Facile synthesis of cyclopentenone B1- and L1-type phytoprostanes

被引:18
作者
Guy, Alexandre [1 ]
Flanagan, Seamus [1 ]
Durand, Thierry [1 ]
Oger, Camille [1 ]
Galano, Jean-Marie [1 ]
机构
[1] Univ Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, France
关键词
phytoprostane; cross-metathesis; natural products; polyunsaturated fatty acids; oxygenated metabolites; CYCLIC OXYGENATED METABOLITES; ALPHA-LINOLENIC ACID; DINOR ISOPROSTANES; OXIDATIVE STRESS; GENERAL STRATEGY; LIPIDS; OLIVE;
D O I
10.3389/fchem.2015.00041
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phytoprostanes (PhytoPs) represent non -enzymatic metabolites of alpha-linolenic acid (ALA), the essential omega-3 polyunsaturated fatty acid (PUFA) derived from plants. PhytoPs are present in the plant kingdom and represent endogenous mediators capable of protecting cells from oxidative stress damages in plants. Recently, it was found that such metabolites are present in cooking oil in high quantities, and also that B-1-PhytoPs protect immature neurons from oxidant injury and promote differentiation of oligodendrocyte progenitors through PPAR-gamma activation. We report a novel and facile synthesis of natural 2,3-substituted cyclopentenone PhytoPs, 16-B-1-PhytoP, and 9-L-1-PhytoP. Our strategy is based on reductive alkylation at the 2-position of 1,3-cyclopentanedione using a recent protocol developed by Ramachary et al. and on a cross-coupling metathesis to access conjugate dienone system. In conclusion, this strategy permitted access to B-1- and L-1-PhytoPs in a relative short sequence process, and afford the possibility to easily develop analogs of PhytoPs.
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页数:10
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