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First published online August 8, 2003
Hepoxilins and trioxilins in barnacles: an analysis of their potential roles in egg hatching and larval settlement
1 School of Biological Sciences, University of Wales Swansea, Singleton
Park, Swansea, SA2 8PP, UK
2 Proteomics Section, Imperial College, Faculty of Medicine, London, W12
ONN, UK
3 School of Marine Science and Technology, University of Newcastle upon
Tyne, Newcastle upon Tyne, NE1 7RU, UK
4 Program in Integrative Biology, Research Institute, The Hospital for Sick
Children, 555-University Avenue, Toronto and the Department of Pharmacology,
University of Toronto, Toronto, Ontario M5G 1X8, Canada
* Author for correspondence (e-mail: a.f.rowley{at}swansea.ac.uk)
Accepted 16 June 2003
The barnacle life cycle has two key stages at which eicosanoids are
believed to be involved in cellular communication pathways, namely the
hatching of nauplii and the settlement of cypris larvae. Barnacle egg-hatching
activity has previously been reported to reside in a variety of eicosanoids,
including 8-hydroxyeicosapentaenoic acid and a number of tri-hydroxylated
polyunsaturated fatty acid derivatives, the trioxilins. The production of the
eicosapentaenoic acid metabolite trioxilin A4
(8,11,12-trihydroxy-5,9,14,17-eicosatetraenoic acid) by the barnacles
Balanus amphitrite and Elminius modestus was confirmed using
a combination of high-performance liquid chromatography and gas
chromatography, both linked to mass spectrometry. In addition, both species
also generated trioxilin A3
(8,11,12-trihydroxy-5,9,14-eicosatrienoic acid; an arachidonic acid-derived
product), 8,11,12-trihydroxy-9,14,17-eicosatrienoic acid (a 
3 analogue
of trioxilin A3; derived from 3 arachidonic acid) and
10,13,14-trihydroxy-4,7,11,16,19-docosapentaenoic acid (a docosahexaenoic
acid-derived product). In contrast to earlier reports, trioxilin A3
had no E. modestus egg-hatching activity at any of the concentrations
tested (10–9–10–6 mol
l–1). The unstable epoxide precursor hepoxilin A3,
however, caused significant levels of hatching at 10–6 mol
l–1. Furthermore, the stable hepoxilin B3 analogue
PBT-3 stimulated hatching at 10–7 mol l–1.
Neither trioxilin A3, hepoxilin A3 or PBT-3 at
0.25–30 µmol l–1 served as settlement cues for
B. amphitrite cypris larvae.
Key words: Elminius modestus, Balanus amphitrite, barnacle egg-hatching activity, larval settlement, hepoxilin, trioxilin, hepoxilin B3, stable analogue, PBT-3
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