iridoids and gentiopicroside

Topics: Alkaloids; Glucosides; Glycosides; Humans; Iridoid Glucosides; Iridoids; Medicine, Chinese Traditional; Medicine, East Asian Traditional; Plants, Medicinal; Pyrans; Pyrones; Triterpenes

Natural products have been the main source of bioactive molecules for centuries. We tested the biological profile of two metabolites extracted from

Topics: Animals; Cell Line; Computational Biology; Cyclooxygenase 2; Doxycycline; Drug Evaluation, Preclinical; Gentiana; In Vitro Techniques; Iridoid Glucosides; Iridoids; Ligands; Metabolome; Mice; Molecular Docking Simulation; Molecular Dynamics Simulation; Proteins

Secoiridoids could be used as a potential new drug for the treatment of hepatic disease. The content of secoiridoids of

Topics: China; Chromatography, High Pressure Liquid; Gentiana; Humans; Iridoid Glucosides; Iridoids; Liver Diseases; Plant Leaves; Plant Roots; Plant Stems; Pyrones; Spectroscopy, Fourier Transform Infrared

Swertia nervosa (Wall. ex G. Don) C. B. Clarke, a promising traditional herbal medicine for the treatment of liver disorders, is endangered due to its extensive collection and unsustainable harvesting practices.. The aim of this study is to discuss the diversity of metabolites (loganic acid, sweroside, swertiamarin, and gentiopicroside) at different growth stages and organs of Swertia nervosa using the ultra-high-performance LC (UPLC)/UV coupled with chemometric method.. UPLC data, UV data, and data fusion were treated separately to find more useful information by partial least-squares discriminant analysis (PLS-DA). Hierarchical cluster analysis (HCA), an unsupervised method, was then employed for validating the results from PLS-DA.. Three strategies displayed different chemical information associated with the sample discrimination. UV information mainly contributed to the classification of different organs; UPLC information was prominently responsible for both organs and growth periods; the data fusion did not perform with apparent superiority compared with single data analysis, although it provided useful information to differentiate leaves that could not be recognized by UPLC. The quantification result showed that the content of swertiamarin was the highest compared with the other three metabolites, especially in leaves at the rooted stage (19.57 ± 5.34 mg/g). Therefore, we speculated that interactive transformations occurred among these four metabolites, facilitated by root formation.. This work will contribute to exploitation of bioactive compounds of S. nervosa, as well as its large-scale propagation.. The roots formation may influence the distribution and accumulation of metabolites.

Topics: Chromatography, High Pressure Liquid; Iridoid Glucosides; Iridoids; Pyrones; Swertia

Hepatic gluconeogenesis plays an important role in regulating fasting plasma glucose levels and is a target of anti-diabetic drugs. Several kinds of iridoid glucosides exhibit hypoglycemic effect, whereas the mechanism was not clear.. In this study, the effects of geniposide and gentiopicroside, two natural iridoid glucosides, on hepatic gluconeogenesis were investigated.. Glucose uptake assay, MTT assay, q-PCR, luciferase assay and western blot assay were performed to investigate the pharmacological effect of geniposide and gentiopicroside on human liver cell line L02. Thereby the fast blood glucose and intraperitoneal glucose tolerance were measured in high fat diet induced hyperglycemic mice after geniposide or gentiopicroside administration.. The results showed that geniposide and gentiopicroside inhibited the transcription of G6PC and PEPCK in L02 cells and in mice. Additional experimental data indicated that these two compounds were able to inhibit the transcriptional activity of FOXO1 by inducing phosphorylation of AKT at Ser473. Furthermore, we found that these two compounds alleviated high fat diet induced hyperglycemia in mice.. Geniposide and gentiopicroside might reduce blood glucose and suppress hepatic gluconeogenesis by regulating the AKT-FOXO1 pathway, and the potential use of these two iridoid glucosides as anti-diabetic agents merits further in-depth exploration.

Topics: Animals; Blood Glucose; Cells, Cultured; Diet, High-Fat; Forkhead Box Protein O1; Gluconeogenesis; Humans; Hypoglycemic Agents; Iridoid Glucosides; Iridoids; Liver; Male; Mice; Mice, Inbred C57BL; Phosphorylation; Proto-Oncogene Proteins c-akt; Signal Transduction

To study the effect of phosphorus( P) and potassium( K) fertilization on four iridoids in axial and lateral root of Gentiana crassicaulis.. Field experiment was conducted based on phosphorus and potassium,and the content of four iridoids was analyzed in the axial and lateral root of Gentiana crassicaulis.. Despite of different proportion of phosphorus and potassium,the content of four iridoids in axial root was always higher than that in the lateral root, and under normal fertilizer condition, the content of axial and lateral root was 12. 36% and 9. 84%, respectively. On the condition of phosphorus and potassium fertilization, the content of gentiopicroside and loganic acid were higher than that of the swertiamarin and sweroside both in the axial and lateral root. And the difference of the two parts could be increased by high potassium with appropriate phosphorus application.. The four iridoids were more likely to accumulate in the axial root of Gentiana crassicaulis, and phosphorus and potassium fertilization, only affected the different degrees on the content of ingredients among two parts. Thus, more attention should be paid to the use of phosphorus and potassium fertilization, and the difference of the active ingredient content in the axial and lateral root of Gentiana crassicaulis.

Topics: Fertilizers; Gentiana; Iridoid Glucosides; Iridoids; Phosphorus; Pyrones

To study the difference in yield and quality of Gentiana crassicaulis with different transplanting period and transplanting methods, and to determine the optimum transplanting technique of Gentiana crassicaulis in Ludian.. The variation in fresh weight,dry weight,dry discount rate, length, diameter, branches,the content of gentiopicroside,loganin acid,alcohol-soluble extract, total ash were measured, and made a comprehensive evaluation of yield and quality by gray relational distance ideal comprehensive evaluation method.. There was a big difference in yield and quality of Gentiana crassicaulis with different transplanting time and transplanting methods. Gentiana crassicaulis were transplanted in March 10 with the density of 25 cm × 24 cm,and overburden 1 cm and flat transplanting had the best comprehensive evaluation of yield and quality.. The transplanting time of Gentiana crassicaulis in Ludian should begin at the end of early March,and reduce overburden soil on the traditional transplanting methods.

Topics: Gentiana; Iridoid Glucosides; Iridoids

To compare the contents of iridoid glycosides in Qingyedan medicinal materials,and to provide the scientific basis for using resources of Qingyedan and rationality of original plant medicinal.. The contens of three iridoid glycosides,including swertiamarin,gentiopicroside and sweroside in Qingyedan medicinal materials were determined by HPLC.. The constituents of 30 samples in nine species were significant difference. And the contents of iridoid glycosides in Swertia bimaculata,Swertia tenuis and Swertia pubescens were reported for the first time.. The results show that the contents of iridoid glycosides in Qingyedan medicinal materials have a significant difference due to the different species and producing areas. Therefore, these medicinal plants should not be used as alternative medicines for clinical application. Swertiamarin and sweroside can be selected as quality control components, this method is an effective method to identify and control the quality of Qingyedan materials.

Topics: China; Chromatography, High Pressure Liquid; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Medicine, Traditional; Plants, Medicinal; Pyrones; Quality Control; Swertia

Gentian root extract is used as a bitter food additive in Japan. We investigated the constituents of this extract to acquire the chemical data needed for standardized specifications. Fourteen known compounds were isolated in addition to a mixture of gentisin and isogentisin: anofinic acid, 2-methoxyanofinic acid, furan-2-carboxylic acid, 5-hydroxymethyl-2-furfural, 2,3-dihydroxybenzoic acid, isovitexin, gentiopicroside, loganic acid, sweroside, vanillic acid, gentisin 7-O-primeveroside, isogentisin 3-O-primeveroside, 6'-O-glucosylgentiopicroside, and swertiajaposide D. Moreover, a new compound, loganic acid 7-(2'-hydroxy-3'-O-β-D-glucopyranosyl)benzoate (1), was also isolated. HPLC was used to analyze gentiopicroside and amarogentin, defined as the main constituents of gentian root extract in the List of Existing Food Additives in Japan.

Topics: Chromatography, High Pressure Liquid; Food Additives; Gentiana; Iridoid Glucosides; Iridoids; Molecular Structure; Plant Extracts; Plant Roots

Gentiana crassicaulis Duthie ex Burk. and Gentiana macrophylla Pall. are two main sources of Radix Gentianae Macrophyllae (Qinjiao) available in markets, which has a wide range of anti-inflammatory effects and has been extensively used for fighting rheumatoid arthritis. However, they vary in terms of chemical compositions, pharmacological activities, and biomass. In this study, a combined chemical and genetic (HPLC and DNA barcoding) approach was used to compare these two plants. Four predominant bioactive compounds, namely, gentiopicroside, loganic acid, swertiamarin, and sweroside, were used to assess the chemical variations. Based on chemical variations, 15 samples were clustered into two groups through PCA analyses. DNA barcoding utilizing the variable nuclear ITS2 regions were sequenced, aligned, and compared. Together with 61 sequences collected from GenBank, 76 batches of Qinjiao were clustered in two groups according to species origin. The genetic relationships indicated by the ITS2-based NJ tree were consistent with the chemical variations. Thus, the chemical profiles determined by HPLC and DNA profiles obtained from ITS2 region could be applied for the quality control of Qinjiao.

Topics: Chromatography, High Pressure Liquid; DNA Barcoding, Taxonomic; Gentiana; Iridoid Glucosides; Iridoids; Pyrones

The flowers of Gentiana macrophylla have been usually applied to cure the joint inflammation and rheumatoid arthritis in Traditional Chinese Medicine.. This work aimed to investigate the anti-rheumatoid arthritic effect and possible mechanism of iridoid glycosides from G. macrophylla (GMI) using an animal model of collagen-induced rheumatoid arthritis (CIA) in rats.. All rats were randomly divided into five groups: normal control, CIA, dexamethasone, 15mg/kg and 30mg/kg GMI.. CIA was induced (day 0) in male Sprague-Dawley rats by intradermal injection of complete Bovine CII at the base of the tail. Dexamethasone was chosen as the positive drug. The administration of different drugs started from day 1 and continued for 28 days. Paw swelling, arthritis score and histopathological changes were examined to assess the severity of arthritis. In addition, the serum levels of tumor necrosis factor α (TNF-α), interleukin-1β (IL-1β), interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expressions in joint synovial tissues were detected.. GMI reduced paw edema, arthritis scores and the index of spleen and thymus from day 7 to 21 after CIA compared with those in the CIA group. Our data also demonstrated that GMI inhibited pro-inflammatory cytokines such as TNF-α, IL-1β and IL-6, regulated the expression of iNOS and COX-2 compared with those in the CIA group. We also obtained four major components from GMI, identified as loganic acid, swertamarin, gentiopicroside and sweroside, and the contents of them were also calculated respectively.. Taken together, our results shed light on the therapeutic efficacy of GMI in rats rheumatoid arthritis model by reducing the levels of IL-1β, IL-6 and TNF-α in serum as well as down-regulating the levels of iNOS and COX-2. Therefore, GMI may be an effective therapy for the treatment of rheumatoid arthritis.

Topics: Animals; Antirheumatic Agents; Arthritis, Experimental; Chromatography, High Pressure Liquid; Cyclooxygenase 2; Cytokines; Flowers; Gentiana; Inflammation Mediators; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Joints; Male; Nitric Oxide Synthase Type II; Organ Size; Phytotherapy; Plant Extracts; Plants, Medicinal; Rats, Sprague-Dawley; Spleen; Thymus Gland; Time Factors

This paper utilized a quantitative (1)H nuclear magnetic resonance (qHNMR) method for assessing the purity of iridoids and secoiridoids. The method was fully validated, including specificity, linearity, accuracy, precision, reproducibility, and robustness. For optimization of experimental conditions, several experimental parameters were investigated, including relaxation delay (D1), scan numbers (NS) and power length (PL1). The quantification was based on the area ratios of H-3 from analytes relative to aromatic protons from 1,4-dinitrobenzene (internal standard) with methanol-d4 as solvent. Five iridoids and secoiridoids (sweroside, swertiamarin, gentiopicroside, geniposide, genipin) were analyzed. Furthermore, the results were validated by the high performance liquid chromatography coupled with ultraviolet detection (HPLC-UV) method. It can be concluded that the qHNMR method was simple, rapid, and accurate, providing a reliable and superior method for assessing the purity of iridoids and secoiridoids.

Topics: Chromatography, High Pressure Liquid; Iridoid Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Molecular Structure; Pyrones; Reproducibility of Results; Sensitivity and Specificity

The root of Gentiana lutea L., famous for its bitter properties, is often used in alcoholic bitter beverages, food products and traditional medicine to stimulate the appetite and improve digestion. This study presents a new, fast, and accurate HPLC method using HPLC/ESI-MS and HPLC/DAD for simultaneous analysis of iridoids (loganic acid), secoiridoids (gentiopicroside, sweroside, swertiamarin, amarogentin) and xanthones (isogentisin) in different populations of G.lutea L., cultivated in the Monti Sibillini National Park, obtained wild there, or purchased commercially. Comparison of HPLC/ESI-MS and HPLC/DAD indicated that HPLC/ESI-MS is more sensitive, reliable and selective. Analysis of twenty samples showed that gentiopicroside is the most dominant compound (1.85-3.97%), followed by loganic acid (0.11-1.30%), isogentisin (0.03-0.48%), sweroside (0.05-0.35%), swertiamarin (0.08-0.30%), and amarogentin (0.01-0.07%). The results confirmed the high quality of the G.lutea cultivated in the Monti Sibillini National Park.

Topics: Alcoholic Beverages; Chromatography, High Pressure Liquid; Gentiana; Iridoid Glucosides; Iridoids; Mass Spectrometry; Plant Roots; Pyrones; Taste; Xanthones

The metabolism of gentiopicroside in vivo was studied by LC/MS following 2,4-dinitrophenylhydrazine derivatization for the first time. The ionization efficiency of the major metabolites erythrocentaurin and gentiopicral were greatly enhanced by the new analytical method developed, and they were successfully detected in rat plasma after oral administration of gentiopicroside. Methyl 4-formylbenzoate was used as the internal standard to quantify erythrocentaurin and gentiopicral in rat plasma in negative mode by UPLC-TOF-MS. It was found that erythrocentaurin reached the maximum plasma concentration of 625.2±246.3 ng/mL at about 2 h and gentiopicral reached the maximum plasma concentration of 157.6±86.6 ng/mL at about 4 h after oral administration of gentiopicroside at a dose of 200 mg/kg. The metabolic pathway of gentiopicroside to erythrocentaurin and gentiopicral was proposed. The monoterpene compound gentiopicroside was found to be metabolized to dihydroisocoumarin in vivo which may be responsible for the pharmacological effect of gentiopicroside. The results may shed light on clinical efficacy of gentiopicroside and the new analytical method developed may assist in studies for the metabolism of other natural iridoids and secoiridoids in vivo.

Topics: Animals; Chromatography, High Pressure Liquid; Iridoid Glucosides; Iridoids; Isocoumarins; Mass Spectrometry; Phenylhydrazines; Plasma; Rats; Rats, Wistar

Swertia chirayita is an endangered medicinal herb widely used as an antidiabetic. It contains two major classes of metabolites, secoiridoids and xanthones, i.e. swertiamarin, mangiferin, amarogentin and amaroswerin. The biosynthetic pathways for these chemical constituents are not completely deciphered due to gaps and redundancy of routes proposed such as for mangiferin. The missing intermediates in pathways were detected through LC-ESI-QToF-HRMS/MS, including the detection of new secoiridoids, amaronitidin and gentiopicroside. The study also reports that the biosynthesis of amaronitidin occurs through the coupling of gentiopicroside and biphenyl acid derivatives such as amarogentin and amaroswerin. This study reports for the first time complete biosynthetic pathways for gentiopicroside, mangiferin, amarogentin, amaroswerin and amaronitidin in S. chirayita with the detection of intermediate metabolites iriflophenone, maclurin, deoxyloganic acid, loganic acid and 1,3,6,7-tetrahydroxy-9H-xanthen-9-one.

Topics: Biosynthetic Pathways; Glucosides; Hypoglycemic Agents; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans; Secondary Metabolism; Swertia; Tandem Mass Spectrometry; Xanthones

In order to optimize the base fertilizer dosage and root size of Gentiana crassicaulis in Ludian,Yulong, Yunnan,the differences in yield and quality of Gentiana crassicaulis caused by different base fertilizer dosage and root size were investigated.. The variation in fresh weight, dry weight, drying rate, length, diameter, branches as well as the contents of gentiopicroside, loganin acid, alcohol-soluble extract and total ash were determined. The ideal distance grey relational degree comprehensive evaluation method was applied to make a comprehensive evaluation on the quality and yield of Gentiana crassicaulis.. There were big differences in yield and quality of Gentiana crassicaulis among different base fertilizer dosage and root size. 2 000 kg/667 m2 of manure, 20 kg/667 m2 of superphosphate, 100 kg/667 m2 of plant ash and mix size of transplanting roots showed the best comprehensive quality and the highest yield.. 2 000 kg/667 m2 of manure, 20 kg/667 m2 of superphosphate,100 kg/667 m2 of plant ash, high quality transplanting roots and stagger certain depth to transplant are highly recommended to produce high quality and high yield of Gentiana crassicaulis in Ludian, Yulong, Yunnan.

Topics: China; Fertilizers; Gentiana; Iridoid Glucosides; Iridoids; Plant Roots; Plants, Medicinal

Gentiana straminea is the famous Tibetan folk medicine thought to cure various diseases. Historically, the Qinghai-Tibetan region has been considered as the geo-authentic production area of "Mahua Jiao," where large quantities of the medicine are grown. However, there is still little known about the phytochemical constituent spatial variation of this species. In order to find the differences between the main phytochemical constituents of G. straminea and to provide comprehensive information for quality evaluation, four main bioactive compounds (loganic acid, swertiamarin, gentiopicroside and sweroside) were analysed in 26 populations grown in areas with elevations ranging from 2320 to 4720 m across the Qinghai-Tibetan Plateau. The results showed that the four phytochemical constitutes' concentrations varied greatly in the spatial profiling of the Qinghai-Tibetan region. Throughout the range of distribution of this species, no altitudinal, latitudinal or longitudinal trends have proven to be significant in any of the four constitutes' concentrations or their summation. Furthermore, hierarchical clustering analysis and statistical tests showed that four populations (Liu0609-18, Liu0609-15, Liu2006-13-9 and Liu0609-22) had total constitute contents that were higher than other populations. The spatial profiling of the four phytochemical constituents suggests that the geo-authentic producing area of this species exists at a few regions within the Qinghai province, which could be attributed to specific environmental or genetic factors.

Topics: Chromatography, High Pressure Liquid; Cluster Analysis; Ethnobotany; Gentiana; Iridoid Glucosides; Iridoids; Phytotherapy; Plant Extracts; Plant Roots; Plants, Medicinal; Pyrones; Tibet

The objective of this work was to investigate the effects of the methanol extracts of Gentiana cruciata L. aerial parts (GCA) and roots (GCR) against carbon tetrachloride-induced liver injury in rats. Pretreatment with GCA and GCR, containing sweroside, swertiamarin and gentiopicrin in high concentrations, dose-dependently and significantly decreased the levels of serum transaminases, alkaline phosphatase and total bilirubin, whereas an increase in the level of total protein was found compared with the CCl4-treated group. Moreover, oral administration of extracts significantly enhanced antioxidant enzyme activities (superoxide dismutase and catalase), increased the content of glutathione and decreased the content of TBARS. Microscopic evaluations of the liver revealed CCl4-induced lesions and related toxic manifestations that were minimal in the liver of rats pretreated with extracts at the dose of 400 mg per kg b.w. The results suggest that the use of G. cruciata extracts has a merit as a potent candidate in protecting the liver against chemical induced toxicity.

Topics: Alanine Transaminase; Alkaline Phosphatase; Animals; Antioxidants; Aspartate Aminotransferases; Bilirubin; Biomarkers; Carbon Tetrachloride; Catalase; Chemical and Drug Induced Liver Injury; Dose-Response Relationship, Drug; Gentiana; Glutathione; Iridoid Glucosides; Iridoids; Liver; Male; Oxidative Stress; Plant Extracts; Plant Roots; Pyrones; Rats; Rats, Wistar; Superoxide Dismutase; Thiobarbituric Acid Reactive Substances

Swertia mussotii Franch. and Swertia chirayita Buch.-Ham. have been commonly used under the same name "Zangyinchen" for the treatment of liver and gallbladder diseases in traditional Tibetan medicine. Detailed characterization and comparison of the complete set of metabolites of these two species are critical for their objective identification and quality control. In this study, a rapid, simple and comprehensive (1)H NMR-based metabolomics method was first developed to differentiate the two species. A broad range of metabolites, including iridoid glycosides, xanthones, triterpenoids, flavonoids, carbohydrates, and amino acids, were identified. Statistical analysis showed evident differences between the two species, and the major markers responsible for the differences were screened. In addition, quantitative (1)H NMR method (qHNMR) was used for the target analysis of the discriminating metabolites. The results showed that S. mussotii had significantly higher contents of gentiopicrin, isoorientin, glucose, loganic acid, and choline, whereas S. chirayita exhibited higher levels of swertiamarin, oleanolic acid, valine, and fatty acids. These findings indicate that (1)H NMR-based metabolomics is a reliable and effective method for the metabolic profiling and discrimination of the two Swertia species, and can be used to verify the genuine origin of Zangyinchen.

Topics: Choline; Fatty Acids; Flavonoids; Glucose; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Luteolin; Magnetic Resonance Spectroscopy; Medicine, Tibetan Traditional; Metabolome; Metabolomics; Oleanolic Acid; Pyrones; Swertia; Terpenes; Valine; Xanthones

A sensitive and efficient liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed for the simultaneous determination of gentiopicroside, geniposide, baicalin, and swertiamarin in rat plasma. To avoid the stress caused by restraint or anesthesia, a freely moving rat model was used to investigate the pharmacokinetics of herbal medicine after the administration of a traditional Chinese herbal prescription of Long-Dan-Xie-Gan-Tang (10 g/kg, p.o.). Analytes were separated by a C18 column with a gradient system of methanol-water containing 1 mM ammonium acetate with 0.1% formic acid. The linear ranges were 10-500 ng/mL for gentiopicroside, geniposide, and baicalin, and 5-250 ng/mL for swertiamarin in biological samples. The intra- and inter-day precision (relative standard deviation) ranged from 0.9% to 11.4% and 0.3% to 14.4%, respectively. The accuracy (relative error) was from -6.3% to 10.1% at all quality control levels. The analytical system provided adequate matrix effect and recovery with good precision and accuracy. The pharmacokinetic data demonstrated that the area under concentration-time curve (AUC) values of gentiopicroside, geniposide, baicalin, and swertiamarin were 1417 ± 83.8, 302 ± 25.8, 753 ± 86.2, and 2.5 ± 0.1 min µg/mL. The pharmacokinetic profiles provide constructive information for the dosage regimen of herbal medicine and also contribute to elucidate the absorption mechanism in herbal applications and pharmacological experiments.

Topics: Administration, Oral; Animals; Area Under Curve; Chromatography, Gel; Drugs, Chinese Herbal; Flavonoids; Iridoid Glucosides; Iridoids; Limit of Detection; Male; Pyrones; Rats, Sprague-Dawley; Tandem Mass Spectrometry

A rapid method combining microwave-assisted extraction (MAE) and high-speed counter-current chromatography (HSCCC) was applied for preparative separation of six bioactive compounds including loganic acid (I), isoorientin-4'-O-glucoside (II), 6'-O-β-d-glucopyranosyl gentiopicroside (III), swertiamarin (IV), gentiopicroside (V), sweroside (VI) from traditional Tibetan medicine Gentiana crassicaulis Duthie ex Burk. MAE parameters were predicted by central composite design response surface methodology. That is, 5.0 g dried roots of G. crassicaulis were extracted with 50 mL 57.5% aqueous ethanol under 630 W for 3.39 min. The extract (gentian total glycosides) was separated by HSCCC with n-butanol/ethyl acetate/methanol/1% acetic acid water (7.5:0.5:0.5:3.5, v/v/v/v) using upper phase mobile in tail-to-head elution mode. 16.3, 8.8, 12., 25.1, 40.7, and 21.8 mg of compounds I-VI were obtained with high purities in one run from 500 mg of original sample. The purities and identities of separated components were confirmed using HPLC with photo diode array detection and quadrupole TOF-MS and NMR spectroscopy. The study reveals that response surface methodology is convenient and highly predictive for optimizing extraction process, MAE coupled with HSCCC could be an expeditious method for extraction and separation of phytochemicals from ethnomedicine.

Topics: Countercurrent Distribution; Gentiana; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Luteolin; Microwaves; Pyrones

Gentiana straminea Maxim. has been used widely as a traditional Chinese medicine for the treatment of rheumarthritis, icterepatitis, constipation, pain and hypertension. Five secoiridoids, gentiopicroside (GTP), 6'-O-(2-hydroxy-3-O-β-D-glucopyranosyl-benzoyl)-sweroside (HGBS), 6'-O-β-D-glucosylgentiopicroside (GGTP), sweroside (SW) and swertiamarin (STM) were isolated from the roots of G. straminea. The effect of these secoiridoids on stimulus-induced superoxide generation in human neutrophils was assayed by measuring the reduction of ferricytochrome c. Tyrosyl or serine/threonine phosphorylation of neutrophil proteins, and translocation of the cytosolic compounds to the cell membrane were also investigated using specific monoclonal antibodies. The five secoiridoids used in the present experiment suppressed N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide generation in a concentration dependent manner. GTP and HGBS also suppressed phorbol 12-myristate 13-acetate (PMA) and arachidonic acid (AA)-induced superoxide generation. However, the other three secoiridoids showed no effect on PMA- and AA-induced superoxide generation. fMLP-, PMA- and AA-induced tyrosyl or serine/threonine phosphorylation and translocation of the cytosolic proteins to the cell membrane were suppressed in parallel with the suppression of the stimulus-induced superoxide generation.

Topics: Arachidonic Acid; Cell Membrane; Cells, Cultured; Gentiana; Humans; Iridoid Glucosides; Iridoids; N-Formylmethionine Leucyl-Phenylalanine; Neutrophils; Phosphorylation; Plant Roots; Protein Transport; Pyrones; Superoxides; Tetradecanoylphorbol Acetate

Gentiopicroside (1) is the major secoiridoid glucoside constituent of Cephalaria kotschyi roots. The mutagenicity, DNA-damaging capacities, and clastogenicity of this molecule were evaluated by the Salmonella typhimurium mutagenicity assay (Ames test) on tester strains TA97a, TA98, TA100, and TA102, the alkaline comet assay, and the micronucleus assay on CHO cells. All tests were performed with and without the metabolization mixture, S9 mix. In the Ames test, the mutagenicity of 1 was limited to TA102 without S9 mix (2.3 rev microg(-1)). The genotoxicity was more evident without S9 mix (0.78 OTMchi(2) units microg(-1) mL) than with the metabolic mixture (0.16 OTMchi(2) units microg(-1) mL) with the comet assay. Similarly, the clastogenicity without S9 mix was 0.99 MNC microg(-1) mL and 0.38 MNC microg(-1) mL with S9 mix in the micronucleus assay. The interaction of 1 with DNA is probably through the involvement of oxidative DNA lesions.

Topics: Animals; Cricetinae; Dipsacaceae; DNA Damage; Glucosides; Iridoid Glucosides; Iridoids; Models, Chemical; Molecular Structure; Mutagenicity Tests; Mutagens; Plant Roots; Plants, Medicinal; Salmonella typhimurium

This study investigated the hepatoprotective effects of gentiopicroside on d-galactosamine (d-GalN) and lipopolysaccharide (LPS)-induced fulminant hepatic failure. Mice were administrated orally with gentiopicroside (40 or 80 mg/kg body weight) at 12h and 1h before d-GalN (700 mg/kg)/LPS (10 microg/kg) injection. Gentiopicroside markedly reduced the increases in serum aminotransferase activities and lipid peroxidation. The glutathione content decreased in d-GalN/LPS alone group, and this decrease was attenuated by gentiopicroside. Increases in serum tumor necrosis factor-alpha (TNF-alpha), which were observed in d-GalN/LPS alone group, were significantly reduced by gentiopicroside. Importantly, gentiopicroside attenuated d-GalN/LPS-induced apoptosis of hepatocytes, as estimated by the caspase-3 cleavage, poly(ADP-ribose) polymerase (PARP) cleavage, and DNA fragmentation. d-GalN/LPS-induced caspase-8 and -9 activation was significantly suppressed by gentiopicroside. Moreover, increased cytosolic cytochrome c protein was reduced by gentiopicroside. Also, the increased ratio of Bax and Bcl-2 protein was significantly attenuated by gentiopicroside. After 6h of d-GalN/LPS injection, phosphorylated c-jun N-terminal kinase (JNK) and extracellular signal regulated kinase (ERK) was significantly increased, whereas phosphorylation JNK and ERK were attenuated by gentiopicroside. Our results suggest that gentiopicroside offers remarkable hepatoprotection against damage induced by d-GalN/LPS related with its anti-apoptotic activities.

Topics: Alanine Transaminase; Animals; Apoptosis; Aspartate Aminotransferases; Blotting, Western; Caspases; Enzyme Activation; Galactosamine; Glucosides; Glutathione; Iridoid Glucosides; Iridoids; Lipid Peroxidation; Lipopolysaccharides; Liver Failure; Male; Mice; Mice, Inbred C57BL; Tumor Necrosis Factor-alpha

Gentiana macrophylla is a traditional Chinese medicinal plant. Its dominant active constituents are secoiridoids, mainly gentiopicrin. The objective of this study was to determine whether endophytic fungi isolated from this plant produce the bioactive ingredient gentiopicrin. Primary screening was done by Dragendorff's reaction and the strain re-selection was done with thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC) to identify the fermentation products of the selected strains. In this study, 20 strains of endophytic fungi were isolated from G. macrophylla, and the extracts from five strains had a positive Dragendorff's reaction. Two strains (QJ16 and QJ18) had a component with the same R(f) value in TLC as that of authentic gentiopicrin and one ingredient of the QJ18 extract had a retention time identical with that of authentic gentiopicrin in HPLC. Therefore, the fungus appears to produce the bioactive ingredient gentiopicrin, as does its host plant, and could be used for the production of gentiopicrin by fermentation.

Topics: Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Fermentation; Gentiana; Iridoid Glucosides; Iridoids; Mycorrhizae; Plant Roots

IN VITRO plant regeneration of Gentiana macrophylla Pall. and determination of gentiopicroside content during somatic embryogenesis are described in the present work. The highest percentage of embryogenic callus formation was observed in Murashige and Skoog (MS) medium supplemented with 1.0 mg/L 2,4-dichlorophenoxyacetic acid (2,4-D) and 1.0 mg/L 6-benzylaminopurine (BA). Calli were subcultured on MS medium containing 1.0 mg/L 2,4-D, 1.0 mg/L BA and 500 mg/L lactalbumin hydrolysate (LH) at intervals of 25 days. A higher frequency of somatic embryo maturation was achieved on MS medium containing B5 vitamins (MB) supplemented with different concentrations of 1-naphthaleneacetic acid (NAA) and BA than with a combination of NAA and kinetin (KT). Addition of AgNO(3) improved maturation of somatic embryos while thidiazuron (TDZ) promoted vitrification. The gentiopicroside contents of embryogenic calli and globular-, heart-, torpedo-, and cotyledon-shaped embryoids were determined by high-performance liquid chromatography (HPLC). Gentiopicroside was not detectable in embryogenic calli, but in all types of somatic embryos. The highest gentiopicroside content was observed in cotyledon-shaped embryoids, reaching more than 12 mg/g dry weight.

Topics: Chromatography, High Pressure Liquid; Culture Media; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Phenylurea Compounds; Seeds; Silver Nitrate; Thiadiazoles; Tissue Culture Techniques

To develop an HPLC method for the quantification of six active components in three species (Swertia davidi, S. nervosa and S. mussotii) .. The determination was performed on a Hypersil BDS colunm (4. 6 mm x 200 mm, 5 microm). Acetonitrile and 0.5% phosphoric acid solution were used as the mobile phases with a gradient elution. The flow rate was 1.0 mL x min(-1). The UV detection wavelength was at 240, 274, 325 and 334 nm. The column oven temperature was at 25 degrees C.. Six components were separated commendably in 60 minutes. The calibration curves of swertiamarin, gentiopicroside, norswertianolin, swertianolin, demethylbellidifolin and bellidifolin were in good linearity over the range of 0.520-20.8, 0.202-8.06, 0.107-4.28, 0.097-3.86, 0.094-3.77, 0.101-4.02 microg, respectively (r = 0.999 9). The average recoveries were 98.7%, 98.1%, 98.3%, 98.8%, 98.1% and 98.6%, respectively, and the RSD were less than 3.0% (n = 6).. The method is accurate,simple and reproducible, and can be used to control the quality of Swertia.

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Iridoid Glucosides; Iridoids; Pyrones; Swertia; Xanthones

A secoiridoid aglycone with an atypical skeleton, named fagraldehyde (1), together with several known secoiridoids (gentiopicroside (2), sweroside (3), and swertiamarin (4)) were isolated from the bark and leaves of Fagraea fragrans collected in Cambodia. The conformations of 1 were evaluated on the basis of molecular modeling and NOESY correlations. A hypothetical biogenesis of fagraldehyde was proposed to explain the unusual skeleton. Compound 1 was weakly active in vitro against Plasmodium falciparum.

Topics: Animals; Cambodia; Glucosides; Iridoid Glucosides; Iridoids; L-Lactate Dehydrogenase; Plant Bark; Plant Leaves; Plants, Medicinal; Plasmodium falciparum; Pyrones

To isolate and identify the chemical constituents of 95% alcohol extract from Swertia delavayi.. The compounds were isolated and purified by column chromatogrphy and their structures were identified by the physicochemical properties and spectral analyses.. Seven compounds were isolated and identified as oleanolic acid (1), gentiopcroside (2), swertiamarin (3), daucosterol (4), swertiadecoraxanthone-II (5), isovitexin (6), isoorientin (7).. Compounds 2-7 were isolated from S. delavayi for the first time. While the compound 6 was firstly reported from the genus Swertia.

Topics: Apigenin; Glucosides; Iridoid Glucosides; Iridoids; Luteolin; Magnetic Resonance Spectroscopy; Oleanolic Acid; Pyrones; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Swertia

To study the chemical constituents of Gentiana veitchiorum.. The chemical constituents were isolated by chromatography and identified by spectral data.. Five glycosides, loganic acid (1), gentiopicroside (2), isoorientin 3'-methyl ether (3), isovitexin (4), isoorientin (5) were isolated and identified.. Compounds 1-5 were isolated from this plant for the first time.

Topics: Apigenin; Chromatography, High Pressure Liquid; Gentiana; Glucosides; Glycosides; Iridoid Glucosides; Iridoids

Gentiopicroside is one of the secoiridoid compound isolated from Gentiana lutea. It exhibits analgesic activities in the mice. The anterior cingulate cortex (ACC) is a forebrain structure known for its roles in pain transmission and modulation. Painful stimuli potentiate the prefrontal synaptic transmission and induce glutamate NMDA NR2B receptor expression in the ACC. But little is known about Gentiopicroside on the persistent inflammatory pain and chronic pain-induced synaptic transmission changes in the ACC. The present study was undertaken to investigate its analgesic activities and central synaptic modulation to the peripheral painful inflammation. Gentiopicroside produced significant analgesic effects against persistent inflammatory pain stimuli in mice. Systemic administration of Gentiopicroside significantly reversed NR2B over-expression during the chronic phases of persistent inflammation caused by hind-paw administration of complete Freunds adjuvant (CFA) in mice. Whole-cell patch clamp recordings revealed that Gentiopicroside significantly reduced NR2B receptors mediated postsynaptic currents in the ACC. Our findings provide strong evidence that analgesic effects of Gentiopicroside involve down-regulation of NR2B receptors in the ACC to persistent inflammatory pain.

Topics: Analgesics, Non-Narcotic; Animals; Blotting, Western; Chronic Disease; Cyclic AMP; Down-Regulation; Excitatory Postsynaptic Potentials; Freund's Adjuvant; Glucosides; Glutamic Acid; Inflammation; Iridoid Glucosides; Iridoids; Mice; Mice, Inbred C57BL; Pain; Pain Measurement; Patch-Clamp Techniques; Receptors, GABA-A; Receptors, N-Methyl-D-Aspartate; Synaptic Transmission

Hairy root cultures of Gentiana macrophylla were established by infecting the different explants four Agrobacterium rhizogenes strains namely A(4)GUS, R1000, LBA 9402 and ATCC11325, and hairy root lines were established with A. rhizogenes strain R1000 in 1/2 MS + B(5) medium. Initially, 42 independent hairy root clones were maintained and seven clones belongs to different category were evaluated for growth, morphology, integration and expression of Ri T-DNA genes, and alkaloid contents in dry root samples. On the basis of total root elongation, lateral root density and biomass accumulation on solid media, hairy root clones were separated into three categories. PCR and Southern hybridization analysis revealed both left and right T-DNA integration in the root clones and RT-PCR analysis confirmed the expression of hairy root inducible gene. GUS assay was also performed to confirm the integration of left T-DNA. The accumulation of considerable amounts of the root-specific secoiridoid glucosides gentiopicroside was observed in GM1 (T +/L and T +/R) and the GM2 (T +/L and T -/R DNA) type clones in considerably higher amount whether as two T -/L but T +/R callus-type clones (GM3) accumulated much less or only very negligible amounts of gentiopicroside. Out of four media composition the 1/2 MS + B(5) vitamin media was found most suitable. We found that initial establishment of root cultures largely depends on root:media ratio. Maximum growth rate was recorded in 1:50 root:media ratio. The maximum biomass in terms of fresh weight (33-fold) was achieved in 1/2 MS + B(5) media composition after 35 days in comparison to sixfold increase in control. The biomass increase was most abundant maximum from 15 to 30 days. Influence of A. rhizogenes strains and Ri plasmid of hairy root induction, the possible role of the T(L)-DNA and T(R)-DNA genes on growth pattern of hairy root, initial root inoculum:media ratio and effect of media composition is discussed.

Topics: DNA, Bacterial; Genome, Plant; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Plant Roots; Plants, Genetically Modified; Plants, Medicinal; Pyrans; Rhizobium; Transformation, Genetic

The biotransformation of gentiopicroside by asexual mycelia of Cordyceps sinensis yielded two products, one of which was proved to be a new pyridine monoterpene alkaloid. The possible mechanisms were discussed.

Topics: Alkaloids; Biotransformation; Cordyceps; Glucosides; Iridoid Glucosides; Iridoids; Monoterpenes; Mycelium; Pyrans

The pharmacokinetics and bioavailability of gentiopicroside (GPS), an active component of the Gentian plant species, from orally administered decoctions of Gentianae (DG), or in combination with other plants in the prescription of Longdan Xiegan Tang (LXT), was compared in rats with oral administration of GPS alone, using doses adjusted to deliver equivalent amounts of GPS (150 mg/kg). Changes in plasma levels of GPS following oral administration of GPS or DG could be fitted to a one compartment open model with elimination half times (T(1/2)Ke) of 3.35+/-0.76 h and 6.21+/-3.07 h, respectively. Kinetics of plasma GPS following oral administration of LXT could be fitted to a two compartments open model with an elimination half time (T((1/2)beta)) of 3.83+/-1.54 h. The bioavailability of GPS from DG was markedly better, and that from LXT markedly worse, compared with GPS alone, as judged by the area under concentration-time curve (AUC) values of 70.0+/-13.9 microgh/ml (DG), 32.7+/-12.9 microgh/ml (GPS) and 19.1+/-5.9 microgh/ml (LXT). The study demonstrates the marked variability in pharmacokinetics and bioavailability of an active component from different herbal preparations.

Topics: Administration, Oral; Animals; Area Under Curve; Biological Availability; Calibration; Chromatography, High Pressure Liquid; Female; Gentiana; Glucosides; Half-Life; Iridoid Glucosides; Iridoids; Male; Molecular Structure; Plant Roots; Pyrans; Rats; Rats, Wistar; Reference Standards; Reproducibility of Results

To develop a HPLC-DAD-ESI-TOF/MS analysis method for the determination of gentiopicroside and loganic acid in Radix gentianae samples and for the research of their fingerprints. The samples were extracted using ASE for 10 min under 100 degrees C and 9.65 MPa, and divided into water phase and chloroform phase and analyzed them with HPLC-DAD-ESI-TOF/MS method respectively. Based on this method, the HPLC fingerprints of Radix gentianae were established. Comparing the spectrogram and mass spectrum of the chromatogram peak with the reference value, three compounds in water phase were identified as gentiopicroside, asafetida acid and loganic acid. There is no report of the compounds in chloroform phase. The content of gentiopicroside and loganic acid in samples of different groups were determined, separately. The fingerprints were compared by the software of the similarity evaluation system for chromatographic fingerprint. The water phase fingerprint congruence coefficients of samples from six different areas were above 0.90, however, the chloroform phase fingerprint congruence coefficients were within 0.62 -0.99. This method can be used for determination of potent component in Radix gentianae and its quality control. Radix gentianae from different producing areas have the largest diversities, and the diversities embodied in the content of chloroform phase compounds.

Topics: Chromatography, High Pressure Liquid; Ecosystem; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Plant Roots; Plants, Medicinal; Reproducibility of Results; Sensitivity and Specificity; Spectrometry, Mass, Electrospray Ionization

To develop a RP-HPLC method for determination of three glycosides in Swertia punicea.. Chromatographic column: Alltimal C18 (4.6 mm x 250 mm, 5 microm). Mobile phase: methanol-water (including 0.05% H3PO4), and gradient elution. Flow rate: 1 mL x min(-1). Wavelength: 254 nm. Column temperture: 30 degrees C.. The calibration curves of gentiopicroside, mangiferin and swertrianolin were in good linearity over the range of 31.3-281.7, 0.31-2.78, 0.55-4.91 microg, (r = 0.9996, 0.9993, 0.9995). The average recoveries were 103.36%, 101.42% and 97.39%, with RSD less then 3% (n = 5).. It is a simple and sensitive meathod in controlling the quality of S. punicea.

Topics: Calibration; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Quality Control; Reproducibility of Results; Swertia; Xanthones

The pharmacokinetics in rats of gentiopicroside (GPS) from orally administered decoctions of Radix Gentianae (DRG) and Gentiana macrophlla (DGM) were compared with that of GPS alone administered at 150 mg/kg orally and 30 mg/kg intravenously. The metabolic profile of GPS after intravenous injection could be fitted to two-compartment model whereas oral administration decoctions DRG or DGM, or GPS alone, could all be fitted to a one-compartment model. After oral administration of GPS alone, GPS was absorbed quickly and reached a maximum plasma concentration (Cmax) value, 5.78 +/- 2.24 microg/mL within 0.75 +/- 0.62 h. The plasma level of GPS declined with a T1/2ke, 3.35 +/- 0.76 h. After oral administration of decoctions DRG and DGM, GPS was absorbed and reached significantly higher maximum concentrations of 10.53 +/- 3.20 microg/mL (p < 0.01) and 7.43 +/- 1.64 microg/mL (p < 0.05) at later time points 1.60 +/- 0.76 (p < 0.01) and 2.08 +/- 0.74 h (p < 0.05), for DRG and DGM respectively, compared with oral GPS alone. Significantly larger AUC values were found for decoctions of GPS (83.49 +/- 20.8 microgxh/mL for DRG and 59.43 +/- 12.9 microgxh/mL for DGM) compared with oral GPS alone (32.67 +/- 12.9 microgxh/mL). The results demonstrate that the bioavailability of GPS was markedly improved when administered as a decoction than as purified GPS. The decoction from Radix Gentianae provided 2.5 times better bioavailability and that from Gentiana macrophlla 1.8 times higher. The study confirms the importance of careful pharmacokinetic analysis in the characterization of herbal medicines when applied for future clinical applications.

Topics: Administration, Oral; Animals; Biological Availability; Chromatography, High Pressure Liquid; Female; Gentiana; Glucosides; Humans; Injections, Intravenous; Iridoid Glucosides; Iridoids; Male; Pyrans; Rats; Rats, Wistar

To develop a method for the preparative separation of gentiopicrin from Radix Gentianae by high-speed counter-current chromatography (HSCCC).. The crude alcohol extracts were eluted on a macroporous resin column and then purified by high speed counter-current chromatography (HSCCC). A two-phase solvent system composed of ethyl acetate: n-butanol: water (2 : 1 : 3) was used, and the lower phase was used as the mobile phase at a flow rate of 1.5 mL x min(-1), while the apparatus rotated at 800 r x min(-1) and the eluate was detected at 254 nm.. 136 mg gentiopicrin with purity of 99.6% determined by HPLC were obtained from 300 mg crude extraction only in one-step separation and less than 200 minutes.. The established method is simple, high efficiency and suitable for large-scale separation of gentiopicrin.

Topics: Chromatography, High Pressure Liquid; Countercurrent Distribution; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Plant Roots; Plants, Medicinal; Resins, Synthetic; Rhizome

To select the best type of macroporous resin for enriching gentiopicroside from the leaves of Gentiana macropylla, and study its optimal conditions and parameters.. Adsorption and desorption characteristics of gentiopieroside were carried out on the resins. HPLC was used to determine the content of gentiopieroside.. The better resin D-101 was chosen, and the optimal parameters were obtained.. The process is feasible to enrich gentiopicroside from the leaves of Gentiana macropylla Pall.

Topics: Adsorption; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Ethanol; Gentianaceae; Glucosides; Humans; Hydrogen-Ion Concentration; Iridoid Glucosides; Iridoids; Plant Leaves; Plant Roots; Plants, Medicinal; Reproducibility of Results; Resins, Synthetic; Technology, Pharmaceutical

Wound healing properties of Gentian (Gentiana lutea ssp. symphyandra) extract and its main constituents, gentiopicroside, sweroside and swertiamarine (compounds 1-3, respectively) were evaluated by comparison with dexpanthenol on cultured chicken embryonic fibroblasts. The extract was also analyzed by HPLC to quantify its constituents. Chicken embryonic fibroblasts from fertilized eggs were incubated with the plant extract and its constituents, compounds 1-3. Using microscopy, mitotic ability, morphological changes and collagen production in the cultured fibroblasts were evaluated as parameters. Wound healing activity of Gentian seems to be mainly due to the increase in the stimulation of collagen production and the mitotic activity by compounds 2 and 3, respectively (p < 0.005 in all cases). All three compounds also exhibited cytoprotective effects, which may cause a synergism in terms of wound healing activity of Gentian. The findings demonstrated the wound healing activity of Gentian, which has previously been based only on ethnomedical data.

Topics: Animals; Cells, Cultured; Chick Embryo; Chickens; Collagen; Fibroblasts; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Phytotherapy; Plant Extracts; Plant Roots; Pyrans; Skin Physiological Phenomena; Wound Healing

To establish a quantitative method of simultaneously determination of swertiamarin, gentiopicroside, mangiferin, swertianolin, isoorientin, 1,8-drihydroxy-3-methoxy-xthanone in Swertia from Qinghai province and Sichuan province by HPLC.. The samples were separated on the column of Kromasil C18 (4. 6 mm x 250 mm, 5 microm) which eluted with methanol and water (content 0.02% phosphoric acid). The ratio of methanol increased from 20% to 80% during 20-50 min, and from 80% to 100% during 50-60 min, with detected wavelength 254 nm, flow rate at 1 mL x min(-1), column temperature 35 degrees C.. Six compounds were base-isolated, the linear ranges of swertiamarin, gentiopicroside, mangiferin, 4-swertianolin, 5-isoorientin, 1,8-drihydroxy-3-methoxy-xthanone were excellent.. The method was rapid and precise, and can be use for controlling medicinal materials quality.

Topics: China; Chromatography, High Pressure Liquid; Glucosides; Iridoid Glucosides; Iridoids; Luteolin; Plants, Medicinal; Pyrans; Pyrones; Quality Control; Reproducibility of Results; Swertia; Xanthones

To establish a sensitive and specific HPLC method for controlling the quality of total glycosides from Swertia franchetiana H. Smith.. HPLC method was applied for quality and quantitative assessment of the pharmaceutical extracts from Swertia franchetiana H. Smith. The preparation of sample, the HPLC column, mobile phase, elution mode (isocratic or gradient) and gradient program were optimized in order to obtain HPLC profile. The HPLC system consisted of a SPD-1OAvp pump, SPD-M1OAVP photodiode-array detector (PAD), SIL-10ADVP auto injector. Data were acquired and processed with the CLASS-VP6.1 workstation. HPLC analysis was performed on a Kromasil C18 column (250 mm x 4. 6 mm ID, 5 microm) with methanol and water as mobile phase. The column temperature was set up at 40 degrees C and the flow-rate was 1 mL x min(-1). The reference solution of chemical standards and sample were injected into HPLC system, separately.. The HPLC chromatographic fingerprinting of the total glycosides, showing 16 characteristic peaks which were partitioned into three parts: one peak in 0-10 min of retention time, nine peaks containing main 1-7 peaks in 10-15 min of retention time, 6 peaks in 15-30 min of retention time, was established from 10 lots of their products. By comparison of the retention time and the on-line UV spectra and their molecule weights of chemical standards, peak 1-7 were identified as swertiamarin (1), gentiopicroside (2), sweroside (3), isoorientin (4), swertisin (5), isoswertisin (6) and swetianolin (7), respectively. The ratios of peak area between 1-16 were in their extent. Moreover, comparison of the HPLC profiles of the total glycosides, the extracts prepared using another process and the plant indicated that they were closely related to each other.. The HPLC profiles and quantitative assessment of the total glycosides from Swertia franchetiana H. Smith with high specificity can be used to control their quality and assure lot to lot consistency.

Topics: Chromatography, High Pressure Liquid; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Luteolin; Molecular Structure; Plants, Medicinal; Pyrans; Pyrones; Quality Control; Swertia

Micellar electrokinetic electrophoresis was employed to determine two active components, gentiopicroside (GE) and swertiamarin (SW) in one Tibetan preparation medicine named shiweilongdankeli, two Tibetan herbal medicines named Gentiana rhodantha and Gentiana kitag and three other Chinese Gentiana medicines named Gentiana scabra, Gentiana rigescens and Gentiana macrophylla. The dissociation constants of gentiopicroside and swertiamarin determined by MEKC were 7.71 and 6.25. The optimum buffer system was 70 mm borate-10 mm sodium dodecylsulfate (SDS) -6% (v/v) ispropanol (pH 9.0). The voltage was 15 kV and detection was at 254 nm. The lower limits of detection (defined as a signal-to-noise ratio of about 3) were approximately 3.86 mg L(-1) for GE and 5.88 mg L(-1) for SW. The relative standard deviation of the migration time and peak area of the GE and SW were 2.33, 2.47 and 1.27, 2.19%, respectively and the recoveries of the two compounds were 96-104% for GE and 92-102% for SW.

Topics: Chromatography, Micellar Electrokinetic Capillary; Drugs, Chinese Herbal; Glucosides; Hydrogen-Ion Concentration; Iridoid Glucosides; Iridoids; Pyrans; Pyrones; Reproducibility of Results

To study the influecnce of gentian leaf blight on the output and quality of rough gentian.. The same grade seedlings were transplanted, disease of every plant was investigated in autumn and the output of gentian was determined. HPLC was applied to determine the content of gentiopicroside and swertiamarin.. The output decreased with the aggravation of the disease, and the decrease was obvious when the index of disease was above 60. The content of gentiopicroside and swertiamarin began to drop when the index of disease was above 70.. The loss of output and the drop of quality are relatively heavy when the disease is serious. The loss of income is not obvious when the index of disease is under 60.

Topics: Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Mitosporic Fungi; Plant Diseases; Plant Leaves; Plants, Medicinal; Pyrans; Pyrones; Quality Control

To study gentiopicroside's determination and comparison of various parts of herb by TLCS and make it impossible to uncover resource of Gentian in Xinjiang area.. Gentiopicroside's determination and comparison of various parts of herb in Gentiana Plants were carried out by TLCS.. The average recovery rate was 98.66% (RSD = 1.33%, n = 5). The Contents were stable. The results kept a high degree of comparable with HPLC ones.. This method was good-steady, high-accurate, simple, convenient, sensitive, reproducible.

Topics: Chromatography, Thin Layer; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Plant Roots; Plant Stems; Plants, Medicinal; Pyrans

To study the correlation between morphological variation and gentiopicroside content in cultivated Gentiana manshurica roots and to investigate the feasibility of breeding new varieties of high effective constituent content.. Gentiopicroside was determined in 5 morphological types of cultivated G. manshurica roots by HPLC, which are normal (or wild) type, white-flowered type, thick-rooted type, broad-leaved type I and broad-leaved type II.. Among different types gentiopicroside content is the highest in the roots of thick-rooted type, the contents decrease as following order: normal type, broad-leaved type I white-flowered type and broad-leaved type II, and the gentiopicroside contents in the same type root system are a positive correlation with root ages, as 3-years-age roots > 2-years-age roots > 1-year-age varied with roots.. The contents of effective constituent vary with the morphological variation in cultivated G. manshurica. It is feasible to breed a new variety with high effective constituent with the morphological character as a selecting index.

Topics: Genetic Variation; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Plant Roots; Plants, Medicinal; Pyrans; Species Specificity

A quantitative method to determine loganic acid and gentiopicroside in Gentiana macrophylla Pall. and Gentiana straminea Maxim. by RP-HPLC was established in this paper. The two compounds were base-isolated on the coloumn of Zorbax SB-C18 (250 mm x 4.6 mm i.d., 5 microm) which eluted with MeOH and H2O (0.04% H3PO4). The methol ratio increased from 18% to 28% in 15 min with detective wave at 254 nm and coloumn temperature at 30 degree C, flow rate at 1 ml/min. A wide range of linearity and the good linear relationships were achieved on above condition. The contents of the two compounds in different parts of the two plants were also determined and compared in this paper.

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Gentianaceae; Glucosides; Hot Temperature; Iridoid Glucosides; Iridoids; Plant Leaves; Plant Roots; Plant Stems; Plants, Medicinal; Pyrans; Tibet

Gentiopicroside (1), a secoiridoid glycoside isolated from the methanol extract of the aerial parts of Centaurium erythraea, has been assessed for antibacterial and free radical scavenging activities. General toxicity of 1 has also been determined by brine shrimp lethality bioassay.

Topics: Animals; Anti-Infective Agents; Artemia; Centaurium; Free Radical Scavengers; Glucosides; Gram-Negative Bacteria; Gram-Positive Bacteria; Iridoid Glucosides; Iridoids; Microbial Sensitivity Tests; Phytotherapy; Plant Extracts; Pyrans

A methanolic extact of Gentiana lutea ssp. symphyandra roots has been investigated for its possible effects on the central nervous system of mice. At doses of 250 and 500 mg/kg (i.p.), the methanol extract of Gentiana roots caused a significant increase in the swimming endurance test and exhibited slight analgesic activity, but no lethality in mice suggesting some activity on the central nervous system. However, there was no indication of sedation or muscular fatigue at the doses employed. HPLC analysis showed that three secoiridoid compounds, gentiopicroside, swertiamarine and sweroside were present and may have been responsible for the CNS effects of the methanol extract of Gentiana lutea ssp. symphyandra roots.

Topics: Analgesics; Animals; Central Nervous System; Chromatography, High Pressure Liquid; Dose-Response Relationship, Drug; Gentiana; Glucosides; Iridoid Glucosides; Iridoids; Male; Mice; Physical Exertion; Phytotherapy; Plant Extracts; Plant Roots; Pyrans; Pyrones; Swimming

To study the metabolism of gentiopicroside by rat intestinal flora in vitro and time profiles of gentiopicroside and its metabolites in rat serum after oral administration of gentiopicroside.. Using high performance liquid chromatography (HPLC) for determination of gentiopicroside, gentianine and gentianal content of rat intestinal flora culture medium in vitro and rat serum sample in vivo.. Gentiopicroside was metabolized quickly in vitro by rat intestinal flora, consequently gentianine and gentianal content appeared. Gentianine and gentianal were observed after gentiopicroside oral administration 4 times in rat serum sample, and gentiopicroside content decreased after oral administration 6 times.. Gentianine and gentianal were the important bioactive metabolites of gentiopicroside in rats.

Topics: Alkaloids; Animals; Chromatography, High Pressure Liquid; Gentiana; Glucosides; Intestines; Iridoid Glucosides; Iridoids; Male; Pyrans; Rats; Rats, Wistar

Bioassay directed fractionation of the (1:1) chloroform-methanol extract of Gentiana spathacea H.B.K (Gentianaceae) led to the isolation of gentiopicroside (gentiopricrin) (1), the major spasmolytic component of the plant. Gentiopicroside inhibited, in a concentration-dependent manner, the spontaneous contractions of isolated guinea pig ileum. Contractions induced by histamine, acetylcholine, BaCl2 and KCl on the ileum were also significantly blocked by this monoterpene glucoside, which suggests that this compound might be interfering with calcium influx into the smooth muscle cells.

Topics: Animals; Glucosides; Guinea Pigs; Ileum; Iridoid Glucosides; Iridoids; Magnoliopsida; Muscle Relaxation; Muscle, Smooth; Pyrans

Repeated fractionations of the methanol extract of the subterranean parts (rhizomes and roots) of Gentiana siphonantha afforded two new and five known secoiridoids, in addition to the widespread plant constituents beta-sitiosterol, daucosterol and oleanolic acid. The structures of the new acyl secoiridoid glycosides were elucidated as 6'-gentisoyl 8-epikingiside and 2'-gentisoyl gelidoside mainly by a combination of high field NMR techniques. The known secoiridoids were identified as gentiolactone, gentiopicroside, sweroside, gelidoside and trifloroside. None of these constituents was active against human pathogenic fungi (Candida albican, Aspergillus flavus and Trichoderma viride). The chemotaxonomic significance of the isolates is discussed briefly.

Topics: Antifungal Agents; Glucosides; Humans; Iridoid Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Plant Extracts; Plants, Medicinal; Pyrans; Rauwolfia; Spectrometry, Mass, Fast Atom Bombardment

High-performance liquid chromatography was employed to determine the contents of several marker substances such as gentiopicroside, mangiferin, palmatine, berberine, baicalin, wogonin and glycyrrhizin in Sann-Joong-Kuey-Jian-Tang. The separation was performed on a Cosmosil 5C18-AR column by gradient elution with 0.03% (v/v) phosphoric acid-acetonitrile (0 min, 90:10; 10 min, 87:13; 17-27 min, 77:23; 40 min, 62:38; 50 min, 55:45) as the mobile phase at a flow-rate of 1.0 ml/min, with detection at 254 nm. n-Propylparaben was used as the internal standard and seven regression equations revealed linear relationships between the peak-area ratios (marker substances/internal standard) and concentrations. The repeatability and reproducibility (relative standard deviation) of the method were in the ranges 0.02-1.78% and 1.44-4.95%, respectively.

Topics: Berberine; Berberine Alkaloids; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavanones; Flavonoids; Glucosides; Glycyrrhetinic Acid; Glycyrrhizic Acid; Iridoid Glucosides; Iridoids; Pyrans; Reproducibility of Results; Xanthenes; Xanthones

Four compounds were isolated from Swertia pubescens. They were identified as isoorientin, gentiopicroside, glucose and oleanolic acid by chemical and physical properties and spectral analysis.

Topics: Drugs, Chinese Herbal; Flavonoids; Glucosides; Iridoid Glucosides; Iridoids; Luteolin; Pyrans

Gentiopicroside (GPS), a main bitter secoiridoid constituent of roots of Gentiana macrophylla Pall., was tested for therapeutic effects on the two hepatic injury models, the CCl4-induced and lipopolysaccharide (LPS)/bacillus Calmette-Guerin (BCG)-induced hepatitides. An increase in serum level of hepatic aminotransferases (GOT: EC 2.6.1.1. and GPT: EC 2.6.1.2.) induced by a p.o. treatment of CCl4 was suppressed by pretreatment with GPS at 30-60 mg/kg/day for 5 consecutive days. An increase of these enzymes triggered by an i.v. treatment with LPS in mice primed with bacillus Calmette-Guerin (BCG) was also inhibited by GPS pretreatment at the same dose of GPS. In the BCG/LPS model, tumor necrosis factor (TNF), a major inflammatory mediator, was increased in serum with a peak at 90-120 min, followed by an increase of serum transaminase activities. GPS treatment significantly suppressed the increase of TNF in serum at the therapeutic doses, suggesting that GPS protected against hepatitis by inhibiting the production of TNF.

Topics: Alanine Transaminase; Animals; Aspartate Aminotransferases; Carbon Tetrachloride Poisoning; Glucosides; Hepatitis, Animal; Iridoid Glucosides; Iridoids; Lipopolysaccharides; Male; Mice; Mice, Inbred C3H; Mice, Inbred ICR; Mycobacterium bovis; Plant Roots; Plants, Medicinal; Pyrans; Tumor Necrosis Factor-alpha

A new and rapid analytical method for the simultaneous determination of five bitter secoiridoid glycosides (gentiopicroside, GTP; swertiamarin, SWT; sweroside, SWO; amarogentin, AMG; amaroswerin, AMS) in the Chinese drug "Long Dan", roots of Gentiana manshurica and 8 allied species by high performance liquid chromatography (HPLC) has been developed. The HPLC system consisting of an apparatus from Shimadzu (model LC-4A), with a UV-detector (SPD-2AS), a data processor (Chromatopac C-R2AX), a column oven (CTO-2AS), and a Zorbax ODS column (25 cm x 4.6 mm ID) was used. Using MeOH--H2O as the mobile phase, the linear concentration-program of methanol was [time (min):C (MeOH)]: [0:20]----[6:20]----[6.01:40]----[23:stop]. The temperature of column oven was 40 degrees C. The bitter secoiridoid glycosides eluted were detected at a wavelength of 254 nm and the analysis was successfully carried out within 23 minutes. This method is sensitive, rapid, accurate and has good reproducibility. Recoveries of each secoiridoid glycoside were 100.0-101.5% with coefficients of variation 0-2.5% (n = 3). The contents of five bitter secoiridoid glycosides in the roots of G. manshurica and eight allied species indigenous to China were determined and reported.

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Iridoid Glucosides; Iridoids; Pyrans; Pyrones

As a part of our studies on the metabolism of crude drug components by intestinal bacteria, gentiopicroside (a secoiridoid glucoside isolated from Gentiana lutea), was anaerobically incubated with various defined strains of human intestinal bacteria. Many species had ability to transform it to a series of metabolites. Among them, Veillonella parvula ss parvula produced five metabolites, which were identified as erythrocentaurin, gentiopicral, 5-hydroxymethylisochroman-1-one,5-hydroxymethylisochromen-1- one and trans-5,6-dihydro-5-hydroxymethyl-6-methyl-1H,3H-pyrano[3,4-c]pyra n-1-one.

Topics: Bacteria; Glucosides; Glycosides; Humans; Intestines; Iridoid Glucosides; Iridoids; Pyrans

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans

Topics: Drugs, Chinese Herbal; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans

Topics: Glucosides; Glycosides; Hot Temperature; Iridoid Glucosides; Iridoids; Medicine, Chinese Traditional; Plants, Medicinal; Pyrans; Seasons; Time Factors; Tissue Distribution

Topics: Chromatography, Thin Layer; Densitometry; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Medicine, Chinese Traditional; Medicine, East Asian Traditional; Plants, Medicinal; Pyrans; Pyrones; Species Specificity

Topics: Chromatography, High Pressure Liquid; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans

Topics: Chromatography, High Pressure Liquid; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans