种及类似的羟基酸（LOHs）是不饱和酸氢过氧化物（LOOHs）的主要生物降解产物，它们的进一步过氧化似乎是有毒醛类的主要来源。
