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Plant Physiol, November 2000, Vol. 124, pp. 1293-1304
Analysis of Oxidative Stress and Wound-Inducible Dinor
Isoprostanes F1 (Phytoprostanes F1) in
Plants1
Ruth
Imbusch and
Martin J.
Mueller*
Julius-von-Sachs-Institute, Pharmaceutical Biology, University of
Wuerzburg, Julius-von-Sachs-Platz 2, D-97082 Wuerzburg, Germany
Isoprostanes F2 are arachidonate autoxidation products
in mammals that have been shown to be induced during several human disorders associated with enhanced free-radical generation.
Isoprostanes F2 represent not only extremely reliable
markers of oxidative stress in vivo, but they also exert potent
biological effects. Therefore, it has been postulated that
isoprostanoids are mediators of oxidant injury in vivo. Higher plants,
however, do not synthesize arachidonic acid or isoprostanes. Here we
show that a series of isoprostane F2 analogs termed
phytoprostanes F1 (previously dinor isoprostanes
F1) are formed by an analogous pathway from  -linolenate in plants. High-performance liquid chromatography and gas
chromatography-mass spectrometry methods using
[18O]3phytoprostanes F1 as
internal standard have been developed to quantify phytoprostanes
F1. In fresh peppermint (Mentha piperita) leaves, phytoprostanes F1 were found in free form (76 ng/g
of dry weight) and at about 150-fold higher levels esterified in lipids. It is notable that these levels of phytoprostanes
F1 are more than two orders of magnitude higher than the
basal levels of isoprostanes F2 in mammalian tissues.
Furthermore, wounding, as well as butyl hydroperoxide or cupric acetate
stress triggered a dramatic increase of free and esterified
phytoprostanes F1. Thus phytoprostanes F1 may
represent a sensitive measure of oxidative damage in plants similar to
isoprostanes in mammals. However, one of the most exciting issues to be
clarified is the possibility that linolenate-derived phytoprostanes
F1 exert biological activities in plants and/or animals.
1
This work was supported by the
Sonderforschungsbereich 369 of the Deutsche Forschungsgemeinschaft, Bonn.
*
Corresponding author; e-mail
Martin.Mueller{at}botanik.uni-wuerzburg.de; fax 49-931-888-6182.
© 2000 American Society of Plant Physiologists
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