iridoids and swertiamarin

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

Topics: Gene Expression Profiling; Gentiana; Humans; Iridoids; Molecular Sequence Annotation

Swertiamarin (SW), which belongs to iridoid glycosides, is one of the main components of Swertia plants in Gentianaceae family, including Swertia pseudochinensis H. Hara and Swertia mileensis T. N. Ho et W. L. Shi. There are mainly used in traditional Chinese medicine for the treatment of hepatic and biliary disease such as jaundice.. This experiment aimed to explore the protective mechanism of SW on cholestasis induced by alpha-naphthylisothiocyanate in rats.. Healthy rats were randomly divided into the control, model (ANIT, 50 mg/kg), ursodeoxycholic acid (UDCA, 80 mg/kg), and low-dose (SW, 80 mg/kg), medium-dose (SW, 100 mg/kg), and high-dose (SW, 150 mg/kg) groups. The hepatic protective effect of SW was preliminarily evaluated by measurement of serum biochemical indicators and liver morphological evaluation. Moreover, metabolomics and proteomics analysis were used to explore the protective mechanism of SW on cholestasis. The expression of related proteins was determined by Western blot and polymerase chain reaction, and the important proteins were verified by cell experiments in vitro.. SW (100 mg/kg) can reduce the serum levels of the model group. The hepatocyte of the medium-dose treatment group was arranged neatly without evident inflammation. SW can partially reverse the changes in cholestasis metabolites, such as taurocholic acid, SM (d18:1/16:0), all-trans-retinoic acid and other products of rats. The main metabolic pathways affected were primary bile acid synthesis, glycerophospholipid metabolism, sphingolipid metabolism and retinol metabolism. SW medium-dose treatment group showed effective reversal of 25 related proteins and it can remarkably reduce the contents of NTCP and CYP27A1 in rat liver and increase the protein expressions of CYP7A1, CYP8B1, bile salt export pump, multidrug resistance-associated protein and FXR.. SW can alleviate ANIT-induced cholestasis, which by activating the farnesoid X receptor and bile acid excretion pathway.

Topics: 1-Naphthylisothiocyanate; Animals; Bile Acids and Salts; Cholestasis; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Liver; Pyrones; Rats; Swertia

One new secoiridoid compound swertiamarin B (

Topics: Carbon-13 Magnetic Resonance Spectroscopy; Cell Death; Cell Line, Tumor; Humans; Inhibitory Concentration 50; Iridoid Glucosides; Iridoids; Plant Components, Aerial; Plant Extracts; Proton Magnetic Resonance Spectroscopy; Pyrones; Swertia

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

In this study, response surface methodology (RSM) and artificial neural network (ANN) was used to construct the predicted models of linear, quadratic and interactive effects of two independent variables viz. salicylic acid (SA) and chitosan (CS) for the production of amarogentin (I), swertiamarin (II) and mangiferin (III) from shoot cultures of Swertia paniculata Wall. These compounds are the major therapeutic metabolites in the Swertia plant, which have significant role and demand in the pharmaceutical industries.. Present study highlighted that different concentrations of SA and CS elicitors substantially influenced the % yield of (I), (II) and (III) compounds in the shoot culture established on modified ½ MS medium (supplemented with 2.22 mM each of BA and KN and 2.54 mM NAA). In RSM, different response variables with linear, quadratic and 2 way interaction model were computed with five-factor-three level full factorial CCD. In ANN modelling, 13 runs of CCD matrix was divided into 3 subsets, with approximate 8:1:1 ratios to train, validate and test. The optimal enhancement of (I) (0.435%), (II) (4.987%) and (III) (4.357%) production was achieved in 14 days treatment in shoot cultures of S. paniculata elicited by 9 mM and 12 mg L

Topics: Chitosan; Glycosides; Iridoid Glucosides; Iridoids; Neural Networks, Computer; Pyrones; Salicylic Acid; Swertia; Xanthones

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

Skeleton-diversity-oriented chemical conversion from pure natural products is a valuable method to obtain natural product-like compounds, especially those with novel architecture. The application of phytochemical methods to iridoids yielded three novel secoiridoid dimers: sweritranslactones A-C (1-3). These molecules possess a 6/6/6/6/6/6-fused hexacyclic skeleton and were obtained from swertiamarin, one of the major constituents of the genus Swertia, via a [4 + 2] cycloaddition and intramolecular nucleophilic addition under aqueous conditions. The structures were established based on extensive spectroscopic characterization and X-ray crystallographic diffraction analysis.

Topics: Crystallography, X-Ray; Cycloaddition Reaction; Dimerization; Iridoid Glucosides; Iridoids; Molecular Structure; Pyrones

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 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

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

Here, we report potential transcripts involved in the biosynthesis of therapeutic metabolites in Swertia japonica , the first report of transcriptome assembly, and characterization of the medicinal plant from Swertia genus. Swertia genus, representing over 170 plant species including herbs such as S. chirata, S. hookeri, S. longifolia, S. japonica, among others, have been used as the traditional medicine in China, India, Korea, and Japan for thousands of years. Due to the lack of genomic and transcriptomic resources, little is known about the molecular basis involved in the biosynthesis of characteristic key bioactive metabolites. Here, we performed deep-transcriptome sequencing for the aerial tissues and the roots of S. japonica, generating over 2 billion raw reads with an average length of 101 bps. Using a combined approach of three popular assemblers, de novo transcriptome assembly for S. japonica was obtained, yielding 81,729 unigenes having an average length of 884 bps and N50 value of 1452 bps, of which 46,963 unigenes were annotated based on the sequence similarity against NCBI-nr protein database. Annotation of transcriptome assembly resulted in the identification of putative genes encoding all enzymes from the key therapeutic metabolite biosynthesis pathways. Transcript abundance analysis, gene ontology enrichment analysis, and KEGG pathway enrichment analysis revealed metabolic processes being up-regulated in the aerial tissues with respect to the roots of S. japonica. We also identified 37 unigenes as potential candidates involved in the glycosylation of bioactive metabolites. Being the first report of transcriptome assembly and annotation for any of the Swertia species, this study will be a valuable resource for future investigations on the biosynthetic pathways of therapeutic metabolites and their regulations.

Topics: Biosynthetic Pathways; Gene Expression Profiling; Gene Expression Regulation, Plant; Gene Ontology; Genes, Plant; Glucosyltransferases; High-Throughput Nucleotide Sequencing; Iridoid Glucosides; Iridoids; Metabolome; Microsatellite Repeats; Molecular Sequence Annotation; Phylogeny; Plant Roots; Pyrones; Swertia; Transcriptome; Up-Regulation

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

Swertia chirayita, an endangered medicinal herb, contains three major secondary metabolites swertiamarin, amarogentin and mangiferin, exhibiting valuable therapeutic traits. No information exists as of today on the biosynthesis of these metabolites in S. chirayita. The current study reports the expression profiling of swertiamarin, amarogentin and mangiferin biosynthesis pathway genes and their correlation with the respective metabolites content in different tissues of S. chirayita. Root tissues of greenhouse grown plants contained the maximum amount of secoiridoids (swertiamarin, 2.8% of fr. wt and amarogentin, 0.1% of fr. wt), whereas maximum accumulation of mangiferin (1.0% of fr. wt) was observed in floral organs. Differential gene expression analysis and their subsequent principal component analysis unveiled ten genes (encoding HMGR, PMK, MVK, ISPD, ISPE, GES, G10H, 8HGO, IS and 7DLGT) of the secoiridoids biosynthesis pathway and five genes (encoding EPSPS, PAL, ADT, CM and CS) of mangiferin biosynthesis with elevated transcript amounts in relation to corresponding metabolite contents. Three genes of the secoiridoids biosynthesis pathway (encoding PMK, ISPD and IS) showed elevated levels (∼57-104 fold increase in roots), and EPSPS of mangiferin biosynthesis showed an about 117 fold increase in transcripts in leaf tissues of the greenhouse grown plants. The study does provide leads on potential candidate genes correlating with the metabolites biosynthesis in S. chirayita as an initiative towards its genetic improvement.

Topics: Iridoid Glucosides; Iridoids; Plant Roots; Plants, Medicinal; Pyrones; Swertia; Xanthones

The genus Swertia is reported to contain potent bitter compounds like iridoids, xanthones and c-glucoflavones that are known to heal many human disorders. In contrast to high ethnomedicinally valued Swertia chirayita, its other species have not been studied extensively, in spite of their common use in traditional medicinal system in Nepalese communities. So, the present study attempts to investigate the content of total polyphenols, flavonoids, antioxidant activity and estimate the rough content of amarogentin, swertiamarin and mangiferin from different species of Swertia from Nepalese Himalayas.. Whole plant parts of S. chirayita (SCH), S. angustifolia (SAN), S. paniculata (SPA), S. racemosa (SRA), S. nervosa (SNE), S. ciliata (SCI) and S. dilatata (SDI) were collected; total phenolic and flavonoid contents were quantified spectrophotometrically and in vitro DPPH free radical scavenging assay was measured. Thin layer chromatography was performed on TLC aluminium plates pre-coated with silica gel for identification of swertiamarin, amarogentin and mangiferin from those species and semi quantitative estimation was done using GelQuant.NET software using their standard compounds.. The phenolic content was highest in the methanol extract of SCH (67.49 ± 0.5 mg GAE/g) followed by SDI, SRA, SNE, SCI, SPA and SAN. The contents of flavonoids were found in the order of SCH, SPA, SRA, SNE, SDI, SCI and SAN. Promising concentration of phenolics and flavonoids produced promising DPPH free radical scavenging values. The IC50 values for the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging test was lowest in SCH (23.35 ± 0.6 μg/ml), even lower than the standard ascorbic acid among the seven studied species. A significant correlation of 0.977 was observed between the polyphenol content and antioxidant values. The TLC profile showed the presence of all three major phytochemicals; amarogentin, swertiamarin and mangiferin in all of the plant samples.. Among the seven studied species, SCH showed anticipating results in total phenol content, flavonoid content and DPPH radical scavenging test. The less considered species of Swertia can be a potential source of bioactive amarogentin, and other useful therapeutic compounds in the alarming status of Swertia chirayita as shown by the phytochemical analysis.

Topics: Antioxidants; Chromatography, Thin Layer; Flavonoids; Free Radical Scavengers; Humans; Iridoid Glucosides; Iridoids; Methanol; Nepal; Phytochemicals; Plant Extracts; Plants, Medicinal; Polyphenols; Pyrones; Species Specificity; Swertia; Xanthones

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

This study presents a new and validated HPLC method for the simultaneous determination of bioactive compounds in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea. The iridoid loganic acid, four secoiridoids and 29 xanthones were separated on a RP-18 column, using aqueous o-phosphoric acid (0.085%, v/v) and acetonitrile as mobile phase. Phytochemical investigation of C. erythraea herb and F. caroliniensis roots resulted into isolation of 25 xanthones and three secoiridoids the structure of which was elucidated by spectroscopic means (NMR, MS and UV). 1,3,8-Trihydroxy-5,6-dimethoxyxanthone, isolated from C. erythraea, turned out to be a novel xanthone. The stability of the analytes was tested by subjecting samples to light, moisture and different temperatures. After six months of storage, decomposition of gentiopicroside and sweroside was observed. The swertiamarin content was nearly unchanged when stored at room temperature or in the refrigerator, but high temperature conditions reduced the content to 85%. In contrast, xanthones were stable under long-term, refrigerated and accelerated conditions. The established chromatographic method has been successfully applied for the quantification of the bioactive compounds in the three plants. The presence and distribution of polyoxygenated xanthones within the three members of the Gentianaceae family and their significance as analytical markers are discussed.

Topics: Centaurium; Chromatography, High Pressure Liquid; Chromatography, Liquid; Gentiana; Gentianaceae; Humans; Iridoid Glucosides; Iridoids; Mass Spectrometry; Phytotherapy; Plant Extracts; Plant Roots; Pyrones; Reproducibility of Results; Xanthones

Diabetic nephropathy (DN) is one of the foremost causes of renal failure and a primary cause of diabetes mellitus related death. Previously, we have reported that aqueous extract of Enicostemma littorale has potential antidiabetic activity. In the present study, we have investigated the effect of aqueous extract of E. littorale 1 g/kg, p.o. and swertiamarin 50 mg/kg, p.o. daily for 3 weeks in type 1 DN complications in SD rats. DN was assessed by serum urea, creatinine, lipid profile and water intake levels. Treatment with aqueous extract of E. littorale and swertiamarin significantly decreased serum urea and creatinine and other parameters associated with the development of DN in type 1 diabetic rats. We have also found considerable improvement in histology of glomerular function of aqueous extract of E. littorale and swertiamarin-treated animals.

Topics: Administration, Oral; Animals; Biomarkers; Blood Glucose; Creatinine; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 1; Diabetic Nephropathies; Drinking; Gentianaceae; Glucosides; Hypertrophy; Hypoglycemic Agents; Iridoid Glucosides; Iridoids; Kidney Glomerulus; Lipids; Male; Plant Extracts; Pyrones; Rats; Rats, Sprague-Dawley; Urea

The whole plant of Enicostemma axillare Raynal (Family: Gentianaceae) is used in variety of diseases in traditional Indian system of medicine including hepatic ailments.. Swertiamarin isolated from Enicostemma axillare Raynal was evaluated for antioxidant and hepatoprotective activity.. Swertiamarin was isolated from successive ethyl acetate extract of the plant Enicostemma axillare belongs to the family Gentianaceae. The concentration of swertiamarin was determined by high performance thin layer chromatography (HPTLC). The hepatoprotective and antioxidant activity of swertiamarin (100 and 200mg/kg body weight) was carried out against d-Galactosamine (d-GalN) (200mg/kg body weight intraperitoneally i.p.) induced liver injury in rats.. Swertiamarin a secoiridoid glycoside was found to contain a major constituent of the extract. d-GalN caused significant hepatotoxicity by alteration of several hepatic parameters. It also caused significant lipid peroxidation and reduced the levels of antioxidant defense mechanisms. The treatment with swertiamarin at 100 and 200mg/kg body weight when administered orally for 8 days prior to d-GalN caused a significant restoration of all the altered biochemical parameters due to d-GalN towards the normal, indicating the potent antioxidant and hepatoprotective nature of swertiamarin.. Swertiamarin isolated from Enicostemma axillare possesses significant antioxidant and hepatoprotective properties against d-GalN induced hepatotoxicity given at 100 and 200mg/kg body weight orally for 8 days, which might be due to its in vitro antioxidant activity.

Topics: Animals; Antioxidants; Female; Galactosamine; Gentianaceae; Glucosides; Iridoid Glucosides; Iridoids; Liver; Male; Plant Extracts; Pyrones; Rats; Rats, Wistar

Swertiamarin, a secoiridoid isolated from the ethyl acetate extract of Enicostemma axillare, was evaluated for antiedematogenic activity using carrageenan-, formalin-, and histamine-induced paw edema methods in rats. In the carrageenan-induced method, the percentages of edema inhibition obtained after 5 h induction were 38.60, 52.50, and 45.44, respectively, for 100 and 200 mg/kg bw swertiamarin and 100 mg/kg bw of standard diclofenac sodium given orally. The activity of swertiamarin at 200 mg/kg bw was found to be superior to that of standard diclofenac sodium in all these methods. Swertiamarin was also screened for IN VITRO antioxidant activity using seven different methods: good activity was observed in ABTS and hydrogen peroxide methods, and moderate activity was observed in hydroxyl radical by deoxyribose and lipid peroxidation methods, with IC50 values of 2.83, 5.70, 52.56, and 78.33 microg/mL, respectively. The total antioxidant capacity was found to be 4.51 mM of ascorbic acid per gram of swertiamarin. Swertiamarin possesses antiedematogenic and in vitro antioxidant activities, and it may be the active constituent responsible for the anti-inflammatory activity of E. AXILLARE.

Topics: Animals; Anti-Inflammatory Agents; Carrageenan; Diclofenac; Edema; Female; Formaldehyde; Free Radical Scavengers; Free Radicals; Gentianaceae; Glucosides; Histamine; Iridoid Glucosides; Iridoids; Male; Pyrones; Rats; Rats, Wistar

Many traditional Indian medicinal plants which contain large quantity of a secoiridoid, swertiamarin are being used to relieve pain. Iridoids present in a wide variety of medicinal plants possess a large number of medicinal properties. In the present study in vivo antinociceptive activity of swertiamarin isolated from E. axillare was carried out using three different methods in mice. In the hot plate method, a significant increase in the latency period was observed for the treatment with swertiamarin at 100 and 200 mg/kg bw after 30 and 45 min. The percent protection observed after 45 min was 109.42, 147.42 and 157.14, respectively, for the standard paracetamol and swertiamarin at 100 and 200 mg/kg bw treatments. A significant increase in the tail withdrawal reflex was observed for the swertiamarin treatment at both the doses with percent protections of 150 and 200, respectively. In both these methods, swertiamarin produced potent activity than that of standard paracetamol. In the acetic acid induced writhing, swertiamarin at 100 and 200 mg/kg bw reduced the number of writhes significantly. Dose dependent results were observed in all the three methods and among the two doses, swertiamarin at 200 mg/kg bw showed potent activity. These results prove that swertiamarin possess both peripheral and central antinociceptive activity.

Topics: Acetaminophen; Acetic Acid; Analgesics; Analgesics, Non-Narcotic; Animals; Gentianaceae; Glucosides; Iridoid Glucosides; Iridoids; Male; Mice; Pain; Phytotherapy; Plant Extracts; Pyrones; Rats; Rats, Wistar; Tail

We have investigated the hypolipidemic effects of swertiamarin an active lead isolated from a perennial herb Enicostemma littorale Blume. in high cholesterol fed rats. Swertiamarin (50 and 75 mg/kg) and atorvastatin (50 mg/kg) was given orally daily for seven consecutive day to the high cholesterol feed rats. Serum total cholesterol, triglycerides, low density lipoprotein and very low density lipoprotein were found to be markedly elevated in the high cholesterol fed control rats and these changes were significantly prevented in swertiamarin treated animals. However, there was no significant effect on serum high density lipoprotein level. The 3-hydroxy 3-methyl glutaryl Co A (HMG-Co A) reductase activity was significantly inhibited in swertiamarin and atorvastatin treated groups compared to high cholesterol fed control group. Swertiamarin was also found to increased excretion of fecal bile acid and total sterols compared to control animals. In conclusion our data suggest that swertiamarin possess high antiatherogenic potential and an effective cholesterol lowering agent and inhibition of HMG-Co A reductase may be one of the main mechanisms of hypolipidemic effect of swertiamarin.

Topics: Animals; Bile Acids and Salts; Cholesterol, Dietary; Feces; Gentianaceae; Glucosides; Hydroxymethylglutaryl CoA Reductases; Hypercholesterolemia; Hypolipidemic Agents; Iridoid Glucosides; Iridoids; Lipids; Male; Pyrones; Rats; Rats, Sprague-Dawley; Sterols

We have investigated antihyperlipidaemic effect of swertiamarin (50 mg/kg, oral once) isolated from the perennial herb Enicostemma littorale Blume in poloxamer 407 (P-407)-induced hyperlipidaemic rats. Rats were made hyperlipidaemic by intraperitoneal administration of P-407 (400 mg/kg). Serum lipid levels such as total cholesterol, triglycerides and low-density lipoprotein cholesterol increased significantly (P < 0.001) compared with normal control rats. All these changes were significantly prevented in the rats treated with swertiamarin. Serum high-density lipoprotein (HDL) cholesterol was found to be reduced in the P-407 control rats. However, administration of swertiamarin significantly (P < 0.01) increased HDL levels and it showed a significant lipid-lowering effect, as well as a high antiatherogenic potential. Overall swertiamarin is an effective lipid-lowering lead compound and can be useful for preventing atherosclerosis.

Topics: Animals; Glucosides; Hyperlipidemias; Hypolipidemic Agents; Iridoid Glucosides; Iridoids; Male; Poloxamer; Pyrones; Rats; Rats, Wistar

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

When cultivated with Aspergillus niger, swertiamarin, an important drug, is rapidly transformed into erythrocentaurin and (5Z)-5-ethylidene-8-hydroxy-3,4,5,6,7,8-hexahydro-1H-pyrano[3,4-c]pyridin-1-one (M(1)), a new compound with high anti-inflammatory activity. A simple and rapid HPLC method for simultaneous determination of swertiamarin and its two metabolites in broth of A. niger is described. The chromatographic separation was achieved on a C(18) ODS column (250 x 4.6 mm i.d.) by gradient elution with 0.04% formic acid in water and 0.04% formic acid in acetonitrile as the gradient mixtures. The flow rate was 1 mL/min, the detection wavelength was 237 nm and the column temperature was kept at 30 degrees C. The retention times of swertiamarin, erythrocentaurin and M(1) were 14.6, 16.8 and 24.8 min, respectively. The mean absolute recoveries of three analysts were over 96%. Quantification limits were 0.02 microg/mL for swertiamarin and 0.05 microg/mL for both of the two metabolites. The method was applied for the quantification of swertiamarin and its two metabolites during the fermentation process and the evaluation of the bioavailabilities in the Caco-2 monolayer.

Topics: Aspergillus niger; Cell Line; Chromatography, High Pressure Liquid; Glucosides; Humans; Iridoid Glucosides; Iridoids; Isocoumarins; Pyrones; Reproducibility of Results

Extracts from Swertia chirata (family Gentianaceae) have antidiabetics and antioxidant activity, largely attributed to the flavonoids and secoiridoids, which are a major class of functional components in methanolic extracts from aerial part of plants. In order to facilitate analysis of systemic exposure to S. chirata derived products in animals, we developed a liquid chromatography tandem mass spectrometry (LC-MS/MS) based method that is capable of routinely monitoring plasma levels of flavonoids and secoiridoids. An LC-MS/MS-based method has been developed for the simultaneous estimation of two bioactive markers, mangiferin and amarogentin along with three other components, amaroswerin, sweroside and swertiamarin in rat plasma. All the analytes including the internal standard (kutkoside) were chromatographed on RP-18 column (250 mm x 4 mm i.d., 5 microm.) coupled with guard column using acetonitrile: 0.5 mM ammonium acetate buffer, pH approximately 3.0 as mobile phase at a flow rate of 1 ml/min in gradient mode. The final flow to source was splitted in 1:1 ratio. The detection of the analytes was performed on API 4000 LC-MS/MS system in the multiple reaction-monitoring (MRM) mode. The quantitation for analytes other than the pure markers was based on relative concentration. The method was validated in terms of establishing linearity, specificity, sensitivity, recovery, accuracy and precision (Intra- and Inter-day), freeze-thaw stability, peltier stability, dry residue stability and long-term stability. The recoveries from spiked control samples were >90% for all analytes and internal standard except mangiferin where recovery was >60%. Intra- and inter-day accuracy and precision of the validated method were within the acceptable limits of <15% at low and <10% at other concentrations. The quantitation method was successfully applied to generate pharmacokinetic (PK) profile of markers as well as to detect other components in plasma after intravenous dose administration of herbal preparation in male Sprague-Dawley (SD) rats.

Topics: Animals; Chromatography, Liquid; Cinnamates; Glucosides; Iridoid Glucosides; Iridoids; Male; Plant Preparations; Pyrones; Rats; Rats, Sprague-Dawley; Reference Standards; Reproducibility of Results; Swertia; Tandem Mass Spectrometry; Xanthones

To establish a RP-HPLC method for the determination of swertiamarin, sweroside, gentiopicrin and oleanolic acid in different parts of Swertia pseudochinesis.. A Zorbax SB-C18 (4.6 mm x 250 mm, 5 microm) column was used with acetonitrile-water (10:90) and methnol-water(86:14) at detection wavelengths of 238 nm, 246 nm, 274 nm and 207 nm for swertiamarin, sweroside, gentiopicrin and oleanolic acid respectively. The flow rate was 1.0 mL x min(-1) and the column temperature was 25 degrees C.. All of the compounds were based--isolated. The linear ranges of swertiamarin, sweroside, gentiopicrin and oleanolic acid were 0.068 9-0.344 4(r = 0.999 2) , 0.001 1-0.014 0 (r2 = 0. 999 8), 0.001 1-0.013 4 (r2 = 0.999 9) and 0.001 1-0.008 8 mg x mL(-1) (r2 = 0. 999 6), respectively.. The method is simple and accurate, which can be used for quality control of S. pseudochinesis.

Topics: Chromatography, High Pressure Liquid; Flowers; Glucosides; Iridoid Glucosides; Iridoids; Oleanolic Acid; Plant Leaves; Plant Roots; Plant Stems; Plants, Medicinal; Pyrones; Reproducibility of Results; Swertia; Triterpenes

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

Concentrations of seven phytochemical constituents (swertiamarin, mangiferin, swertisin, oleanolic acid, 1,5,8-trihydroxy-3-methoxyxanthone, 1,8-dihydroxy-3,7-dimethoxyxanthone and 1,8-dihydroxy-3,5-dimethoxyxanthone) of "ZangYinChen" (Swertia mussotii, a herb used in Tibetan folk medicine) were determined and compared in plants collected from naturally distributed high-altitude populations and counterparts that had been artificially cultivated at low altitudes. Levels of mangiferin, the most abundant active compound in this herb, were significantly lower in cultivated samples and showed a negative correlation with altitude. The other constituents were neither positively nor negatively correlated with cultivation at low altitude. Concentrations of all of the constituents varied substantially with growth stage and were highest at the bud stage in the cultivars, but there were no distinct differences between flowering and fruiting stages in this respect.

Topics: Agriculture; Altitude; Drug Evaluation, Preclinical; Flowers; Geography; Glucosides; Iridoid Glucosides; Iridoids; Medicine, Tibetan Traditional; Oleanolic Acid; Plant Physiological Phenomena; Plants, Medicinal; Pyrones; Seeds; Swertia; Time Factors; 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

As part of our on-going search for bioactive compounds from Scottish plants, two secoiridoid glycosides, swertiamarin and sweroside, have been isolated from the aerial parts of Centaurium erythraea Rafn (Family: Gentianaceae) by reversed-phase preparative HPLC coupled with a photo-diode-array detector. The structures of these compounds were elucidated unambiguously by UV, FABMS and extensive 1D and 2D NMR spectroscopic analyses and also by comparing experimental data with literature data. Antibacterial, free radical scavenging activities and general toxicity of these glycosides have been assessed. Both compounds inhibited the growth of Bacillus cereus, Bacillus subtilis, Citrobacter freundii and Escherichia coli. While swertiamarin was also active against Proteus mirabilis and Serratia marcescens, sweroside inhibited the growth of Staphylococcus epidermidis. Swertiamarin and sweroside exhibited significant general toxicity in brine shrimp lethality bioassay and the LD50 values were 8.0 microg/ml and 34 microg/ml, respectively, whereas that of the positive control podophyllotoxin, a well known cytotoxic lignan, was 2.79 microg/ml. Chemotaxonomic implications of these compounds in the family Gentianaceae have also been discussed briefly.

Topics: Animals; Anti-Bacterial Agents; Artemia; Centaurium; Chromatography, High Pressure Liquid; Glucosides; Gram-Negative Bacteria; Gram-Positive Bacteria; Humans; Iridoid Glucosides; Iridoids; Lethal Dose 50; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Phytotherapy; Plant Extracts; Pyrones

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

Swertia herb (florescent whole plantof Swertia japonica, Gentianaceae) has long been utilized as a folk medicine in Japan. It is often blended in general gastroenteric drugs as a bitter stomachic. Swertiamarin, a bitter secoiridoid glycoside, is the representative constituent of this crude drug and Swertia herb is normally evaluated by the swertiamarin content. To date, papers have described the discrimination of Swertia herbs from other bitter crude drugs, estimation of swertiamarin and seasonal variation in swertiamarin content using thin-layer chromatography, while other papers have reported quantitative determination of swertiamarin using high-performance liquid chromatography (HPLC). In our previous papers, we reported analyses of the constituents of some crude drugs using capillary electrophoresis (CE). To aid in the evaluation of crude drugs, we succeeded in our attempt to separate and determine the quantity of swertiamarin in Swertia herb. Subsequently, we applied the same analytical condition to estimate the swertiamarin contents in Japanese pharmacopoeia stomachic preparations, in OTC gastroenteric drugs and in OTC hair tonics containing Swertia herb.

Topics: Chromatography, High Pressure Liquid; Drug Industry; Electrophoresis, Capillary; Glucosides; Iridoid Glucosides; Iridoids; Kinetics; Models, Chemical; Plant Preparations; Pyrones; Swertia; Time Factors; Water

A new secoiridoid glycoside, swertiapunimarin (I), was isolated from the whole plant of Swertia punicea Hemsl. The structure was elucidated as 6'-O-beta-D-glucopyranosylsweroside on the basis of chemical and spectroscopic analysis. The other seven known compounds were identified as sweroside (II), swertiamarin (III), oleanolic acid (IV), daucosterol (V), beta-sitosterol (VI), 2,3-dihydroxy-1,4-benzodicarboxylic acid (VII) and methylswertianin (VIII).

Topics: Drugs, Chinese Herbal; Glucosides; Iridoid Glucosides; Iridoids; Molecular Structure; Pyrans; Pyrones

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

The biotransformation of swertiamarin [1, a seco-iridoid glucoside isolated from Swertia japonica (Schult.) Makino] by human intestinal bacteria was investigated. Three metabolites were isolated and identified as erythrocentaurin (2), 5-hydroxymethylisochroman-1-one (3), and gentianine (4) by spectroscopic methods. Through screening of various defined strains of intestinal bacteria (25 species), it was found that all these species had the ability to metabolize 1 to 2 and 3, whereas only a few species had the ability to produce 4. This is the first report to show that one of the metabolic intermediates of the secoiridoid compound is further transformed to a nitrogen-containing compound through metabolic processes by human intestinal bacteria.

Topics: Feces; Glucosides; Glycosides; Humans; Iridoid Glucosides; Iridoids; Molecular Structure; Plants, Medicinal; Pyrans; Pyrones

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

Topics: Animals; Biotransformation; Chemical Phenomena; Chemistry; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Mutagenicity Tests; Mutagens; Plant Extracts; Pyrans; Pyrones; Rats; Salmonella typhimurium

Topics: Drug Stability; Glucosides; Hydrogen-Ion Concentration; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans; Pyrones

Topics: Flavonoids; Glucosides; Iridoid Glucosides; Iridoids; Japan; Luteolin; Plant Extracts; Plants, Medicinal; Pyrones; Xanthenes; Xanthones

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