Format

Send to

Choose Destination
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.

Author information

1
Lehrstuhl für Pflanzenphysiologie, Ruhr-Universität, Bochum, Germany.

Abstract

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.

PMID:
9073358
DOI:
10.1006/abio.1997.2012
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Elsevier Science
Loading ...
Support Center