18-hydroxyoleic Acid Research Articles

Epoxy acids in the lipid polymer, cutin and their role in the biosynthesis of cutin

In apple skin slices oleic acid-1- 14C was incorporated specifically into 18-hydroxyoleic acid, 10,18-dihydroxystearic acid and 9,10, 18-trihydroxystearic acid of cutin, whereas stearic acid-1- 14C was not converted into these acids. Palmitic acid-1- 14C, but neither palmitoleic acid-10- 14C nor palmitelaidic acid-10- 14C, was converted into 16-hydroxypalmitic acid and 10,16-dihydroxypalmitic acid. Based on this tracer evidence a pathway for the biosynthesis of hydroxy C 18 acids is proposed which involves hydration of the double bond of ω-hydroxyoleic acid and epoxidation followed by hydration. The proposed epoxy intermediate was identified in cutin by LiAlD 4 treatment followed by mass spectrometry.