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J. Biol. Chem., Vol. 261, Issue 36, 17040-17047, 12, 1986
L Meijer, AR Brash, RW Bryant, K Ng, J Maclouf and H Sprecher
Oocyte maturation (meiosis reinitiation) in starfish is induced by the
natural hormone 1-methyladenine. This induction of meiotic divisions can be
triggered also by four fatty acids: 5,8,11-20:3; 5,8,11,14-20:4
(arachidonic acid); 6,9,12,15-20:4; 5,8,11,14,17-20:5, all other fatty
acids being completely inactive. This maturation triggered by eicosanoids
occurs in the micromolar range and is facilitated by the presence of
calcium. A variety of arachidonic acid derivatives (esters, epoxides, etc.)
and metabolites (cyclooxygenase and lipoxygenase products) has been tested;
the biological activity is restricted to 8- hydroxyeicosatetraenoic acid
(8-HETE), other mono- and poly-HETEs being completely inactive. Maturation
triggered by 8-HETE occurs around 10 nM and is insensitive to the presence
of calcium. 8-HETE methyl ester and 8-hydroperoxyeicosatetraenoic acid are
able to induce maturation at higher concentrations. Both (8S) and (8R)
stereoisomers have been tested; the biological activity is strictly
restricted to the (8R) isomer. 8-HETE triggers a complete maturation, i.e.
maturation- promoting factor appearance, germinal vesicle breakdown,
emission of the polar bodies, and formation of a female pronucleus.
(8R)-HETE, but not (8S)-HETE, triggers the typical decrease in cyclic AMP
concentration induced by 1-methyladenine and the burst of protein
phosphorylation associated with maturation. Starfish oocytes oxidize
exogenous arachidonic acid into 8-HETE and other HETEs. 8-HETE was
identified, after high pressure liquid chromatography purification, by gas
chromatography mass spectrometry. Furthermore, it was found that the
starfish oocytes only produce the (8R)-HETE isomer. This highly
stereospecific induction of oocyte maturation by (8R)-HETE suggests that
this fatty acid, or a very closely related fatty acid, may play a role in
the transduction of the 1-methyladenine message at the plasma membrane
level.
Stereospecific induction of starfish oocyte maturation by (8R)- hydroxyeicosatetraenoic acid
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