5-9-12-octadecatrienoic-acid and eicosa-5-11-14-trienoic-acid

Δ5-Olefinic acids have been characterized in gymnosperm plants and have been reported to have several biological health benefits. Δ5-Olefinic acids from pine nut oil were effectively concentrated by repeated lipase-catalyzed esterification. The pine nut oil contained three major Δ5-olefinic acids, namely taxoleic acid (C18:2 Δ5,9), pinolenic acid (C18:3 Δ5,9,12), and sciadonic acid (C20:3 Δ5,11,14). The fatty acids present in pine nut oil were selectively esterified with ethanol using Lipozyme RM IM from Rhizomucor miehei as a biocatalyst. The Δ5-olefinic acids were concentrated in the unesterified fatty acid fraction. The optimum molar ratio of the substrates (fatty acid:ethanol), temperature, the enzyme loading, and the reaction time were 1:7, 25°C, 5% of total substrate weight, and 6 h, respectively. There was no significant effect in the concentration of Δ5-olefinic acids when water was added in the reaction mixture. The same protocol and optimum conditions were employed for two times repeated lipase-catalyzed esterifications. In first lipase-catalyzed esterification, the Δ5-olefinic acids content in the pine nut oil increased from 17 mol% to 51 mol% with a yield of 40 mol%. In a second lipase-catalyzed esterification, with the Δ5-olefinic acids-concentrated fatty acids obtained from the first reaction as the substrate, the Δ5-olefinic acids content increased to 86 mol% with a yield of 15 mol%. Finally, a maximum Δ5-olefinic acids content of ca. 96 mol% with a yield of 6 mol% was obtained via a third lipase-catalyzed esterification.

Topics: Alkenes; Arachidonic Acids; Biocatalysis; Chemistry, Organic; Esterification; Ethanol; Linolenic Acids; Lipase; Nuts; Pinus; Plant Oils; Rhizomucor; Temperature

Sciadonic acid (SCA), pinolenic acid (PNA), and Δ7-eicosatrienoic acid (Δ7-ETrA) are three non-methylene-interrupted fatty acids (NMIFA). Using murine microglial BV-2 cells, this study determined how NMIFA incorporation modulated phospholipid fatty acid composition and the production of pro-inflammatory mediators. Each NMIFA was rapidly taken up and incorporated in BV-2 cells, resulting in the differential redistribution of total lipids. The cellular phospholipid fatty acid compositions were altered, and a significant decrease in the proportions of total monounsaturated fatty acids (MUFA) was observed while the proportions of NMIFA and its metabolites accounted for 38% of the fatty acid total. Incubation of microglial cells with NMIFA suppressed production of LPS-stimulated pro-inflammatory mediators, including nitric oxide (NO), prostaglandin E2 (PGE2), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α), as well as the over-expression of inducible nitric oxide synthase (iNOS) and type 2 cyclooxygenase (COX-2). These inhibitory effects could be accounted for, in part, by the inactivation of mitogen-activated protein kinases (MAPK) signaling. In conclusion, Δ7-ETrA, PNA, and SCA are anti-inflammatory NMIFA that may be useful in suppressing in vitro immune responses involved in neural inflammation.

Topics: Animals; Anti-Inflammatory Agents; Arachidonic Acids; Cell Line; Cyclooxygenase 2; Dinoprostone; Dose-Response Relationship, Drug; Down-Regulation; Enzyme Activation; Fatty Acids, Monounsaturated; Inflammation Mediators; Interleukin-6; Linolenic Acids; MAP Kinase Signaling System; Mice; Microglia; Mitogen-Activated Protein Kinases; Nitric Oxide; Nitric Oxide Synthase Type II; Phospholipids; Tumor Necrosis Factor-alpha