Analysis of phenolic choline esters from seeds of Arabidopsis thaliana and Brassica napus by capillary liquid chromatography/electrospray‐ tandem mass spectrometry

Abstract

Total phenolic choline ester fractions prepared from seeds of Arabidopsis thaliana and Brassica napus were analyzed by capillary LC/ESI-QTOF-MS and direct infusion ESI-FTICR-MS. In addition to the dominating sinapoylcholine, 30 phenolic choline esters could be identified based on accurate mass measurements, interpretation of collision-induced dissociation (CID) mass spectra, and synthesis of selected representatives. The compounds identified so far include substituted hydroxycinnamoyl- and hydroxybenzoylcholines, respective monohexosides as well as oxidative coupling products of phenolic choline esters and monolignols. Phenolic choline esters are well separable by reversed-phase liquid chromatography and sensitively detectable using electrospray ionization mass spectrometry in positive ion mode. CID mass spectra obtained from molecular ions facilitate the characterization of both the type and substitution pattern of such compounds. Therefore, LC/ESI-MS/MS represents a valuable tool for comprehensive qualitative and quantitative analysis of this compound class.

Reprogramming the Phenylpropanoid Metabolism in Seeds of Oilseed Rape by Suppressing the Orthologs ofREDUCED EPIDERMAL FLUORESCENCE1

“…Compounds were then putatively annotated/characterized by interpretation of characteristic fragment ions and neutral losses (Supplemental Tables S2 and S3). Putative annotations of a total of 26 compounds could be verified by an analysis of noncommercial reference compounds that were synthesized (Böttcher et al, 2009) or isolated from oilseed rape seeds and structurally characterized by NMR Wolfram et al, 2010) in previous studies.…”

Simultaneous quantification of lignans in Arabidopsis thaliana by highly sensitive capillary liquid chromatography-electrospray ionization-ion trap mass spectrometry

“…Since the sensitivity of LC-ESI-MS can be increased by lowering the flow rate of the mobile phase, capillary LC-ESI-MS systems with narrow diameter LC columns are more sensitive than conventional LC-ESI-MS systems (Abian et al 1999;Hopfgartner et al 1993). Highly sensitive capillary LC-ESI-MS has been applied in peptide mapping ) and in quantification of flavonoids (Bottcher et al 2009) and plant hormones (Izumi et al 2009), but has not been used for lignan analysis. Here we established a highly sensitive analytical system based on capillary liquid chromatography-electrospray ionization-ion trap mass spectrometry (LC-ESI-IT-MS/MS) that enables lignan profiling of A. thaliana.…”

Peroxisomal ATP-Binding Cassette Transporter COMATOSE and the Multifunctional Protein ABNORMAL INFLORESCENCE MERISTEM Are Required for the Production of Benzoylated Metabolites in Arabidopsis Seeds

“…S1; Supplemental Table S1) was analyzed for glucosinolates, including BGs (Reichelt et al, 2002), and phenolic choline esters such as hydroxycinnamoylcholine and hydroxybenzoylcholine esters (Böttcher et al, 2009). Most of these mutants were analyzed previously for potential roles in fatty acid or auxin metabolism, but the specific functions of the genes involved remain unknown (Wiszniewski et al, 2009).…”

“…1191425-45-2), m/z 296. The compounds were identified based on comparison of mass spectra with those in the literature (Böttcher et al, 2009). …”