isorhamnetin-3-o-glucoside and 3-methylquercetin

The chromatographic reinvestigation the methanol extract of

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Flavonoids; Flavonols; Interleukin-6; Lipopolysaccharides; Mice; Molecular Structure; Nitric Oxide; Quercetin; RAW 264.7 Cells; Tumor Necrosis Factor-alpha; Zygophyllaceae

Prickly pear fruit peel constitutes a high percentage of the fruit and could be a natural, economic agro-industrial waste of potential use in the nutraceutical industry. This study aimed to isolate and characterize the main constituents of the fruit peel and evaluate its antibacterial activity. A methanol extract was successively fractionated using hexane, chloroform and ethyl acetate. The n-hexane fraction was evaluated for its fatty acid content using gas chromatography mass spectrometry (GC-MS), revealing linolenic acid (omega-3) as the major fatty acid (60.56%), while an ethyl acetate fraction was analyzed using ultra-performance liquid chromatography electrospray tandem mass spectrometry (UPLC-ESI-MS/MS), resulting in the identification of 6 phenolic acids and 9 flavonoids, where caffeic acid (43.69%) and quercetin (14%) were found the most abundant. The ethyl acetate fraction was subjected to column chromatography, resulting in the isolation of four flavanols, viz. astragalin (1), quercetin 5,4'-dimethyl ether (2), isorhamnetin-3-O-glucoside (3) and isorhamnetin (4). Antibacterial evaluation revealed that the EtOAc fraction is the most potent active fraction against the selected pneumonia pathogens, and quercetin 5,4'-dimethyl ether (2) is the most active among the isolated compounds. Virtual docking of the isolated compounds showed promising in silico anti-quorum sensing efficacy, indicating that they could represent natural antibacterial agents. These findings indicate that the unused waste from prickly pear fruits contains valuable constituents that have beneficial potential against some pneumonia pathogens.

Topics: Anti-Bacterial Agents; Bacteria; Fatty Acids; Flavonoids; Flavonols; Fruit; Kaempferols; Microbial Sensitivity Tests; Molecular Docking Simulation; Opuntia; Phytochemicals; Pneumonia, Bacterial; Quercetin

This work aimed to evaluate the mechanisms involved in the apoptosis induction of isorhamnetin-3-O-glucosyl-pentoside (IGP) in metastatic human colon cancer cells (HT-29). To achieve this, we assessed phosphatidylserine (PS) exposure, cell membrane disruption, chromatin condensation, cell cycle alterations, mitochondrial damage, ROS production, and caspase-dependence on cell death. Our results showed that IGP induced cell death on HT-29 cells through PS exposure (48%) and membrane permeabilization (30%) as well as nuclear condensation (54%) compared with control cells. Moreover, IGP treatment induced cell cycle arrest in G2/M phase. Bax/Bcl-2 ratio increased and the loss of mitochondrial membrane potential (63%) was observed in IGP-treated cells. Finally, as apoptosis is a caspase-dependent cell death mechanism, we used a pancaspase-inhibitor (Q-VD-OPh) to demonstrate that the cell death induced by IGP was caspase-dependent. Overall these results indicated that IGP induced apoptosis through caspase-dependent mitochondrial damage in HT-29 colon cancer cells.

Topics: Apoptosis; Caspases; Cell Cycle Checkpoints; Colonic Neoplasms; Flavonols; Glycosides; HT29 Cells; Humans; Membrane Potential, Mitochondrial; Mitochondria; Opuntia; Plant Extracts; Quercetin

The aim of this study is to investigate the change in flavonoid composition and antioxidative activity during fermentation of onion (Allium cepa L.) by Leuconostoc mesenteroides with different NaCl concentrations. In order to qualify and quantify the flavonoids during fermentation of onion, 7 flavonoids, [quercetin 3,7-O-β-d-diglucopyranoside (Q3,7G), quercetin 3,4'-O-β-d-diglucopyranoside (Q3,4'G), quercetin 3-O-β-d-glucopyranoside (Q3G), quercetin 4'-O-β-d-glucopyranoside (Q4'G), isorhamnetin 3-O-β-d-glucopyranoside (IR3G), quercetin (Q), and isorhamnetin (IR)], were isolated and identified from onion. During fermentation, the contents of flavonoid glucosides (Q3,7G, Q3,4'G, Q3G, Q4'G, and IR3G) gradually decreased, whereas the contents of flavonoid aglycones (Q, IR) gradually increased. Decline rates of the flavonoid glucosides increased with the addition of L. mesenteroides. Furthermore, the activity of β-glucosidase, which is produced by L. mesenteroides, is dose-dependently inhibited with different NaCl concentrations during fermentation. The presence of L. mesenteroides enhanced the antioxidative activity of onion as demonstrated using the 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), and reducing power assays. The enhancement of antioxidative activity was considered because the content of flavonoid aglycones increased during fermentation. However, the addition of NaCl may decrease the antioxidative activity; we surmise that this phenomenon occurs because of the inhibition of β-glucosidase by NaCl. Therefore, we conclude that the addition of NaCl may be useful for the regulation of antioxidative activity via the control of β-glucosidase action, during the fermentation of flavonoid glucoside-rich foods.

Topics: beta-Glucosidase; Biphenyl Compounds; Fermentation; Flavonoids; Flavonols; Food Handling; Glucosides; Humans; Leuconostoc mesenteroides; Onions; Oxidation-Reduction; Picrates; Plant Extracts; Quercetin; Sodium Chloride

To study the chemical constituents of flowers of Prunus mume.. Compounds were separated by silica gel. Their structures were identified and elucidated by spectral analysis and chemical methods.. Eight compounds were obtained and identified as benzoic acid (I), isorhamnetin (II), quercetin (III), kaempferol-3-O-beta-D-galactopyranoside (IV), isorhamnetin-3-O-beta-D-glucopyranoside (V), isoquercitrin (VI), hypericin (VII) and rutin (VIII).. Among them, II-VII are isolated from this plant for the first time.

Topics: Anthracenes; Benzoic Acid; Flavonols; Flowers; Molecular Structure; Perylene; Plants, Medicinal; Prunus; Quercetin

Seedcoats of 16 almond varieties were screened for flavonol glycosides by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Flavonol glycosides were extracted by a simple methanolic extraction followed by a quick cleanup procedure with a Sep-Pak C(18) cartridge. Each of the 16 seedcoat samples exhibited a unique composition. Four flavonol glycosides, isorhamnetin rutinoside, isorhamnetin glucoside, kaempferol rutinoside, and kaempferol glucoside, were detected and quantified with use of rutin as an internal standard. Individual peak ratios were very consistent across triplicate analyses of all samples; the average standard deviation was 9%. In all almond varieties, isorhamnetin rutinoside was the most abundant flavonol glycoside, and the total content ranged from 75 to 250 microg/g.

Topics: Flavonoids; Flavonols; Glycosides; Kaempferols; Methanol; Prunus; Quercetin; Rutin; Seeds; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization