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Mead acid

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Mead acid
Names
Preferred IUPAC name
(5Z,8Z,11Z)-Icosa-5,8,11-trienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15- ☒N
    Key: UNSRRHDPHVZAHH-YOILPLPUSA-N ☒N
  • InChI=1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-
    Key: UNSRRHDPHVZAHH-YOILPLPUBD
  • CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O
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 checkY☒N ?)

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.[2] Mead acid is found in large quantities in cartilage.

Chemistry

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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, as is typical for polyunsaturated fatty acids. 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 hydroperoxy (HpETE) products.[3][4]

Physiology

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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 about 13-fold higher than reference subjects.[5] Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate oleic acid to make mead acid, (20:3, n−9).[6] This has been documented to a lesser extent in vegetarians and semi-vegetarians following an unbalanced diet.[7][8]

Mead acid has been found to decrease osteoblastic activity. This may be important in treating conditions where inhibition of bone formation is desired.[9]

Role in inflammation

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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 (AA). AA has the same chain length as Mead acid but an additional ω-6 double bond. When physiological levels of arachidonic acid are low, other unsaturated fatty acids including mead and linoleic acid are oxidized by COX. Cyclooxygenase breaks the bisallylic C-H bond of AA to synthesize prostaglandin H2, but breaks a stronger allylic C-H bond when it encounters Mead acid instead.[3]

Mead acid is also converted to leukotrienes C3 and D3.[10]

Mead acid is metabolized by 5-lipoxygenase to 5-hydroxyeicosatrienoic acid (5-HETrE)[11] and then by 5-hydroxyeicosanoid dehydrogenase to 5-oxoeicosatrienoic acid (5-oxo-ETrE).[12] 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;[13] 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

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References

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  1. ^ Siegel, George J.; Albers, R. Wayne (2006). Basic neurochemistry: molecular, cellular, and medical aspects, Volume 1 (7th ed.). Elsevier. p. 40. ISBN 9780080472072. One of these is 20:3ω9, termed 'Mead acid' after its discovery by James Mead....
  2. ^ Ichi I; Kono N; Arita Y; Haga S (January 2014). "Identification of genes and pathways involved in the synthesis of Mead acid (20:3n−9), an indicator of essential fatty acid deficiency". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1841 (1): 204–213. doi:10.1016/j.bbalip.2013.10.013. PMID 24184513.
  3. ^ a b Oliw, E.H.; Hornsten, L.; Sprecher, H.; Hamberg, M. (1993). "Oxygenation of 5,8,11-Eicosatrienoic Acid by Prostaglandin Endoperoxide Synthase and by Cytochrome P450 Monooxygenase: Structure and Mechanism of Formation of Major Metabolites". Archives of Biochemistry and Biophysics. 305 (2): 288–297. doi:10.1006/abbi.1993.1425. PMID 8373167.
  4. ^ Cyberlipid Center. "PROSTAGLANDINS AND RELATED COMPOUNDS". Archived from the original on April 13, 2018. Retrieved October 24, 2007.
  5. ^ EN Siguel; KM Chee; JX Gong; 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. doi:10.1093/clinchem/33.10.1869. PMID 3665042. Archived from the original on September 27, 2011. Retrieved October 24, 2007.
  6. ^ Geissler C, Powers H (2017). Human Nutrition. Oxford University Press. p. 174. ISBN 9 78-0-19-876802-9.
  7. ^ Phinney SD, Odin RS, Johnson SB, Holman RT (1990). "Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans". Am. J. Clin. Nutr. 51 (3): 385–92. doi:10.1093/ajcn/51.3.385. PMID 2106775.
  8. ^ 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 October 23, 2007.
  9. ^ Hamazaki, Tomohito; Suzuki, Nobuo; Widyowati, Retno; Miyahara, Tatsuro; Kadota, Shigetoshi; Ochiai, Hiroshi; Hamazaki, Kei (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. ISSN 0024-4201. PMID 18941818. S2CID 4011759.
  10. ^ Hammarström S (1981). "Conversion of 5,8,11-Eicosatrienoic Acid to Leukotrienes C3 and D3" (PDF). Journal of Biological Chemistry. 256 (3): 2275–2279. doi:10.1016/S0021-9258(19)69773-5. PMID 6780563.
  11. ^ Wei YF, Evans RW, Morrison AR, Sprechert H, Jakschik BA (1985). "Double bond requirement for the 5-lipoxygenase pathway". Prostaglandins. 29 (4): 537–45. doi:10.1016/0090-6980(85)90078-4. PMID 2988021.
  12. ^ a b Powell, William S.; Rokach, Joshua (2013). "The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor". Progress in Lipid Research. 52 (4): 651–665. doi:10.1016/j.plipres.2013.09.001. ISSN 0163-7827. PMC 5710732. PMID 24056189.
  13. ^ Patel, P.; Cossette, C.; Anumolu, J. R.; Gravel, S.; Lesimple, A.; Mamer, O. A.; Rokach, J.; Powell, W. S. (2008). "Structural Requirements for Activation of the 5-Oxo-6E,8Z, 11Z,14Z-eicosatetraenoic Acid (5-Oxo-ETE) Receptor: Identification of a Mead Acid Metabolite with Potent Agonist Activity". Journal of Pharmacology and Experimental Therapeutics. 325 (2): 698–707. doi:10.1124/jpet.107.134908. ISSN 0022-3565. PMID 18292294. S2CID 19936422.
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