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Structure Database (LMSD)

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Common Name

bishomo-gamma-linolenic acid

Systematic Name

8Z,11Z,14Z-eicosatrienoic acid

Synonyms

dihomo-gamma-linolenic acid
8, 11, 14-eicosatrienoic acid
C20:3n-6,9,12
gamma-Homolinolenic acid

LM ID

LMFA01030158

Formula

C₂₀H₃₄O₂

Exact Mass

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306.25588

Sum Composition

FA 20:3

Status

Curated

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Classification

Biological Context

Dihomo-γ-Linolenic Acid (DGLA, 20:3), an elongation product of γ-linolenic acid (18:3), is rapidly metabolized by fatty acid desaturases to produce arachidonic acid (20:4). DGLA is metabolized through the cyclooxygenase pathway to produce 1-series prostaglandins, including PGE1.1,2 In mice, DGLA supplementation in the diet can reduce atopic dermatitis and atherosclerosis.^3,4

This information has been provided by Cayman Chemical

References

1. Bell, J.G., Tocher, D.R., and Sargent, J.R. Effect of supplementation with 20:3(n-3), 20:4(n-6) and 20:5(n-3) on the production of prostaglandins E and F of the 1-, 2- and 3-series in turbot (Scophthalmus maximus) brain astroglial cells in primary culture. Biochim. Biophys. Acta 1211, 335-342 (1994).

2. Levin, G., Duffin, K.L., Obukowicz, M.G., et al. Differential metabolism of dihomo-γ-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: Implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem. J. 365(Pt 2), 489-496 (2002).

3. Takai, S., Jin, D., Kawashima, H., et al. Anti-atherosclerotic effects of dihomo-γ-linolenic acid in ApoE-deficient mice. J. Atheroscler. Thromb. 16(4), 480-489 (2009).

4. Kawashima, H., Tateishi, N., Shiraishi, A., et al. Oral administration of dihomo-γ-linolenic acid prevents development of atopic dermatitis in NC/Nga mice. Lipids 43(1), 37-43 (2007).