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J. Biol. Chem., Vol. 276, Issue 16, 12832-12838, April 20, 2001
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From the The cyclic derivative of
13(S)-hydroperoxolinolenic acid, 12-oxophytodienoic acid,
serves as a signal transducer in higher plants, mediating
mechanotransductory processes and plant defenses against a
variety of pathogens, and also serves as a precursor for the
biosynthesis of jasmonic acid, a mediator of plant herbivore defense.
Biosynthesis of 12-oxophytodienoic acid from
A Novel Class of Oxylipins,
sn1-O-(12-Oxophytodienoyl)-sn2-O-(hexadecatrienoyl)-monogalactosyl
Diglyceride, from Arabidopsis thaliana*
,,§,
Lehrstuhl für Pflanzenphysiologie,
Ruhr-Universität, D-44780 Bochum, Germany and the
¶ Institut für Pharmazeutische Chemie, Johann Wolfgang
Goethe-Universität, D-60439 Frankfurt am Main, Germany
-linolenic acid occurs
in plastids, mainly in chloroplasts, and is thought to start with free
linolenic acid liberated from membrane lipids by lipase action. In
Arabidopsis thaliana, the glycerolipid fraction contains
esterified 12-oxophytodienoic acid, which can be released enzymatically
by sn1-specific, but not by sn2-specific,
lipases. The 12-oxophytodienoyl glycerolipid fraction was isolated,
purified, and characterized. Enzymatic, mass spectrometric, and NMR
spectroscopic data allowed us to establish the structure of the novel
oxylipin as
sn1-O-(12-oxophytodienoyl)-sn2-O-(hexadecatrienoyl)-monogalactosyl diglyceride. The novel class of lipids is localized in plastids. Purified monogalactosyl diglyceride was not converted to the
sn1-(12-oxophytodienoyl) derivative by the combined action
of (soybean) lipoxygenase and (A. thaliana) allene oxide
synthase, an enzyme ensemble that converts free -linolenic acid to
free 12-oxophytodienoic acid. When leaves were wounded, a significant
and transient increase in the level of
(12-oxophytodienoyl)-monogalactosyl diglyceride was observed. In
A. thaliana, the major fraction of 12-oxophytodienoic acid occurs esterified at the sn1 position of the plastid-specific glycerolipid, monogalactosyl diglyceride.
*
This work was supported by the Deutsche
Forschungsgemeinschaft, Bonn and by Fonds der Chemischen Industrie,
Frankfurt (literature provision).The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in
accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
To whom correspondence should be addressed: Lehrstuhl
für Pflanzenphysiologie, Ruhr-Universität Bochum,
Universitätsstra
e 150, D-44801 Bochum, Germany. Tel.: 49 234 3224291; Fax: 49 234 3214187; E-mail:
Elmar.Weiler@ruhr-uni-bochum.de.
Copyright © 2001 by The American Society for Biochemistry and Molecular Biology, Inc.
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