Sciadonic acid: Difference between revisions

|ImageFile = Sciadonic acid Structural Formula V.1Sciadonic_Acid.svg

'''Sciadonic acid''', also known as '''eicosatrienoic acid''', is a [[polyunsaturated fatty acid]].<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><ref>Sciadonic acid. ChemSpider. (n.d.). Retrieved November 10, 2022, from http://www.chemspider.com/Chemical-Structure.392828.html </ref> In regard to its structure, 5Z5''Z'',11Z11''Z'',14Z14''Z''-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-'' conformationconfiguration. 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 verticillateverticillata]]''.<ref>{{cite journal | doi = 10.1007/s11746-999-0102-7 | title = All-cis 5,11,14-20:3 acid: Podocarpic acid or sciadonic acid? | year = 1999 | last1 = Wolff | first1 = Robert L. | journal = Journal of the American Oil Chemists' Society | volume = 76 | issue = 10 | pages = 1255–1256 | s2cid = 94058769 }}</ref>

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">{{cite journal | doi = 10.1104/pp.107.098202 | title = Cloning and Characterization of Unusual Fatty Acid Desaturases from ''Anemone leveillei'': Identification of an Acyl-Coenzyme aA C20 Δ5-Desaturase Responsible for the Synthesis of Sciadonic Acid | year = 2007 | last1 = Sayanova | first1 = Olga | last2 = Haslam | first2 = Richard | last3 = Venegas Caleron | first3 = Monica | last4 = Napier | first4 = Johnathan A. | journal = Plant Physiology | volume = 144 | issue = 1 | pages = 455–467 | pmid = 17384161 | pmc = 1913799 }}</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>{{cite journal | doi = 10.5650/jos.ess18136 | title = Preparation of High Purity Δ5-Olefinic Acids from Pine Nut Oil via Repeated Lipase-Catalyzed Esterification | year = 2018 | last1 = Kim | first1 = Heejin | last2 = Choi | first2 = Nakyung | last3 = Kim | first3 = Hak-Ryul | last4 = Lee | first4 = Junsoo | last5 = Kim | first5 = In-Hwan | journal = Journal of Oleo Science | volume = 67 | issue = 11 | pages = 1435–1442 | pmid = 30404964 | doi-access = free }}</ref>

Sciadonic acid and several other Δ⁵-olefinic acids are found to be relatively abundant in [[gymnospermsgymnosperm]]s. ''[[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>{{cite journal | doi = 10.1007/s11746-999-0195-z | title = The phylogenetic significance of sciadonic (All-cis 5,11,14-20:3) acid in gymnosperms and its quantitative significance in land plants | year = 1999 | last1 = Wolff | first1 = Robert L. | journal = Journal of the American Oil Chemists' Society | volume = 76 | issue = 12 | pages = 1515–1516 | s2cid = 84666529 }}</ref><ref>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 [[conifersconifer]]s. Indicating that plant families can be characterized by the fatty acid composition of their seed, leaves, and wood oils.

[[EicosanoidsEicosanoid]]s 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 desaturasesdesaturase]]s, FADS 1,2 and 3 are [[enzyme]] coding genes found in [[chromosome 11q13]], in which alterations can be attributed to several types of [[cancerscancer]]s such as breast, ovarian and cervical cancer. In particular, the FADS2 enzyme, responsible for Δ⁶ desaturation is no longer functional.<ref name="auto">{{cite journal | doi = 10.1016/j.plefa.2018.05.002 | title = A rare eicosanoid precursor analogue, sciadonic acid (5Z,11Z,14Z–20:3), detected in vivo in hormone positive breast cancer tissue | year = 2018 | last1 = Park | first1 = H.G. | last2 = Zhang | first2 = J.Y. | last3 = Foster | first3 = C. | last4 = Sudilovsky | first4 = D. | last5 = Schwed | first5 = D.A. | last6 = Mecenas | first6 = J. | last7 = Devapatla | first7 = S. | last8 = Lawrence | first8 = P. | last9 = Kothapalli | first9 = K.S.D. | last10 = Brenna | first10 = J.T. | journal = Prostaglandins, Leukotrienes and Essential Fatty Acids | volume = 134 | pages = 1–6 | pmid = 29886893 | pmc = 5999340 }}</ref> In healthy tissues sciadonic acid is usually not within detectable concentrations. However, detectable concentrations have been found in human breast cancer tissues<ref name="auto" /> and in pooled human blood plasma.<ref>{{Cite journal |lastlast1=Menzel |firstfirst1=Jan Philipp |last2=Young |first2=Reuben S. E. |last3=Benfield |first3=Aurélie H. |last4=Scott |first4=Julia S. |last5=Wongsomboon |first5=Puttandon |last6=Cudlman |first6=Lukáš |last7=Cvačka |first7=Josef |last8=Butler |first8=Lisa M. |last9=Henriques |first9=Sónia T. |last10=Poad |first10=Berwyck L. J. |last11=Blanksby |first11=Stephen J. |date=2023-07-04 |title=Ozone-enabled fatty acid discovery reveals unexpected diversity in the human lipidome |url=https://www.nature.com/articles/s41467-023-39617-9 |journal=Nature Communications |language=en |volume=14 |issue=1 |pages=3940 |doi=10.1038/s41467-023-39617-9 |pmid=37402773 |issn=2041-1723|pmc=10319862 |bibcode=2023NatCo..14.3940M }}</ref> Due to structural similarity, Sciadonic acid has shown potential as a substitute for [[arachidonic acid]] in cellular [[phospholipid]] pools in signaling pathways.<ref name="auto"/> 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 [[prostaglandinProstaglandin E2|prostaglandin E₂]].<ref name="auto2">{{cite journal | doi = 10.1016/j.fct.2012.07.057 | title = Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine macrophages through NF-κB and MAPK signaling pathways | year = 2012 | last1 = Chen | first1 = Szu-Jung | last2 = Huang | first2 = Wen-Cheng | last3 = Yang | first3 = Tzu-Ting | last4 = Lu | first4 = Jui-Hua | last5 = Chuang | first5 = Lu-Te | journal = Food and Chemical Toxicology | volume = 50 | issue = 10 | pages = 3687–3695 | pmid = 22889893 }}</ref> Reduction of pro-inflammatory mediator molecules also occurs in murine macrophages, regulating the activation of NF-κΒ and MAPK pathways.<ref name="auto2"/>