Benedetti A, Comporti M, Fulceri R, Esterbauer H
Biochim Biophys Acta. 1984 Feb 9;792(2):172-81. doi: 10.1016/0005-2760(84)90219-4.
During the NADPH-Fe-induced peroxidation of liver microsomal lipids products are formed which are provided with cytopathological activities. In a previous study one of the major products was identified as an aldehyde of the 4-hydroxyalkenal class, namely 4-hydroxynonenal. In the present study another cytotoxic product has been isolated and identified as 4,5-dihydroxy-2,3-decenal. The isolation was performed by means of thin-layer chromatography and high-pressure liquid chromatography and the structure was ascertained mainly by means of mass spectroscopy of the free aldehyde and of its derivatives. In the absence of NADPH-Fe liver microsomes produced no 4,5-dihydroxydecenal. The inhibitory activity of 4,5-dihydroxydecenal on microsomal glucose-6-phosphatase is somewhat lower than that exhibited by 4-hydroxynonenal. This lower inhibitory activity correlates with the lower capacity to bind to the microsomal protein of 4,5-dihydroxydecenal as compared to 4-hydroxynonenal. The reactivities of the two aldehydes with cysteine were comparable. The production of toxic aldehydes may represent a mechanism by which lipid peroxidation causes deleterious effects on cellular functions.
在NADPH-铁诱导的肝微粒体脂质过氧化过程中，会形成具有细胞病理学活性的产物。在先前的一项研究中，一种主要产物被鉴定为4-羟基烯醛类的醛，即4-羟基壬烯醛。在本研究中，另一种细胞毒性产物已被分离并鉴定为4,5-二羟基-2,3-癸烯醛。分离是通过薄层色谱法和高压液相色谱法进行的，结构主要通过游离醛及其衍生物的质谱法确定。在没有NADPH-铁的情况下，肝微粒体不产生4,5-二羟基癸烯醛。4,5-二羟基癸烯醛对微粒体葡萄糖-6-磷酸酶的抑制活性略低于4-羟基壬烯醛。这种较低的抑制活性与4,5-二羟基癸烯醛与微粒体蛋白结合的能力低于4-羟基壬烯醛有关。两种醛与半胱氨酸的反应性相当。有毒醛的产生可能是脂质过氧化对细胞功能造成有害影响的一种机制。
