Sciadonic Acid Research Articles

Occurrence of a novel cannabimimetic molecule 2-sciadonoylglycerol (2-eicosa-5',11',14'-trienoylglycerol) in the umbrella pine Sciadopitys verticillata seeds.

The umbrella pine Sciadopitys verticillata seeds were found to contain a substantial amount (16.7 nmol/g) of sciadonic acid (all-cis-5,11,14-eicosatrienoic acid)-containing 2-monoacylglycerol, i.e., 2-sciadonoylglycerol (2-eicosa-5',11',14'-trienoylglycerol). Because the structure of 2-sciadonoylglycerol closely resembles that of 2-arachidonoylglycerol, the endogenous natural ligand for the cannabinoid receptor, we examined whether or not 2-sciadonoylglycerol exhibits cannabimimetic activity using NG108-15 neuroblastomaxglioma hybrid cells which express the cannabinoid CB1 receptor. We found that 2-sciadonoylglycerol induces rapid transient elevation of intracellular free Ca2+ concentration in NG108-15 cells through a cannabinoid CBI receptor-dependent mechanism similar to the case of 2-arachidonoylglycerol, yet the activity of 2-sciadonoylglycerol was apparently lower than that of 2-arachidonoylglycerol. The activity of 2-sciadonoylglycerol was detectable from 3-10 nM, reaching a maximum at around 10 microM. To our knowledge, this is the first report showing the occurrence of a cannabimimetic monoacylglycerol in higher plants.

The phylogenetic significance of sciadonic (all‐cis 5,11,14–20:3) acid in gymnosperms and its quantitative significance in land plants

The phylogenetic significance of sciadonic (all‐<i>cis</i> 5,11,14–20:3) acid in gymnosperms and its quantitative significance in land plants

The seed fatty acid composition and the distribution of Δ5‐olefinic acids in the triacylglycerols of some taxares (Cephalotaxus and Podocarpus)

AbstractThe fatty acid compositions of the seeds from four Cephalotaxus species or varieties (plum yews; Cephalotaxaceae) and two Podocarpus species (podocarps; Podocarpaceae) have been established. These compositions were compared with those previously published for some Taxaceae species (Taxus and Torreya). Cephalotaxaceae, Podocarpaceae, and Taxaceae belong to the Taxares suborder. Δ5‐Olefinic acids are present in the seed lipids from all species analyzed. In Cephalotaxus, Podocarpus, and Torreya, the prominent Δ5‐olefinic acid that occurs is the trienoic acid 5,11,14–20:3 (sciadonic) acid, comprising from 6.7 to 26.4% of total fatty acids. In these species, the Δ5,11 structure is largely favored over the Δ5,9 structure: the 5,9–18:2 (taxoleic) and 5,9,12–18:3 (pinolenic) acids are at the limit of detection, in contrast to Taxus and most Pinaceae species, where these two Δ5‐olefinic acids generally predominate. 14‐Methylhexadecanoic acid, an habitual though minor component of Pinaceae and Ginkgo biloba seed lipids, could not be detected in Cephalotaxus species studied here and was tentatively identified in trace amounts only in one Podocarpus species. In addition to sciadonic acid, Cephalotaxus and Podocarpus seeds are characterized by unusually high amounts of 11,14–20:2 acid, in the range of 3.1–12.0%. This contrasts with most of the 170 species of conifers analyzed so far (from the families Pinaceae, Cupressaceae, Taxodiaceae, Taxaceae, and Sciadopityaceae, which belong to the Pinares suborder), where this acid is generally ≤2%. A close resemblance between Torreya grandis and three of the Cephalotaxus species analyzed might be indicative of some phyletic relationship between the families Cephalotaxaceae and Taxaceae. 13C nuclear magnetic resonance spectroscopy of the seed oils from C. drupaceae and P. andinus has shown that Δ5‐olefinic acids are apparently excluded from the internal position of triacylglycerols, which is a characteristic common to all Coniferales species analyzed so far, and consequently of great antiquity.

Fatty acids of the seeds from pine species of the Ponderosa‐Banksiana and Halepensis sections. The peculiar taxonomic position of Pinus pinaster

AbstractThe fatty acid compositions of pine seed oils were determined from 11 species of the Banksiana subsection and three species of the Ponderosa subsection. All were collected in North America (United States, Mexico, and Cuba). These analyses also included the seed oils from the unique European species of the Ponderosa‐Banksiana section (Banksiana subsection), Pinus pinaster, and from three pine species of the Halepensis section, which are related to the Banksiana subsection. Emphasis was placed on their Δ5‐olefinic acid content and profile. Principal‐component analysis of fatty acid compositions showed that all North American species constituted a fairly homogeneous group. However, P. jeffreyi was slightly eccentric, and P. pinaster, a west‐Mediterranean species, was completely isolated from the North American group. Other species from the Banksiana and Ponderosa subsections could not be distinguished on the basis of their seed oil fatty acid compositions. With respect to Δ5‐olefinic acids, the North American species (except for P. jeffreyi) had 5,9‐18:2, 5,9,12‐18:3, 5,11‐20:2, and 5,11,14‐20:3 acid concentrations in the ranges 1.9 to 3.2, 17.7 to 22.9, 0.2 to 0.4, and 2.0 to 3.5%, respectively (sum, 22.7–28.5%). Levels of corresponding acids in P. pinaster were 0.9, 7.9, 0.9, and 7.0%, respectively (sum, 16.7%). Other differences were observed for linoleic acid (42.6 to 48.6% vs. 52.2%) and α‐linolenic acid (0.3 to 0.6% vs. 1.4%). Pinus pinaster was close to species of the Halepensis section (5,9‐18:2, 0.5 to 1.0%; 5,9,12‐18:3, 3.1 to 4.4%; 5,11‐20:2, 0.4 to 0.5%; 5,11,14‐20:3, 3.6 to 5.4%; sum, 8.6–11.1%), which were clearly separated from the Ponderosa‐Banksiana section. Among all pines analyzed, P. pinaster presented the highest level of sciadonic (5,11,14‐20:3) acid, a component that has three ethylenic bonds in common with arachidonic and eicosapentaenoic acids.

Prostaglandins and inflammation

Candida albicans is an important opportunistic pathogen in humans. During infection, arachidonic acid (ω6) is released from host phospholipids, leading to the production of host and yeast derived prostaglandin E2 (PGE2). This stimulates yeast hyphal formation, is immunomodulatory and causes cell damage during infection. Although supplementation of mammalian cells with ω3 fatty acids has received attention due to their immunomodulatory and anti-inflammatory activities, increased production of ω3 fatty acid metabolites could lower the host's ability to combat infections. Since mammalian cells cannot produce PGE2 from sciadonic acid (SA), a non-methylene interrupted ω6 fatty acid (NMIFA), supplementation of cells with SA may decrease the production of PGE2 without increasing levels of ω3 fatty acid metabolites. Our study evaluated PGE2 production by SA supplemented epithelial cells in response to Candida albicans and C. dubliniensis. We show that PGE2 production during infection can be modulated by incorporation of SA into host lipids and that this does not influence the levels of ω3 fatty acids in the epithelial cells.