Convenient identification of desulfoglucosinolates on the basis of mass spectra obtained during liquid chromatography–diode array–electrospray ionisation mass spectrometry analysis: Method verification for sprouts of different Brassicaceae species extracts

Kusznierewicz, Barbara; Iori, Renato; Piekarska, Anna; Namieśnik, Jacek; Bartoszek, Agnieszka

doi:10.1016/j.chroma.2012.12.075

Cited by 66 publications

(51 citation statements)

References 32 publications

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“…was identical to the UV spectrum of m-hydroxylated d12R (Agerbirk and Olsen, 2012), with significantly lower k max values than found for the p-hydroxylated isomers leading to absence of a distinct maximum near 220 nm in contrast to presence of this maximum in UV spectra of p-hydroxyl derivatives (Agerbirk et al, 2001(Agerbirk et al, , 2008. Tandem MS of desulfoGSLs has rarely been discussed , most authors have only reported masses of the intact desulfoGSL adducts (Mithen et al, 2010;Kusznierewicz et al, 2013). Analysis of desulfated GSLs may offer the advantage that the charge needed for detection is in the form of an exogenous ion that can form adducts with any polar part of the molecule .…”

Section: Analytical Distinction Of Isomersmentioning

confidence: 81%

Multiple hydroxyphenethyl glucosinolate isomers and their tandem mass spectrometric distinction in a geographically structured polymorphism in the crucifer Barbarea vulgaris

et al. 2015

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Section: Analytical Distinction Of Isomersmentioning

confidence: 81%

Multiple hydroxyphenethyl glucosinolate isomers and their tandem mass spectrometric distinction in a geographically structured polymorphism in the crucifer Barbarea vulgaris

et al. 2015

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“…For identification of GS, some desulfoglucosinolate extracts were run on an LC-ESI-IonTrap-MS-system (Bruker Esquire6000) in positive ionization mode and compared to known GS from A. thaliana ecotype Col-0 leaf and seed extracts and for 3MSOOP to an Erysimum cheiri (type: Borntal-Lichter; Chrestensen) seed extract. Obtained mass spectral data of desulfoglucosinolates were compared to data shown in Kusznierewicza et al (2013).…”

Section: Methodsmentioning

confidence: 99%

Flowering Locus C (FLC) Is a Potential Major Regulator of Glucosinolate Content across Developmental Stages of Aethionema arabicum (Brassicaceae)

et al. 2017

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The biochemical defense of plants can change during their life-cycle and impact herbivore feeding and plant fitness. The annual species Aethionema arabicum is part of the sister clade to all other Brassicaceae. Hence, it holds a phylogenetically important position for studying crucifer trait evolution. Glucosinolates (GS) are essentially Brassicales-specific metabolites involved in plant defense. Using two Ae. arabicum accessions (TUR and CYP) we identify substantial differences in glucosinolate profiles and quantities between lines, tissues and developmental stages. We find tissue specific side-chain modifications in aliphatic GS: methylthioalkyl in leaves, methylsulfinylalkyl in fruits, and methylsulfonylalkyl in seeds. We also find large differences in absolute glucosinolate content between the two accessions (up to 10-fold in fruits) that suggest a regulatory factor is involved that is not part of the quintessential glucosinolate biosynthetic pathway. Consistent with this hypothesis, we identified a single major multi-trait quantitative trait locus controlling total GS concentration across tissues in a recombinant inbred line population derived from TUR and CYP. With fine-mapping, we narrowed the interval to a 58 kb region containing 15 genes, but lacking any known GS biosynthetic genes. The interval contains homologs of both the sulfate transporter SULTR2;1 and FLOWERING LOCUS C. Both loci have diverse functions controlling plant physiological and developmental processes and thus are potential candidates regulating glucosinolate variation across the life-cycle of Aethionema. Future work will investigate changes in gene expression of the candidates genes, the effects of GS variation on insect herbivores and the trade-offs between defense and reproduction.

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“…In liquid chromatography-mass spectroscopy (LC-MS) analysis, peak 4 had mass-to-charge ratio (m/z) values of 178, 340, and 362, which corresponded to the previously reported m/z values of desulfo-glucoraphasatin for [M+H2Glc], [M+H], and [M+Na], respectively ( Fig. 4B; Kusznierewicz et al, 2013). Similarly, the mass spectra of peak 3 were identical to that of desulfo-glucoerucin (data not shown).…”

Section: Analysis Of Transgenic Arabidopsis Overexpressing Orf3mentioning

confidence: 99%

A 2-Oxoglutarate-Dependent Dioxygenase Mediates the Biosynthesis of Glucoraphasatin in Radish

et al. 2017

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Glucosinolates (GSLs) are secondary metabolites whose degradation products confer intrinsic flavors and aromas to Brassicaceae vegetables. Several structures of GSLs are known in the Brassicaceae, and the biosynthetic pathway and regulatory networks have been elucidated in Arabidopsis (Arabidopsis thaliana). GSLs are precursors of chemical defense substances against herbivorous pests. Specific GSLs can act as feeding blockers or stimulants, depending on the pest species. Natural selection has led to diversity in the GSL composition even within individual species. However, in radish (Raphanus sativus), glucoraphasatin (4-methylthio-3-butenyl glucosinolate) accounts for more than 90% of the total GSLs, and little compositional variation is observed. Because glucoraphasatin is not contained in other members of the Brassicaceae, like Arabidopsis and cabbage (Brassica oleracea), the biosynthetic pathways for glucoraphasatin remain unclear. In this report, we identified and characterized a gene encoding GLUCORAPHASATIN SYNTHASE 1 (GRS1) by genetic mapping using a mutant that genetically lacks glucoraphasatin. Transgenic Arabidopsis, which overexpressed GRS1 cDNA, accumulated glucoraphasatin in the leaves. GRS1 encodes a 2-oxoglutarate-dependent dioxygenase, and it is abundantly expressed in the leaf. To further investigate the biosynthesis and transportation of GSLs in radish, we grafted a grs1 plant onto a wild-type plant. The grafting experiment revealed a leaf-to-root long-distance glucoraphasatin transport system in radish and showed that the composition of GSLs differed among the organs. Based on these observations, we propose a characteristic biosynthesis pathway for glucoraphasatin in radish. Our results should be useful in metabolite engineering for breeding of high-value vegetables.

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Convenient identification of desulfoglucosinolates on the basis of mass spectra obtained during liquid chromatography–diode array–electrospray ionisation mass spectrometry analysis: Method verification for sprouts of different Brassicaceae species extracts

Cited by 66 publications

References 32 publications

Multiple hydroxyphenethyl glucosinolate isomers and their tandem mass spectrometric distinction in a geographically structured polymorphism in the crucifer Barbarea vulgaris

Multiple hydroxyphenethyl glucosinolate isomers and their tandem mass spectrometric distinction in a geographically structured polymorphism in the crucifer Barbarea vulgaris

Flowering Locus C (FLC) Is a Potential Major Regulator of Glucosinolate Content across Developmental Stages of Aethionema arabicum (Brassicaceae)

A 2-Oxoglutarate-Dependent Dioxygenase Mediates the Biosynthesis of Glucoraphasatin in Radish

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