Differentiation of flavonol glucoside and galactoside isomers combining chemical isopropylidenation with liquid chromatography–mass spectrometry analysis

Souza, Lauro Mera de; Dartora, Nessana; Scoparo, Camila T.; Gorin, Philip A.J.; Iacomini, Marcello; Sassaki, Guilherme L.

doi:10.1016/j.chroma.2016.03.069

Cited by 18 publications

(10 citation statements)

References 22 publications

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“…Different flavonol glycosides were found in this study, mainly containing quercetin as a glycone moiety originating from the protonated fragment at m/z 303.05, and myricetin was also found, as confirmed by the fragment at m/z 319.04. The most common monosaccharides attached to the flavonols were hexoses (e.g., glucose and/or galactose), deoxyhexose (rhamnose), and pentoses (e.g., arabinose and/or xylose) [13]. The flavonol glycosides observed in our extracts had similar characteristics, with peak 7, at m/z 617.1177, identified as quercetin-galloyl-hexoside.…”

Section: Chemical Evaluation Of M Albicans Solvent Fractionsmentioning

confidence: 51%

“…In a previous investigation, phenolic compounds of M. albicans leaves were well characterized, identifying various flavonoids, including quercetin and several glycosylated derivatives, such as rutin, along with ellagic acid derivatives [8]. Phenolic compounds are known for their potential benefits to human health, mainly related to their antioxidant capabilities [13]. On the other hand, some phenolics are known to be cytotoxic; therefore, plant extracts rich in phenolics should be investigated for safety [14].…”

Section: Resultsmentioning

confidence: 99%

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Phytochemical Evaluation and Anti-Inflammatory Potential of Miconia albicans (Sw.) Triana Extracts

et al. 2022

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The plant Miconia albicans (Sw.) Triana has been popularly used in Brazil to treat chronic inflammatory disturbances, such as osteoarthritis. This disease affects 250 million people worldwide, and is associated with intense pain and loss of articular function. There is a lack of information about the phytochemistry and bioactivity of M. albicans. Therefore, this study determined the chemical composition of some extracts and evaluated their cytotoxicity, along with their antioxidant and anti-inflammatory, activities using in vitro models. Aqueous and ethanolic extracts were prepared. Afterwards, a liquid–liquid partition was developed using chloroform, ethyl acetate, and n-butanol. The extracts were characterized by LC–MS, and their biological activities were evaluated on epithelial cells (Vero), tumoral hepatic cells (Hep-G2), and THP-1 macrophages. LC–MS analyses identified several flavonoids in all fractions, such as quercetin, myricetin, and their glycosides. The crude extracts and n-butanol fractions did not present cytotoxicity to the cells. The non-toxic fractions presented significant antioxidant activity when evaluated in terms of DPPH scavenging activity, lipid peroxidation, and ROS inhibition. THP-1 macrophages treated with the n-butanol fraction (250 µg/mL) released fewer pro-inflammatory cytokines, even in the presence of LPS. In the future, it will be necessary to identify the phytochemicals that are responsible for anti-inflammatory effects for the discovery of new drugs. In vivo studies on M. albicans extracts are still required to confirm their possible mechanisms of action.

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Section: Chemical Evaluation Of M Albicans Solvent Fractionsmentioning

confidence: 51%

Section: Resultsmentioning

confidence: 99%

Phytochemical Evaluation and Anti-Inflammatory Potential of Miconia albicans (Sw.) Triana Extracts

et al. 2022

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“…Take isoquercitrin as an example, in the negative ion mode, m/z 299.94183 and m/z 301.01648 fragment ions appeared simultaneously. The flavonoid aglycones will continue to disintegrate after deglycosylation, producing fragment ions such as [Y 0 -HCO] − , [Y 0 -HCO-CO] − , for example, the product ion at m/z 271.06042 [Y 0 -H-HCO] − in the mass spectrum of isoquercitrin ( Shahat et al, 2005 ; Gonzales et al, 2014 ; de Souza et al, 2016 ; Qin et al, 2017 ).…”

Section: Resultsmentioning

confidence: 99%

Integrated UPLC-MS and Network Pharmacology Approach to Explore the Active Components and the Potential Mechanism of Yiqi Huoxue Decoction for Treating Nephrotic Syndrome

Feng

Wang

et al. 2022

Front. Pharmacol.

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Background: Yiqi Huoxue Decoction (YQHXD) is a traditional Chinese medicine that promotes blood circulation, removes blood stasis, facilitates diuresis, and alleviates edema. It is composed of 10 herbal medicines and has extensive application in treating nephrotic syndrome (NS). However, the active components and the potential mechanism of YQHXD for treating NS remain unclear.Methods: We set up a sensitive and rapid method based on Ultra-High Performance Liquid Chromatograph-Mass (UPLC-MS) to identify the compounds in YQHXD and constituents absorbed into the blood. Disease genes were collected through GeneCards, DisGeNET, and OMIM database. Genes of compounds absorbed into blood were predicted by the TCMSP database. We constructed Disease-Drug-Ingredient-Gene (DDIG) network using Cytoscape, established a Protein-protein interaction (PPI) network using String, Gene biological process (GO), and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway analysis was performed using DAVID. Cellular experiments were performed to validate the results of network pharmacology.Result: A total of 233 compounds in YQHXD and 50 constituents absorbed into the blood of rats were identified. The 36 core targets in the PPI network were clustered in the phosphatidylinositol 3 kinase-RAC serine/threonine-protein kinase (PI3K-AKT) and nuclear factor kappa-B (NF-κB) signaling pathways. Luteolin, Wogonin, Formononetin, and Calycosin were top-ranking components as potentially active compounds.Conclusion: The results of our studies show that YQHXD is able to enhance renal function, alleviate podocyte injury, and improve adriamycin nephrotic syndrome.

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“…Peak 18 at m/z 595.165 with main fragments at m/z 449.107 and 287.055 was characteristic of kaempeferol diglycoside, such as kaempferol rutinoside or its isomers ( Souza et al, 2008b ). Compound 19 at m/z 449.107 with a main fragment at m/z 287.055 was identified as a kaempferol-O-hexoside, being glucosides and galactosides the most commonly found in plants ( Souza et al, 2016 ).…”

Section: Resultsmentioning

confidence: 99%

Croton urucurana Baill. Ameliorates Metabolic Associated Fatty Liver Disease in Rats

et al. 2022

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Background: Metabolic associated fatty liver disease (MAFLD) affects a quarter of the worldwide population, but no drug therapies have yet been developed. Croton urucurana Baill. (Euphorbiaceae) is a medicinal species, that is, widely distributed in Brazil. It is used in popular medicine to treat gastrointestinal, cardiovascular, and endocrine system diseases. However, its hepatoprotective and lipid-lowering effects have not yet been scientifically investigated.Aim of the study: The present study investigated the effects of an extract of C. urucurana in a rat model of MAFLD that was associated with multiple risk factors, including hypertension, smoking, and dyslipidemia.Material and Methods: The phytochemical composition of C. urucurana was evaluated by liquid chromatography-mass spectrometry. Spontaneously hypertensive rats received a 0.5% cholesterol-enriched diet and were exposed to cigarette smoke (9 cigarettes/day for 10 weeks). During the last 5 weeks, the animals were orally treated with vehicle (negative control [C-] group), C. urucurana extract (30, 100, and 300 mg/kg), or simvastatin + enalapril (two standard reference drugs that are commonly used to treat dyslipidemia and hypertension, respectively). One group of rats that were not exposed to these risk factors was also evaluated (basal group). Blood was collected for the analysis of cholesterol, triglyceride, alanine aminotransferase (ALT), and aspartate aminotransferase (AST) levels. The liver and feces were collected for lipid quantification. The liver was also processed for antioxidant and histopathological analysis.Results: The main constituents of the C. urucurana extract were flavonoids, glycosides, and alkaloids. The model successfully induced MAFLD, reflected by increases in AST and ALT levels, and induced oxidative stress in the C- group. Treatment with the C. urucurana extract (300 mg/kg) and simvastatin + enalapril decreased plasma and hepatic lipid levels. In contrast to simvastatin + enalapril treatment, C. urucurana reduced AST and ALT levels. Massive lesions were observed in the liver in the C- group, which were reversed by treatment with the C. urucurana extract (300 mg/kg).Conclusion:C. urucurana extract exerted promising hepatoprotective and lipid-lowering effects in a preclinical rat model of MAFLD.

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Differentiation of flavonol glucoside and galactoside isomers combining chemical isopropylidenation with liquid chromatography–mass spectrometry analysis

Cited by 18 publications

References 22 publications

Phytochemical Evaluation and Anti-Inflammatory Potential of Miconia albicans (Sw.) Triana Extracts

Phytochemical Evaluation and Anti-Inflammatory Potential of Miconia albicans (Sw.) Triana Extracts

Integrated UPLC-MS and Network Pharmacology Approach to Explore the Active Components and the Potential Mechanism of Yiqi Huoxue Decoction for Treating Nephrotic Syndrome

Croton urucurana Baill. Ameliorates Metabolic Associated Fatty Liver Disease in Rats

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