iridoids and sweroside

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

To study the chemical composition and their anti-inflammatory activities of honeysuckle (Lonicera japonica Thunb.) roots, seventeen compounds were isolated from the roots of L. japonica Thunb. by various chromatography, including silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by MS, IR, and nuclear magnetic resonance spectra, as 1-oxo-(1H)-cyclopenta[b]benzofuran-7-carbaldehyde (1), 4-hydroxycinnamic acid (2), chlorogenic acid (3), loganin aglycone (4), caffeic acid (5), secologanin dimethyl acetal (6), korolkoside (7), coniferin (8), sweroside (9), secoxyloganin (10), 5-O-caffeoylquinic acid (11), chlorogenic acid methyl ester (12), chlorogenic acid ethyl ester (13), 3,5-O-dicaffeoylquinic acid (14), 4,5-O-dicaffeoylquinic acid (15), grandifloroside (16), and 4,5-O-dicaffeoylquinic acid (17). Among those, compound 1 is a new compound, and compound 8 is found in L. japonica for the first time. Compounds 1, 3, 14-17 showed significant anti-inflammatory activities against macrophage in zebrafish.

Topics: Animals; Anti-Inflammatory Agents; Chlorogenic Acid; Chromatography, High Pressure Liquid; Iridoid Glucosides; Iridoids; Lonicera; Macrophages; Plant Roots; Quinic Acid; Zebrafish

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

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

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

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

A novel lactone, tripterospermumcins E (1), along with four known compounds, sweroside (2), loganic acid (3), 8-epi-kingiside (4) and bergenin (5), were isolated from the aerial parts of Tripterospermum chinense. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and chemical methods. Compound 1 is rare beta-lactone with a glucoside.

Topics: Benzopyrans; Drugs, Chinese Herbal; Gentianaceae; Iridoid Glucosides; Iridoids; Lactones; Molecular Structure; Plant Components, Aerial; Plants, Medicinal

The ethanolic extract from stems of a Thai medicinal plant, Alstonia macrophylla Wall. ex G. Don (Apocynaceae) showed a significant inhibitory effect on acetylcholinesterase (AChE) determined by using Ellman assay. Four compounds i.e., a bisindole alkaloid, macralstonine (1), a new bisindole alkaloid, thungfaine (2), a secoiridoid glycoside, sweroside (3) and a new secoiridoid glycoside, naresuanoside (4) were isolated. Compound 4 showed moderate AChE and butyrylcholinesterase (BChE) inhibitory effects. Interestingly, compound 4 inhibited cell growth on human androgen-sensitive prostate cancer cell line (LNCaP) but no effect on viability of human foreskin fibroblast cells (HF).

Topics: Acetylcholinesterase; Alstonia; Animals; Butyrylcholinesterase; Cell Line, Tumor; Cell Proliferation; Cells, Cultured; Electrophorus; Fibroblasts; Foreskin; Glycosides; Horses; Humans; Indole Alkaloids; Inhibitory Concentration 50; Iridoid Glucosides; Iridoids; Male; Medicine, East Asian Traditional; Plant Extracts; Plant Stems; Plants, Medicinal; Thailand

Allergy-preventive activity of flower buds of Lonicera japonica THUNB. was found in the 35% EtOH extract (LJ) using an in vivo assay, The assay system uses monitoring of a decrease in blood flow (BF) in the tail vein of mice subjected to sensitization with hen-egg white lysozyme (HEL). Bioassay-guided fractionation of the 35% EtOH extract led to isolation of chlorogenic acid (1) and three known iridoid derivatives, loganin (2), secoxyloganin (3) and sweroside (4), all of which inhibited the BF decrease. This suggested that the flower buds of L. japonica and compounds isolated from them have allergy-preventive properties. The structure-activity relationship of iridoid derivatives, morroniside (5), geniposide (6), asperuloside (7), aucubin (8) and catalpol (9), were also tested using the same bioassay method. Compounds 2-5 and 9 having the sp(3) atom at C-8 showed an allergy-preventive effect, while compounds 6, 7 and 8 having a double bond at C-7, C-8 did not.

Topics: Animals; Anti-Allergic Agents; Chickens; Chlorogenic Acid; Female; Flowers; Hypersensitivity; Iridoid Glucosides; Iridoids; Lonicera; Male; Mice; Mice, Inbred Strains; Muramidase; Phytotherapy; Plant Extracts; Structure-Activity Relationship; Veins

To establish a method of microwave-assisted extraction and high performance liquid chromatographic (HPLC) for simultaneous determination of three iridoid glycosides including loganin, sweroside and cornuside in Cornus officinalis.. The extraction conditions of microwave power,ethanol concentration, liquid to sample ratio were optimized with a response surface methodology (RSM); Three constituents were separated on an Agilent TC-C18 column by gradient elution using acetonitrile and water as the mobile phase. The flow rate was 1.0 mL/min. The detection wave length was 240 nm.. The optimal conditions of microwave extraction were as follows: microwave power 400 W, ethanol concentration 72%, liquid to sample ratio 15 mL/g, the extraction time 10 min, the extraction times 2; The HPLC peak areas of all the constituents showed good linearity (r>0.9994) in the range of the tested concentration,the average recoveries of the method were 98.68%, 98.24% and 98.29%, respectively.. The established method of microwave-assisted extraction and HPLC simultaneously determination has the advantages of convenient, precision and reliability. It can be used in simultaneous determination of three iridoid glycosides in Cornus officinalis.

Topics: Chromatography, High Pressure Liquid; Cornus; Fruit; Glucosides; Iridoid Glucosides; Iridoids; Microwaves; Pyrans; Quality Control; Reproducibility of Results; Solvents

The parenteral route has many merits over the oral route, including greater predictability, reproducibility of absorption, and rapid drug action, but injectable phytomedicines are uncommon due to protein precipitating tannin and hemolytic saponin components. In this study, in an effort to develop a safe injectable analgesic phytomedicine, we prepared a tannin and saponin-free Lonicera japonica extract, SKLJI, through fractionation and column purification, and evaluated its anti-inflammatory and analgesic activities in in vivo experimental models of inflammation and pain. The removal of tannin and saponin resulted in loganin and sweroside-enriched SKLJI and it showed reduced hemolysis and protein precipitation. In efficacy tests, SKLJI inhibited croton oil- and arachidonic acid-induced ear edema, acetic acid-induced writhing, and carrageenan-induced rat hind paw hyperalgesia. Inhibition of cylcooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS), and 5-lipoxyfenase (5-LO) activities by SKLJI appeared to be the mechanism underlying anti-inflammatory and analgesic efficacy. Loganin and sweroside also showed anti-inflammatory and analgesic activities, suggesting that they might be active principles in the efficacy of SKLJI. These results suggest that SKLJI is a viable candidate for a new anti-inflammatory and analgesic phytomedicine that can be administered by the parenteral route.

Topics: Analgesics; Animals; Anti-Inflammatory Agents; Arachidonate 5-Lipoxygenase; Cyclooxygenase 2; Enzyme Inhibitors; Hemolysis; Inflammation; Injections, Intravenous; Iridoid Glucosides; Iridoids; Lonicera; Male; Mice; Nitric Oxide Synthase Type II; Plant Extracts; Rats; Rats, Sprague-Dawley

Sweroside is an active ingredient of iridoid glycoside isolated from the flower buds of Lonicera japonica THUNB. A quantitative HPLC-UV method was developed for monitoring sweroside in rat plasma, urine, feces and bile. The method was successfully applied for a basic pharmacokinetic study. The obtained data of pharmacokinetics were applied to evaluate the oral bioavailabilities of sweroside and the active ingredients of purified herbal extracts (IGEs-1). The absolute bioavailability was estimated to F(sweroside) 0.31% and F(IGEs-1) 0.67%. The majority of sweroside excreted to feces revealed one reason of the low oral bioavailability. The values of F(IGEs-1) much higher than that of F(sweroside) reveals that ingredients in IGEs-1 such as loganin, secoxyloganin and some phenolic acids may promote the absorption of sweroside. The study of hepatobiliary excretion was achieved by an in vivo microdialysis sampling method after intravenous administration of sweroside. The percentage of accumulation of free form sweroside in bile duct was 31.2+/-7.2% of the total dosage. It may be one reason why sweroside possesses strong hepatoprotective effect.

Topics: Animals; Bile; Biliary Tract; Biological Availability; Chromatography, High Pressure Liquid; Feces; Glucosides; Iridoid Glucosides; Iridoids; Liver; Molecular Structure; Rats

A Diels-Alder cycloaddition approach to the sweroside aglycone intermediate of iridoids was explored using silylated butenolides and levoglucosenone as dienophiles under both Lewis acid and thermal conditions. Results of this study reveal no evidence that using less sterically demanding derivatives compromise the diastereofacial selectivity of the cycloaddition using silylated butenolides. Further chemistry performed on cycloadducts concentrated on the identification and management of methodologies suitable for its conversion into sweroside aglycone. During the course of these studies, a dehydrative cyclisation onto a preformed tetrahydrofuran ring to a bis-tetrahydrofuranoid moiety was unravelled. In addition studies on levoglucosenone-derived cycloadducts provide extensive insight into the conformational behaviour and reactivity. Further, the X-ray crystal structure of an alcohol intermediate from one-carbon homologation studies provided the first structural evidence confirming the diastereoselectivity of the cycloaddition procedure.

Topics: 4-Butyrolactone; Carbon; Crystallography, X-Ray; Glucosides; Iridoid Glucosides; Iridoids; Molecular Conformation; Organic Chemistry Phenomena

To study the chemical constituents of the root of Hemerocallis fulva.. Compounds were isolated by repeated silica gel, Sephadex LH-20, MCI gel, etc. column chromatography and their structures were determined by spectral analyses and physicochemical properties.. From the n-butanol fraction of the EtOH extract of the roots of H. fulva, 9 glycosides were isolated and identified as sweroside (1), laganin (2), picraquassioside C (3), puerarin (4), 3'-methoxypuerarin (5), 7-hydro xylnaphthalide-O-beta-D-glucopyranoside (6), orcinol-3-O-beta-glucopyranoside (7), HN saponin F (8), hederagenin-3-0-beta D-glucopyranosyl-(1-3)-alpha-L-arabinopyranoside-28-O-beta-D-glucopyranosyl ester (9).. Compounds 1-9 were isolated from the genus Hemerocallis for the first time.

Topics: Glucosides; Hemerocallis; Iridoid Glucosides; Iridoids; Isoflavones; Magnetic Resonance Spectroscopy; Plant Roots; Saponins

A simple and rapid HPLC method was established for simultaneously determining six active components in Fructus Corni. The six components were separated on an Agilent Zorbax Extend C18 column (250 mmx4.6 mm, 5 microm) and detected by diode array detector (DAD). Mobile phase was composed of (A) aqueous phosphoric acid (0.1%, v/v) and (B) acetonitrile phosphoric acid (0.1%, v/v) using a gradient elution. Analyses were performed at 30 degrees C with a flow rate of 1.0 mL/min and UV detection at 218 nm, 240 nm and 284 nm. All calibration curves showed good linear regression (r2>or=0.9999) within tested ranges. The LOD and LOQ were 0.11-1.69 microg/mL and 1.48-16.60 microg/mL, respectively. Overall intra-day and inter-day variations were less than 4.72%, and the average recoveries were 97.97-102.51% for the analytes. The developed method can be applied to the intrinsic quality control of Fructus Corni.

Topics: Biological Assay; Calibration; Chromatography, High Pressure Liquid; Cornus; Drugs, Chinese Herbal; Furaldehyde; Gallic Acid; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Molecular Structure; Pyrans; Reproducibility of Results; Time Factors

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 elucidate the promoting effect of the constituents in plasma after oral administration of Liuwei Dihuangwan on proliferation of rat osteoblast.. To add the constituents in plasma after oral administration of Liuwei Dihuangwan with rational concentration into culture solution of rat osteoblast, later using MT method for determining the proliferation rate of rat osteoblast.. The Mixed group including morroniside, sweroside and loganin with different dose all significantly promoted proliferation of rat osteoblast.. This study preliminarily elucidated the constituents such as morroniside, sweroside and loganin in plasma after oral administration of Liuwei Dihuangwan were main biological constituents which contributed to anti-osteoporosis bioactivity of Liuwei Dihuangwan.

Topics: Administration, Oral; Animals; Cell Proliferation; Cells, Cultured; Drugs, Chinese Herbal; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Osteoblasts; Plasma; Rats; Rats, Wistar

This study presents a new HPLC method for the simultaneous determination of seven major components, namely chlorogenic acid, caffeic acid, loganin, sweroside, secoxyloganin, rutin and luteolin 7-O-glucoside in Caulis Lonicerae Japonicae, a commonly used traditional Chinese medicinal herb derived from the caulis of Lonicera japonica Thunb. These seven compounds, belonging to the chemical types of phenolic acids, iridoids and flavonoids, were separated on a C18 column (250 x 4.6 mm, 5.0 microm) with the column temperature at 30 degrees C. The mobile phase was composed of (A) aqueous acetic acid (0.4%, v/v) and (B) acetonitrile using a gradient elution of 10% B at 0-12 min, 10-17% B at 12-25 min and 17% B at 25-35 min. The flow rate was 1.0 mL/min and detection wavelength was set at 245 nm. The limit of detection (S/N = 3) ranged from 0.10 to 0.23 microg/mL and the limit of quantification (S/N = 10) ranged from 0.69 to 3.56 microg/mL. All calibration curves showed good linear regression (r2 > 0.9990) within the test ranges. The intra- and inter-day precisions as determined from sample solutions were below 1.24 and 2.28%, respectively. The recoveries for seven compounds were found to range from 94.2 to 103.6%. This verified method has been successfully applied to evaluation of commercial samples of Caulis Lonicerae Japonicae from different markets in China.

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonoids; Glucosides; Hydroxybenzoates; Iridoid Glucosides; Iridoids; Linear Models; Lonicera; Luteolin; Molecular Structure; Reproducibility of Results; Rutin; Sensitivity and Specificity; Spectrophotometry, Ultraviolet

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

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 investigate the chemical constituents of water-soluble part of stem of Nauclea officinalis.. The compounds were isolated and purified by resins, silica gel, and Sephadex LH20 column chromatography repeatedly, and their structures were identified by spectral analysis.. Seven compounds were isolated and identified as: naucleamide A-10-O-beta-D-glucopyranoside (I), 5-beta-carboxystrictosidin (II), sweroside (III), loganin (IV), 3,4-dimethoxyphenyl-beta-D-glucopyranoside (V), 3, 4, 5-trimethoxyphenyl-beta-D-glucopyranoside (VI), 2-phenethylrutinoside (VII).. Compound I is a new indole alkaloid glucoside, compounds I-VII were isolated from this plant for the first time.

Topics: Carbolines; Glucosides; Glycosides; Indole Alkaloids; Iridoid Glucosides; Iridoids; Molecular Conformation; Molecular Structure; Plant Stems; Plants, Medicinal; Rubiaceae

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

From the rootstock of Scabiosa columbria L. loganin and sweroside were isolated. Sweroside showed moderate antibacterial activity. Pure sweroside was converted to the sweroside aglycone 1-acetoxy derivative (DABCO/Ac2O) after hydrolysis of the glucose unit. X-ray crystallography of the monoacetate showed unambiguously that it had been transformed to a new seco-iridoid having the novel trans diaxial configuration for the protons on C-1, C-9 and C-5. The mechanism for the rearrangement is discussed.

Topics: Acetylation; Biotransformation; Crystallography, X-Ray; Glucosides; Iridoid Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Pyrans; Spectrometry, Mass, Electrospray Ionization

A new iridoid glycoside 6'-O-beta-apiofuranosylsweroside was isolated from the ethanolic extract of the roots of Lonicera quinquelocularis along with the known compounds loganin and sweroside.

Topics: Disaccharides; Glucosides; Glycosides; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Magnetic Resonance Spectroscopy; Plant Extracts; Plant Roots; Plant Shoots; Plants, Medicinal; Pyrans; Pyrones

A chemical and biological screening of 25 species of the Gentianaceae family has been undertaken. Both methanolic and dichloromethane extracts of Swertia calycina exhibited a strong antifungal activity against Cladosporium cucumerinum and Candida albicans. The compound responsible for this activity has been isolated and identified as 2-methoxy-1,4-naphthoquinone. It is the first naphthoquinone to be described in Gentianaceae species. LC-UV and LC-TSP-MS analysis of the crude extracts of Swertia calycina also allowed on-line identification of six known xanthones and secoiridoids.

Topics: Antifungal Agents; Chromatography, High Pressure Liquid; Glucosides; Iridoid Glucosides; Iridoids; Mass Spectrometry; Microbial Sensitivity Tests; Naphthoquinones; Plant Extracts; Pyrans; Rwanda

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