acteoside and 1-1-diphenyl-2-picrylhydrazyl

Analytical methods used for quality control of plants and plant extracts are based on the identification and quantification of chemical markers to manage batch reproducibility and efficacy. The aim of this work was to assess the performance of a High Performance Thin Layer Chromatography (HPTLC) method developed for quality control of industrial dry extracts of ribwort plantain (P. lanceolata L.), using 2,2-diphenyl 1-picrylhydrazyle (DPPH) effect directed chemical reaction for antioxidant activity of acteoside, a phenylethanoid glycoside commonly used as a marker for P. lanceolata L., and to demonstrate the applicability of the Life Cycle Management of Analytical Methods concept to quantitative HPTLC-DPPH methods. The first step was the determination of the Analytical Target Profile (ATP) and Target Measurement Uncertainty (TMU), taking into account the quality control requirements for such extracts and the detection method applicable range. Once the desired range was established, an evaluation of the calibration function was conducted using several calibration models. Due to the lack of reference samples, spiked samples were used to evaluate the accuracy of the method by means of Total Analytical Error (TAE) determination, using prediction intervals calculation for the selected calibration functions. Measurement Uncertainty (MU) was also estimated, allowing the final choice of the calibration function to be used for quality control, giving the most fit for purpose performance level in accordance with the product specifications. As Life Cycle Management of the method also includes its routine use, the Measurement Uncertainty was checked on spiked and unspiked extract samples with different dilution levels, in order to verify the accordance of results between spiked and unspiked samples and to prepare a replication strategy to be applied during the routine use of the method.

Topics: Biphenyl Compounds; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Glucosides; Limit of Detection; Linear Models; Phenols; Picrates; Plant Extracts; Plantago; Reproducibility of Results

Verbascoside is found in many medicinal plant families such as Verbenaceae. Important biological activities have been ascribed to verbascoside. Investigated in this study is the potential of verbascoside as an adjuvant during tuberculosis treatment. The present study reports on the in vitro metabolism in human hepatic microsomes and cytosol incubations as well as the presence and quantity of verbascoside within

Topics: Antioxidants; Biphenyl Compounds; Cell Proliferation; Chromatography, High Pressure Liquid; Cytochrome P-450 Enzyme System; Enzyme Activation; Glucosides; Hep G2 Cells; Humans; Nitric Oxide; Oxidation-Reduction; Phenols; Phytochemicals; Picrates; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Xiao-Ke-An formula (XKA) is a Chinese medicine widely used for treating diabetes and associated complications. Endothelial protection is thought to be one of its therapeutic mechanisms. However, the protective effect of XKA on endothelial cells remains unclear, especially in oxidative injury induced endothelial dysfunction.. A novel strategy to rapidly screen and identify potential endothelial protective substances from XKA was established by combining the 2,2'-diphenyl-1-picrylhydrazyl high performance liquid chromatography coupled with mass spectrometry (DPPH-HPLC-MS) approach with cell-based verification. Firstly, the DPPH-HPLC-MS approach was employed to identify the antioxidants in XKA. Then, the potent endothelial protective effect of XKA, and the potential active substances and mechanism of action were revealed in EA.hy926 cells injured by tert-butyl hydroperoxide (t-BHP).. XKA exhibited potent antioxidant activity and endothelial protective effect. Phenolic acids derived from Salvia miltiorrhiza Bunge, root and rhizome, xanthones from Anemarrhena asphodeloides Bunge, rhizome, and acteoside from Rehmannia glutinosa (Gaertn.) DC., root, were identified as the major endothelial protective components in XKA.. An efficient method for rapid identifying endothelial protective substances from complex mixtures was developed and used to identify the major endothelial protective components in XKA. This method would help reveal the material base of herbal medicine with endothelial protective effect, and could also be applied to discover novel natural-origin endothelial protective substances.

Topics: Biphenyl Compounds; Cell Line; Cell Survival; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Endothelium, Vascular; Glucosides; Humans; Hydroxybenzoates; Mass Spectrometry; Phenols; Picrates; Protective Agents; Reactive Oxygen Species; Superoxide Dismutase; Xanthones

Moussonia deppeana, known as Tlachichinole, is a Mexican medicinal plant used for treatment of inflammatory diseases, influenza, diarrhea, gastrointestinal disorders and arthritis.. In this paper the antioxidant and anti-inflammatory activities as well as the acute and sub-acute toxicological effects were evaluated for the ethanolic extract from aerial parts of M. deppeana, also its phytochemical analysis is described.. Phytochemical analysis and compound isolation were performed with thin layer chromatography. The chemical identification of the main compound was performed by (1)H NMR (COSY, NOESY, HSQC and HMBC) spectra. In vitro antioxidant capacity and total phenolic content for the ethanolic extract and its primary fractions was determined by DPPH and Folin-Ciocalteu reagent. Acute and subacute toxicity tests were evaluated on Balb/C mice. Finally acute anti-inflammatory evaluation was tested for a local (TPA) and systemic (carrageenan) murine model.. The main compound isolated from the ethanolic extract of M. deppeana was Verbascoside, which was isolated from F3 and was identified by (1)H NMR and COSY data. Furthermore oleanolic and ursolic acids were isolated from primary fractions F1 and F2. Ethanolic extract showed IC50 = 6.71mg/mL for DPPH test and 664.12µg QE/mL for the total phenolic content. The LD50 value was >2g/kg by i.g. route in male and female mice. Sub-acute administration (28 days) of the ethanolic extract (1g/kg) did not cause lethality or alter any hematological and biochemical parameters, in addition, histological analysis of the major organs exhibited no structural changes. Anti-inflammatory activity of the ethanolic extract showed an ED50 = 1.5mg/ear and 450mg/kg for TPA and carrageenan test, respectively. Primary fractions generated moderate local and systemic anti-inflammatory activity.. The ethanolic extract from the aerial parts of M. deppeana did not cause any lethality or adverse effect in either of the acute and sub-acute toxicity tests. This exhibited an important local and systemic anti-inflammatory activity and also moderate antioxidant capacity. Moreover, the primary fraction F2 was more active for the TPA model while the primary fraction F3 was most active in the carrageenan model in vivo. The main compound isolated from F3 was verbascoside; on the other hand also ursolic and oleanolic acids were isolated from F1 and F2.

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Biphenyl Compounds; Carrageenan; Edema; Female; Glucosides; Magnoliopsida; Male; Medicine, Traditional; Mexico; Mice, Inbred BALB C; Oleanolic Acid; Phenols; Phorbol Esters; Phytochemicals; Phytotherapy; Picrates; Plant Components, Aerial; Plant Extracts; Triterpenes; Ursolic Acid

Because of its good sensorial attributes, lemon verbena is used as a primary ingredient in infusions and nonalcoholic drinks. The present study was designed to assess the antioxidant activity (AA) of lemon verbena infusion (LVI) as well as the thermal stability of its AA and the content of polyphenolic compounds. The values reflecting the AA of LVI, including AA index, fast scavenging rate against 2,2-diphenyl-1-picrylhydrazyl, Trolox equivalent antioxidant capacity, and hydroxyl radical scavenging, are higher than those of many herbal infusions and antioxidant drinks estimated from reported data. In addition, the slope lag time and specific oxyradical antioxidant capacity values of LVI are comparable to those of a commercial antioxidant drink based on green tea. Hence, LVI is a source of bifunctional antioxidants, and thus in vivo studies of the antioxidant capacity of LVI would be useful to evaluate its potential as an ingredient in antioxidant drinks.

Topics: Antioxidants; Beverages; Biphenyl Compounds; Chromans; Chromatography, High Pressure Liquid; Flavonoids; Glucosides; Linear Models; Phenols; Picrates; Plant Extracts; Plant Leaves; Polyphenols; Reactive Oxygen Species; Spectrometry, Mass, Electrospray Ionization; Temperature; Verbena

In our continual course toward the valorization of traditionally used endemic flora through the analysis of its chemobiodiversity, the phytochemical analysis of aerial parts of Marrubium deserti de Noé was undertaken. Dichloromethane and methanol extracts led to the isolation of terpenoid derivatives among which two were new labdane diterpenes named marrulibacetal A and desertine, respectively. Six of them were known compounds (a mixture of the isomers cyllenin A and 15-epi-cyllenin A, marrubiin, marrulactone, marrulibacetal and β-stigmasterol) and seven known phenolic compounds were also isolated: apigenin and several 7-O-substituted derivatives (apigenin-7-O-β-neohesperidoside, apigenin-7-O-glucoside, terniflorin and apigenin-7-O-glucuronide) together with two phenylethanoid glucosides (acteoside and forsythoside B). The structures and relative configurations of the new compounds were elucidated by MS and a series of 1D and 2D NMR analyses. Some pure compounds have been evaluated for their antioxidant activities through different methods: DPPH and ABTS assays as well as CUPRAC assay. Genotoxic and antigenotoxic activities of extracts and pure compounds were also evaluated in vitro on Escherichia coli PQ37 cells by the SOS Chromotest. Some of the isolated compounds like phenylethanoid derivatives showed stronger antioxidant capacity than trolox and were also able to significantly inhibit β-galactosidase induction caused by the mutagen agent nitrofurantoin.

Topics: Antioxidants; Apigenin; Benzothiazoles; Biphenyl Compounds; Caffeic Acids; Diterpenes; DNA Damage; Flavones; Glucosides; Glycosides; Magnetic Resonance Spectroscopy; Marrubium; Methanol; Methylene Chloride; Phenols; Picrates; Plant Extracts; Sulfonic Acids

A new phenylpropanoid glycoside, dolichandroside-A, together with seven known compounds alpha-lapachone, lapachol, aloesaponarin II, 8-hydroxydehydroiso-alpha-lapachone, beta-sitosterol, 3,8-dihydroxydehydroiso-alpha-lapachone and verbascoside were isolated from the active ethyl acetate soluble extract of heartwood of Dolichandrone falcata. All except for dolichandroside-A are known compounds, but have been isolated for the first time from this plant. The structure of all these compounds was determined on the basis of 1D- and 2D-NMR spectral data. All the isolates were tested for alpha-glucosidase inhibitory and DPPH radical scavenging activity. This is the first report identifying DPPH scavenging activity and alpha-glucosidase inhibitory activity in D. falcata. Furthermore, along with a new compound, dolichandroside-A, this study also assigns for the first time alpha-glucosidase inhibitory activity to verbascoside and aloe saponarin-II.

Topics: Anthraquinones; Bignoniaceae; Biphenyl Compounds; Enzyme Inhibitors; Free Radical Scavengers; Glucosides; Glycoside Hydrolase Inhibitors; Glycosides; Molecular Structure; Phenols; Picrates; Plant Extracts

The chromatographic separation of MeOH extract from Clerodendron trichotomum Thunberg leaves led to the isolation of three phenylpropanoid compounds. Using spectroscopic methods, the structures of these compounds were determined as beta-(3', 4'-dihydroxyphenyl)ethyl-O-alpha-L-rhamnopyranosyl (1-->3)-beta-D-(4-O-caffeoyl)-glucopyranoside, acteoside (verbascoside) (1), beta-(3', 4'-dihydroxyphenyl)ethyl-O-alpha-L-rhamnopyranosyl (1-->3)-beta-D-(6-O-caffeoyl)-glucopyranoside, isoacteoside (2), beta-(3', 4'-dihydroxyphenyl) ethyl-O-alpha-L-rhamnopyranosyl (1-->3)-beta-D-glucopyranoside, and decaffeoylacteoside (3). We measured the anti-inflammatory activity of these three phenylpropanoid compounds both in vitro (DPPH reduction assay, TBARS assay on Cu (2+)-induced oxidized LDL, PGE(2) assay) and in vivo (acetic acid induced vascular permeability in mice and carrageenan-induced hind paw edema in rats). 80% methanol fraction and acteoside had the activity.

Topics: Acetic Acid; Animals; Anti-Inflammatory Agents; Biphenyl Compounds; Capillary Permeability; Carrageenan; Catechols; Cell Line; Clerodendrum; Dinoprostone; Disaccharides; Disease Models, Animal; Dose-Response Relationship, Drug; Free Radical Scavengers; Glucosides; Humans; Inflammation; Magnetic Resonance Spectroscopy; Mast Cells; Mice; Molecular Structure; Phenols; Picrates; Plant Leaves; Rats; Thiobarbituric Acid Reactive Substances

The aim of the study was to determine the mechanism of the whitening effect of acteoside.. We used tyrosinase activity and melanin production stimulated in B16 melanoma cells by alpha-melanocyte stimulating hormone (alpha-MSH) or forskolin to measure the whitening effect of acteoside.. Acteoside did not directly inhibit mushroom tyrosinase activity, but dose-dependently inhibited tyrosinase activity and melanin production in B16 melanoma cells stimulated by 1 micromol/l alpha-MSH. Acteoside also reduced cyclic AMP levels in cells stimulated by 1 micromol/l alpha-MSH, suggesting direct inhibition of adenyl cyclase. Acteoside also inhibited production of both melanin and cyclic AMP in cells stimulated by 1 micromol/l forskolin, an adenyl cyclase activator. Acteoside showed antioxidant activity in a cell-free DPPH (1-diphenyl-2-picrylhydroazyl) assay and inhibited generation of intracellular reactive oxygen species.. These results suggest that the whitening activity of acteoside results from inhibition of adenyl cyclase and alpha-MSH signalling.

Topics: Adenylyl Cyclases; alpha-MSH; Antioxidants; Biphenyl Compounds; Cell Line, Tumor; Cell Survival; Colforsin; Cyclic AMP; Glucosides; Humans; Melanins; Melanoma, Experimental; Monophenol Monooxygenase; Phenols; Picrates; Reactive Oxygen Species

In this study the influence of liposomal incorporation on both the stability and the in vitro (trans) dermal delivery of verbascoside was evaluated. The effect of drug entrapment into vesicles on its radical scavenging activity was also studied. Liposomes were obtained from soy phosphatidylcholine and cholesterol according to the film hydration method. Stability of verbascoside-loaded vesicles was studied over 6 months. Results showed that verbascoside can be incorporated in liposomes (E% = 57-66%), preventing its degradation. Stability studies (dynamic lager light scattering [DLLS] measurements and transmission electron microscopy [TEM] visualization) pointed out that vesicles were stable for 90 days and neither verbascoside leakage nor vesicle size alteration occurred during this period. The effects of vesicular incorporation on verbascoside diffusion through skin were investigated in vitro using newborn pig skin. Results showed that liposomes promoted drug accumulation into the stratum corneum but they did not give rise to any significant transdermal verbascoside delivery. Finally, results obtained from a 1, 1-diphenyl-2-pierylhydrazyl (DPPH) radical assay demonstrated that liposomes did not interfere with the radical scavenging activity of verbascoside.

Topics: Animals; Antineoplastic Agents, Phytogenic; Biphenyl Compounds; Drug Delivery Systems; Free Radical Scavengers; Free Radicals; Glucosides; Hydrazines; Light; Liposomes; Microscopy, Electron, Transmission; Models, Biological; Permeability; Phenols; Picrates; Scattering, Radiation; Skin; Swine

Rapid production of reactive oxygen species (ROS) and upregulation of beta2 integrin by leucocytes are two important inflammatory responses in human leucocytes. To evaluate whether three phenylpropanoid glycosides (acteoside, crenatoside, and rossicaside B) and two iridoid glucosides (boschnaloside and 8-epideoxyloganic acid) identified from two medicinal plants with similar indications (Orobanche caerulescens and Boschniakia rossica) exhibited anti-inflammatory activity, their effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol-12-myristate-13-acetate (PMA)-activated peripheral human neutrophils (PMNs) and mononuclear cells were examined. Pretreatment with 1-50 microM phenylpropanoid glycoside concentration-dependently diminished PMA- and fMLP-induced ROS production with IC50 values of approximately 6.8-23.9 and 3.0-8.8 muM, respectively. Iridoid glucoside was less effective than phenylpropanoid glycoside with an IC50 value of approximately 8.9-28.4 microM in PMA-activated PMNs and 19.1-21.1 microM in fMLP-activated mononuclear cells. Phenylpropanoid glycosides also effectively inhibited NADPH oxidase (NOX) and displayed potent free radical-scavenging activity, but did not interfere with pan-protein kinase C (PKC) activity. Furthermore, all compounds, except rossicaside B, significantly inhibited PMA- and fMLP-induced Mac-1 (a beta2 integrin) upregulation at 50 microM but not that of fMLP-induced intracellular calcium mobilization. These drugs had no significant cytotoxicity as compared with the vehicle control. Our data suggested that inhibition of ROS production, possibly through modulation of NOX activity and/or the radical scavenging effect, and beta2 integrin expression in leucocytes indicated that these compounds had the potential to serve as anti-inflammatory agents during oxidative stress.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Biphenyl Compounds; Caffeic Acids; CD18 Antigens; Cells, Cultured; Free Radicals; Glucosides; Humans; Hydrazines; Iridoids; Leukocytes, Mononuclear; Macrophage-1 Antigen; N-Formylmethionine Leucyl-Phenylalanine; NADPH Oxidases; Neutrophils; Phenols; Picrates; Protein Kinase C; Reactive Oxygen Species; Tetradecanoylphorbol Acetate

The protective effect of acteoside against membrane lipid oxidation and free radical-mediated impairment of endothelial function was investigated. Results showed that iron-mediated oxidative modification of the cell membrane in cultured bovine pulmonary endothelial cells (PAECs) was significantly attenuated by acteoside as measured by thiobarbituric acid-reactive substances (TBARS). Fenton's reagent (H2O2/Fe2+) was used to generate hydroxyl radicals (*OH) and induce oxidative stress. Acteoside not only effectively minimized the loss of cell viability induced by hydroxyl radicals in cultured endothelial cells but also countered the free radical-induced destruction of the endothelium-dependent relaxation to acetylcholine in rat aorta. Furthermore, acteoside showed a dose-dependent scavenging effect of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radicals and appeared to be the most efficient in comparison with the four reference compounds (alpha-tocopherol, vitamin C, probucol and resveratrol). These data suggested that acteoside protects the cell from oxidative stress and that scavenging of free radicals could be a key mechanism contributing to the cytoprotective effect of acteoside.

Topics: Animals; Antioxidants; Aorta, Thoracic; Biphenyl Compounds; Cattle; Cell Death; Cells, Cultured; Endothelium, Vascular; Glucosides; Hydrazines; In Vitro Techniques; Male; Membrane Lipids; Oxidative Stress; Phenols; Picrates; Pulmonary Artery; Rats; Rats, Sprague-Dawley; Thiobarbituric Acid Reactive Substances; Vasodilation

A new phenylethanoid glycoside, samioside, was isolated from the aerial parts of Phlomis samia and identified as 1-O-3,4-(dihydroxyphenyl)ethyl beta-D-apiofuranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->3)-4-O-caffeoyl-beta-D-glucopyranoside (1). In addition, one known phenylethanoid glycoside and three known flavonoids were identified as acteoside (2), apigenin, chrysoeriol, and ermanin, respectively. The structure of 1 was elucidated on the basis of its spectroscopic data. Samioside (1) demonstrated scavenging properties toward the DPPH radical and antimicrobial activity against Gram-positive and -negative bacteria.

Topics: Anti-Bacterial Agents; Anti-Infective Agents; Apigenin; Bepridil; Biphenyl Compounds; Candida; Chromatography, Thin Layer; Enterobacter cloacae; Escherichia coli; Flavones; Flavonoids; Free Radical Scavengers; Glucosides; Glycosides; Greece; Klebsiella pneumoniae; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Phenols; Picrates; Plants, Medicinal; Pseudomonas aeruginosa; Spectrophotometry, Infrared; Staphylococcus aureus; Staphylococcus epidermidis; Stereoisomerism

Topics: Animals; Bepridil; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Free Radicals; Glucosides; In Vitro Techniques; Lipid Peroxidation; Liver; Male; Mitochondria, Liver; Oxygen Consumption; Phenols; Picrates; Plant Extracts; Rats; Rats, Wistar; Reperfusion Injury; Vitamin E