title: A previously undescribed jasmonate compound in flowering Arabidopsis thaliana - The identification of cis-(+)-OPDA-Ile.
abstract: Jasmonates (JAs) are plant hormones that integrate external stress stimuli with physiological responses. (+)-7-iso-JA-L-Ile is the natural JA ligand of COI1, a component of a known JA receptor. The upstream JA biosynthetic precursor cis-(+)-12-oxo-phytodienoic acid (cis-(+)-OPDA) has been reported to act independently of COI1 as an essential signal in several stress-induced and developmental processes. Wound-induced increases in the endogenous levels of JA/JA-Ile are accompanied by two to tenfold increases in the concentration of OPDA, but its means of perception and metabolism are unknown. To screen for putative OPDA metabolites, vegetative tissues of flowering Arabidopsis thaliana were extracted with 25% aqueous methanol (v/v), purified by single-step reversed-phase polymer-based solid-phase extraction, and analyzed by high throughput mass spectrometry. This enabled the detection and quantitation of a low abundant OPDA analog of the biologically active (+)-7-iso-JA-L-Ile in plant tissue samples. Levels of the newly identified compound and the related phytohormones JA, JA-Ile and cis-(+)-OPDA were monitored in wounded leaves of flowering Arabidopsis lines (Col-0 and Ws) and compared to the levels observed in Arabidopsis mutants deficient in the biosynthesis of JA (dde2-2, opr3) and JA-Ile (jar1). The observed cis-(+)-OPDA-Ile levels varied widely, raising questions concerning its role in Arabidopsis stress responses.
authors.affiliation: Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic.
authors.forename: Kristýna
authors.initials: K
authors.lastname: Floková
authors.affiliation: Department of Plant Biochemistry, Albrecht-von-Haller-Institute for Plant Sciences, Georg-August-University, Justus-von-Liebig-Weg 11, D-37077 Göttingen, Germany.
authors.forename: Kirstin
authors.initials: K
authors.lastname: Feussner
authors.affiliation: Department of Plant Biochemistry, Albrecht-von-Haller-Institute for Plant Sciences, Georg-August-University, Justus-von-Liebig-Weg 11, D-37077 Göttingen, Germany.
authors.forename: Cornelia
authors.initials: C
authors.lastname: Herrfurth
authors.affiliation: Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic.
authors.forename: Otto
authors.initials: O
authors.lastname: Miersch
authors.affiliation: Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic.
authors.forename: Václav
authors.initials: V
authors.lastname: Mik
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany AS CR & Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic.
authors.forename: Danuše
authors.initials: D
authors.lastname: Tarkowská
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany AS CR & Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic.
authors.forename: Miroslav
authors.initials: M
authors.lastname: Strnad
authors.affiliation: Department of Plant Biochemistry, Albrecht-von-Haller-Institute for Plant Sciences, Georg-August-University, Justus-von-Liebig-Weg 11, D-37077 Göttingen, Germany.
authors.forename: Ivo
authors.initials: I
authors.lastname: Feussner
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany AS CR & Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic; Department of Molecular Signal Processing, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Claus
authors.initials: C
authors.lastname: Wasternack
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany AS CR & Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic. Electronic address: novako@ueb.cas.cz.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Novák
mesh_terms: D017360:Arabidopsis / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry / Q000302:isolation & purification*; D003979:Diazonium Compounds; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D035264:Flowers / Q000737:chemistry; D007532:Isoleucine / Q000031:analogs & derivatives / Q000737:chemistry; D054883:Oxylipins / Q000737:chemistry / Q000302:isolation & purification*; D010937:Plant Growth Regulators / Q000378:metabolism; D018515:Plant Leaves / Q000378:metabolism; D011725:Pyridines; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D003979:Diazonium Compounds; D005231:Fatty Acids, Unsaturated; D054883:Oxylipins; D010937:Plant Growth Regulators; D011725:Pyridines; C532883:jasmonoyl-isoleucine; D007532:Isoleucine; C056727:2-(2'-pyridyldithio)benzyldiazoacetate; C025999:12-oxophytodienoic acid; C011006:jasmonic acid
keywords: Arabidopsis thaliana (Brassicaceae); Cis-(+)-12-oxo-phytodienoyl-l-isoleucine (cis-(+)-OPDA-Ile); Jasmonates; Solid-phase extraction (SPE); Tandem mass spectrometry (MS/MS); Ultra-high performance liquid chromatography (UHPLC)