isorhamnetin-3-o-glucoside and 1-1-diphenyl-2-picrylhydrazyl

Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.

Topics: Antioxidants; Biphenyl Compounds; Free Radical Scavengers; Molecular Structure; Picrates; Quercetin; Structure-Activity Relationship

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

Seven flavonoids have been isolated from the aerial parts of Halostachys caspica C. A. Mey. (Chenopodiaceae) for the first time. By means of physicochemical and spectrometric analysis, they were identified as luteolin (1), chrysin (2), chrysin 7-O-β-D-glucopyranoside (3), quercetin (4), quercetin 3-O-β-D-glucopyranoside (5), isorhamentin-3-O-β-D-glucopyranoside (6), and isorhamentin-3-O-β-D-rutinoside (7). All flavonoids were evaluated to show a broad antimicrobial spectrum of activity on microorganisms including seven bacterial and one fungal species as well as pronounced antioxidant activity. Among them, the aglycones with relatively low polarity had stronger bioactivity than their glycosides. The results suggested that the isolated flavonoids could be used for future development of antimicrobial and antioxidant agents, and also provided additional data for supporting the use of H. caspica as forage.

Topics: Anti-Infective Agents; Antioxidants; Bacteria; Biological Assay; Biphenyl Compounds; Chenopodiaceae; Flavonoids; Flavonols; Fungi; Glucosides; Luteolin; Magnetic Resonance Spectroscopy; Picrates; Quercetin

Isorhamnetin 3-O-beta-D-glucopyranoside (1) was isolated from Salicornia herbacea. The inhibitory effects of compound 1 on oxidative stress were evaluated in free-cellular and cellular systems. An increased concentration of compound 1 not only exhibited dose-dependent scavenging activities on the generation of 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl and carbon-centered radicals, but also significantly decreased levels of intracellular reactive oxygen species (ROS) in a dose-dependent manner. Further, antioxidative mechanisms by compound 1 were examined by measuring the intracellular glutathione (GSH) level and expression levels of antioxidant enzymes such as superoxide dismutase (SOD), catalase, glutathione reductase and heme oxygenase-1 (HO-1). Compound 1 significantly elevated GSH level as well as expression levels of antioxidant enzymes which were closely related with amount of cellular ROS. In addition, it significantly inhibited oxidative damage of purified genomic DNA and suppressed activity of myeloperoxidase (MPO), a generator of potent oxidant (hypochlorous acid), in tumor necrosis factor-alpha (TNF-alpha) stimulated human myeloid cells. Therefore, these results suggested that compound 1 has a therapeutic effectiveness in prevention of ROS-induced cellular damage and is a candidate worthy of being developed as a potential natural antioxidant related to oxidative stress.

Topics: Antioxidants; Biphenyl Compounds; Blotting, Western; Cell Survival; Chenopodiaceae; DNA Damage; Flavonols; Free Radicals; Glutathione; Humans; Hydrogen Peroxide; Hydroxyl Radical; Oxidants; Oxidative Stress; Picrates; Protective Agents; Reactive Oxygen Species; Reverse Transcriptase Polymerase Chain Reaction; U937 Cells