New bioactive oxylipins formed by non-enzymatic free-radical-catalyzed pathways: the phytoprostanes.
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.
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. Thierry.Durand@univ-montp1.fr
Thierry
T
Durand
Valérie
V
Bultel-Poncé
Alexandre
A
Guy
Susanne
S
Berger
Martin J
MJ
Mueller
Jean-Marie
JM
Galano
D000818:Animals; D002384:Catalysis; D003517:Cyclopentanes / Q000032:analysis / Q000378:metabolism*; D005231:Fatty Acids, Unsaturated / Q000032:analysis / Q000378:metabolism* / Q000502:physiology; D005609:Free Radicals / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D028421:Isoprostanes / Q000032:analysis / Q000378:metabolism / Q000502:physiology; D054883:Oxylipins / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D015398:Signal Transduction / Q000502:physiology
D003517:Cyclopentanes; D005231:Fatty Acids, Unsaturated; D005609:Free Radicals; D028421:Isoprostanes; D054883:Oxylipins; C486066:phytoprostane F1