Mass Spectrometry of Flavonoid Vicenin-2, Based Sunlight Barriers in Lychnophora species

In a comprehensive study, more than 60 phenolic compounds were detected in methanolic extracts from different tissues of pineapple infructescence by high-performance liquid chromatography with diode array detection and electrospray ionisation multiple-stage mass spectrometry (HPLC-DAD-ESI-MS (n) ) as well as by gas chromatography-mass spectrometry (GC-MS). The analytical workflow combining both methods revealed numerous compounds assigned for the first time as pineapple constituents by their mass fragmentations. Pineapple crown tissue was characterised by depsides of p-coumaric and ferulic acid. In contrast, major phenolic compounds in pineapple pulp extracts were assigned to diverse S-p-coumaryl, S-coniferyl and S-sinapyl derivatives of glutathione, N-L-γ-glutamyl-L-cysteine and L-cysteine, which were also identified in the peel. The latter was additionally characterised by elevated concentrations of p-coumaric, ferulic and caffeic acid depsides and glycerides, respectively. Two peel-specific cyanidin hexosides were found. Elevated concentrations of isomeric N,N'-diferuloylspermidines may be a useful tool for the detection of fraudulent peel usage for pineapple juice production. Mass fragmentation pathways of characteristic pineapple constituents are proposed, and their putative biological functions are discussed.

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“…For instance, the flavonoid vicenin-2 (42) was recently proposed to be an efficient UV screen on the surface of Lychnophora spp. leaves [54].…”

Section: Phenolic Pattern Of Different Fruit Tissuesmentioning

confidence: 98%

Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

et al. 2015

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“…(45) MALDI-MS imaging has also revealed that, unlike other flavonoids, vicenin-2 is produced at the top of Lychnophora salicifolia leaves. (46) The combination of the localization and UV absorption properties of vicenin-2 indicate that it could act as a UV-light barrier to protect plants. Thus, MALDI-MS imaging provides information vital for understanding the ecological and physiological functions of metabolites in plants.…”

Section: Visualization Of Polyphenol Distributions In Edible Plants Bmentioning

confidence: 99%

“…Thus, MALDI-MS imaging provides information vital for understanding the ecological and physiological functions of metabolites in plants. (46) The presence of hesperidin in leaves and stems of Citrus limonia after Xylella fastidiosa infection has been visualized by MALDI-MS imaging, revealing that hesperidin plays a role in the plant-pathogen interaction. (38) Thus, MALDI-MS imaging could overcome the limitations of conventional analytical methods in research into the distribution of polyphenols in plant tissues, providing new analytical information regarding the biological roles and biosynthesis of phytochemicals in plants.…”

Section: Visualization Of Polyphenol Distributions In Edible Plants Bmentioning

confidence: 99%

Detection and Visualization of Food-derived Polyphenols by Matrix-assisted Laser Desorption/Ionization Mass Spectrometry Imaging

Nguyen¹,

Ham²,

Matsui³

et al. 2019

Sensors and Materials

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Food-derived polyphenols have health benefits owing to their ability to prevent some diseases. Knowledge of their bioavailabilities and metabolism is important for understanding the mechanisms underlying their benefits. Thus, mass spectrometry (MS)-based analytical techniques, such as liquid chromatography-MS (LC-MS), that are capable of highly sensitive and simultaneous detection of absorbed polyphenols and their metabolites are essential tools in this field. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) imaging is currently used in biological sciences for visualizing the spatial information of various compounds, such as peptides, proteins, lipids, drugs, and food compounds, in various biological tissues. However, the application of MALDI-MS imaging to polyphenols is challenging owing to the lack of appropriate matrix reagents for visualizing (or detecting) polyphenols absorbed in target biological tissues. This review highlights the development of the MALDI-MS imaging technique for the detection and visualization of food-derived polyphenols. First, the development of new matrices and matrix additives for the detection and visualization of polyphenols is discussed, followed by their introduction to inhibitor-aided MALDI-MS imaging for the elucidation of intestinal absorption routes and the metabolic behaviors of polyphenols. The MALDI-MS imaging technique shows great potential as a novel analytical tool for elucidating the bioavailabilities of food-derived polyphenols.

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“…1) were evaluated by MALDI, in which six are aglycones and five are O-glycosides. The aglycones having fewer hydroxyl substituents, as kaempferol (18) and galangin (17), did not suffer in-source fragmentation when low laser intensity was applied, but they easily lost CO and were fragmented by RDA reactions in high laser intensities (>25% for analyses without matrix) ( Fig. 3C and Supporting Information Fig.…”

Section: Flavonolsmentioning

confidence: 99%

“…[15] However, MALDI has been employed for the analysis of secondary metabolites in extracts, tissues and single plant cells. [16,17] The first evidence of a chemical barrier for sunlight absorption in plants, reported by the simultaneous quantification and structural elucidation of a di-C-glycosyl flavonoid, was described using MALDI imaging, [18] which combines molecular mass analysis and spatial information in tissues. [19] The tissue distributions of flavonoids in leaves of the Citrus species infected by Xylella fastidiosa were analyzed by MALDI imaging.…”

Section: Introductionmentioning

confidence: 99%

MALDI-MS of flavonoids: a systematic investigation of ionization and in-source dissociation mechanisms

Silva

Lopes

2015

J. Mass Spectrom.

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Matrix assisted laser desorption ionization (MALDI) is a technique widely employed in the analysis of proteins and peptides, and nowadays it has also been applied to small molecules. There is little significant information regarding the in-source dissociation processes on MALDI for natural products. Twenty-six flavonoids (flavanones, flavones and flavonols) were analyzed by MALDI using different methods (with different matrices) and without matrix to comprehend the in-source reactions and establish good analysis methods for these compounds. Depending on the class, structure and the laser intensity applied, methoxylated flavonoid aglycones can eliminate methyl radicals (˙CH3) in the source, such as flavonols, but lithium 2,4-dihydroxybenzoate matrix suppresses the ˙CH3 eliminations and retro-Diels-Alder cleavages in the source. All of the flavonoid O-glycosides evaluated herein eliminated the sugar in source, even in the presence of the matrix, and its product radical ions ([M-H-sugar](-)˙) were observed in the negative mode. The flavone C-glycosides suffered intense dissociation, which was reduced by the addition of a matrix and the application of low laser intensity, mainly in the negative mode. Depending on the hydroxyl substituents, the [M-H-H](-)˙ ion was observed with variable relative intensity in the spectra.

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Mass Spectrometry of Flavonoid Vicenin-2, Based Sunlight Barriers in Lychnophora species

Cited by 67 publications

References 33 publications

Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis

Detection and Visualization of Food-derived Polyphenols by Matrix-assisted Laser Desorption/Ionization Mass Spectrometry Imaging

MALDI-MS of flavonoids: a systematic investigation of ionization and in-source dissociation mechanisms

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