Skip to main content
Fig. 1 | Lipids in Health and Disease

Fig. 1

From: Delta-5® oil, containing the anti-inflammatory fatty acid sciadonic acid, improves skin barrier function in a skin irritation model in healthy female subjects

Fig. 1

Structure of sciadonic acid (SA). SA is a non-methylene interrupted fatty acid present in Delta-5 oil as a triacylglycerol, representing 20–25% of total fatty acids in the oil. It is a 20-carbon fatty acid, with 3 double bonds present in Δ-5, 11, and 14 positions in cis-configuration. As a result of having only 2 methylene-interrupted fatty acids, it has good oxidative stability like a dienoic fatty acid. In skin, sciadonic acid exerts anti-inflammatory properties by displacing arachidonic acid from lipid pools; but may also potentially form bioactive, aborted cyclooxygenase and lipoxygenase and other eicosanoid products (a very poorly studied area). In our example herein, the C13-hydrogen at the center of the 1,4 cis, cis pentadiene system is extracted, following oxygen attack at C-15, forming 15-hydroxy-5,11,13-eicosatrienoic acid by the cyclooxygenase system. Another cyclooxygenase product (not shown) is 11-hydroxy-5,12,14-eiosatrienoic acid [64]. If SA were acted on by a skin 12-lipoxygenase, then 12-hydroxy-5,10,14-eicosatrienoic acid would be theoretically formed (not shown). See the "Introduction" section for further discussion and references

Back to article page