Anthocyanidins structural study using positive electrospray ionization triple quadrupole mass spectrometry and H/D exchange

Poliseli, Camila B.; Ribeiro, Matheus Henrique Dal Molin; Tonin, Angélica Priscila Parussolo; Vagula, Julianna M.; Santos, Oscar Oliveira; Visentainer, Jesuí V.; Pontes, Rodrigo M.; Moraes, Luiz Alberto Beraldo; Meurer, Eduardo C.

doi:10.1002/jms.4293

Cited by 3 publications

(1 citation statement)

References 19 publications

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“…Because the permanent positive charge of anthocyanin is located on the oxygen atom of the benzopyrylium, the number of phenolic hydroxyl groups in the structure of anthocyanin metabolites can be determined by the number of deuterium atoms in MS1 of the HDX-MS experiments [ 33 ]. In MS2, the possible structures of unknown anthocyanin metabolites may be deduced from HDX-MS experiments by comparing the fragmented mechanisms of known anthocyanin analogs [ 34 ]. Quantum chemistry can facilitate the interpretation, prediction, and analysis of MS data, particularly those obtained by MS/MS [ 35 , 36 ].…”

Section: Discussionmentioning

confidence: 99%

Mass Spectrometric Behavior and Molecular Mechanisms of Fermented Deoxyanthocyanidins to Alleviate Ulcerative Colitis Based on Network Pharmacology

Bai¹,

Wang²,

Lan

et al. 2022

International Journal of Analytical Chemistry

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Aims. Ulcerative colitis (UC) is a type of chronic idiopathic inflammatory bowel disease with a multifactorial pathogenesis and limited treatment options. The aim of the present study is to investigate the hydrogen deuterium exchange mass spectrometry (HDX-MS) behaviors of fermented deoxyanthocyanidins and their molecular mechanisms to alleviate UC by using quantum chemistry and network pharmacology. Methods. Tandem MS indicated at least two fragmentation pathways through which deuterated vinylphenol-deoxyanthocyanidins could generate different product ions. Quantum calculations were conducted to determine the transition states of the relevant molecules and analyze their optimized configuration, vibrational characteristics, intrinsic reaction coordinates, and corresponding energies. The potential targets of deoxyanthocyanidins in UC were screened from a public database. The R package was used for Gene Ontology (GO) and KEGG pathway analyses, and the protein–protein interactions (PPIs) of the targets were assessed using Search Tool for the Retrieval of Interacting Genes (STRING). Finally, molecular docking was implemented to analyze the binding energies and action modes of the target compounds through the online tool CB-Dock. Results. Quantum calculations indicated two potential fragmentation pathways involving the six-membered ring and dihydrogen cooperative transfer reactions of the vinylphenol-deoxyanthocyanidins. A total of 146 and 57 intersecting targets of natural and fermented deoxyanthocyanidins were separately screened out from the UC database and significant overlaps in GO terms and KEGG pathways were noted. Three shared hub targets (i.e., PTGS2, ESR1, and EGFR) were selected from the two PPI networks by STRING. Molecular docking results showed that all deoxyanthocyanidins have a good binding potential with the hub target proteins and that fermented deoxyanthocyanidins have lower binding energies and more stable conformations compared with natural ones. Conclusions. Deoxyanthocyanidins may provide anti-inflammatory, antioxidative, and immune system regulatory effects to suppress UC progression. It is proposed for the first time that fermentation of deoxyanthocyanidins can help adjust the structure of the intestinal microbiota and increase the biological activity of the natural compounds against UC. Furthermore, HDX-MS is a helpful strategy to analyze deoxyanthocyanidin metabolites with unknown structures.

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Section: Discussionmentioning

confidence: 99%

Mass Spectrometric Behavior and Molecular Mechanisms of Fermented Deoxyanthocyanidins to Alleviate Ulcerative Colitis Based on Network Pharmacology

Bai¹,

Wang²,

Lan

et al. 2022

International Journal of Analytical Chemistry

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Cyanidin Ameliorates Bisphenol A-Induced Alzheimer’s Disease Pathology by Restoring Wnt/β-Catenin Signaling Cascade: an In Vitro Study

Suresh,

Vellapandian

2023

Mol Neurobiol

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A Direct Infusion Probe for Rapid Metabolomics of Low-Volume Samples

et al. 2022

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Targeted and nontargeted metabolomics has the potential to evaluate and detect global metabolite changes in biological systems. Direct infusion mass spectrometric analysis enables detection of all ionizable small molecules, thus simultaneously providing information on both metabolites and lipids in chemically complex samples. However, to unravel the heterogeneity of the metabolic status of cells in culture and tissue a low number of cells per sample should be analyzed with high sensitivity, which requires low sample volumes. Here, we present the design and characterization of the direct infusion probe, DIP. The DIP is simple to build and position directly in front of a mass spectrometer for rapid metabolomics of chemically complex biological samples using pneumatically assisted electrospray ionization at 1 μL/min flow rate. The resulting data is acquired in a square wave profile with minimal carryover between samples that enhances throughput and enables several minutes of uniform MS signal from 5 μL sample volumes. The DIP was applied to study the intracellular metabolism of insulin secreting INS-1 cells and the results show that exposure to 20 mM glucose for 15 min significantly alters the abundance of several small metabolites, amino acids, and lipids.

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Anthocyanidins structural study using positive electrospray ionization triple quadrupole mass spectrometry and H/D exchange

Cited by 3 publications

References 19 publications

Mass Spectrometric Behavior and Molecular Mechanisms of Fermented Deoxyanthocyanidins to Alleviate Ulcerative Colitis Based on Network Pharmacology

Mass Spectrometric Behavior and Molecular Mechanisms of Fermented Deoxyanthocyanidins to Alleviate Ulcerative Colitis Based on Network Pharmacology

Cyanidin Ameliorates Bisphenol A-Induced Alzheimer’s Disease Pathology by Restoring Wnt/β-Catenin Signaling Cascade: an In Vitro Study

A Direct Infusion Probe for Rapid Metabolomics of Low-Volume Samples

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