nonclassic eicosanoid
Nonclassic eicosanoids are biologically active signaling molecules made by oxygenation of twenty-carbon fatty acids other than the classic eicosanoids.
Terminology
:{{Main article|Eicosanoid}}
"Eicosanoid" is the collective{{cite journal
| author=Funk, Colin D. | journal=Science |date=30 November 2001
| volume= 294| issue= 5548 |pages= 1871–1875 |doi = 10.1126/science.294.5548.1871
| title= Prostaglandins and Leukotrienes: Advances in Eicosanoid Biology
| pmid=11729303| bibcode=2001Sci...294.1871F }}
term for oxygenated derivatives of three different 20-carbon essential fatty acids—Eicosapentaenoic acid (EPA), Arachidonic acid (AA) and Dihomo-gamma-linolenic acid (DGLA).
Current usage limits the term to the leukotrienes (LT) and three types of prostanoids—prostaglandins (PG) prostacyclins (PGI), and thromboxanes (TX).
However, several other classes can technically be termed eicosanoid, including the eoxins, hepoxilins, resolvins, isofurans, isoprostanes, lipoxins, epi-lipoxins, epoxyeicosatrienoic acids (EETs) and endocannabinoids.
LTs and prostanoids are sometimes termed 'classic eicosanoids' {{cite journal
|vauthors=Van Dyke TE, Serhan CN |title=Resolution of inflammation: a new paradigm for the pathogenesis of periodontal diseases |journal=J. Dent. Res.
| volume=82 |issue=2 |pages=82–90 |year=2003 |pmid=12562878 |doi=10.1177/154405910308200202
|journal=Prostaglandins Other Lipid Mediat. |volume=73 |issue=3–4 |pages=155–72 |year=2004 |pmid=15290791
|doi=10.1016/j.prostaglandins.2004.03.005}}{{
cite journal |vauthors=Anderle P, Farmer P, Berger A, Roberts MA |title=Nutrigenomic approach to understanding the mechanisms by which dietary long-chain fatty acids induce gene signals and control mechanisms involved in carcinogenesis
|journal=Nutrition (Burbank, Los Angeles County, Calif.) |volume=20 |issue=1 |pages=103–8 |year=2004 |pmid=14698023 |
doi=10.1016/j.nut.2003.09.018
}}
in contrast to the 'novel', 'nonclassic' or 'eicosanoid-like' eicosanoids.{{
cite journal |author=Evans AR |title=Isoprostanes, novel eicosanoids that produce nociception and sensitize rat sensory neurons |journal=J. Pharmacol. Exp. Ther. |volume=293 |issue=3 |pages=912–20 |year=2000 |pmid=10869392 |name-list-style=vanc|author2=Junger H |author3=Southall MD |display-authors=3 |last4=Nicol |first4=GD |last5=Sorkin |first5=LS |last6=Broome |first6=JT |last7=Bailey |first7=TW |last8=Vasko |first8=MR}}{{cite journal |vauthors=O'Brien WF, Krammer J, O'Leary TD, Mastrogiannis DS |title=The effect of acetaminophen on prostacyclin production in pregnant women |journal=Am. J. Obstet. Gynecol. |volume=168 |issue=4 |pages=1164–9 |year=1993 |pmid=8475962 |doi=10.1016/0002-9378(93)90362-m}}{{cite journal |vauthors=Behrendt H, Kasche A, Ebner von Eschenbach C, Risse U, Huss-Marp J, Ring J |title=Secretion of proinflammatory eicosanoid-like substances precedes allergen release from pollen grains in the initiation of allergic sensitization |journal=Int. Arch. Allergy Immunol. |volume=124 |issue=1–3 |pages=121–5 |year=2001 |pmid=11306946 |doi= 10.1159/000053688|s2cid=53331 }}{{cite journal |author=Sarau HM |title=In vitro and in vivo pharmacological characterization of SB 201993, an eicosanoid-like LTB4 receptor antagonist with anti-inflammatory activity |journal=Prostaglandins Leukot. Essent. Fatty Acids |volume=61 |issue=1 |pages=55–64 |year=1999 |pmid=10477044 |doi= 10.1054/plef.1999.0074 |name-list-style=vanc|author2=Foley JJ |author3=Schmidt DB |display-authors=3 |last4=Martin |first4=L.D. |last5=Webb |first5=E.F. |last6=Tzimas |first6=M.N. |last7=Breton |first7=J.J. |last8=Chabot-Fletcher |first8=M. |last9=Underwood |first9=D.C.}}
The classic eicosanoids are autocrine and paracrine mediators, active at micromolar concentrations (or lower), produced with high stereospecificity. They are produced from EFAs (chiefly AA) from either cyclooxygenase (COX) or 5-lipoxygenase.
Broadly, the nonclassic eicosanoids are the products of 20-carbon EFAs and
|title=Prostanoids and Related Products
|url=http://www.cyberlipid.org/prost1/pros0001.htm
|author=Cyberlipid Center
|accessdate=2007-11-02
|website=
|archive-url=https://web.archive.org/web/20070208145938/http://www.cyberlipid.org/prost1/pros0001.htm
|archive-date=2007-02-08
|url-status=dead
}}
- Other oxygenation enzymes, (eoxins, hepoxilins, resolvins, lipoxins, epi-lipoxins, epoxyeicosatrienoic acids (EETs));
- Uncatalyzed oxygenation reactions, (isofurans, isoprostanes, phytoprostanes);
- Addition reactions other than oxygenation (endocannabinoids).
Also included are
- Side products from the classic eicosanoid biosynthesis, (levuglandins, Oxoeicosanoids);
- Reactions between other fatty acids and these pathways (the COX products of pinolenic and mead acid).