acteoside and luteolin-7-glucoside

Topics: Caffeic Acids; Chlorogenic Acid; Coumaric Acids; Coumarins; Flavones; Flavonoids; Glucosides; Lamiaceae; Phenols; Plant Development; Propionates; Succinates

Lippia alba is a popular Brazilian herb known as 'cidreira' that presents several chemotypes which exhibit different chemical profile and they are widely used as seasonings and traditional medicine. This work describes the seasonal variation of metabolites of polar extracts of carvone and linalool chemotypes, identified by GC-MS analyses of the essential oils. A methodology was elaborated in order to obtain a seasonal variation in the chemical composition of leaf employing HPLC-DAD. Acteoside, isoacteoside, geneposidic acid, 8-epi-loganin, mussaenoside, luteolin 7-O-glucoside, apigenin 7-O-glucuronide and tricin 7-O-diglucuronide have been isolated and identified for validation procedures and chromatographic analysis. Geneposidic acid was presented in all samples, in contrast to the 8-epi-loganin and, mussaenoside which were presented only in the carvone-chemotype. Acteoside was the major metabolite detected from July to November while tricin-7-O-diglucuronide was the major compound in all other months. Besides, phenylpropanoids are predominant in winter and flavonoids in summer season.

Topics: Acyclic Monoterpenes; Brazil; Chromatography, High Pressure Liquid; Flavones; Flavonoids; Gas Chromatography-Mass Spectrometry; Glucosides; Glucuronides; Lippia; Monoterpenes; Oils, Volatile; Phenols; Plant Leaves; Reproducibility of Results; Seasons; Secondary Metabolism

The antimicrobial properties of olive leaf extract (OLE) have been well recognized in the Mediterranean traditional medicine. Few studies have investigated the antimicrobial properties of OLE. In this preliminary study, commercial OLE and its major phenolic secondary metabolites were evaluated in vitro for their antimicrobial activities against Escherichia coli and Staphylococcus aureus, both individually and in combination with ampicillin. Besides luteolin 7-O-glucoside, OLE and its major phenolic secondary metabolites were effective against both bacteria, with more activity on S. aureus. In combination with ampicillin, OLE, caffeic acid, verbascoside and oleuropein showed additive effects. Synergistic interaction was observed between ampicillin and hydroxytyrosol. The phenolic composition of OLE and the stability of olive phenols in assay medium were also investigated. While OLE and its phenolic secondary metabolites may not be potent enough as stand-alone antimicrobials, their abilities to boost the activity of co-administered antibiotics constitute an imperative future research area.

Topics: Ampicillin; Anti-Bacterial Agents; Bacteria; Caffeic Acids; Drug Synergism; Escherichia coli; Flavones; Glucosides; Herb-Drug Interactions; Iridoid Glucosides; Iridoids; Medicine, Traditional; Olea; Phenols; Phenylethyl Alcohol; Plant Extracts; Plant Leaves; Staphylococcus aureus

Olive leaves are rich in bioactive compounds, which are beneficial for humans. The objective of this work was to assess the influence of processing conditions (drying and extraction) of olive leaves on the extract's bioaccessibility. Thus, extracts obtained from dried olive leaves (hot air drying at 70 and 120 °C or freeze-drying) by means of conventional or ultrasound-assisted extraction were subjected to in vitro digestion. Antioxidant capacity, total phenolic content, and HPLC-DAD/MS/MS analysis were carried out during digestion. The dehydration treatment used for the olive leaves did not have a meaningful influence on bioaccessibility. The digestion process significantly (p<0.05) affected the composition of the extracts. Oleuropein and verbascoside were quite resistant to gastric digestion but were largely degraded in the intestinal phase. Nevertheless, luteolin-7-O-glucoside was the most stable polyphenol during the in vitro simulation (43% bioaccessibility). Therefore, this compound may be taken into consideration in further studies that focus on the bioactivity of olive leaf extracts.

Topics: Agriculture; Antioxidants; Dietary Supplements; Digestion; Food Handling; Glucosides; Humans; Hydrolysis; Industrial Waste; Iridoid Glucosides; Iridoids; Luteolin; Models, Biological; Olea; Phenols; Phytochemicals; Plant Extracts; Plant Leaves; Spain

Olive leaves, an easily available natural low-cost material, constitute a source of extracts with significant antitumor activity that inhibits cell proliferation in several breast-cancer-cell models. In this work, a metabolite-profiling approach has been used to assess the uptake and metabolism of phenolic compounds from an olive-leaf extract in the breast-cancer-cell line SKBR3 to evaluate the compound or compounds responsible for the cytotoxic activity. For this, the extract was firstly characterized quantitatively by high-performance liquid chromatography coupled to electrospray ionization-quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS). Then, SKBR3 cells were incubated with 200 μg/mL of the olive-leaf extract at different times (15 min, 1, 2, 24, and 48 h). A metabolite-profiling approach based on HPLC-ESI-QTOF-MS was used to determine the intracellular phenolic compounds, enabling the identification of 16 intact phenolic compounds from the extract and four metabolites derived from these compounds in the cell cytoplasm. The major compounds found within the cells were oleuropein, luteolin-7-O-glucoside and its metabolites luteolin aglycone and methyl-luteolin glucoside, as well as apigenin, and verbascoside. Neither hydroxytyrosol nor any of its metabolites were found within the cells at any incubation time. It is proposed that the major compounds responsible for the cytotoxic activity of the olive-leaf extract in SKBR3 cells are oleuropein and the flavones luteolin and apigenin, since these compounds showed high uptake and their antitumor activity has been previously reported.

Topics: Apigenin; Breast Neoplasms; Carcinoma; Cell Line, Tumor; Chromatography, High Pressure Liquid; Cytoplasm; Female; Flavones; Glucosides; Humans; Iridoid Glucosides; Iridoids; Luteolin; Olea; Phenols; Plant Extracts; Plant Leaves; Pyrans; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry

In this article, an efficient method was developed to screen, isolate and identify the major radical scavengers in the leaves of Olea europaea L. by DPPH-HPLC-DAD, HSCCC and NMR. The method of DPPH-HPLC-DAD was used to screen the major radical scavengers. It was found that three major constituents (A, B, C) in the extract of the leaves of O. europaea L. possessed potential antioxidant activities. In order to identify the chemical structures of those compounds, the HSCCC method with a two-phase solvent system composed of petroleum ether-ethyl acetate-water at an optimized volume ratio of 6:600:700 (v/v/v) together with column chromatography was developed to isolate and purify the active compounds. Pure compounds A (225 mg), B (10 mg) and C (12 mg) with purities 92.6, 95.1 and 96.4%, respectively, were obtained from the crude sample (500 mg). Their structures were identified as oleuropein (A), luteolin-7-O-glucoside (B) and verbascoside (C) by (1) H-NMR and (13) C-NMR.

Topics: Acetates; Chromatography, High Pressure Liquid; Flavones; Free Radical Scavengers; Glucosides; Iridoid Glucosides; Iridoids; Olea; Phenols; Plant Extracts; Plant Leaves; Pyrans

To study the chemical constituents of Phlomis younghusbandii.. Column chromatography was used in the isolation procedure. The structures of isolated compounds were elucidated by spectral data. Eight compounds were isolated and their structures were identified as barlerin (1), sesamoside (2), phloyoside II (3), salidroside (4), shanzhiside methyl ester (5), acteoside (6), luteolin-7-O-glucoside (7), daucosterol (8).. Compound 4 is firstly isolated from Phlomis genus. Compound 4 and 6 are obtained from this plant for the first time.

Topics: Flavones; Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Molecular Structure; Phenols; Phlomis; Plant Roots; Plants, Medicinal; Pyrans

Leaf extracts of Buddleja globosa (Buddlejaceae) are used in Chilean folk medicine for wound healing. The anti-inflammatory (topic and per os), analgesic (per os) effects and the antioxidant activity of Buddleja globosa were for the first time reported by us.. Assess the antinociceptive activity of the methanol sequential and global extracts using complementary chemical and thermal models of pain, characterize pharmacologically the antinociception induced, evaluate seasonal influence to support Buddleja globosa medicinal use.. Global methanol, sequential methanol and ethanol (leaves collected in autumn and summer) extracts were evaluated for oral and topic analgesia in tail flick, formalin and writhing models, verbascoside and 7-O-luteolin glucoside were assayed in tail flick and writhing. Ibuprofen was used as reference. For characterization of induced antinociception, naltrexone, naltrindole, tropisetron, nor-binaltorphimine, prazosin, yohimbine, atropine, and N-nitro-l-arginine methyl ester were used as antagonists and inhibitors drugs.. Seasonal influence was observed since autumn extract resulted less active. Extracts showed a dose-dependent antinociceptive activity in all assays, the highest effects were obtained for the formalin and writhing test. Verbascoside was more active than ibuprofen in the writhing test (67.6% and 50.0% at equimolar doses) and showed similar effects in the tail flick (topic and oral) near 25% at equivalent doses - ED25 or EC25 - to ibuprofen. Luteolin 7-O-glucoside was slightly more active in the tail flick test and nearly half active than verbascoside in the writhing assay. Effectiveness was higher for the sequential than for global alcoholic extracts, and can be increased by selective blocking of opioid receptors. Global methanol extract seems modulated only by naltrexone.. Analgesic effect of Buddleja globosa is here demonstrated validating its use in traditional medicine. Season influence is important to be considered.

Topics: Administration, Cutaneous; Administration, Oral; Analgesics; Animals; Buddleja; Chile; Disease Models, Animal; Dose-Response Relationship, Drug; Glucosides; Ibuprofen; Luteolin; Male; Medicine, Traditional; Mice; Pain; Pain Measurement; Phenols; Plant Extracts; Plant Leaves; Seasons

A continuous approach assisted by ultrasound for direct enrichment of edible oils (olive, sunflower, and soya) with the main phenols in olive leaves (i.e., oleuropein, verbascoside, apigenin-7-glucoside, and luteolin-7-glucoside) has been developed. Multivariate methodology was used to carry out a detailed optimization of the enrichment, and quantitation of the transferred compounds was based on LC-MS-MS in multiple reaction monitoring optimizing the most sensitive transition for each biophenol. Under the optimal working conditions, only 20 min is necessary to enrich the edible oils with 14.45-9.92 microg/mL oleuropein, 2.29-2.12 microg/mL verbascoside, 1.91-1.51 microg/mL apigenin-7-glucoside, and 1.60-1.42 microg/mL luteolin-7-glucoside. The enrichment method is carried out at room temperature and is organic-solvent-free; thus, the healthy properties of the edible oils improve as does their quality. Also, the low acquisition and maintenance costs of an ultrasound source and its application in a dynamic system make advisable the industrial implementation of the proposed method.

Topics: Apigenin; Dietary Fats, Unsaturated; Food, Fortified; Glucosides; Iridoid Glucosides; Iridoids; Luteolin; Olea; Phenols; Plant Leaves; Pyrans; Ultrasonics

The edible flower of Torenia fournieri Linden ex E. Fourn was found to possess potent antioxidative activity in a rat brain homogenate model. Bioassay-guided isolation of the active compounds from a CH(2)Cl(2)-MeOH (1:1) extract led to the isolation of acteoside (1), luteolin-7-O-beta-glucoside (2), apigenin-7-O-alpha-rhamnosyl-(1-->6)-beta-glucoside (3), and apigetrin (4).

Topics: Animals; Antioxidants; Apigenin; Brain; Disaccharides; Flavones; Flowers; Free Radical Scavengers; Glucosides; In Vitro Techniques; Lipid Peroxidation; Phenols; Plant Extracts; Rats; Scrophulariaceae