title: An in planta technique for cis-/trans-stereochemical analysis of jasmonoyl isoleucine.
abstract: A novel technique for determining the cis-/trans-stereochemistry of jasmonoyl-isoleucine by coupling its alcoholic derivatives by sodium borohydride with high performance liquid chromatography-tandem mass spectrometry is described. Resolving cis- and trans-stereochemistry of the jasmonates in Achyranthes plants exposed to airborne (exogenous) trans-d(2)MeJA was demonstrated as an example. This novel application firmly establishes for the first time that trans-d(2)MeJA is converted exclusively into trans-JA-Ile in Achyranthes leaves, whereas the subsequent de novo biosynthesized JA-Ile possesses cis-stereochemistry. The method is simple, reproducible and could be employed for in vivo cis-/trans-stereochemistry analysis of jasmonates in plants.
authors.affiliation: Department of Biological Production, Laboratory of Biologically Active Compounds, Akita Prefectural University, Akita 010-0195, Japan.
authors.forename: Shigeru
authors.initials: S
authors.lastname: Tamogami
authors.forename: Ganesh Kumar
authors.initials: GK
authors.lastname: Agrawal
authors.forename: Randeep
authors.initials: R
authors.lastname: Rakwal
mesh_terms: D029044:Achyranthes / Q000737:chemistry* / Q000378:metabolism*; D001894:Borohydrides / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000737:chemistry / Q000378:metabolism*; D007532:Isoleucine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D054883:Oxylipins / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry
chemical_list: D001894:Borohydrides; D003517:Cyclopentanes; D054883:Oxylipins; C532883:jasmonoyl-isoleucine; D007532:Isoleucine; C011006:jasmonic acid; C025364:sodium borohydride