Identification and egg hatching activity of monohydroxy fatty acid eicosanoids in the barnacle Balanus balanoides.
Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography-mass spectrometry (GC-MS) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic acids and 9-, 13- and 15-hydroxyoctadecadienoic acids. Each monohydroxy fatty acid was tested for egg hatching activity in a bioassay using Elminius modestus egg masses, but 8-hydroxy-5, 9, 11, 14, 17-eicosapentaenoic acid (8-HEPE) was the only MHFA with barnacle egg hatching activity. Studies on the egg hatching activity of MHFAs prepared from the oxidation of polyunsaturated fatty acids showed that activity was confined to the 8-hydroxy isomer of eicosapentaenoic acid and arachidonic acid, and that unsaturation at C5 and C14, but not C17, was essential for activity. In addition, the 8(R) conformation is necessary for activity, as 8(R)-HEPE caused egg hatching at 10(-7) M whereas the enantiomer 8(S)-HEPE was inactive.
Hill
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EM
School of Ocean Sciences, University College of North Wales, Anglesey, U.K.
Holland
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DL
D000818:Animals; D001681:Biological Assay; D002851:Chromatography, High Pressure Liquid; D015777:Eicosanoids / Q000302:isolation & purification* / Q000494:pharmacology*; D004625:Embryo, Nonmammalian / Q000187:drug effects / Q000502:physiology*; D008401:Gas Chromatography-Mass Spectrometry; D006880:Hydroxy Acids / Q000302:isolation & purification* / Q000494:pharmacology*; D007536:Isomerism; D013329:Structure-Activity Relationship; D001468:Thoracica / Q000502:physiology*
D015777:Eicosanoids; D006880:Hydroxy Acids