hyperoside and quercitrin

Quercetin, one of the most abundant flavonoids in plant-based foods, commonly occurs in nature in various glycosylated forms. There is still a less explored aspect regarding the cause of diversity of its glycosides, depending on the sugar moiety attached. This work focuses on four wide-spread quercetin glycosides-hyperoside, isoquercitrin, quercitrin and rutin-by testing the property-tuning capacity of different sugar moieties and thus explains and predicts some of their functions in plant-based foods. The electron paramagnetic spectra of the semiquinone anion radicals of these glycosides were interpreted in terms of hyperfine coupling constants and linewidths, highlighting a clear link between spin density trends, the identity of the bound sugar, and their reactivity corroborated with their modelled structures. Redox potential and lipophilicity were connected to a specific flavonoid-enzyme interaction and correlated with their prooxidant reactivity assessed by oxidation of ferrous hemoglobin. Hyperoside and isoquercitin-galactose and glucose glycosides-exhibit the highest prooxidant reactivity owing to their lowest redox potential and lipophilicity whereas rutin and quercitrin-rutinose and rhamnose glycosides-behave vice versa. The ability of the tested glycosides to undergo HAT or SET-type reactions has also been tested using five different analytical assays, including inhibition of cytochrome c-triggered liposome peroxidation. In most cases, rutin proved to be the most unreactive of the four tested glycosides considering either steric or redox reasons whereas the reactivity hierarchy of the other three glycosides were rather assay dependent.

Topics: Antioxidants; Electron Spin Resonance Spectroscopy; Electrons; Free Radical Scavengers; Glycosides; Hydrogen; Lipids; Oxidants; Oxidation-Reduction; Quercetin; Rutin

As the interest in heirloom cultivars of apple trees, their fruit, and processed products is growing worldwide, studies of the qualitative and quantitative composition of biological compounds are important for the evaluation of the quality and nutritional properties of the apples. Studies on the variations in the chemical composition of phenolic compounds characterized by a versatile biological effect are important when researching the genetic heritage of the heirloom cultivars in order to increase the cultivation of such cultivars in orchards. A variation in the qualitative and quantitative composition of phenolic compounds was found in apple samples of cultivars included in the Lithuanian collection of genetic resources. By the high-performance liquid chromatography (HPLC) method flavan-3-ols (procyanidin B1, procyanidin B2, procyanidin C2, (+)-catechin and (-)-epicatechin), flavonols (rutin, hyperoside, quercitrin, isoquercitrin, reynoutrin and avicularin), chlorogenic acids and phloridzin were identified and quantified in fruit samples of heirloom apple cultivars grown in Lithuania. The highest sum of the identified phenolic compounds (3.82 ± 0.53 mg/g) was found in apple fruit samples of the 'Koštelė' cultivar.

Topics: Biflavonoids; Catechin; Chlorogenic Acid; Chromatography, High Pressure Liquid; Dietary Supplements; Flavonoids; Fruit; Glycosides; Lithuania; Malus; Phenols; Phlorhizin; Proanthocyanidins; Quercetin; Rutin

Dried achene or anthocarpous accessory fruits of Rosa multiflora Thunb., Rosae fructus ("Eijitsu" in Japanese), have been used in clinical practice to improve constipation within traditional Japanese medicine. Recently, it has been claimed that the efficacy of this crude drug is decreasing, and multiflorin A, the purgative component, was not detected within the tested samples. In order to clarify the causes of this issue, we investigated Rosa section Synstylae (Rosaceae), including R. multiflora, growing in Japan and South Korea with a focus on the secondary metabolite, multiflorin A. We recognize that there are two chemotypes based on the presence (Type I) or absence (Type II) of multiflorin A. Type I contains quercitrin, multinoside A, multiflorin B, and multinoside A acetate as major index compounds. Type II contains hyperin, isoquercitrin, quercetin 3-O-glucuronide, and 3'-methoxy-isoquercitrin as the major index compounds. The chemotype of Rosa section Synstylae (Rosaceae) plants collected in Japan (excluding Tsushima Island) were all classified as Type I with exception of two species, R. luciae and R. sambucina. On the other hand, both Type I and Type II were detected within Rosae fructus obtained from R. multiflora collected in South Korea and Tsushima Island, Japan. The results indicate that Rosae fructus from R. multiflora (Type I) from Japan, excluding Tsushima Island, should be employed clinically, which we describe as purgative.

Topics: Chromones; Flavonols; Fruit; Glycosides; Japan; Medicine, Traditional; Phytochemicals; Quercetin; Republic of Korea; Rosa

Accumulation of selected secondary metabolites in two Hypericum species (H. perforatum and H. annulatum) was compared in their vegetative parts (stems and leaves) and in terms of the extraction solvent (80% aq. methanol or 60% aq. ethanol). The presence of chlorogenic acid and quercitrin was not detected in stem of both species. Almost all metabolites were more accumulated in the leaves than in the stems (rutin, hyperoside, quercetin and hypericin) but epicatechin showed the opposite in both species and hyperforin in H. annulatum. Extraction solvents showed rather species-specific differences with EtOH being more suitable for the extraction of hypericin, quercetin, quercitrin, and hyperoside (on average, for both the leaves and stems, extraction increased by approximately 130, 30, 25, and 15%, respectively) while MeOH for the extraction of epicatechin, rutin, and hyperforin (increased extraction by approximately 50, 40, and 35%, respectively). On the other hand, content of total soluble phenols did not differ in relation to solvent in any organ or species. Various ages of H. annulatum plants did not show dramatic impact on the amount of metabolites. Subsequently, the usefulness of capillary electrophoresis (CE) as an alternative to HPLC for the quantification of metabolites in H. perforatum was tested and results showed non-significant differences between CE and HPLC with the methods we developed (the difference did not exceed 10%).

Topics: Anthracenes; Catechin; Chlorogenic Acid; Chromatography, High Pressure Liquid; Hypericum; Perylene; Phloroglucinol; Plant Extracts; Plant Leaves; Plant Stems; Quercetin; Rutin; Terpenes

Quercitrin, hyperoside, rutin, and afzelin are the dominant flavonoids compounds from Zanthoxylum bungeanum leaves, and they play major roles in the antioxidant activity. Macroporous adsorption resin (MAR) treatment, a simple, low-cost and efficient method, was combined with ultrasound-assisted extraction (UAE) to enrich and purify these four flavonoids from Z. bungeanum leaves efficiently. The optimal conditions for UAE based on Response Surface Methodology (RSM) were determined to be an ethanol concentration of 60%, leaves size of 40 mesh, temperature of 50 °C and ultrasonic power of 400 W with four flavonoids contents of 120.84 mg/g. After the extraction process, five kinds of MARs (D4020, D-101, NKA-9, AB-8, and X-5) were tested through static adsorption/desorption to enrich and purify the ultrasonic-assisted extracts, and D-101 was selected as the most suitable resin. The optimal adsorption conditions were 5 bed volumes (BV) of sample solution with an initial concentration of 7.5 mg/mL and pH 5.0. Meanwhile, the optimal desorption parameters were 5 BV each of deionized water and 30% ethanol, then 10 BV 70% ethanol, and a flow rate of 2 BV/hr. Under the optimized conditions, the contents of quercitrin, hyperoside, rutin, and afzelin increased by 276.39%, 187.46%, 221.81%, and 288.45%, respectively, and the recovery yields were 85.47%, 73.53%, 81.35%, and 65.06%. In addition, laboratory preparative-scale separation indicated that the preparative separation of four flavonoids was feasible and easy. Moreover, the antioxidant activities of the purified products were significantly increased after enrichment. In conclusion, all of the results indicated that these methods are highly efficient, low cost, environmentally friendly and easy to scale up.. This study provided an environmentally friendly, rapid, and highly productive method for the extraction and purification of four active compounds from Zanthoxylum bungeanum leaves. The results can be used for the utilization of Z. bungeanum leaves as a kind of food supplement in an industrial setting.

Topics: Adsorption; Flavonoids; Mannosides; Plant Extracts; Plant Leaves; Proanthocyanidins; Quercetin; Resins, Synthetic; Rutin; Ultrasonics; Zanthoxylum

To clarify the substantial basis of the excellent antioxidant capacity of

Topics: Agrimonia; Catechin; DNA Damage; Flavonoids; Molecular Structure; Oxidative Stress; Plant Extracts; Quercetin; Rutin; Structure-Activity Relationship

To study the chemical consituents of Hypericum ascyron.. The constituents were isolated and purified by chromatography on silica gel; the structure of the compound was determined by MS and NMR spectral analysis.. On the basis of spectroscopic analysis and comparison with the reported data, they were identified as hyperoside( 1),hypercalin B( 2),hypercalin C( 3),1,7-dihydroxyxanthone( 4),2,3-dimethoxyxanthone( 5),1-hydroxy-7-methoxyxanthone( 6),rutin( 7),kaempferol( 8),toxyloxanthone B( 9),quercetin( 10),quercitrin( 11),β-daucosterol( 12) and β-sitosterol( 13).. Compounds 2,3,6 and 9 are obtained from this plant for the first time.

Topics: Acetates; Hypericum; Kaempferols; Quercetin; Rutin; Sitosterols

In this study, an aqueous two-phase system (ATPS) based on ethanol/NaH2 PO4 was developed for the extraction and purification of quercitrin, hyperoside, rutin, and afzelin from Zanthoxylum bungeanum Maxim leaves. These 4 flavonoids were 1st extracted from dried Z. bungeanum leaves using a 60% ethanol solution and subsequently added to the ATPS for further purification. The partition behavior of the 4 flavonoids in ATPS was investigated. The optimal ATPS conditions were: 29% (w/w) NaH2 PO4 , 25% (w/w) ethanol concentration, 1% (w/w) added amount of leaf extracts, no pH adjustment, and repeated 1 h extractions at 25 °C. Under the optimal conditions for the 10 g ATPS, the absolute recovery of quercitrin, hyperoside, rutin, and afzelin reached 90.3%, 83.5%, 92.3%, and 89.1%, respectively. Compared to the 60% ethanol extracts, the content of quercitrin (44.8 mg/g), hyperoside (65.6 mg/g), rutin (56.4 mg/g), and afzelin (6.84 mg/g) in the extracts increased by 49.9%, 38.8%, 45.6%, and 36.8% respectively. The extracts after ATPS also exhibited stronger antioxidant activities, the 2,2-diphenyl-1-picrylhydrazyl IC50 value (10.5 μg/mL) decreased by 41.8%, and the 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt value (966 μmol Trolox/g) and ferric reducing power value (619 μmol Trolox/g) increased by 29.8% and 53.7%, respectively. Furthermore, scale-up experiments indicated that a larger scale experiment was feasible for the purification of the 4 flavonoids.

Topics: Antioxidants; Benzothiazoles; Biphenyl Compounds; Flavonoids; Mannosides; Oxidation-Reduction; Picrates; Plant Extracts; Plant Leaves; Proanthocyanidins; Quercetin; Rutin; Sulfonic Acids; Water; Zanthoxylum

Sixteen subsequent fractions were prepared from the ethyl acetate fraction of Zanthoxylum bungeanum leaves after bio-guided chromatographic separation. The HPLC profiles and antioxidant activity of the various fractions indicated that the content of eight phenolic compounds (chlorogenic acid, epicatechin, rutin, hyperoside, trifolin, quercitrin, afzelin and quercetin) and antioxidant activity vary significantly, and high concentrations of a combination of eight phenolic compounds would result in an increase of the antioxidant activity. These results suggested that the eight compounds could be used as chemical markers for quality assessment of Z. bungeanum leaves. Correlation between chromatographic fingerprint and antioxidant activity of the fractions showed that quercitrin and hyperoside play crucial roles in the antioxidant activity, and they can be seen as the milestone for quality control. The findings also suggested that five obtained fractions (E-3-3, E-2-4, E-7, E-5 and E-4) could become useful supplements for functional food ingredients and health-related products.

Topics: Antioxidants; Chromatography, High Pressure Liquid; Flavonoids; Phenols; Plant Leaves; Quercetin; Zanthoxylum

The aerial parts of Houttuynia cordata used for treating inflammation-related disorders contain flavonoids as major constituents. Since certain flavonoids possess anti-inflammatory activity, especially in the lung, the pharmacological activities of H. cordata and the flavonoid constituents were evaluated using in vitro and in vivo models of lung inflammation. The 70 % ethanol extract of the aerial parts of H. cordata inhibited the production of inflammatory biomarkers IL-6 and NO in lung epithelial cells (A549) and alveolar macrophages (MH-S), respectively. And the same plant material, administered orally (100 and 400 mg/kg), significantly inhibited lung inflammatory response in a mouse model of lipopolysaccharide (LPS)-induced acute lung injury. From the extract, major flavonoids including afzelin, hyperoside and quercitrin were successfully isolated and they also attenuated LPS-induced lung inflammation in mice by oral administration. In particular, quercitrin showed most potent activity at 100 mg/kg. These results demonstrate for the first time that H. cordata and three flavonoid constituents have a therapeutic potential for treating lung inflammatory disorders.

Topics: Animals; Anti-Inflammatory Agents; Cells, Cultured; Epithelial Cells; Flavonoids; Houttuynia; Humans; Interleukin-6; Lipopolysaccharides; Macrophages, Alveolar; Male; Mannosides; Mice; Nitric Oxide; Phytotherapy; Plant Components, Aerial; Plant Extracts; Pneumonia; Proanthocyanidins; Quercetin

Quercetin is a plant-derived flavonoid and its cytotoxic properties have been widely reported. However, in nature, quercetin predominantly occurs as various glycosides. Thus far the cytotoxic activity of these glycosides has not been investigated to the same extent as quercetin, especially in animal models. In this study, the cytotoxic properties of quercetin (1), hyperoside (quercetin 3-O-galactoside, 2), isoquercitrin (quercetin 3-O-glucoside, 3), quercitrin (quercetin 3-O-rhamnoside, 4), and spiraeoside (quercetin 4'-O-glucoside, 5) were directly compared in vitro using assays of cancer cell viability. To further characterize the influence of glycosylation in vivo, a novel zebrafish-based assay was developed that allows the rapid and experimentally convenient visualization of glycoside cleavage in the digestive tract. This assay was correlated with a novel human tumor xenograft assay in the same animal model. The results showed that 3 is as effective as 1 at inhibiting cancer cell proliferation in vivo. Moreover, it was observed that 3 can be effectively deglycosylated in the digestive tract. Collectively, these results indicate that 3 is a very promising drug candidate for cancer therapy, because glycosylation confers advantageous pharmacological changes compared with the aglycone, 1. Importantly, the development of a novel and convenient fluorescence-based assay for monitoring deglycosylation in living vertebrates provides a valuable platform for determining the metabolic fate of naturally occurring glycosides.

Topics: Animals; Flavonoids; Glucosides; Glycosides; Glycosylation; HCT116 Cells; Humans; Molecular Structure; Quercetin; Structure-Activity Relationship; Vertebrates; Zebrafish

In Chinese traditional medicine, Agrimonia pilosa Ledeb (APL) exhibits great effect on treatment of type 2 diabetes mellitus (T2DM), however its mechanism is still unknown. Considering that T2DM are correlated with postprandial hyperglycemia and oxidative stress, we investigated the α-glucosidase inhibitory activity and the antioxidant activity of flavonoid compound (FC) and triterpenoid compound (TC) from APL.. Entire plants of APL were extracted using 95% ethanol and 50% ethanol successively. The resulting extracts were partitioned and isolated by applying liquid chromatography using silica gel column and Sephadex LH 20 column to give FC and TC. The content of total flavonoids in FC and the content of total triterpenoids in TC were determined by using UV spectrophotometry. HPLC analysis was used to identify and quantify the monomeric compound in FC and TC. The α-glucosidase inhibitory activities were determined using the chromogenic method with p-nitrophenyl-α-D-glucopyranoside as substrate. Antioxidant activities were assessed through three kinds of radical scavenging assays (DPPH radical, ABTS radical and hydroxyl radical) & β-carotene-linoleic acid assay.. The results indicate FC is abundant of quercitrin, and hyperoside, and TC is abundant of 1β, 2β, 3β, 19α-tetrahydroxy-12-en-28-oic acid (265.2 mg/g) and corosolic acid (100.9 mg/g). The FC & the TC have strong α-glucosidase inhibitory activities with IC50 of 8.72 μg/mL and 3.67 μg/mL, respectively. We find that FC show competitive inhibition against α-glucosidase, while the TC exhibits noncompetitive inhibition. Furthermore, The FC exhibits significant radical scavenging activity with the EC50 values of 7.73 μg/mL, 3.64 μg/mL and 5.90 μg/mL on DPPH radical, hydroxyl radical and ABTS radical, respectively. The FC also shows moderate anti-lipid peroxidation activity with the IC50 values of 41.77 μg/mL on inhibiting β-carotene bleaching.. These results imply that the FC and the TC could be responsible for the good clinical effects of APL on T2MD through targeting oxidative stress and postprandial hyperglycaemia. So APL may be good sources of natural antioxidants and α-glucosidase inhibitors exhibiting remarkable potential value for the therapy of T2DM.

Topics: Agrimonia; alpha-Glucosidases; Antioxidants; beta Carotene; Chromatography, High Pressure Liquid; Diabetes Mellitus, Type 2; Flavonoids; Free Radical Scavengers; Glucosides; Glycoside Hydrolase Inhibitors; Hyperglycemia; Kinetics; Lipid Peroxidation; Oxidation-Reduction; Oxidative Stress; Plant Extracts; Postprandial Period; Quercetin; Triterpenes

The aim of this study was to determine the composition and content of phenolic compounds in the ethanol extracts of apple leaves and to evaluate the antioxidant activity of these extracts. The total phenolic content was determined spectrophotometrically, as well as the total flavonoid content in the ethanol extracts of apple leaves and the antioxidant activity of these extracts, by the ABTS, DPPH, and FRAP assays. The highest amount of phenolic compounds and flavonoids as well as the highest antioxidant activity was determined in the ethanol extracts obtained from the apple leaves of the cv. Aldas. The analysis by the HPLC method revealed that phloridzin was a predominant component in the ethanol extracts of the apple leaves of all cultivars investigated. The following quercetin glycosides were identified and quantified in the ethanol extracts of apple leaves: hyperoside, isoquercitrin, avicularin, rutin, and quercitrin. Quercitrin was the major compound among quercetin glycosides.

Topics: Antioxidants; Benzothiazoles; Biphenyl Compounds; Flavonoids; Malus; Oxidation-Reduction; Phenols; Picrates; Plant Extracts; Plant Leaves; Quercetin; Rutin; Sulfonic Acids

To Set up a method for determining the contents of the five flavonoids simultaneously in the HuangKui capsule and analyze their specific chromatograms.. HPLC method was used. The analytical column was Thermo scientific Hypersil GOLD (250 mm x 4.6 mm, 5 microm). The mobile phase was composed of acetonitrile (A) and 0.2% orthophosphoric acid (B) with gradient elution. The flow rate was 0.8 mL/min and detection wavelength was 360 nm. The column temperature was maintained at 30 degrees C.. Contents of the five flavonoids (Rutin, Hyperoside, Isoquercitrin, Myricetin, Quercitrin) had good resolution with the correlation coefficients exceed 0.9999 and the average percent recovery lied in 98.46% to 100.33%. The chromatograms of the HuangKui capsule shared 15 common peaks in which 5 of them were recognized by the reference standard. Chromatograms of 10 lots of HuangKui capsule were analyzed with the similarities over 0.95.. The proposed method of contents determination and chromatogram analysis has strong characteristic and specificity. This method is fast, easy and reliable, and can be applied for quality control of the preparation.

Topics: Abelmoschus; Capsules; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonoids; Quality Control; Quercetin; Reproducibility of Results; Rutin

To study the constituents of ethyl acetate fraction form Hypericum hengshanense.. The constituents were isolated and purified by chromatography on silica gel and their structures were elucidated by MS and NMR spectral analysis.. Ten compounds were isolated and identified as: hyperoside (1), hypericin (2), quercetin (3), quercitrin (4), sesamin (5), betulonic acid (6), rutin (7), kaempferol (8), beta-daucosterol (9), beta-sitosterol (10).. All compounds are obtained from this plant for the first time.

Topics: Acetates; Anthracenes; Hypericum; Kaempferols; Magnetic Resonance Spectroscopy; Perylene; Plant Components, Aerial; Plants, Medicinal; Quercetin; Rutin

To investigate the chemical constituents of Psidium guajava L, the EtOH/H(2)O extract of the fresh leaves was subjected to various chromatography. One diphenylmethane, one benzophenone, and eight flavonoids were isolated and elucidated as 2,6-dihydroxy-3-formaldehyde-5-methyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-diphenylmethane (1), 2,6-dihydroxy-3,5-dimethyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-benzophenone (2), kaempferol (3), quercetin (4), quercitrin (5), isoquercitrin (6), guaijaverin (7), avicularin (8), hyperoside (9), reynoutrin (10) by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS spectrometry as well as by comparison with published data. Compounds 5 and 10 are obtained from P. guajava for the first time, and compound 1 is a new diphenylmethane compound.

Topics: Benzhydryl Compounds; Benzophenones; Flavonoids; Gallic Acid; Glucosides; Glycosides; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Leaves; Psidium; Quercetin; Spectrometry, Mass, Electrospray Ionization

We verified the hypothesis that the consumption of polyphenol concentrate (PC), rich in quercetin and its glycosides (36 g/100 g), in association with different dietary fiber matrices, that is, an easily fermentable fructo-oligosaccharides (FOS) or non-fermentable cellulose (CEL), causes a disparate adaptive response of the cecal microbial activity in rats. This in turn facilitates further utilization of biologically active polyphenolic compounds, which are not, as usual, digested in the foregut.. Four-week experimental feeding of male Wistar rats consisted of diets containing 5% FOS or CEL, as a source of dietary fiber, with or without 0.3% addition of PC.. Positive changes in rat cecum were observed resulting from the ingestion of an FOS-containing diet, such as decreased pH and increased the production of short-chain fatty acids in the digesta, compared with a CEL-containing diet. The addition of PC to the FOS diet did not eliminate the positive effects of the latter, except for a slight increase in cecal pH and a decrease in microbial glycolytic activity. However, a simultaneous increase in the cecal butyrate pool was also observed. An adaptation process of the microflora enzymatic system to dieting with PC and FOS was proven in further enhanced susceptibility of rutin (quercetin 3-O-glucorhamnoside), hyperoside (quercetin 3-O-galactoside), and quercitrin (quercetin 3-O-rhamnoside) to hydrolysis by the cecal digesta solution.. Especially when consumed together, PC and FOS are important dietary factors affecting the susceptibility of quercetin glycosides to microbial metabolism in the cecum. The intensification of the hydrolysis of quercetin glycosides by dietary treatments leads also to the increased metabolism of quercetin itself.

Topics: Animals; Bacteria; Butyrates; Cecum; Cellulose; Diet; Fatty Acids, Volatile; Flavonoids; Glycosides; Hydrogen-Ion Concentration; Male; Oligosaccharides; Phenols; Plant Extracts; Polyphenols; Quercetin; Rats; Rats, Wistar; Rutin

Two bioactive flavonol glucosides, hyperoside and quercitrin, were successfully isolated in one step from the phytochemically unknown medicinal plant Osteomeles schwerinae by high-speed counter-current chromatography using a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (0.5:5.5:1.5:4.5 v/v). From 160 mg of crude extract, 2.1 mg of hyperoside (98.6% purity, 83.3% recovery) and 4.5 mg of quercitrin (99.2% purity, 81.7% recovery) were separated and then their chemical structures were identified by (1)H and (13)C NMR analysis. In addition, the isolates were subjected to an in vitro bioassay to evaluate their inhibitory activity on rat lens aldose reductase. Both quercitrin and hyperoside showed excellent inhibitory activities toward rat lens aldose reductase with the IC(50) values of 0.16 and 4.33 microM, respectively, as compared with positive control, 3,3-tetramethyleneglutaric acid (28.7 microM). So far, chemical constituents and biological activities of O. schwerinae have never been reported. This is the first report on the chemical constituents and biological activity of this plant using semi-preparative high-speed counter-current chromatography separation technique.

Topics: Aldehyde Reductase; Animals; Countercurrent Distribution; Flavonols; Glucosides; Inhibitory Concentration 50; Lens, Crystalline; Magnetic Resonance Spectroscopy; Molecular Structure; Organic Chemicals; Plant Extracts; Plant Leaves; Plant Stems; Quercetin; Rats; Rosaceae; Water

The phloroglucinol derivative hyperforin, the naphthodianthrones hypericin and pseudohypericin, the phenylpropane chlorogenic acid, and the flavonoids rutin, hyperoside, apigenin-7-O-glucoside, kaempferol, quercitrin, quercetin and amentoflavone were investigated in Hypericum confertum growing wild in Turkey. After drying at room temperature, the plant materials were assayed for secondary metabolite concentrations by HPLC. All the listed compounds were detected at various levels. This is the first report on the chemistry of H. confertum.

Topics: Anthracenes; Apigenin; Biflavonoids; Bridged Bicyclo Compounds; Chlorogenic Acid; Hypericum; Perylene; Phloroglucinol; Plant Components, Aerial; Quercetin; Rutin; Terpenes

The present study was conducted out to determine hyperforin, hypericin, pseudohypericin, chlorogenic acid, rutin, hyperoside, quercitrin, quercetin, kaempferol, apigenin-7-O-glucoside and amentoflavone contents of Hypericum adenotrichum, an endemic plant species to Turkey. The aerial parts representing a total of 30 individuals were collected at full flowering, dried at room temperature and assayed for secondary metabolite concentrations by HPLC. All of the chemicals were detected at various levels except for hyperforin. This is the first report on polar chemistry of this endemic species.

Topics: Anthracenes; Bridged Bicyclo Compounds; Chromatography, High Pressure Liquid; Hypericum; Kaempferols; Perylene; Phloroglucinol; Quercetin; Terpenes; Turkey

Agrimonia pilosa Ledeb is used as the tonic for asthenia and fatigue in China. Considering that the energizing effect might be correlated with antioxidant properties, we investigated the antioxidant activities of aqueous extract (AE) from Agrimonia pilosa Ledeb by assessing radical-scavenging and anti-lipid-peroxidation abilities. We found that AE shows a moderate antioxidant activity to scavenge DPPH*, O2(-)* and *OH and inhibit beta-carotene bleaching with IC(50) values of 13.0, 33.2, 351, and 11.9 microg/ml, respectively, while its AcOEt-soluble fraction (ESF) and BuOH soluble fraction (BSF) exhibit remarkable efficiencies. The ESF's IC(50) values of scavenging DPPH*, O2(-)*, and *OH, and inhibiting beta-carotene bleaching are 5.6, 5.8, 171, and 7.6 mircog/ml, respectively, and those of BSF are 7.5, 8.4, 82.0, and 6.2 microg/ml, respectively. In addition, we found that there is a significant correlation between total phenol content and the antioxidant activity determined by O2(-)* and *OH scavenging, and beta-carotene-bleaching assays. Furthermore, HPLC analysis revealed the presence of quercetin, hyperoside, quercitrin, taxifoliol, luteolin-7-O-beta-D-glucopyranoside, and rutin in Agrimonia pilosa Ledeb. Thus, we suggest that the extracts from Agrimonia pilosa Ledeb, could be considered as natural antioxidant sources and dietary nutritional supplements to prevent oxidation-related diseases.

Topics: Agrimonia; Antioxidants; beta Carotene; Chromatography, High Pressure Liquid; Dietary Supplements; Drugs, Chinese Herbal; Free Radical Scavengers; Glucosides; Inhibitory Concentration 50; Lipid Peroxidation; Luteolin; Oxidation-Reduction; Phenols; Plant Extracts; Quercetin; Rutin; Solvents; Water

The leaves and fruits of strawberry tree - Arbutus unedo L., collected from two separate geographic locations in Croatia were investigated to determine their flavonoid composition and content. Quercitrin, isoquercitrin, hyperoside and rutin were identified in all leaf samples by means of thin-layer chromatography; the fruits contained only isoquercitrin. Chlorogenic acid was present in some leaf samples. The content of flavonoids depended on the plant organ investigated, date of collection and the locality. Spectrophotometric determination of the flavonoids indicated that the leaves are richer in flavonoids (0.52-2.00%) than fruits (0.10-0.29%).

Topics: Croatia; Ericaceae; Flavonoids; Fruit; Plant Leaves; Quercetin

Mimosa, an excellent energy crop candidate because of its high growth yield, also contains, on a dry basis, 0.83% hyperoside and 0.90% quercitrin. Hyperoside has been documented as having anti-inflammatory and diurectic properties, whereas quercitrin may play a role in intestinal repair following chronic mucosal injury. Thus, mimosa might first be extracted for important antioxidant compounds and then used as a feedstock for energy production. This article presents results from studies aimed at determining the effect of three extraction parameters (temperature, solvent composition, and time) on the yield of these important quercetin compounds. Conditions are sought which maximize yield and concentration, whereas complementing subsequent biomass pretreatment, hydrolysis and fermentation.

Topics: Chemical Fractionation; Energy-Generating Resources; Mimosa; Plant Leaves; Quercetin

Quercetin is an important dietary flavonoid with putative beneficial effects in the prevention of cancer and CVD. The in vivo bioactivity of quercetin depends on its bioavailability, which varies widely between foods. We used an in situ rat intestinal perfusion model to study whether differential small intestinal hydrolysis of the sugar moiety of five naturally occurring quercetin glycosides determines the small intestinal uptake and subsequent biliary excretion of quercetin. After 30 min perfusion, a decrease of intact quercetin glycoside in perfusate was observed for quercetin-3-O-ss-glucoside (20.9 (sem 1.4) micromol/l) and quercetin-4'-O-ss-glucoside (23.5 (sem 1.6) micromol/l), but not of quercetin-3-O-ss-galactoside, quercetin-3-O-ss-rhamnoside and quercetin-3-O-alpha-arabinopyranoside. Appearance of free quercetin in perfusate and conjugated quercetin metabolites (quercetin, isorhamnetin, and tamarixetin) in portal and peripheral plasma and bile were also significantly greater after treatment with quercetin-3-O-ss-glucoside or quercetin-4'-O-ss-glucoside compared with any of the other glycosides. Thus, the type of sugar moiety is a major determinant of the small intestinal absorption of quercetin glycosides, but the position (3 or 4') of the glucose moiety does not further influence absorption. The poor bioavailability of important dietary quercetin glycosides has implications for their in vivo bioactivities.

Topics: Animals; Bile; Biological Availability; Diet; Glycosides; Intestinal Absorption; Intestine, Small; Male; Perfusion; Portal Vein; Quercetin; Rats; Rats, Wistar

Miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is one of the flavonoids of St. John's wort (Hypericum perforatum L.) whose antidepressant activity has been shown by the forced swimming test, an in vivo pharmacological model with rats. However, nothing is known about its ability to reach the CNS after oral administration. We examined the pathway of miquelianin from the small intestine to the central nervous system using three in vitro membrane barrier cell systems. In the Caco-2 cell line, miquelianin showed a higher uptake (1.93 +/- 0.9 pmol x min(-1) x cm(-2)) than hyperoside (quercetin 3-O-beta-D-galactopyranoside; 0.55 +/- 0.18 pmol x min(-1) x cm(-2)) and quercitrin (quercetin 3-O-alpha-L-rhamnopyranoside; 0.22 +/- 0.08 pmol x min(-1) x cm(-2)). The permeability coefficient of miquelianin (Pc = 0.4 +/- 0.19 x 10(-6) cm/sec) was in the range of orally available drugs assuming sufficient absorption from the small intestine. Uptake and permeability of the examined compounds was increased by the MRP-2 inhibitor MK-571 indicating a backwards transport by this membrane protein. Porcine cell cultures of brain capillary endothelial cells were used as a model of the blood-brain barrier (bbb) and epithelial cells of the plexus chorioidei as a model of the blood-CSF barrier (bcb). Results indicate no active transport in one direction. Although moderate, the permeability coefficients (bbb: Pc = 1.34 +/- 0.05 x 10(-6) cm/sec; bcb: Pc = 2.0 +/- 0.33 x 10(-6) cm/sec) indicate the ability of miquelianin to cross both barriers to finally reach the CNS.

Topics: Administration, Oral; Animals; Biological Availability; Blood-Brain Barrier; Brain; Caco-2 Cells; Cells, Cultured; Glucosides; Humans; Hypericum; Intestinal Absorption; Intestinal Mucosa; Multidrug Resistance-Associated Protein 2; Phytotherapy; Plant Preparations; Quercetin; Swine

Monarda didyma L. is a herbaceous perennial with the square stems and opposite leaves characteristic of herbs in the Labiate family. Monarda didyma L. is often used as a domestic medicine, being particularly useful in the treatment of digestive disorders. The leaves and flowering stems are antihelmintic, carminative, diuretic, expectorant, febrifuge, rubefacient and stimulant. Monarda didyma L. has twenty-six compounds in the essential oil, of which thymol, with smaller amounts of para-cymene, d-limonene, carvacrol, linalool, and hydrothymoquinone. A new method was used for the determining of the amount of separate flavonols by high-performance liquid chromatography. The flavonoids (rutin, hyperoside, quercitrin, luteolin, quercetin) were found in leaves and flowers of beebalm. The quantity of flavonoids was higher in flowers than in leaves of Monarda didyma L.

Topics: Chromatography, High Pressure Liquid; Flavonoids; Flowers; Humans; Luteolin; Monarda; Phytotherapy; Plant Leaves; Quercetin; Rutin

In contrast to chemically defined drugs, most herbal medicinal products (HMPs) are poorly characterized in terms of their pharmaceutical properties. In many cases it is assumed that the plant extract as a whole is the active moiety, since it is often difficult to identify the individual components responsible for the pharmacological activity and even more difficult to assess synergies among the various components. However, where the active components have been identified, it should be possible to compare products with respect not only to content uniformity but also to their biopharmaceutical properties. The aim of this study was to investigate and compare the dissolution characteristics of several St John's wort products under biorelevant conditions. Components of St John's wort known, or suspected, to play a role in its antidepressant activity include phloroglucines, naphthodianthrones and the flavonoids. Since these groups have a broad spectrum of polarity and solubility, dissolution was studied for representative compounds from each group. Although the labelling indicates that several of the products studied should be pharmaceutically equivalent, dissolution under biorelevant conditions revealed that they have quite different release profiles and cannot be considered switchable. It was concluded that biorelevant dissolution testing can be a powerful tool for comparing HMPs as well as synthetically produced drug products.

Topics: Antidepressive Agents; Bridged Bicyclo Compounds; Capsules; Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Ethanol; Hypericum; Kinetics; Methanol; Phloroglucinol; Plant Extracts; Quercetin; Reproducibility of Results; Rutin; Solubility; Solvents; Terpenes; Time Factors

To investigate the chemical constituents from the aerial parts of Hyperricum monogynum.. Compounds were isolated by various column chromatography and identified by spectral analysis.. Ten compounds were isolated and identified as quercetin, quercitrin, hyperoside, rutin, (-)-epicatechin, 3,5-dihydroxy-1-methoxy-xanthone, 3,4-O-isopropylidenyl shikimic acid, shikimic acid, daucosterol, and oleanoic acid.. All compounds were isolated from this plant for the first time.

Topics: Hypericum; Plant Components, Aerial; Plants, Medicinal; Quercetin

The traditional herbal remedy from Psidium guajava leaves has been medically proposed in Mexico as effective treatment of acute diarrhea. A methanolic leaf extract was subjected to a bioassay-guided isolation of spasmolytic constituents. Six fractions were separated on a polyvinylpolypyrrolidine (PVPP) column using a water methanol-gradient. The fraction containing flavonols inhibited peristalsis of guinea pig ileum in vitro. A trace of quercetin aglycone together with five glycosides was isolated from this active fraction and identified as quercetin 3-O-alpha-L-arabinoside (guajavarin); quercetin 3-O-beta-D-glucoside (isoquercetin); quercetin 3-O-beta-D-galactoside (hyperin); quercetin 3-O-beta-L-rhamnoside (quercitrin) and quercetin 3-O-gentobioside. Biological activity of each pure compound was studied in the same bioassay. Obtained results suggest that the spasmolytic activity of the Psidium guajava leaf remedy is mainly due to the aglycone quercetin, present in the leaf and in the extract mainly in the form of five flavonols, and whose effect is produced when these products are hydrolyzed by gastrointestinal fluid.

Topics: Animals; Antidiarrheals; Drug Evaluation, Preclinical; Gastric Acid; Glycosides; Guinea Pigs; Hydrolysis; Ileum; Male; Methanol; Mexico; Muscle Relaxation; Muscle, Smooth; Parasympatholytics; Plant Extracts; Plants, Medicinal; Quercetin

A new flavonol glycoside, C27H28O10, mp 151-152 degrees C (MeOH), named acuminatin (I), was isolated from the aerial part of Epimedium acuminatum Franch in addition to four known compounds. By means of UV, FAB-MS, EI-MS, 1HNMR, 13CNMR and chemical evidences, the structure of acuminatin was established as 6", 6"-dimethylpyrano (2", 3": 7, 8) 4'-methyl kaempferol-3-O-alpha-L-rhamnopyranoside. The known compounds were identified as kaempferol-3-O-alpha-L-rhamnopyranoside (II), quercitrin (III), hyperin (IV) and daucosterol (V).

Topics: Drugs, Chinese Herbal; Flavonoids; Glycosides; Molecular Structure; Quercetin