Stearidonic acid
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Pin(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid

Stearidonic acid (SDA: C18H28O2; 18:4, n-3) is an ω-3 fatty acid, sometimes called moroctic acid.

Biosynthesis

It is biosynthesized from alpha-linolenic acid (ALA: C18H30O2; 18:3, n-3) by the enzyme delta-6-desaturase, which removes two hydrogen (H) atoms.

Metabolism

Stearidonic acid is involved in the synthesis of longer-chain ω-3 fatty acids in animals (including humans), plants, and bacteria.[1] It is a precursor to eicosapentaenoic acid via a[2] eicosatetraenoic acid (20:4 ω-3) intermediate. Studies in human volunteers and cell cultures suggest that SDA increases EPA levels more efficiently than an equimolar amount of ALA.[3]

SDA is also a precursor to N-acylethanolamine (NAEs).[1][failed verification][4]

Sources

Natural sources of this fatty acid are the seed oils of hemp (between 0.16 and 1.54% of the oil),[1] blackcurrant (between 2.5 and 4.5%),[5] Buglossoides arvensis (corn gromwell),[6] and Echium plantagineum, and the cyanobacterium Spirulina[citation needed].

As it is a precursor to other fatty acids, there has been efforts to enhance the content off stearidonic acid in various crops, such as soybeans.[7] A GMO soybean source is approved by the European Food Safety Authority.[8]

SDA can also be synthesized in a lab.

See also

References

  1. ^ Galasso, Incoronata; Russo, Roberto; Mapelli, Sergio; Ponzoni, Elena; Brambilla, Ida M.; Battelli, Giovanna; Reggiani, Remo (2016-05-20). "Variability in Seed Traits in a Collection of Cannabis sativa L. Genotypes". Frontiers in Plant Science. 7: 688. Bibcode:2016FrPS....7..688G. doi:10.3389/fpls.2016.00688. ISSN 1664-462X. PMC 4873519. PMID 27242881
  2. ^ Calder, Philip C. (2012). "Mechanisms of Action of (N-3) Fatty Acids". The Journal of Nutrition. 142 (3): 592S–599S. Bibcode:2012JNut..142S.592C. doi:10.3945/jn.111.155259. PMID 22279140
  3. ^ Seidel, U; Eberhardt, K; Wiebel, M; Luersen, K; Ipharraguerre, IR; Haegele, FA; Winterhalter, P; Bosy-Westphal, A; Schebb, NH; Rimbach, G (2024). "Stearidonic acid improves eicosapentaenoic acid status: studies in humans and cultured hepatocytes.". Frontiers in Nutrition. 11. doi:10.3389/fnut.2024.1359958. PMID 38974810
  4. ^ PubChem. "Stearidonic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-22.
  5. ^ Ruiz Del Castillo, Maria Luisa; Dobson, Gary; Brennan, Rex; Gordon, Sandra (2004). "Fatty Acid Content and Juice Characteristics in Black Currant ( Ribes nigrum L.) Genotypes". Journal of Agricultural and Food Chemistry. 52 (4): 948–952. Bibcode:2004JAFC...52..948R. doi:10.1021/jf034950q. PMID 14969555
  6. ^ "Corn Gromwell". NIAB. Archived 2011-07-04 at the Wayback Machine.
  7. ^ Garg, Monika; Sharma, Natasha; Sharma, Saloni; Kapoor, Payal; Kumar, Aman; Chunduri, Venkatesh; Arora, Priya (2018). "Biofortified Crops Generated by Breeding, Agronomy, and Transgenic Approaches Are Improving Lives of Millions of People around the World". Frontiers in Nutrition. 5. doi:10.3389/fnut.2018.00012. PMC 5817065. PMID 29492405
  8. ^ "Scientific Opinion on genetically modified soybean MON 87769". European Food Safety Authority. 2014-05-16. Retrieved 2019-02-18.