Profiling of potential brassinosteroids in different tissues of rape flower by stable isotope labeling - liquid chromatography/mass spectrometry analysis

Yu, Lei; Ye, Tiantian; Bai, Ya-Li; Cai, Wen-Jing; Ding, Jun; Feng, Yu‐Qi

doi:10.1016/j.aca.2017.08.038

Cited by 16 publications

(11 citation statements)

References 33 publications

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“…To verify the feasibility of 4-PAMBA as the derivatization reagent for the LC–PCD–MS detection of monosaccharides, six monosaccharides (Ery, Ri, Fuc, Glc, GlcN, and Sor) were selected as model compounds and their 4-PAMBA derivatives were directly detected by MS. As shown in Figure B, the precursor ions of these derivatives were detected. The MS/MS spectra (Figure S3 of the Supporting Information) of these precursor ions show a neutral loss of 93.0 Da (phenylamine) from the moiety of the derivatization reagent, resulting in a [M – 93] + fragment ion that is quite similar to the fragmentation of the derivatives of 4-PAMBA and BRs. , These results confirmed that the reaction between six monosaccharides and 4-PAMBA can occur and produce the desired derivatives. Subsequently, the six model monosaccharides were detected in MRM mode by a LC–PCD–MS device (Figure ).…”

Section: Resultssupporting

confidence: 59%

“…The MS/MS spectra (Figure S3 of the Supporting Information) of these precursor ions show a neutral loss of 93.0 Da (phenylamine) from the moiety of the derivatization reagent, resulting in a [M − 93] + fragment ion that is quite similar to the fragmentation of the derivatives of 4-PAMBA and BRs. 32,33 These results confirmed that the reaction between six monosaccharides and 4-PAMBA can occur and produce the desired derivatives. Subsequently, the six model monosaccharides were detected in MRM mode by a LC−PCD−MS device (Figure 2).…”

Section: ■ Experimental Sectionsupporting

confidence: 68%

“…For the rapid analysis of monosaccharides by LC–PCD–MS, a derivatization reagent that satisfies the requirements of PCD is required. Boronic acid reagents have been widely used to label cis -diols. − In our previous study, 4-PAMBA has been used as the derivatization reagent for the highly sensitive detection of brassinosteroids (BRs). , However, the derivatization products of boronic acid reagents with cis -diol compounds, such as monosaccharides, are easily decomposed during LC separation . Therefore, pre-column derivatization is not suitable for the determination of monosaccharides by LC–MS using 4-PAMBA as the derivatization reagent.…”

Section: Resultsmentioning

confidence: 99%

“…NaBH 3 CN (97%) was purchased from Aladdin Regent Co. (Shanghai, China). The derivatization reagent 4-PAMBA was synthesized according to our previously reported method . Ultrapure water was prepared on a Milli-Q system (Milford, MA, U.S.A.).…”

Section: Experimental Sectionmentioning

confidence: 99%

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Rapid Analysis of Monosaccharides in Sub-milligram Plant Samples Using Liquid Chromatography–Mass Spectrometry Assisted by Post-column Derivatization

Cai

Wang

et al. 2020

J. Agric. Food Chem.

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Monosaccharides play important roles in plant growth and development, and their biofunctions are closely related to their endogenous contents. Therefore, the determination of monosaccharides is beneficial for the further study of monosaccharide biofunction. In this work, we developed a liquid chromatography–mass spectrometry analytical method assisted by a post-column derivatization technique (LC–PCD–MS) for the fast and automatic determination of 16 monosaccharides in samples. Post-column chemical derivatization of monosaccharides was performed by a reaction of monosaccharides with 4-benzylaminobenzeneboronic acid (4-PAMBA) through boronate ester formation in a three-way connector. 4-PAMBA worked as a derivatization reagent to improve the selectivity and sensitivity of monosaccharide detection by MS. The developed LC–PCD–MS method integrates LC separation, chemical derivatization, and MS detection in one run, thus greatly reducing the analysis time for each sample. The limits of detection and limits of quantification for 16 monosaccharides were in the range of 0.002–0.1 and 0.007–0.5 ng/mL, respectively. Good linearity was obtained from the linear regression, with a determination coefficient (R 2) ranging from 0.9928 to 1.0000. The relative recoveries were in the range of 80.7–117.8%, with the intra- and interday relative standard deviations less than 19.7 and 16.5%, respectively, indicating good accuracy and acceptable reproducibility of the method. Finally, the method was successfully applied to investigate the spatial and temporal distribution of 16 monosaccharides in the developing flower and germinating seed of Arabidopsis thaliana.

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Section: Resultssupporting

confidence: 59%

Section: ■ Experimental Sectionsupporting

confidence: 68%

Section: Resultsmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

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Rapid Analysis of Monosaccharides in Sub-milligram Plant Samples Using Liquid Chromatography–Mass Spectrometry Assisted by Post-column Derivatization

Cai

Wang

et al. 2020

J. Agric. Food Chem.

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“…26−28 Furthermore, the profiling of cis-diolcontaining metabolites was pioneeringly exemplified by introducing a pair of boronate reagents, 4-PAMBA and 4-PAMBA-d 5 , to label potential brassinosteroids in plant extracts followed by LC−MS analysis. 29 Brassinosteroid candidates were annotated by retention time (RT) and peak intensity matching of the H/D isotope-labeled derivatives. However, in the proposed profiling strategy, a pair of isotope reagents were required for metabolite screening and annotation, which were of high cost and difficult to obtain.…”

Section: ■ Introductionmentioning

confidence: 99%

Boron Isotope Tag-Assisted Ultrahigh-Performance Liquid Chromatography Coupled with High-Resolution Mass Spectrometry for Discovery and Annotation of cis-Diol-Containing Metabolites

et al. 2021

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cis-Diol-containing metabolites are widely distributed in living organisms, and they participate in the regulation of various important biological activities. The profiling of cis-diolcontaining metabolites could help us in fully understanding their functions. In this work, based on the characteristic isotope pattern of boron, we employed a boronic acid reagent as the isotope tag to establish a sensitive and selective liquid chromatography−highresolution mass spectrometry method for the screening and annotation of cis-diol-containing metabolites in biological samples. Boronic acid reagent 2-methyl-4-phenylaminomethylphenylboronic acid was used to label the cis-diol-containing metabolites in biological samples to improve the selectivity and MS sensitivity of cis-diol-containing metabolites. Based on the characteristic 0.996 Da mass difference of precursor ions and the peak intensity ratio of 1:4 originating from 10 B and 11 B natural isotopes, the potential cis-diol-containing metabolites were rapidly screened from biological samples. Potential cis-diol-containing metabolites were annotated by database searching and analysis of fragmentation patterns obtained by multistage MS (MS n ) via collision-induced dissociation. Importantly, the cis-diol position could be readily resolved by the MS 3 spectrum. With this method, a total of 45 cisdiol-containing metabolites were discovered in rice, including monoglycerides, polyhydroxy fatty acids, fatty alcohols, and so forth. Furthermore, the established method showed superiority in avoiding false-positive results in profiling cis-diol-containing metabolites.

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The Brassinosteroids Family – Structural Diversity of Natural Compounds and Their Precursors

Zullo

Bajguz

2019

Brassinosteroids: Plant Growth and Development

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Profiling of potential brassinosteroids in different tissues of rape flower by stable isotope labeling - liquid chromatography/mass spectrometry analysis

Cited by 16 publications

References 33 publications

Rapid Analysis of Monosaccharides in Sub-milligram Plant Samples Using Liquid Chromatography–Mass Spectrometry Assisted by Post-column Derivatization

Rapid Analysis of Monosaccharides in Sub-milligram Plant Samples Using Liquid Chromatography–Mass Spectrometry Assisted by Post-column Derivatization

Boron Isotope Tag-Assisted Ultrahigh-Performance Liquid Chromatography Coupled with High-Resolution Mass Spectrometry for Discovery and Annotation of cis-Diol-Containing Metabolites

The Brassinosteroids Family – Structural Diversity of Natural Compounds and Their Precursors

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