Univ Lyon, UMR 1060 Inserm & 1397 Inrae (CarMeN laboratory), IMBL, INSA-Lyon, 69621 Villeurbanne Cedex, France.
Univ Lyon, UMR 1060 Inserm & 1397 Inrae (CarMeN laboratory), IMBL, INSA-Lyon, 69621 Villeurbanne Cedex, France.
Prostaglandins Leukot Essent Fatty Acids. 2020 Nov;162:102185. doi: 10.1016/j.plefa.2020.102185. Epub 2020 Oct 1.
Double lipoxygenation of polyunsaturated fatty acids having at least three methylene-interrupted double bonds can be made by two lipoxygenases, e.g. 5- and 12-LOX, or 15-LOX only, followed by reduction of the hydroperoxide products through the glutathione peroxidase action. Several biological activities have been reported for such a double 15-LOX product of docosahexaenoic acid, called protectin DX to differentiate it from protectin D1, a stereo and geometric isomer described for its potent anti-inflammatory potential. The geometric characteristic of the double lipoxygenase products is the conjugated triene E,Z,E (trans,cis,trans), which appears crucial in their biological activities. A focus is also done on single lipoxygenation of mono-hydroxylated products first made by aspirin-treated cyclooxygenase-2. The resulting (R,S)-diOH, E,Z,E conjugated trienes, instead of the (S,S)-diOH isomer in case of double lipoxygenation, seem to be even more active for some biological effects, making biologically relevant the single lipoxygenation in aspirin-treated situations.
多不饱和脂肪酸中至少有三个亚甲基中断双键的双键双加氧作用可由两种脂氧合酶（如 5-和 12-LOX）或仅由 15-LOX 完成，随后通过谷胱甘肽过氧化物酶作用还原氢过氧化物产物。已经报道了二十二碳六烯酸（DHA）的这种双 15-LOX 产物（称为保护素 DX，以将其与保护素 D1 区分开来，后者是一种立体和几何异构体，因其具有强大的抗炎潜力而被描述）的几种生物活性。双脂氧合酶产物的几何特征是共轭三烯 E,Z,E（反式、顺式、反式），这在其生物活性中似乎至关重要。本文还重点研究了首先由阿司匹林处理的环氧化酶-2 生成的单羟基化产物的单脂氧合作用。所得的（R，S）-二 OH、E，Z，E 共轭三烯，而不是双键双加氧作用的（S，S）-二 OH 异构体，对于某些生物学效应似乎更为活跃，使阿司匹林处理情况下的单脂氧合作用具有生物学相关性。
