Durand Thierry, Bultel-Poncé Valérie, Guy Alexandre, Berger Susanne, Mueller Martin J, Galano Jean-Marie
Institut des Biomolécules Max Mousseron, IBMM, UMR 5247, CNRS, Université Montpellier I, Université Montpellier II, Faculté de Pharmacie, 15. Av. Ch. Flahault, 34093, Montpellier Cedex 05, France.
Lipids. 2009 Oct;44(10):875-88. doi: 10.1007/s11745-009-3351-1. Epub 2009 Sep 30.
In animals and plants, fatty acids with at least three double bonds can be oxidized to prostaglandin-like compounds via enzymatic and non-enzymatic pathways. The most common fatty acid precursor in mammals is arachidonic acid (C20:4) (AA) which can be converted through the cyclooxygenase pathway to a series of prostaglandins (PG). Non-enzymatic cyclization of arachidonate yields a series of isoprostanes (IsoP) which comprises all PG (minor compounds) as well as PG isomers that cannot be formed enzymatically. In contrast, in plants, alpha-linolenic acid (C18:3) (ALA) is the most common substrate for the allene oxide synthase pathway leading to the jasmonate (JA) family of lipid mediators. Non-enzymatic oxidation of linolenate leads to a series of C18-IsoPs termed dinor IsoP or phytoprostanes (PP). PP structurally resemble JA but cannot be formed enzymatically. We will give an overview of the biological activity of the different classes of PP and also discuss their analytical applications and the strategies developed so far for the total synthesis of PP, depending on the synthetic approaches according to the targets and which key steps serve to access the natural products.
在动植物中，具有至少三个双键的脂肪酸可通过酶促和非酶促途径氧化为类前列腺素化合物。哺乳动物中最常见的脂肪酸前体是花生四烯酸（C20:4）（AA），它可通过环氧化酶途径转化为一系列前列腺素（PG）。花生四烯酸的非酶促环化产生一系列异前列腺素（IsoP），其中包括所有的PG（次要化合物）以及无法通过酶促形成的PG异构体。相比之下，在植物中，α-亚麻酸（C18:3）（ALA）是导致茉莉酸（JA）类脂质介质的丙二烯氧化物合酶途径最常见的底物。亚麻酸的非酶促氧化导致一系列称为去甲二烯IsoP或植物前列腺素（PP）的C18-IsoP。PP在结构上类似于JA，但无法通过酶促形成。我们将概述不同类别的PP的生物活性，还将讨论它们的分析应用以及迄今为止根据目标合成方法和用于获取天然产物的关键步骤而开发的PP全合成策略。
