Arachidonic acid

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Arachidonic acid
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Names
Preferred IUPAC name
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid[1]
Other names
5,8,11,14-all-cis-Eicosatetraenoic acid
all-cis-5,8,11,14-Eicosatetraenoic acid
Identifiers
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3D model (JSmol)
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1713889
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EC Number Page Template:Plainlist/styles.css has no content.
58972
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MeSH Arachidonic+acid
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  • InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22) ☒N
    Key: YZXBAPSDXZZRGB-UHFFFAOYSA-N ☒N
  • InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
  • Key: YZXBAPSDXZZRGB-DOFZRALJSA-N
  • CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Properties
C20H32O2
Molar mass 304.474 g·mol−1
Density 0.922 g/cm3
Melting point −49 °C (−56 °F; 224 K)
Boiling point 169 to 171 °C (336 to 340 °F; 442 to 444 K) at 0.15 mmHg
log P 6.994
Acidity (pKa) 4.752
Hazards
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1
1
0
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related compounds
 Eicosatetraenoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega−6 fatty acid 20:4(ω−6), or 20:4(5,8,11,14).[2][3] It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes.[4]

Together with omega−3 fatty acids and other omega−6 fatty acids, arachidonic acid provides energy for body functions, contributes to cell membrane structure, and participates in the synthesis of eicosanoids, which have numerous roles in physiology as signaling molecules.[2][5]

It was named after the similarly structured Arachidic acid, a constituent of peanut oil whose name in turn derives from the ancient Greek neologism arachis 'peanut'.[6] Peanut oil does not contain any arachidonic acid, itself.[7] Arachidonate is the name of the derived carboxylate anion (conjugate base of the acid), salts, and some esters.

Chemistry

File:AAnumbering.png

In chemical structure, arachidonic acid is a carboxylic acid with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end.

Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids. However, almost all writings in biology, medicine, and nutrition limit the term to all cis-5,8,11,14-eicosatetraenoic acid.

Biology

Arachidonic acid is a polyunsaturated fatty acid present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain, muscles, and liver. Skeletal muscle is an especially active site of arachidonic acid retention, accounting for roughly 10–20% of the phospholipid fatty acid content typically.[8]

In addition to being involved in cellular signaling as a lipid second messenger involved in the regulation of signaling enzymes, such as PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms, arachidonic acid is a key inflammatory intermediate and can also act as a vasodilator.[9] (Note separate synthetic pathways, as described in section below.)

Biosynthesis and cascade in humans

De novo

File:Linoleic Acid Metabolism.gif
Linoleic acid metabolism

Arachidonic acid is synthesized from linoleic acid (LA) via a process starting with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6 desaturase.[10]

By hydrolysis

File:Eicosanoid synthesis.svg
Eicosanoid synthesis

Arachidonic acid is freed from phospholipids that contain an arachidonic acid sidechain by hydrolysis, catalyzed by the phospholipase A2 (PLA2).[9]

Arachidonic acid for signaling purposes appears to be derived by the action of group IVA cytosolic phospholipase A2 (cPLA2, 85 kDa), whereas inflammatory arachidonic acid is generated by the action of a low-molecular-weight secretory PLA2 (sPLA2, 14-18 kDa).[9]

Arachidonic acid is a precursor to a wide range of eicosanoids:

The production of these derivatives and their actions in the body are collectively known as the "arachidonic acid cascade"; see Essential fatty acid interactions and the enzyme and metabolite linkages given in the previous paragraph for more details.

PLA2 activation

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Furthermore, any agent increasing intracellular calcium may cause activation of some forms of PLA2.[22]

PLC activation

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Receptors that activate this pathway include:

PLC may also be activated by MAP kinase. Activators of this pathway include PDGF and FGF.[22]

In the body

Cell membranes

Along with other omega−6 and omega−3 fatty acids, arachidonic acid contributes to the structure of cell membranes.[2] When incorporated into phospholipids, the omega fatty acid affects cell membrane properties, such as permeability and the activity of enzymes and cell-signaling mechanisms.[2]

Brain

Arachidonic acid, one of the most abundant fatty acids in the brain, is present in similar quantities to docosahexaenoic acid, with the two accounting for about 20% of brain fatty-acid content.[23] Arachidonic acid is involved in the early neurological development of infants.[24]

Dietary supplement

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Arachidonic acid is marketed as a dietary supplement.[2][5] A 2019 review of clinical studies investigating the potential health effects of arachidonic acid supplementation of up to 1500 mg per day on human health found there were no clear benefits.[25] There were no adverse effects in adults of using high daily doses (1500 mg) of arachidonic acid on several biomarkers of blood chemistry, immune function, and inflammation.[25]

A 2009 review indicated that consumption of 5−10% of food energy from omega−6 fatty acids including arachidonic acid may reduce the risk of cardiovascular diseases compared to lower intakes.[26] A 2014 meta-analysis of possible associations between heart disease risk and individual fatty acids reported a significantly reduced risk of heart disease with higher levels of EPA, DHA, and arachidonic acid.[27]

Veterinary medicine

Cats have low Δ6 desaturase activity and cannot efficiently convert linoleic acid into arachidonic acid. As a result, they need to acquire it from food.[28]

See also

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References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Pubchem. "5,8,11,14-Eicosatetraenoic acid | C20H32O2 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-03-31.
  2. ^ a b c d e Page Module:Citation/CS1/styles.css has no content."Essential fatty acids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. June 2019. Retrieved 13 May 2024.
  3. ^ Page Module:Citation/CS1/styles.css has no content."IUPAC Lipid nomenclature: Appendix A: names of and symbols for higher fatty acids". www.sbcs.qmul.ac.uk.
  4. ^ Page Module:Citation/CS1/styles.css has no content."Dorland's Medical Dictionary – 'A'". Archived from the original on 11 January 2007. Retrieved 2007-01-12.
  5. ^ a b Page Module:Citation/CS1/styles.css has no content."Omega-3 fatty acids". Office of Dietary Supplements, US National Institutes of Health. 15 February 2023. Retrieved 13 May 2024.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Martin S, Brash A, Murphy R (2016). "The discovery and early structural studies of arachidonic acid". J Lipid Res. 57 (7): 1126–1132.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Truswell A, Choudhury N, Peterson D, Mann J, Agostoni C, Riva E, Giovannini M, Marangoni F, Galli C (1994). "Arachidonic acid and peanut oil". The Lancet. 344 (8928): 1030–1031. doi:10.1016/S0140-6736(94)91695-0. PMID 7999151. S2CID 1522233.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Smith GI, Atherton P, Reeds DN, Mohammed BS, Rankin D, Rennie MJ, Mittendorfer B (Sep 2011). "Omega-3 polyunsaturated fatty acids augment the muscle protein anabolic response to hyperinsulinaemia-hyperaminoacidaemia in healthy young and middle-aged men and women". Clinical Science. 121 (6): 267–78. doi:10.1042/cs20100597. PMC 3499967. PMID 21501117.
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  14. ^ Page Module:Citation/CS1/styles.css has no content.Brash AR, Boeglin WE, Chang MS (Jun 1997). "Discovery of a second 15S-lipoxygenase in humans". Proc Natl Acad Sci U S A. 94 (12): 6148–52. Bibcode:1997PNAS...94.6148B. doi:10.1073/pnas.94.12.6148. PMC 21017. PMID 9177185.
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  24. ^ Page Module:Citation/CS1/styles.css has no content.Crawford MA, Sinclair AJ, Hall B, et al. (July 2023). "The imperative of arachidonic acid in early human development". Progress in Lipid Research. 91 101222. doi:10.1016/j.plipres.2023.101222. hdl:10044/1/103039. PMID 36746351.
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