Description
Adrenic acid is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-
carbon chain elongation of arachidonic acid. It is present in the adrenal glands, brain, testis, and kidney. Although there is trace metabolism of adrenic acid in the forebrain, the renal medulla is the only tissue which readily metabolizes the acid through cyclooxygenase activity. The primary metabolite of adrenic acid in the rabbit kidney is 1a,1b-
dihomo prostaglandin E
2.
Chemical Properties
Docosa tetra enoic acid designates any straight chain 22:4 fatty acid.
One isomer is of particular interest :
all-cis-7,10,13,16-docosa tetra enoic acid is an ω-6 fatty acid with the trivial name adrenic acid. 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.
Uses
cis-7,10,13,16-Docosatetraenoic Acid has been identified as a protein kinase inhibitor, affecting serotonin levels in studies.
Uses
Adrenic acid is considered a sort of storage form of arachidnoic acid because it can be retro-converted into arachidonic acid by enzymes. Arachidonic acid is relatively abundant especially in the phospholipids that are found in cellular membranes, and it is precursor for many hormone-like signaling molecules, e.g. prostaglandins and leukotrienes. It shall be liberated from the phospholipids by phospholipase enzymes before it can be converted into these signaling molecules. Omnivorous humans also consume small amounts of arachidonic acid with the diet, since arachidonic acid is found in small amounts in all animal products. Arachidonic acid is not found in higher plants. Arachidonic acid serves many important functions in the body, e.g. as a structural element in membrane phospholipids, and as precursor for signalling.
Definition
ChEBI: All-cis-docosa-7,10,13,16-tetraenoic acid is the all-cis-isomer of a C22 polyunsaturated fatty acid having four double bonds in the 7-, 10-, 13- and 16-positions. One of the most abundant fatty acids in the early human brain. It has a role as a human metabolite and an algal metabolite. It is a docosatetraenoic acid and an omega-6 fatty acid. It is a conjugate acid of an all-cis-docosa-7,10,13,16-tetraenoate.
Enzyme inhibitor
This long-chain, unsaturated fatty acid (FWfree-acid = 332.53 g/mol; CAS 28874-58-0), also known as adrenic acid and (7Z,10Z,13Z,16Z)- docosatetraenoic acid, inhibits arachidonyl-CoA synthetase, orarachidonate:CoA ligase and prostaglandin biosynthesis.
References
[1] H SPRECHER. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney.[J]. The Journal of Biological Chemistry, 1982, 257 7: 3912-3918.
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] CHONG YUAN. Cyclooxygenase Allosterism, Fatty Acid-mediated Cross-talk between Monomers of Cyclooxygenase Homodimers.[J]. The Journal of Biological Chemistry, 2009, 284 15: 10046-10055. DOI:
10.1074/jbc.m808634200
