کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1925675 | 1536402 | 2011 | 6 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Nitric oxide converts fatty acid alkoxyl radicals into fatty acid allyl radicals Nitric oxide converts fatty acid alkoxyl radicals into fatty acid allyl radicals](/preview/png/1925675.png)
Nitric oxide (NO) is thought to react with fatty acid alkoxyl radical, which is generated from fatty acid hydroperoxide via one-electron reduction. However, detail in the reaction remains obscure. In the present study, we examined the reaction of nitric oxide with fatty acid alkoxyl radical generated in the lipoxygenase/linoleate/13-hydroperoxyoctadecadienoate (13-HpODE) system under anaerobic conditions via HPLC equipped with mass spectrometry and photodiode array detections. In this reaction system, nitric oxide can scavenge linoleate alkoxyl radical, producing 13-ONO-9Z,11E-ODE. However, instead of 13-ONO-9Z,11E-ODE, 13-NO-9E,11E-ODE and 9-NO-10E,12E-ODE were alternatively detected in the reaction solution. To explain this contradiction, we proposed a mechanism as follows: (1) 13-ONO-9E/11Z-ODE undergoes homolytic cleavage at >CHONO bond into the linoleate allyl radical and nitrogen dioxide, (2) the allyl radical undergoes resonance stabilization into the E/E-form, and (3) nitric oxide scavenges the E/E-pentadiene radical at C9 or C13 position. Consequently, we concluded that nitric oxide immediately converts fatty acid alkoxyl radical into allyl radical.
► A model system for fatty acid alkoxyl radical generation was established.
► NO scavenges lipid alkoxyl radical through radical–radical combination.
► Fatty acid alkoxyl radical-nitric oxide adduct dissociates into allyl radical.
► NO should consequently prevent β-elimination of fatty acid alkoxyl radical.
Journal: Archives of Biochemistry and Biophysics - Volume 516, Issue 2, 15 December 2011, Pages 154–159