Sciadonic acid

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 verticillata.{{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 }}

Oftentimes, the acid is found in conifers together with other fatty acids (juniperonic, pinolenic, taxoleic, coniferonic acid) that have a double bond in the position 5, separated by more than one methylene group from the next double bond.{{cite journal |last1=Pédrono |first1=Frédérique |last2=Boulier-Monthéan |first2=Nathalie |last3=Boissel |first3=Françoise |last4=Ossemond |first4=Jordane |last5=Viel |first5=Roselyne |last6=Fautrel |first6=Alain |last7=Marchix |first7=Justine |last8=Dupont |first8=Didier |title=Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase |journal=Scientific Reports |date=10 April 2020 |volume=10 |issue=1 |pages=6223 |doi=10.1038/s41598-020-63301-3 |url=https://www.nature.com/articles/s41598-020-63301-3 |access-date=19 May 2025 |language=en |issn=2045-2322|pmc=7148351 }}

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.{{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 A 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 }} 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. 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.{{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 }}

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.{{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 }}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)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) 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.

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 the 11q13 region of chromosome 11, 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.{{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 }} In healthy tissues sciadonic acid is usually not within detectable concentrations. However, detectable concentrations have been found in human breast cancer tissues and in pooled human blood plasma.{{Cite journal |last1=Menzel |first1=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 |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 }} Due to structural similarity, Sciadonic acid has shown potential as a substitute for arachidonic acid in cellular phospholipid pools in signaling pathways. 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.{{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 }} Reduction of pro-inflammatory mediator molecules also occurs in murine macrophages, regulating the activation of NF-κΒ and MAPK pathways.

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{{Fatty acids}}

Category:Fatty acids

Category:Polyunsaturated compounds