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Anal Biochem. 1997 Mar 15;246(2):211-7.

Analysis of 12-oxo-phytodienoic acid enantiomers in biological samples by capillary gas chromatography-mass spectrometry using cyclodextrin stationary phases.

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Lehrstuhl für Pflanzenphysiologie, Ruhr-Universität, Bochum, Germany.


The octadecanoid plant growth regulator 12-oxo-phytodienoic acid (12-oxo-PDA), which is also an intermediate in the biosynthesis of jasmonic acid, is obtained from 13-hydroperoxylinolenic acid via an unstable allene oxide generated by the enzyme allene oxide synthase. Recombinant, bacterially expressed and purified allene oxide synthase from Arabidopsis thaliana yields racemic 12-oxo-PDA as a mixture of 94:6 cis:trans diastereomers. In the presence of allene oxide cyclase from Solanum tuberosum, a product of high enantiomeric purity was obtained, which was shown to be (+)-cis-12-oxo-PDA (98:2 cis:trans diastereomers). Based on this coupled reaction, a preparative procedure was developed that yields pure (+)-cis-12-oxo-PDA in milligram quantities. Furthermore, an analytical technique employing capillary gas chromatography-mass spectrometry and beta- or gamma-cyclodextrin stationary phases was developed that enables the direct analysis of nanogram amounts of enantiomers of 12-oxo-PDA, as their methyl esters, in plant tissues. In the species analyzed, endogenous cis-12-oxo-PDA is the (+)-enantiomer.

[Indexed for MEDLINE]

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