Mead acid

Mead acid
Names
IUPAC name
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acid
Identifiers
20590-32-3 YesY
ChEBI CHEBI:72865 N
ChemSpider 4471956 N
Jmol interactive 3D Image
PubChem 5312531
Properties
C20H34O2
Molar mass 306.48276
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Mead acid is an omega-9 fatty acid, first characterized by James F. Mead.[1] As with some other omega-9 polyunsaturated fatty acids, animals can make Mead acid de novo. Its elevated presence in the blood is an indication of essential fatty acid deficiency. Mead acid is found in large quantities in cartilage.

Chemistry

Mead acid, also referred to as eicosatrienoic acid, is chemically a carboxylic acid with a 20-carbon chain and three methylene-interrupted cis double bonds. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3 (n-9). (See Fatty Acid#Nomenclature for an explanation of the naming system.) In the presence of lipoxygenase, cytochrome p450 or cyclooxygenase Mead acid can form various hydroxyeicosatetraenoic acid (HETE) and hydoperoxy (HpETE) products.[2]

Physiology

Two fatty acids, linoleic acid and alpha-linolenic acid, are considered essential fatty acids (EFAs) in humans and other mammals. Both are 18 carbon fatty acids unlike mead acid, which has 20 carbons. Linoleic is an ω-6 fatty acid whereas linolenic is ω-3 and mead is ω-9. One study examined patients with intestinal fat malabsorption and suspected EFA deficiency. They were found to have blood-levels of Mead acid 1263% higher than reference subjects.[3] Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate oleic acid to make mead acid, (20:3, n−9).[4] This has been documented to a lesser extent in vegetarians and semi-vegetarians following an unbalanced diet.[5][6]

Mead acid has been found to decrease osteoblastic activity. This may be important in treating conditions where inhibition of bone formation is desired.[7]

Role in inflammation

Cyclooxygenases are enzymes known to play a large role in inflammatory processes through oxidation of unsaturated fatty acids. Most notably, the formation of prostaglandin H2 from arachidonic acid which is very similar in structure to mead acid. When physiological levels of arachidonic acid are low, other unsaturated fatty acids including mead and linoleic acid are oxidized by COX.

Mead acid is also converted to leukotrienes C3 and D3.[8]

Mead acid is metabolized by 5-lipoxygenase to 5-hydroxyeicosatrieonic acid (5-HETrE)[9] and then by 5-Hydroxyeicosanoid dehydrogenase to 5-oxoeicosatrienoic acid (5-oxo-ETrE).[10] 5-Oxo-ETrE is as potent as its arachidonic acid-derived analog, 5-oxo-eicosatetraenoic acid (5-oxo-ETE), in stimulating human blood eosinophils and neutrophils;[11] it presumably does so by binding to the 5-oxo-ETE receptor (OXER1) and therefore may be, like 5-oxo-ETE, a mediator of human allergic and inflammatory reactions.[12]

See also

References

  1. ↑ Siegel, George J.; Albers, R. Wayne (2006). Basic neurochemistry: molecular, cellular, and medical aspects, Volume 1 (7th ed.). p. 40. One of these is 20:3ω9, termed 'Mead acid' after its discovery by James Mead....
  2. ↑ Cyberlipid Center. "PROSTAGLANDINS AND RELATED COMPOUNDS". Retrieved 2007-10-24.
  3. ↑ EN Siguel, KM Chee, JX Gong and EJ Schaefer (October 1, 1987). "Criteria for essential fatty acid deficiency in plasma as assessed by capillary column gas–liquid chromatography". Clinical Chemistry 33 (10): 1869–1873. PMID 3665042. Retrieved 2007-10-24.
  4. ↑ Lipomics. "Mead acid". Retrieved February 14, 2006.
  5. ↑ Phinney, SD, RS Odin, SB Johnson and RT Holman (1990). "Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans". Retrieved February 11, 2006.
  6. ↑ Hornstra, Gerard (September 2007). "Essential Polyunsaturated Fatty Acids and Early Human Development". Fats of Life Newsletter. Archived from the original on June 7, 2008. Retrieved 2007-10-23.
  7. ↑ Hamazaki, Tomohito; Suzuki, Nobuo; Widyowati, Retno; Miyahara, Tatsuro; Kadota, Shigetoshi; Ochiai, Hiroshi; Hamazaki, Kei (October 22, 2008). "The Depressive Effects of 5,8,11-Eicosatrienoic Acid (20:3n-9) on Osteoblasts". Lipids 44 (2): 97–102. doi:10.1007/s11745-008-3252-8. Retrieved October 19, 2012. Check date values in: |year= / |date= mismatch (help)
  8. ↑ , Conversion of 5,8,11-Eicosatrienoic Acidt o Leukotrienes C3 and D3 Journal of Biological Chemistry (1981) vol. 256, p. 2275
  9. ↑ Prostaglandins. 1985 Apr;29(4):537-45.
  10. ↑ Prog Lipid Res. 2013 Oct;52(4):651-65. doi: 10.1016/j.plipres.2013.09.001. Epub 2013 Sep 19
  11. ↑ J Pharmacol Exp Ther. 2008 May;325(2):698-707. doi: 10.1124/jpet.107.134908. Epub 2008 Feb 21
  12. ↑ Prog Lipid Res. 2013 Oct;52(4):651-65. doi: 10.1016/j.plipres.2013.09.001. Epub 2013 Sep 19. Review
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