Benzoic acid glucosinolate esters and other glucosinolates from Arabidopsis thaliana.
The spectacular recent progress in Arabidopsis thaliana molecular genetics furnishes outstanding tools for studying the formation and function of all metabolites in this cruciferous species. One of the major groups of secondary metabolites in A. thaliana is the glucosinolates. These hydrophilic, sulfur-rich glycosides appear to serve as defenses against some generalist herbivores and pathogens, and as feeding and oviposition stimulants to specialist herbivores. To help study their biosynthesis and role in plant-insect interactions, we wanted to determine the complete glucosinolate content of A. thaliana. In previous studies, 24 glucosinolates had been identified from ecotype Columbia. We reinvestigated Columbia as well as additional ecotypes and mutant lines, and identified 12 further glucosinolates, including five novel compounds. Structures were elucidated by MS and NMR spectroscopy of their desulfated derivatives, and by enzymatic cleavage of the attached ester moieties. Four of the novel glucosinolates are benzoate esters isolated from the seeds. In all but one of these compounds, esterification is on the glucose moiety rather than the side chain, a very unusual feature for glucosinolates. Among additional glucosinolates identified were the first non-chain elongated, methionine-derived glucosinolate from A. thaliana and the first compounds that appear to be derived from leucine.
Reichelt
Michael
M
Max-Planck Institute for Chemical Ecology, Beutenberg Campus, Winzerlaer Strasse 10, D-07745 Jena, Germany.
Brown
Paul D
PD
Schneider
Bernd
B
Oldham
Neil J
NJ
Stauber
Einar
E
Tokuhisa
Jim
J
Kliebenstein
Daniel J
DJ
Mitchell-Olds
Thomas
T
Gershenzon
Jonathan
J
D017360:Arabidopsis / Q000737:chemistry*; D001565:Benzoates / Q000737:chemistry; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification; D005961:Glucosinolates / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012639:Seeds / Q000737:chemistry*
D001565:Benzoates; D004952:Esters; D005961:Glucosinolates