Reaction: Elongation of gamma-lenolenoyl-CoA to dihomo-gamma-lenolenoyl-CoA
- in pathway: Linoleic acid (LA) metabolism
Gamma-linolenoyl-CoA (6,9,12-20:3(n-6)) is rapidly elongated to dihomo-gamma-linolenoyl-CoA (DGL-CoA; 8,11,14-20:3(n-6)) by the action of C18-PUFA-specific elongase 5 (ELOVL5). Two carbon atoms are added during this reaction. DGL-CoA later undergoes desaturation to form arachidonic acid (AA, 5,8,11,14-20:4(n-6)).
Depending on the cell type, DGL-CoA can also be metabolized by cyclooxygenases and lipoxygenases to produce anti-inflammatory eicosanoids (prostaglandins of series 1 (PGE1) and 15-hydroxyeico- satrienoic acid (15-HETrE)). GLA and these two oxidative metabolites exert clinical effects in a variety of diseases, including suppression of chronic inflammation, vasodilation and lowering of blood pressure, inhibition of platelet aggregation and thrombosis. (Fan et al. 2001, Fan & Chapkin 1998, Kapoor & Huang. 2006)
Depending on the cell type, DGL-CoA can also be metabolized by cyclooxygenases and lipoxygenases to produce anti-inflammatory eicosanoids (prostaglandins of series 1 (PGE1) and 15-hydroxyeico- satrienoic acid (15-HETrE)). GLA and these two oxidative metabolites exert clinical effects in a variety of diseases, including suppression of chronic inflammation, vasodilation and lowering of blood pressure, inhibition of platelet aggregation and thrombosis. (Fan et al. 2001, Fan & Chapkin 1998, Kapoor & Huang. 2006)
Reaction - small molecule participants:
H2O [endoplasmic reticulum lumen]
NADP+ [endoplasmic reticulum lumen]
CoA-SH [endoplasmic reticulum lumen]
CO2 [endoplasmic reticulum lumen]
DGL-CoA [endoplasmic reticulum lumen]
Malonyl-CoA [endoplasmic reticulum lumen]
GLA-CoA [endoplasmic reticulum lumen]
NADPH [endoplasmic reticulum lumen]
Reactome.org reaction link: R-HSA-2046094
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Reaction input - small molecules:
malonyl-CoA(5-)
gamma-linolenoyl-CoA
NADPH
Reaction output - small molecules:
water
NADP(+)
coenzyme A(4-)
carbon dioxide
all-cis-icosa-8,11,14-trienoyl-CoA
Reactome.org link: R-HSA-2046094