Biosynthesis of 14,15-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D(1) pathway.
A novel group of cyclopentenone prostaglandin-like compounds, deoxy phytoprostanes J(1), together with their precursors, phytoprostanes D(1), were identified in tobacco, tomato and Arabidopsis. Previously, it was thought that 14,15-dehydro-12-oxo-phytodienoic acid, a member of the deoxy phytoprostanes J(1) family, is derived from either 12-oxo-phytodienoic acid or diketols via the allene oxide synthase pathway. Results suggest that 14,15-dehydro-12-oxo-phytodienoic acid as well as structurally related cyclopentenones of the chromomoric acid family are synthesized via the phytoprostane D(1) pathway in planta. Notably, 14,15-dehydro-12-oxo-phytodienoic acid is more abundant than 12-oxo-phytodienoic acid in all three species so far analyzed.
Krischke
Markus
M
Julius-von-Sachs-Institute for Biosciences, Pharmaceutical Biology, University of Wuerzburg, Julius-von-Sachs-Platz 2, D-97082 Wuerzburg, Germany.
Loeffler
Christiane
C
Mueller
Martin J
MJ
D017360:Arabidopsis / Q000378:metabolism; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000737:chemistry / Q000378:metabolism*; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis* / Q000737:chemistry* / Q000378:metabolism*; D018551:Solanum lycopersicum / Q000378:metabolism; D010936:Plant Extracts / Q000378:metabolism; D010937:Plant Growth Regulators / Q000096:biosynthesis; D013237:Stereoisomerism; D014026:Nicotiana / Q000378:metabolism
D003517:Cyclopentanes; D005231:Fatty Acids, Unsaturated; D010936:Plant Extracts; D010937:Plant Growth Regulators; C424244:Prostane, herbal preparation; C473305:phytoprostane D1; C025999:12-oxophytodienoic acid; C013905:cyclopentenone