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Identification and hatching factor activity of monohydroxyeicosapentaenoic acid in homogenates of the barnacle Elminius modestus

A crude eicosanoid extract of the barnacle Elminius modestus caused hatching of isolated egg masses from both E. modestus and Balanus balanoides. On thin-layer chromatography (TLC) two bands containing hatching factor activity were identified, a monohydroxy fatty acid (MHFA) band with potent hatching factor activity and a less active trihydroxy fatty acid (THFA) band. Gas chromatography-mass spectrometry (GC-MS) of the MHFA band showed that it consisted mainly of positional isomers of monohydroxyeicosapentaenoic acid, predominantly 8-hydroxyeicosapentaenoic acid (8-HEPE). A range of positional isomers of monohydroxyeicosapentaenoic acid was produced by autoxidation of the methyl ester and this mixture was highly active in hatching E. modestus eggs. The commercially available stereoisomer 8(S)-HEPE hatched E. modestus eggs at concentrations as low as 10-8 M. The saturated derivative 8-hydroxyeicosanoic acid did not show hatching factor activity.