Sciadonic acid: Difference between revisions

▲| IUPACName = (5Z, 11Z, 14Z)-icosa-5,11,14-trienoic acid

▲CCCCC/C=C\C/C=C\CCCC/C=C\CCCC(=O)O

▲'''Eicosatrienoic Acid''', more commonly referred to as Sciadonic acid is a [[polyunsaturated fatty acid]]. In regard to its structure, 5Z,11Z,14Z-eicosa-5,11,14-trienoic acid (sciadonic acid) has 3 double bonds in the 5, 11, and 14 positions all of which are in the cis- conformation. It is further classified as Δ⁵-fatty, and an [[omega-6]] acid due to the methylene interrupted double bond at carbon-5 and a final double bond 6 carbons away from the methylene tail of the [[hydrocarbon]]. Sciadonic acid is a naturally occurring compound and has been found to play a role as a plant metabolite, commonly found in pine nut oil.<ref>U.S. National Library of Medicine. (n.d.). Sciadonic acid. National Center for Biotechnology Information. PubChem Compound Database. Retrieved November 10, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Sciadonic-acid</ref>. Furthermore, there have been propositions of several health applications for sciadonic acid as an [[anti-inflammatory agent]]. Sharing close structural similarity to [[arachidonic acid]], sciadonic acid acts as a replacement [[phospholipid]] in the corresponding [[biochemical pathways]].

▲The root behind the [[nomenclature]] of sciadonic acid comes from its high abundance in the seed, leaves, and wood oils of the plant species [[Sciadopitys verticillate]].<ref>Wolff, R. L. (1999). All-CIS 5,11,14-20:3 acid: Podocarpic acid or sciadonic acid? Journal of the American Oil Chemists' Society, 76(10), 1255–1256. https://doi.org/10.1007/s11746-999-0102-7 </ref>

▲== Synthetic Methods ==

▲There are a few methods reagarding the synthesis of sciadonic acid and other Δ5-fatty acids. One method is through [[desaturase]] enzyme complexes in which the [[biosynthesis]] of sciadonic acid has been achieved in the organism [[Anemone leveillei]] via two Δ⁵-desaturases, AL10 and AL21.<ref name="auto1">Sayanova O, Haslam R, Venegas Caleron M, Napier JA. Cloning and characterization of unusual fatty acid desaturases from Anemone leveillei: identification of an acyl-coenzyme A C20 Delta5-desaturase responsible for the synthesis of sciadonic acid. Plant Physiol. 2007 May;144(1):455-67. doi: 10.1104/pp.107.098202. Epub 2007 Mar 23. PMID: 17384161; PMCID: PMC1913799.</ref> Both desaturases have shown success in the synthesis of sciadonic acid, however, the mechanisms show different substrate specificity. AL21 has broad substrate specificity and acts on both saturated (16:0 and 18:0) and unsaturated (20:2, ω-6) fatty acids.<ref name="auto1"/> In contrast AL10 has a much greater substrate specificity binding only to a C20 unsaturated fatty acid (20:2, n-6) When AL10 is co-expressed with a Δ⁹-elongase the biosynthesis of sciadonic acid is achieved in [[transgenic plants]]. A second synthetic method is achieved through an [[esterification]] reaction catalyzed via Lipozyme RM IM and pine nut oil. Lipase-catalyzed esterification reactions leading to the development of Δ⁵-fatty acids can be achieved in solvent-free conditions using water-[[jacketed vessel]].<ref>Kim, H., Choi, N., Kim, H.-R., Lee, J., & Kim, I.-H. (2018). Preparation of high purity Δ5-olefinic acids from pine nut oil via repeated lipase-catalyzed esterification. Journal of Oleo Science, 67(11), 1435–1442. https://doi.org/10.5650/jos.ess18136 </ref>

▲== Phylogenetic Significance in Gymnosperms ==

▲Sciadonic acid and several other Δ⁵-olefinic acids are found to be relatively abundant in [[gymnosperms]]. [[Setaria verticillata]] seeds and their fatty acid compositions allow for distinction between different Coniferophytes such as species from families such as [[Cupressaceae]] and [[Taxodiaceae]].<ref>Wolff, R. L. (1999). The phylogenetic significance of sciadonic (all-cis 5,11,14-20:3) acid in gymnosperms and its quantitative significance in land plants. Journal of the American Oil Chemists' Society, 76(12), 1515–1516. https://doi.org/10.1007/s11746-999-0195-z </ref><ref>73:765–771 (1996). 14. Wolff, R.L., L.G. Deluc, A.M. Marpeau, and B. Comps, Chemotaxonomic Differentiation of Conifer Families and Genera Based on the Seed Oil Fatty Acid Compositions: Multivariate Analyses, Trees 12:57–65 (1997)</ref><ref>Wolff, R.L., Clarification on the Taxonomic Position of Sciadopitys verticillata Among Coniferophytes Based on the Seed Oil Fatty Acid Compositions, J. Am. Oil Chem. Soc. 75:757–758 (1998)</ref>. Sciadonic acid is a distinctive fatty acid that shows presence in the oils of seeds, leaves, and woods of [[conifers]]. Indicating that plant families can be characterized by the fatty acid composition of their seed, leaves, and wood oils.

▲== Health Implications ==

▲[[Eicosanoids]] and metabolites found to be biologically active have correlated to tumor progression by several mechanisms such as interruption of [[cell signaling]]. In humans, [[fatty acid desaturases]], FADS 1,2 and 3 are [[enzyme]] coding genes found in [[chromosome 11q13]], in which alterations can be attributed to several types of [[cancers]] such as breast, ovarian and cervical cancer. In particular, the FADS2 enzyme, responsible for Δ⁶ desaturation is no longer functional.<ref name="auto">Park, H. G., Zhang, J. Y., Foster, C., Sudilovsky, D., Schwed, D. A., Mecenas, J., Devapatla, S., Lawrence, P., Kothapalli, K. S. D., & Brenna, J. T. (2018). A rare eicosanoid precursor analogue, sciadonic acid (5Z,11z,14Z–20:3), detected in vivo in hormone positive breast cancer tissue. Prostaglandins, Leukotrienes and Essential Fatty Acids, 134, 1–6. https://doi.org/10.1016/j.plefa.2018.05.002 </ref> In healthy tissues sciadonic acid is not within detectable concentrations however in human breast cancer tissues detectable concentrations have been found. Sciadonic acids structural similarity has shown potential as a substitute for [[arachidonic acid]] in cellular [[phospholipid]] pools in the signaling pathways.<ref name="auto"/><ref>Chen, S.-J., Huang, W.-C., Yang, T.-T., Lu, J.-H., & Chuang, L.-T. (2012). Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine [[macrophages through NF-ΚB and MAPK signaling pathways. Food and Chemical Toxicology, 50(10), 3687–3695. https://doi.org/10.1016/j.fct.2012.07.057 </ref>In keratinocytes, sciadonic acids release from the cellular membrane phospholipid pool reduces levels of pro-inflammatory arachidonic acid and the corresponding pro-inflammatory down-stream mediator [[prostaglandin E2]].<ref name="auto2">Chen, S.-J., Huang, W.-C., Yang, T.-T., Lu, J.-H., & Chuang, L.-T. (2012). Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine macrophages through NF-ΚB and MAPK signaling pathways. Food and Chemical Toxicology, 50(10), 3687–3695. https://doi.org/10.1016/j.fct.2012.07.057 </ref> Reduction of pro-inflammatory mediator molecules is also occurs in murine macrophages, regulating the activation of NF-κΒ and MAPK pathways.<ref name="auto2"/>

▲== References ==

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