Negative atmospheric pressure chemical ionisation low-energy collision activation mass spectrometry for the characterisation of flavonoids in extracts of fresh herbs

Justesen, Ulla

doi:10.1016/s0021-9673(00)00861-x

Cited by 231 publications

(203 citation statements)

References 29 publications

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“…H-1″ of the sugar residue appears as a broad singlet, which is only compatible with an α-configuration. Note that despite the fact that luteolin-O-glucuronide has been previously described in several Thymus plants (Justesen, 2000;Miron, Plaza, Bahrim, Ibanez, & Herrero, 2011), only the 7-O-β-isomer has been previously identified by NMR analysis (Fecka & Turek, 2008;Ozgen et al, 2011).…”

Section: Flavonesmentioning

confidence: 94%

Simultaneous characterization and quantification of phenolic compounds in Thymus x citriodorus using a validated HPLC–UV and ESI–MS combined method

Pereira

Peres

Silva

et al. 2013

Food Research International

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Thymus x citriodorus is a Lamiaceae plant extensively cultivated in the Mediterranean region and used for centuries in culinary and in traditional medicine. The present work describes the detailed phenolic composition of T. x citriodorus for the first time, by means of HPLC-DAD, ESI-MS and MS n and nuclear magnetic resonance (NMR) analyses. The ethanolic extract of T. x citriodorus was analyzed by reversed phase HPLC. The method of analysis was also validated concerning its linearity, instrumental and method precision (for repeatability, immediate precision and intermediate precision) and accuracy (absolute recovery study). The technique was combined with electrospray mass spectrometry in order to identify the phenolic compounds and the structure of the main phenolics was also confirmed by NMR analysis. The in-house validated HPLC-DAD method showed good linearity for the tested reference compounds as well as satisfactory repeatability and immediate precision values, for both instrument and method. Furthermore, the satisfactory results of intermediate precision analysis and recovery assays indicated that the chromatographic method could be used to quantify the main phenolic compounds of T. x citriodorus with adequate precision and accuracy. The extract was rich in rosmarinic acid (10.4 ± 0.6 mg/g extract) that is a widespread phenolic acid in Thymus plants, but also in luteolin-7-O-α-glucuronide (12 ± 2 mg/g extract), that was herein reported in Thymus for the first time. Other novel compounds comprised one eriodictyol dihexoside with O-glycosidic linkages, two eriodictyol-O-monohexosides, one quercetagetin dimethyl ether-O-hexoside, one naringenin-O-hexoside and chrysoeriol-7-β-O-glucoside. Having in mind the health-promoting properties reported in literature for some of the main polyphenols found in T. x citriodorus, we suggest that this plant has a high potential for being used as a functional food.

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Section: Flavonesmentioning

confidence: 94%

Simultaneous characterization and quantification of phenolic compounds in Thymus x citriodorus using a validated HPLC–UV and ESI–MS combined method

Pereira

Peres

Silva

et al. 2013

Food Research International

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“…The MS 2 spectra of peaks representing similar compounds are often highly similar (Figure 4) (Justesen, 2000;Morreel et al, 2004;Fabre et al, 2007). Consequently, in addition to the correlation coefficient between the peak abundances, MS 2 spectral matching can be regarded as a second optional filter to decide whether or not a CSPP is associated with a true biochemical conversion.…”

Section: Including a Ms 2 Spectral Similarity Search Algorithmmentioning

confidence: 99%

Systematic Structural Characterization of Metabolites in Arabidopsis via Candidate Substrate-Product Pair Networks

et al. 2014

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Plant metabolomics is increasingly used for pathway discovery and to elucidate gene function. However, the main bottleneck is the identification of the detected compounds. This is more pronounced for secondary metabolites as many of their pathways are still underexplored. Here, an algorithm is presented in which liquid chromatography-mass spectrometry profiles are searched for pairs of peaks that have mass and retention time differences corresponding with those of substrates and products from well-known enzymatic reactions. Concatenating the latter peak pairs, called candidate substrate-product pairs (CSPP), into a network displays tentative (bio)synthetic routes. Starting from known peaks, propagating the network along these routes allows the characterization of adjacent peaks leading to their structure prediction. As a proof-of-principle, this high-throughput cheminformatics procedure was applied to the Arabidopsis thaliana leaf metabolome where it allowed the characterization of the structures of 60% of the profiled compounds. Moreover, based on searches in the Chemical Abstract Service database, the algorithm led to the characterization of 61 compounds that had never been described in plants before. The CSPP-based annotation was confirmed by independent MS n experiments. In addition to being high throughput, this method allows the annotation of low-abundance compounds that are otherwise not amenable to isolation and purification. This method will greatly advance the value of metabolomics in systems biology.

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“…The molecular ion mass is 86 amu larger than that of the glucosyl group (162 amu) and corresponds to a malonyl group (−OCCH 2 -COOH) (20)(21)(22)(23)(24)(25). Therefore, peak 12 was identified as luteolin 7-O-glucoside malonate.…”

Section: Identification Of Celery Flavonoidsmentioning

confidence: 99%

Detection and Quantification of Glycosylated Flavonoid Malonates in Celery, Chinese Celery, and Celery Seed by LC-DAD-ESI/MS

Lin

Harnly

2007

J. Agric. Food Chem.

122

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A screening method using LC-DAD-ESI/MS was applied to the analysis of flavonoids in celery, Chinese celery, and celery seeds (Apium graveolens L. and varieties). Fifteen flavonoid glycosides were detected in the three celery materials. They were identified as luteolin 7-O-apiosylglucoside, luteolin 7-O-glucoside, apigenin 7-O-apiosylglucoside, chrysoeriol 7-O-apiosylglucoside, chrysoeriol 7-O-glucoside, and more than 10 malonyl derivatives of these glycosides. The identification of the malonyl derivatives was confirmed by their conversion into glycosides upon heating and by comparison of some of the malonates with malonates that had previously been identified in red bell pepper and parsley. The concentrations of the glycosides and the malonyl glycosides in the three materials were estimated by comparison to aglycone standards. This is the first report of the presence of these glycosylated flavonoid malonates in celery.

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Negative atmospheric pressure chemical ionisation low-energy collision activation mass spectrometry for the characterisation of flavonoids in extracts of fresh herbs

Cited by 231 publications

References 29 publications

Simultaneous characterization and quantification of phenolic compounds in Thymus x citriodorus using a validated HPLC–UV and ESI–MS combined method

Simultaneous characterization and quantification of phenolic compounds in Thymus x citriodorus using a validated HPLC–UV and ESI–MS combined method

Systematic Structural Characterization of Metabolites in Arabidopsis via Candidate Substrate-Product Pair Networks

Detection and Quantification of Glycosylated Flavonoid Malonates in Celery, Chinese Celery, and Celery Seed by LC-DAD-ESI/MS

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