Juniperonic Acid Biosynthesis is Essential in Caenorhabditis elegans Lacking Δ6 Desaturase (fat-3) and Generates New ω-3 Endocannabinoids

In eukaryotes, the C20:4 polyunsaturated fatty acid arachidonic acid (AA) plays important roles as a phospholipid component, signaling molecule and precursor of the endocannabinoid-prostanoid axis. Accordingly, the absence of AA causes detrimental effects. Here, compensatory mechanisms involved in AA deficiency in Caenorhabditis elegans were investigated. We show that the ω-3 C20:4 polyunsaturated fatty acid juniperonic acid (JuA) is generated in the C. elegans fat-3(wa22) mutant, which lacks Δ6 desaturase activity and cannot generate AA and ω-3 AA. JuA partially rescued the loss of function of AA in growth and development. Additionally, we observed that supplementation of AA and ω-3 AA modulates lifespan of fat-3(wa22) mutants. We described a feasible biosynthetic pathway that leads to the generation of JuA from α-linoleic acid (ALA) via elongases ELO-1/2 and Δ5 desaturase which is rate-limiting. Employing liquid chromatography mass spectrometry (LC-MS/MS), we identified endocannabinoid-like ethanolamine and glycerol derivatives of JuA and ω-3 AA. Like classical endocannabinoids, these lipids exhibited binding interactions with NPR-32, a G protein coupled receptor (GPCR) shown to act as endocannabinoid receptor in C. elegans. Our study suggests that the eicosatetraenoic acids AA, ω-3 AA and JuA share similar biological functions. This biosynthetic plasticity of eicosatetraenoic acids observed in C. elegans uncovers a possible biological role of JuA and associated ω-3 endocannabinoids in Δ6 desaturase deficiencies, highlighting the importance of ALA.

Fatty Acid Composition of Juniperus Species (Juniperus Section) Native to Turkey

Fatty acid compositions of seeds of five taxa of the Juniperus section of the genus Juniperus L. (Cupressaceae), i. e. J. drupacea Lab., J. communis L. var. communis, J. communis var. saxatilis Pall., J. oxycedrus L. subsp. oxycedrus, and J. oxycedrus subsp. macrocarpa (Sibth. & Sm.) Ball, were investigated. Methyl ester derivatized fatty acids of the lipophylic extracts of the five species were comparatively analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Juniperus taxa showed uniform fatty acid patterns, among which linoleic (25.8–32.5%), pinolenic (11.9–24.1%) and oleic acids (12.4–17.2%) were determined to be the main fractions in the seed oils. Juniperonic acid was found to be remarkably high in J. communis var. saxatilis (11.4 %), J. oxycedrus subsp. oxycedrus (10.4 %), and J. communis var. communis (10.1 %). To the best of our knowledge, the present work discloses the first report on the fatty acid compositions of seeds of this Juniperus section grown in Turkey.