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| One isomer is of particular interest: | One isomer is of particular interest: | ||
| * all-''cis''-7,10,13,16-docosatetraenoic acid is an ] with the ] '''adrenic acid''' (AdA). This is a naturally occurring ] formed through a 2-carbon chain elongation of ]. It is one of the most abundant fatty acids in the early human brain.<ref name=Martinez >{{cite journal |author=Martinez M |title=Tissue levels of polyunsaturated fatty acids during early human development |journal=J Pediatr |volume=120 |issue=4 Pt 2 |pages=S129–38 |year=1992 |pmid=1532827 |doi=10.1016/S0022-3476(05)81247-8}}</ref> This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins,<ref name=Campbell>{{cite journal |vauthors=Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS |title=Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells |journal=Biochim. Biophys. Acta |volume=837 |issue=1 |pages=67–76 |year=1985 |pmid=3931686 |doi=10.1016/0005-2760(85)90086-4}}</ref> and epoxydocosatrienoic acids (EDTs, also known as dihomo-]s).<ref name="pmid20038752">{{cite journal | vauthors = Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB | title = Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors | journal = Hypertension | volume = 55 | issue = 2 | pages = 547–54 | year = 2010 | pmid = 20038752 | pmc = 2819927 | doi = 10.1161/HYPERTENSIONAHA.109.144147 }}</ref> <ref name=Yi>{{cite journal |journal= Am J Physiol Heart Circ Physiol |date =May 2007| volume=292|issue=5|pages=H2265–74 | title=Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries. |vauthors=Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB |pmid=17209008 | doi=10.1152/ajpheart.00947.2006}}<!--|accessdate=2007-10-30 --></ref> <ref name=Singh>{{cite journal |journal= ACS Omega |date =March 2021| volume=6|issue=10|pages=7165-7174 | title=Adrenic Acid-Derived Epoxy Fatty Acids Are Naturally Occurring Lipids and Their Methyl Ester Prodrug Reduces Endoplasmic Reticulum Stress and Inflammatory Pain. |vauthors=Singh N, Barnych B, Wagner KM, Wan D, Morisseau C, Hammock BD | doi=10.1021/acsomega.1c00241|pmc=7970556|doi-access=free}}</ref> In addition to being ]s, EDTs have demonstrated anti-] stress and anti-] activities. They are hydrolyzed by the ] (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors. | * all-''cis''-7,10,13,16-docosatetraenoic acid is an ] with the ] '''adrenic acid''' (AdA). This is a naturally occurring ] formed through a 2-carbon chain elongation of ]. It is one of the most abundant fatty acids in the early human brain.<ref name=Martinez >{{cite journal |author=Martinez M |title=Tissue levels of polyunsaturated fatty acids during early human development |journal=J Pediatr |volume=120 |issue=4 Pt 2 |pages=S129–38 |year=1992 |pmid=1532827 |doi=10.1016/S0022-3476(05)81247-8}}</ref> This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins,<ref name=Campbell>{{cite journal |vauthors=Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS|author2-link=John R. Falk |title=Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells |journal=Biochim. Biophys. Acta |volume=837 |issue=1 |pages=67–76 |year=1985 |pmid=3931686 |doi=10.1016/0005-2760(85)90086-4}}</ref> and epoxydocosatrienoic acids (EDTs, also known as dihomo-]s).<ref name="pmid20038752">{{cite journal | vauthors = Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB | title = Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors | journal = Hypertension | volume = 55 | issue = 2 | pages = 547–54 | year = 2010 | pmid = 20038752 | pmc = 2819927 | doi = 10.1161/HYPERTENSIONAHA.109.144147 }}</ref> <ref name=Yi>{{cite journal |journal= Am J Physiol Heart Circ Physiol |date =May 2007| volume=292|issue=5|pages=H2265–74 | title=Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries. |vauthors=Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB |pmid=17209008 | doi=10.1152/ajpheart.00947.2006}}<!--|accessdate=2007-10-30 --></ref> <ref name=Singh>{{cite journal |journal= ACS Omega |date =March 2021| volume=6|issue=10|pages=7165-7174 | title=Adrenic Acid-Derived Epoxy Fatty Acids Are Naturally Occurring Lipids and Their Methyl Ester Prodrug Reduces Endoplasmic Reticulum Stress and Inflammatory Pain. |vauthors=Singh N, Barnych B, Wagner KM, Wan D, Morisseau C, Hammock BD | doi=10.1021/acsomega.1c00241|pmc=7970556|doi-access=free}}</ref> In addition to being ]s, EDTs have demonstrated anti-] stress and anti-] activities. They are hydrolyzed by the ] (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors. | ||
| ==See also== | ==See also== | ||
Revision as of 20:46, 25 February 2022
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| Names | |
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| Preferred IUPAC name (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
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| CompTox Dashboard (EPA) | |
InChI
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| Properties | |
| Chemical formula | C22H36O2 |
| Molar mass | 332.5 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
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Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See essential fatty acid for nomenclature.)
One isomer is of particular interest:
- all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs). In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.
See also
References
- Martinez M (1992). "Tissue levels of polyunsaturated fatty acids during early human development". J Pediatr. 120 (4 Pt 2): S129–38. doi:10.1016/S0022-3476(05)81247-8. PMID 1532827.
- Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS (1985). "Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells". Biochim. Biophys. Acta. 837 (1): 67–76. doi:10.1016/0005-2760(85)90086-4. PMID 3931686.
- Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB (2010). "Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors". Hypertension. 55 (2): 547–54. doi:10.1161/HYPERTENSIONAHA.109.144147. PMC 2819927. PMID 20038752.
- Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB (May 2007). "Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries". Am J Physiol Heart Circ Physiol. 292 (5): H2265–74. doi:10.1152/ajpheart.00947.2006. PMID 17209008.
- Singh N, Barnych B, Wagner KM, Wan D, Morisseau C, Hammock BD (March 2021). "Adrenic Acid-Derived Epoxy Fatty Acids Are Naturally Occurring Lipids and Their Methyl Ester Prodrug Reduces Endoplasmic Reticulum Stress and Inflammatory Pain". ACS Omega. 6 (10): 7165–7174. doi:10.1021/acsomega.1c00241. PMC 7970556.
Further reading
- Ferretti, A., Flanagan, V.P. Mass spectrometric evidence for the conversion of exogenous adrenate to dihomo-prostaglandins by seminal vesicle cyclo-oxygenase. A comparative study of two animal species. J Chromatogr 383 241-250 (1986).
- Sprecher, H., VanRollins, M., Sun, F., et al. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. J Biol Chem 257 3912-3918 (1982).