Abstract
Phytoprostanes (PhytoPs) represent non-enzymatic metabolites of α-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 B1-PhytoPs protect immature neurons from oxidant injury and promote differentiation of oligodendrocyte progenitors through PPAR-γ activation. We report a novel and facile synthesis of natural 2,3-substituted cyclopentenone PhytoPs, 16-B1-PhytoP, and 9-L1-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 B1- and L1-PhytoPs in a relative short sequence process, and afford the possibility to easily develop analogs of PhytoPs.
Highlights
Non-enzymatic production of biologically relevant compounds seems rather scarce in nature
While this idea is only starting to grow in the field of oxidative stress and the production of non-enzymatically formed metabolites of polyunsaturated fatty acid (PUFA), it is still rather uncommon
In 1998, Mueller and coworkers discovered that peroxidation of α-linolenic acid in plant (C18:3 n-3, ALA) lead to dinor-isoprostanes, later called Phytoprostanes (PhytoPs) (Parchmann and Mueller, 1998; Jahn et al, 2010)
Summary
Non-enzymatic production of biologically relevant compounds seems rather scarce in nature. In 1990, Morrow and Roberts discovered isoprostanes (IsoPs), compounds produced in human fluids and tissues by non-enzymatic free radical peroxidation of arachidonic acid (C20:4 n-3, AA) in phospholipid membranes (Morrow et al, 1990) These compounds later became the “gold standard” biomarker of lipid oxidative stress (Kadiiska et al, 2005), and showed many relevant biological activities (Jahn et al, 2008; Galano et al, 2015). In 1998, Mueller and coworkers discovered that peroxidation of α-linolenic acid in plant (C18:3 n-3, ALA) lead to dinor-isoprostanes, later called Phytoprostanes (PhytoPs) (Parchmann and Mueller, 1998; Jahn et al, 2010) They represent a standard of oxidative stress in plants (Durand et al, 2009), and are considered, like the jasmonate compounds, to be able to activate genes implicated in the detoxification response, and many other response signals to protect the plants (Durand et al, 2009). PhytoPs are relevant to human, to human diet, being present in vegetable oil (Karg et al, 2007; Collado-González et al, 2015a,b), and it was demonstrated that their level in humans can increase after high consumption of ALA
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