Wachtel Ellen, Bach Diana, Epand Raquel F, Tishbee Arye, Epand Richard M
Chemical Research Infrastructure Unit, Weizmann Institute of Science, Rehovot, Israel.
Biochemistry. 2006 Jan 31;45(4):1345-51. doi: 10.1021/bi0516778.
There is evidence that some products of the reaction of ozone with cholesterol contribute to atherosclerosis. One of these compounds is 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al. We have synthesized this compound and have demonstrated that it reacts with phosphatidylethanolamine to form a Schiff base. The 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al also affects the physical properties of phosphatidylethanolamines. We show by both DSC and X-ray diffraction that it increases the negative curvature of the membrane. In addition, 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al causes the lamellar phase to become disorganized, resulting in the loss of lamellar periodicity. The chemical and physical interactions of 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al with phosphatidylethanolamines may contribute to damaging effects of this lipid on cell membranes, resulting in pathology.
有证据表明，臭氧与胆固醇反应的某些产物会导致动脉粥样硬化。其中一种化合物是3β-羟基-5-氧代-5,6-断胆甾烷-6-醛。我们已经合成了这种化合物，并证明它与磷脂酰乙醇胺反应形成席夫碱。3β-羟基-5-氧代-5,6-断胆甾烷-6-醛还会影响磷脂酰乙醇胺的物理性质。我们通过差示扫描量热法（DSC）和X射线衍射表明，它会增加膜的负曲率。此外，3β-羟基-5-氧代-5,6-断胆甾烷-6-醛会使层状相变得无序，导致层状周期性丧失。3β-羟基-5-氧代-5,6-断胆甾烷-6-醛与磷脂酰乙醇胺的化学和物理相互作用可能会导致这种脂质对细胞膜产生破坏作用，从而引发病变。
