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Find video protocols related to scientific articles indexed in Pubmed.
Toxicity assessment of Arisaematis Rhizoma in rats by a (1)H NMR-based metabolomics approach.
Mol Biosyst
PUBLISHED: 11-20-2014
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Arisaematis Rhizoma (AR), a famous traditional Chinese medicine, has been widely used in Asia over thousands of years. Documented with noticeable toxicity in ancient books, AR has been used to treat various diseases in the clinic. Therefore, it is important to assess the toxicity of AR dynamically and holistically. In this study, a (1)H NMR-based metabolomics approach complemented with serum chemistry and histopathology has been applied to investigate the toxicity of AR. Rats were intragastrically administered with AR (0, 0.5 and 1 g kg(-1) body weight) for 30 days, and serum and urine samples were collected. Their (1)H NMR profiles were analyzed by multivariate pattern recognition techniques to denote metabolic variations induced by AR, and 13 metabolites in urine and 6 metabolites in serum were significantly altered, which suggested that disturbances in energy metabolism, perturbation of the gut microflora environment, membrane damage, folate deficiency and injury of kidneys are produced by AR. Histopathology showed a slight vacuolization of the glomerular matrix and edema of renal tubular epithelial cells in kidneys of AR administered rats, which were evidenced by increased levels of blood urea nitrogen and creatinine in serum chemistry. Our results indicated that oral administration of crude AR was found to induce slight renal toxicity. Therefore, precautions should be made to monitor the potential nephrotoxicity of AR in clinical use. The metabolomics approach provided a promising tool for the study and better understanding of TCM-induced toxicity dynamically and holistically.
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Simultaneous enrichment and separation of flavonoids from Herba Epimedii by macroporous resins coupled with preparative chromatographic method.
Nat. Prod. Res.
PUBLISHED: 10-03-2014
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An efficient, feasible enrichment and separation method of epimedins A, B, C and icariin from Herba Epimedii was developed by the combination of microwave-assisted extraction, macroporous resins and preparative HPLC. WDX-5 macroporous resin shows better recoveries at 96.2%, 97.0%, 98.2% and 97.1% for epimedins A, B, C and icariin than other macroporous resins used in the experiments. As a result, epimedins A (5.1 mg), B (15.3 mg), C (7.6 mg) and icariin (14.3 mg) were obtained from 6.0 g crude Herba Epimedii with the recoveries at 70.8%, 68.9%, 66.7% and 95.3%, respectively. The method developed in this study may provide scientific references for the enrichment and separation of flavonoids from Herba Epimedii.
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Directly utilizing an endogenous gene to dissect regulatory elements in the biosynthetic gene cluster of nosiheptide.
Chem. Commun. (Camb.)
PUBLISHED: 07-26-2014
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The regulatory elements for nosiheptide biosynthesis were identified by a novel host-vector system with an endogenous gene within the biosynthetic gene cluster as a reporter gene. The present study offers a rapid and reliable method for the identification of regulatory elements in the biosynthesis of various bioactive natural products.
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Arctigenin but not arctiin acts as the major effective constituent of Arctium lappa L. fruit for attenuating colonic inflammatory response induced by dextran sulfate sodium in mice.
Int. Immunopharmacol.
PUBLISHED: 07-19-2014
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The crude powder of the fruit of Arctium lappa L. (ALF) has previously been reported to attenuate experimental colitis in mice. But, its main effective ingredient and underlying mechanisms remain to be identified. In this study, ALF was extracted with ethanol, and then successively fractionated into petroleum ether, ethyl acetate, n-butanol and water fraction. Experimental colitis was induced by dextran sulfate sodium (DSS) in mice. Among the four fractions of ALF, the ethyl acetate fraction showed the most significant inhibition of DSS-induced colitis in mice. The comparative studies of arctigenin and arctiin (the two main ingredients of ethyl acetate fraction) indicated that arctigenin rather than arctiin could reduce the loss of body weight, disease activity index and histological damage in the colon. Arctigenin markedly recovered the loss of intestinal epithelial cells (E-cadherin-positive cells) and decreased the infiltration of neutrophils (MPO-positive cells) and macrophages (CD68-positive cells). Arctigenin could down-regulate the expressions of TNF-?, IL-6, MIP-2, MCP-1, MAdCAM-1, ICAM-1 and VCAM-1 at both protein and mRNA levels in colonic tissues. Also, it markedly decreased the MDA level, but increased SOD activity and the GSH level. Of note, the efficacy of arctigenin was comparable or even superior to that of the positive control mesalazine. Moreover, it significantly suppressed the phosphorylation of MAPKs and the activation of NF-?B, including phosphorylation of I?B? and p65, p65 translocation and DNA binding activity. In conclusion, arctigenin but not arctiin is the main active ingredient of ALF for attenuating colitis via down-regulating the activation of MAPK and NF-?B pathways.
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Analysis and pharmacokinetics studies of gastrodin and p-hydroxybenzyl alcohol in dogs using ultra fast liquid chromatography-tandem mass spectrometry method.
J Pharm Biomed Anal
PUBLISHED: 07-12-2014
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A simple, sensitive and reliable ultra fast liquid chromatography-electrospray ionization-tandem mass spectrometry (UFLC-ESI-MS/MS) method was developed for simultaneously quantifying gastrodin (p-hydroxy-methyl-phenol-?-d-glucoside) and its metabolite p-hydroxybenzyl alcohol (HBA) in dog plasma. Separation was performed on an ultra fast liquid chromatography (UFLC) system. Detection was carried out on a tandem mass spectrometry (MS/MS) in multiple reaction monitoring (MRM) mode via an electrospray ionization (ESI) interface. MRM mode of precursor-product ion transitions was used for gastrodin, HBA and the internal standard (IS, bergeninum) at m/z 285.0?123.0, 123.0?105.0 and 326.9?192.2, respectively. The lower limits of quantification (LLOQ) of this method for both gastrodin and HBA were 1ng/mL, with their linear concentration ranging from 0.001 to 10?g/mL. The methods were validated for selectivity, calibration curves, accuracy and precision, extraction recoveries, matrix effects, carry-over, cross talk, dilution integrity, stability and incurred sample reanalysis (ISR). Using this validated method, pharmacokinetic behaviors of gastrodin and HBA after intragastric administration (ig) of gastrodin to dogs were studied for the first time.
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A new acorane sesquiterpene from the aerial parts of Psychotria yunnanensis.
Nat. Prod. Res.
PUBLISHED: 07-10-2014
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Psycacoraone A (1), a new acorane-type sesquiterpene possessing rare spirobicyclic carbon skeleton, was isolated from the aerial parts of Psychotria yunnanensis. Its structure was elucidated on the basis of spectroscopic methods including HR-ESI-MS, 1D and 2D NMR. The absolute configuration of 1 was determined by calculation of electronic circular dichroism using density functional theory.
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NMR-based metabolomics approach to study the chronic toxicity of crude ricin from castor bean kernels on rats.
Mol Biosyst
PUBLISHED: 07-04-2014
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Ricin, a large, water soluble toxic glycoprotein, is distributed majorly in the kernels of castor beans (the seeds of Ricinus communis L.) and has been used in traditional Chinese medicine (TCM) or other folk remedies throughout the world. The toxicity of crude ricin (CR) from castor bean kernels was investigated for the first time using an NMR-based metabolomic approach complemented with histopathological inspection and clinical chemistry. The chronic administration of CR could cause kidney and lung impairment, spleen and thymus dysfunction and diminished nutrient intake in rats. An orthogonal signal correction partial least-squares discriminant analysis (OSC-PLSDA) of metabolomic profiles of rat biofluids highlighted a number of metabolic disturbances induced by CR. Long-term CR treatment produced perturbations on energy metabolism, nitrogen metabolism, amino acid metabolism and kynurenine pathway, and evoked oxidative stress. These findings could explain well the CR induced nephrotoxicity and pulmonary toxicity, and provided several potential biomarkers for diagnostics of these toxicities. Such a (1)H NMR based metabolomics approach showed its ability to give a systematic and holistic view of the response of an organism to drugs and is suitable for dynamic studies on the toxicological effects of TCM.
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New cassane-type diterpenoids from Caesalpinia bonduc.
Chem. Pharm. Bull.
PUBLISHED: 07-04-2014
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Six new cassane diterpenoids, named caesalls H-M (1-6), were isolated from the seed kernels of Caesalpinia bonduc. Their structures were elucidated on the basis of spectroscopic analysis, mainly NMR and MS. The absolute configurations of compounds 1 and 3 were determined by a single-crystal X-ray study using a mirror CuK? radiation and circular dichroism (CD) spectra, respectively. None of the compounds were cytotoxic against HepG-2, MCF-7 and MG-63 cells.
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Flavonostilbenes from Sophora alopecuroides L. as multidrug resistance associated protein 1 (MRP1) inhibitors.
Nat. Prod. Res.
PUBLISHED: 06-23-2014
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Flavonoids have always attracted much attention due to their reversal activity on multidrug resistance (MDR). Eight flavonoids isolated from traditional Chinese medicine Sophora alopecuroides L. were applied to test their effect on MDR associated protein 1 (MRP1) through the established predicting assay. Three flavonostilbenes (alopecurone A, B and D) were first found exhibiting potent inhibitory activity on MRP1. All of them dramatically increased 6-carboxyfluorescein diacetate and doxorubicin accumulation in MRP1-transfected U-2 OS cells. The compounds significantly increased the cytotoxicity and decreased the IC?? value of doxorubicin on the MDR cells (12-, 5- and 8-fold, respectively) at a non-toxic concentration (20 ?M). Besides, Q-PCR analysis reveals that the MRP1 mRNA level in U-2 OS/MRP1 was also markedly decreased by the three compounds. These findings indicate a new therapeutic role of the herb. The three flavonostilbenes may have the possibility for further development as novel therapeutic reversal agents against MDR.
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Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa.
J. Nat. Prod.
PUBLISHED: 04-28-2014
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A total of 10 new indole alkaloids, tabercarpamines A-J (1-10), were isolated from the leaves of Tabernaemontana corymbosa. Tabercarpamines C-F (3-6) are rare C-14/C-15-seco-tabersonine-type monoterpenoid indole alkaloids, and 5 and 6 are the first examples with a lactone linkage between C-14 and C-20. The structures of these alkaloids were elucidated using spectroscopic methods, and the absolute configurations of 1 and 2 were determined using the ECD exciton chirality method. In addition, an MTT assay was used to examine the growth-inhibitory effects of all new isolates and of two known isolates on MCF-7, HepG2, and SMMC-7721 cells; 1 exhibited significant inhibitory effects against these three human cancer cell lines with IC50 values of 8.54, 3.31, and 6.76 ?M, respectively. Additionally, the results from the annexin-V/PI double-staining assay indicated that 1 might inhibit the proliferation of HepG2 cells by inducing apoptosis.
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A new alkaloid glycoside from the rhizomes of Aristolochia fordiana.
Nat. Prod. Res.
PUBLISHED: 04-09-2014
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A new alkaloid glycoside named fordianoside (1), together with three known compounds arabinothalictoside (2), 6-O-p-coumaroyl-?-fructofuranosyl-(2 ? 1)-?-d-glucopyranoside (3) and 4-[formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (4), was isolated from the rhizomes of Aristolochia fordiana. The structure of 1 was established as (1S)-1,2,3,4-tetrahydro-7-hydroxy-1-[(4-hydroxybenzyl) methyl]-2,2-dimethyl-8-O-isoquinolinyl ?-d-glucopyranoside by using chemical and spectroscopic methods including HR-ESI-MS, 1D and 2D NMR.
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(1)H NMR-based metabolomics study on a goldfish model of Parkinson's disease induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP).
Chem. Biol. Interact.
PUBLISHED: 03-26-2014
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A goldfish (Carassius auratus) model of Parkinson's disease (PD) was constructed by a single dose of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) according to previously reported methods. Global metabolite changes in brain of the MPTP induced goldfish model of PD were investigated. (1)H NMR-based metabolomics combined with various statistical methods such as orthogonal partial least squares discriminant analysis (OPLS-DA) and two-dimensional statistical total correlation spectroscopy (2D-STOCSY) found significant increase of leucine, isoleucine, valine, alanine, alanylalanine, creatinine, myo-inositol, 18:2 fatty acid, total fatty acids, arachic alcohol, taurine and significant decrease of N-acetylaspartate, (phospho)creatine, (phospho)choline, betaine, glutamine, 3-hexenedioate, acetamide, malonate, isocitrate, scyllo-inositol, phosphatidylcholines, cholesterols, n-3 fatty acids, polyunsaturated fatty acids (PUFAs) in brain of MPTP induced PD goldfish. These disturbed metabolite levels were involved in oxidative stress, energy failure, neuronal cell injury and death, consistent with those observed in clinical PD patients, and rodents and primates model of PD, indicating that the acute MPTP model of goldfish was an ideal and valuable model for PD research. In addition, several unusual metabolites in brain were significantly changed between MPTP induced PD and control goldfish, which might also play an important role in the pathogenesis of PD. This study also demonstrated the applicability and potential of (1)H NMR-based metabolomics approach for evaluation of animal models of disease induced by chemicals, such as MPTP-induced PD goldfish.
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Identification and analysis of gastrodin and its five metabolites using ultra fast liquid chromatography electrospray ionization tandem mass spectrometry to investigate influence of multiple-dose and food.
J Chromatogr A
PUBLISHED: 03-04-2014
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A reliable and highly sensitive ultra performance liquid chromatography electrospray ionization tandem mass spectrometry (UFLC-ESI-MS/MS) analytical method was developed for identification and quantification of gastrodin (GAS) and its metabolites in rat plasma. Five metabolites were identified: p-formylphenyl-?-d-glucopyranoside (M1), p-hydroxybenzonic acid (M2), p-hydroxybenzyl alcohol (M3), p-formaldehydephenyl-?-d-glucopyranoside (M4), p-hydroxybenzaldehyde (M5). The molecular structures of metabolites were proposed based on the characters of their precursor ions, product ions and chromatographic retention time. Four of them were reported firstly in rat plasma. This method involved the addition of bergeninum as the internal standard (IS), UFLC separation, and quantification by MS/MS system using negative electrospray ionization in the multiple reaction monitoring (MRM) mode. The lower limit of quantification of gastrodin and five metabolites were all 1ng/mL. The method was linear in the concentration range of 0.001-10?g/mL. The intra- and inter-day precisions (R.S.D %) were within 15.0% for all analytes. No interference was noted due to endogenous substances. All analytes were stable in rat plasma stored at room temperature and 4°C for at least 4h, -20°C combined with three freeze-thaw cycles for at least 1 month. By this method, the influence of multiple-dose and food on the pharmacokinetics behaviors of GAS and its metabolites were studied for the first time. We hope pharmacokinetic data of present study may inspire rational clinical usage of GAS.
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Discovery of highly potent DPP-4 inhibitors by hybrid compound design based on linagliptin and alogliptin.
Eur J Med Chem
PUBLISHED: 02-24-2014
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Highly potent DPP-4 inhibitors have been identified by hybrid compound design based on linagliptin and alogliptin. The most promising compound 2h (IC50 = 0.31 nM) exhibited 8.5-fold and 2.5-fold more potent activity than that of alogliptin (IC50 = 2.63 nM) and linagliptin (IC50 = 0.77 nM), respectively. Compound 2h had a good inhibition selectivity for DPP-4 over DPP-8/9 and thus was selected for further biological evaluation, including oral glucose tolerance, plasma DPP-4 inhibitory activity, pharmacokinetic profile, acute toxicity and hERG inhibition. The assay results showed that 2h displayed significant in vivo glucose-lowering effect and low risk of toxicity. Further studies are expected to confirm 2h as a potential drug candidate for the treatment of type 2 diabetes.
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A new neo-clerodane diterpene from Ajuga decumbens.
Nat. Prod. Res.
PUBLISHED: 01-27-2014
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A new neo-clerodane diterpene, named ajugacumbin J (1), together with 13 known compounds (2-14) was isolated from Ajuga decumbens. The structure of ajugacumbin J (1) was elucidated by 1D and 2D NMR spectra and MS. Ajugacumbin J (1) and ajugacumbin D (5) exhibited inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages with an IC50 value of 46.2 and 35.9 ?M, respectively.
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Cassane-type diterpenoids from the seed kernels of Caesalpinia bonduc.
Fitoterapia
PUBLISHED: 01-03-2014
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Seven new cassane diterpenoids (1-7), along with three known compounds (8-10), were isolated from the seed kernels of Caesalpinia bonduc. The structures were elucidated by extensive 1D and 2D NMR (HSQC, HMBC and ROESY) and mass (HRESIMS) spectroscopic data analyses. The structure and absolute configuration of compound 1 were confirmed by a single-crystal X-ray diffraction experiment. All isolates were tested for their cytotoxicity against HepG-2, MCF-7 and MG-63 cells, and 8-10 showed weak inhibitory activities.
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Development and validation of a sensitive and selective LC-MS/MS method for the determination of trans ?-veniferin, a resveratrol dehydrodimer, in rat plasma and its application to pharmacokinetics and bioavailability studies.
J. Chromatogr. B Analyt. Technol. Biomed. Life Sci.
PUBLISHED: 01-02-2014
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In this study, an accurate and reliable LC-MS/MS assay was firstly developed and validated for the quantitative determination of trans ?-veniferin (TVN) in rat plasma. Chlorzoxazone was used as the internal standard (IS). After one-step protein precipitation with methanol, the analyte and IS were separated on an ODS column by gradient elution with mobile phase of acetonitrile-0.2% formic acid at a flow rate of 0.3mL/min. Negative electrospray ionization was performed using multiple reactions monitoring (MRM) mode with transitions of m/z 453.0>410.9 for TVN, and m/z 168.0>132.0 for IS. Good linearity (R?0.996) was observed over the concentration range of 5-5000ng/mL for TVN with a lower limit of quantification (LLOQ) of 5ng/mL. The mean recoveries for TVN and IS were 91.05% and 96.68%, respectively. The intra- and inter-day precisions (RSD) were no more than 10.5% and accuracies (RE) were within the range of -6.3% to 2.1%. The validated method was suitable for quantification of TVN and successfully applied to the pharmacokinetic study of TVN after oral and intravenous administration to rats. The oral absolute bioavailability of TVN was 14.2% in rat.
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Synthesis and biological evaluation of novel pentacyclic triterpene derivatives as potential PPAR? agonists.
Med Chem
PUBLISHED: 09-11-2013
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Synthesis and biological evaluation of a novel series of substituted pentacyclic triterpene derivatives as potential PPAR? agoinsts and glycogen phosphorylase inhibitors have been described. Compounds 11 and 17 showed potent PPAR? agonistic activity and activated the transcription activity of PPAR? in a dose-dependent manner. On the other hand, eleven compounds exhibited moderate inhibitory activity against rabbit muscle glycogen phosphorylase a (RMGPa), and triterpene 10 was the best one. Structure-activity relationship (SAR) is also discussed.
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NMR-based metabolomics approach to study the toxicity of lambda-cyhalothrin to goldfish (Carassius auratus).
Aquat. Toxicol.
PUBLISHED: 08-30-2013
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In this study, a (1)H nuclear magnetic resonance (NMR) based metabolomics approach was applied to investigate the toxicity of lambda-cyhalothrin (LCT) in goldfish (Carassius auratus). LCT showed tissue-specific damage to gill, heart, liver and kidney tissues of goldfish. NMR profiling combined with statistical methods such as orthogonal partial least squares discriminant analysis (OPLS-DA) and two-dimensional statistical total correlation spectroscopy (2D-STOCSY) was developed to discern metabolite changes occurring after one week LCT exposure in brain, heart and kidney tissues of goldfish. LCT exposure influenced levels of many metabolites (e.g., leucine, isoleucine and valine in brain and kidney; lactate in brain, heart and kidney; alanine in brain and kidney; choline in brain, heart and kidney; taurine in brain, heart and kidney; N-acetylaspartate in brain; myo-inositol in brain; phosphocreatine in brain and heart; 2-oxoglutarate in brain; cis-aconitate in brain, and etc.), and broke the balance of neurotransmitters and osmoregulators, evoked oxidative stress, disturbed metabolisms of energy and amino acids. The implication of glutamate-glutamine-gamma-aminobutyric axis in LCT induced toxicity was demonstrated for the first time. Our findings demonstrated the applicability and potential of metabolomics approach for the elucidation of toxicological effects of pesticides and the underlying mechanisms, and the discovery of biomarkers for pesticide pollution in aquatic environment.
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Enantioseparation of racemic trans-?-viniferin using high speed counter-current chromatography based on induced circular dichroism technology.
J Chromatogr A
PUBLISHED: 07-01-2013
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A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate trans-?-viniferin (TVN) enantiomers successfully. The important parameters for the chiral HSCCC separation process, including the type of chiral selector (CS), the concentration of chiral selector and the equilibrium temperature, were optimized using induced circular dichroism spectrum. The final separation procedure was established with a biphasic solvent system composed of n-hexane-ethyl acetate-25mmolL(-1) hydroxypropyl-?-cyclodextrin aqueous solution (5:5:10, v/v/v) in the head-to-tail elution mode at 5°C. Under optimum chiral HSCCC separation conditions, 8.2mg of (7S, 8S)-TVN (1) and 9.4mg of (7R, 8R)-TVN (2) were successfully separated from 20mg TVN enantiomers with the purity of 99.51% and 99.36%, respectively.
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Labdane diterpenes from Chloranthus serratus.
Fitoterapia
PUBLISHED: 06-27-2013
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Five new labdane diterpenes (1-5), serralabdanes A-E, were isolated from the whole plant of Chloranthus serratus. Their structures were elucidated by spectroscopic methods, and the absolute configuration of the 12,13-diol moiety in serralabdane C (3) was determined by observing the induced circular dichroism (ICD) after addition of dimolybdenum teracetate in DMSO solution. Serralabdanes A-E (1-5) showed inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells.
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Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities.
Phytochemistry
PUBLISHED: 06-27-2013
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Six partially acylated pentasaccharide resin glycosides, cairicosides A-F, were isolated from the aerial parts of Ipomoea cairica. These compounds were characterized as a group of macrolactones of simonic acid A, partially acylated with different organic acids. The lactonization site of 11S-hydroxyhexadecanoic acid (jalapinolic acid) was bound to the second saccharide moiety at C-3 in cairicosides A-E, while at C-2 in cairicoside F. Structures were established by spectroscopic and chemical methods. Compounds cairicosides A-E exhibited moderate cytotoxicity against a small panel of human tumor cell lines with IC50 values in the range of 4.28-14.31?M.
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A new steroidal glycoside from the seeds of Hyoscyamus niger.
Nat. Prod. Res.
PUBLISHED: 06-08-2013
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A new steroidal glycoside hyoscyamoside G (1), together with two known analogues hyoscyamoside E (2) and hyoscyamoside F1 (3), was isolated from the seeds of Hyoscyamus niger. The structure of 1 was established as (22R,24Z)-1?,3?,7?,22,26-pentakishydroxylergost-22-O-?-d-gulcopyranosyl-5,24-diene-26-O-?-d-glucopyranoside, by means of chemical and spectroscopic methods including HRESI-MS, 1D and 2D NMR. In vitro, compound 2 showed cytotoxicity against human lung cancer cell H460 with IC50 value of 66 ?g/mL.
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Simultaneous separation of triterpenoid saponins and flavonoid glycosides from the roots of Glycyrrhiza uralensis Fisch by pH-zone-refining counter-current chromatography.
J Sep Sci
PUBLISHED: 04-19-2013
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Glycosides including triterpenoid saponins and flavonoid glycosides are the main constituents of Glycyrrhiza uralensis Fisch (licorice) and exhibit prominent pharmacological activities. However, conventional methods for the separation of glycosides always cause irreversible adsorption and unavoidable loss of sample due to their high hydrophilicities. The present paper describes a convenient method for the simultaneous separation of triterpenoid saponins and flavonoid glycosides from licorice by pH-zone-refining counter-current chromatography. Ethyl acetate/n-butanol/water (2:3:5, v/v) with 10 mM TFA in the upper organic stationary phase and 10 mM ammonia in the lower aqueous mobile phase was used as the biphasic solvent system. Three triterpenoid saponins and two flavonoid glycosides including licorice-saponin A3 (63.3 mg), glycyrrhizic acid (342.2 mg), 3-O-[?-D-glucuronopyranosyl-(1 ? 2)-?-D-galactopyranosyl]glycyrrhetic acid (56.0 mg), liquiritin apioside (232.6 mg), and liquiritin (386.5 mg) were successfully obtained from licorice ethanol extract (2 g) in one step. This method subtly takes advantage of the common acidic properties of triterpenoid saponins and flavonoid glycosides, and obviously is much more efficient and convenient than the previous methods. It is also the first time that the separation of acidic triterpenoid saponins by using pH-zone-refining counter-current chromatography has been reported.
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¹H NMR-based metabolomics approach to evaluate the effect of Xue-Fu-Zhu-Yu decoction on hyperlipidemia rats induced by high-fat diet.
J Pharm Biomed Anal
PUBLISHED: 02-09-2013
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An NMR-based metabolomics approach was conducted to holisticly explore the effect of XFZYD (a traditional Chinese medicine formula) on high-fat diet induced hyperlipidemia rats with one of the commonly used antihyperlipidemic agents, simvastatin as the positive control. NMR spectra from blood plasma combined with statistical analysis revealed compounds distinguishing hyperlipidemia rats from normal control rats. XFZYD could ameliorate hyperlipidemia by intervening in some major metabolic pathways, such as decreasing the accumulation of ketone body (?-hydroxybutyrate) and acetyl-glycoproteins, enhancing glutathione (GSH) biosynthesis, partially reversing energy and lipid metabolism disturbance. Oral administration of XFZYD could also be helpful to hyperlipidemia rats in bettering the serum chemistry profile. The combined results demonstrated that XFZYD could ameliorate the hyperlipidemic symptoms in a global scale and restore the abnormal metabolic state to a near normal level in a time-dependent pattern.
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A rapid and sensitive LC-MS/MS assay for the determination of berbamine in rat plasma with application to preclinical pharmacokinetic study.
J. Chromatogr. B Analyt. Technol. Biomed. Life Sci.
PUBLISHED: 02-04-2013
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Berbamine (BBM), a natural compound from Chinese herb Berberis amurensis, has recently received a great deal of attention due to its anti-leukemia activity. In this study, a rapid and sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the determination of BBM in rat plasma was developed for the first time. Caffeine was used as an internal standard. Chromatographic separation was performed on an ODS column with gradient elution using methanol-1% formic acid as mobile phase at a flow rate of 0.3mL/min. Quantification was through tandem mass spectrometry with positive electrospray ionization (ESI) and multiple reaction monitoring (MRM) at m/z 305.2?566.3 and 195.1?138.0 for BBM and IS, respectively. The lower limit of quantification was 1ng/mL with a linear range of 1-1000ng/mL. The intra- and inter-day assay precision (RSD) ranged from 2.0-6.4% to 2.5-5.5%, respectively, and the intra- and inter-day assay accuracy (RE) was between -5.8-6.0% and -6.5-1.4%, respectively. The validated method was successfully applied to the preclinical pharmacokinetic studies of BBM in rats. The elimination half-lives (t1/2) were (472.4±66.1), (509.6±97.0) and (486.2±94.6) min after single intravenous administration of 2, 4 and 8mg/kg BBM, respectively. The area under the plasma concentration versus time curve (AUC0-24h) and initial plasma concentration (C0) were linearly related to dose.
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Paeoniflorin attenuates amyloid-beta peptide-induced neurotoxicity by ameliorating oxidative stress and regulating the NGF-mediated signaling in rats.
Brain Res.
PUBLISHED: 01-04-2013
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Paeoniflorin is a monoterpene glycoside isolated from the aqueous extract of the dry root of Paeonia. It has been identified to exhibit many pharmacological effects including enhancing the cognitive ability, producing anti-depressant-like effect and reducing the MTPT-induced toxicity. In our previous study, it has shown that paeoniflorin improved the cognitive ability and attenuated the oxidative stress in the A?((1-42))-treated rats. In order to further elucidate the possible molecular mechanisms of paeoniflorin on the cognitive ability, rats were injected with A?((1-42)) (1?g/?L) and later with paeoniflorin (15mg/kg and 30mg/kg, i.p.) and donepezil hydrochloride (2mg/kg, i.p.) daily for 20 days in this study. The results showed that the long-term treatment of paeoniflorin or donepezil enhanced the cognitive performances in the Morris water maze test, restored the decreased activities of superoxide dismutase and catalase and the increased level of malondialdehyde, and reversed the alterations of matrix metallopeptidase-9 and tissue-inhibitor of metalloproteinase-1 in the hippocampus of A?((1-42))-treated rats. Paeoniflorin also up-regulated the activity of choline acetyltrasferase and the expression of tyrosine kinase A receptor, and down-regulated the activity of acetylcholine esterase in the hippocampus of A?((1-42))-treated rats. These results demonstrate that paeoniflorin ameliorates the spatial learning and memory deficits by attenuating oxidative stress and regulating the nerve growth factor-mediated signaling to reinforce cholinergic functions in the hippocampus of the A?((1-42))-treated rats.
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Phenylethyl cinnamides as potential alpha-glucosidase inhibitors from the roots of Solanum melongena.
Nat Prod Commun
PUBLISHED: 08-06-2011
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Bioassay-guided fractionation against alpha-glucosidase resulted in isolation and identification of six phenolic compounds (1-6) from the 70% EtOH extract of the roots of Solanum melongena L. (Solanaceae). Of these, three phenylethyl cinnamides, N-trans-feruloyl tyramine (1), N-trans-p-coumaroyl tyramine (2) and N-cis-p-coumaroyl tyramine (3) possessed inhibitory activity against alpha-glucosidase with IC50 values of 500.6, 5.3 and 46.3 microM, respectively. Mechanism analysis revealed these phenylethyl cinnamides were non-competitive inhibitors. This is the first study of the alpha-glucosidase inhibitory activities of the roots of S. melongena, and this preliminary observation suggested potential medicinal use of this herb.
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Qualitative and quantitative analysis of the major constituents in Chinese medicinal preparation Guan-Xin-Ning injection by HPLC-DAD-ESI-MS(n).
J Pharm Biomed Anal
PUBLISHED: 05-31-2011
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Guan-Xin-Ning (GXN) injection, a traditional Chinese medicinal preparation consisting of Radix Salvia miltiorrhiza and Rhizoma Ligusticum chuanxiong, has been used to treat coronary heart disease and angina pectoris in China for decades. In this paper, a HPLC/DAD/ESI-MS(n) method was successfully developed for qualitative and quantitative analysis of the active components in GXN injection for the first time. 28 compounds were identified by comparison of their retention times and MS spectra (HPLC/DAD/ESI-MS(n)) with those elucidated standards or recorded literature. 19 of them (danshensu, furoic acid, 3-O-caffeoylquinic acid, protocatechuic aldehyde, p-hydroxybenzoic acid, chlorogenic acid, caffeic acid, 4-O-caffeoylquinic acid, vanillin, 1,3-dicaffeoylquinic acid, 4-hydroxycinnamic acid, ferulic acid, senkyunolide I, senkyunolide H, isosalvianolic acid A, rosmarinic acid, salvianolic acid B, salvianolic acid A and isosalvianolic acid C) were simultaneously determined by HPLC-DAD quantitatively. The analytical method was validated and successfully applied for simultaneous determination of major components in GXN injections from seven different production batches, indicating that the proposed approach was applicable for the routine analysis and quality control of GXN injection.
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Complete 1H and 13C NMR data assignment of protolimonoids from the stem barks of Aphanamixis grandifolia.
Magn Reson Chem
PUBLISHED: 04-20-2011
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Seven new protolimonoids, named aphagranins A-G (1-7), along with four known compounds, were isolated from the ethanol extract of the stem barks of Aphanamixis grandifolia. Structure elucidation and signal assignments were achieved on the basis of spectral and chemical evidences.
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Application of complexation high-speed counter-current chromatography in the separation of 5-hydroxyisoflavone isomers from Belamcanda chinensis (L.) DC.
J Chromatogr A
PUBLISHED: 02-01-2011
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A novel separation technique of complexation high-speed counter-current chromatography (HSCCC) using copper ion as a complexation agent was first developed to isolate 5-hydroxyisoflavone isomers from Belamcanda chinensis (L.) DC. According to the partition coefficient and separation factor, the two-phase solvent system composed of light petroleum-ethyl acetate-methanol-water (3:5:3:5, v/v) and copper nitrate (0.10mol/L in the lower phase) was selected. 9.2mg isoirigenin (1), 46.4mg irigenin (2) and 1.2mg 5,7,4-trihydroxy-6,3,5-trimethoxyisoflavone (3) were simultaneously purified from 100mg crude extract by HSCCC with the purity of 95.06%, 96.98% and 93.69%, respectively. As evidenced by the results of UV-Vis spectroscopy, the stoichiometries of the copper ion with the three 5-hydroxyisoflavones were all 1:1 and their chelating power was 3>2>1. Those explained the complexation HSCCC behavior. It is the first report that includes the practical application of complexation HSCCC and explanation of its chromatographic behavior.
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Steroidal alkaloid saponins and steroidal saponins from Solanum surattense.
Phytochemistry
PUBLISHED: 01-12-2011
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A rare 16?-H steroidal alkaloid saponin (1), an avenacoside-type saponin (2), two steroidal saponins (4, 5), one revised-structure steroidal saponin (3) and six known compounds (6-11) were isolated from aerial parts of Solanum surattense Burm. f. Their structures were established on the basis of physical data, as well as by using spectroscopic (HRESIMS, 1D and 2D NMR), and chemical analysis methods. Compounds 1 and 11 showed cytotoxicity against A549 cell line with IC(50) values of 20.3 and 15.7?M, respectively.
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Preparative separation of atropine and scopolamine from Daturae metelis Flos using pH-zone-refining counter-current chromatography with counter-rotation and dual-mode elution procedure.
J Sep Sci
PUBLISHED: 01-10-2011
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To isolate atropine and scopolamine from Daturae metelis Flos, three different elution modes have been applied in pH-zone-refining counter-current chromatography. These separations were performed with a two-phase solvent system composed of ethyl acetate/n-butanol/water (4:1:5? v/v) with 0.50% triethylamine in the organic phase and 0.15% hydrochloric acid in the aqueous phase. As a result, the best separation was obtained by counter-rotation and dual-mode elution procedure. In this new separation mode, the mobile phase and stationary phase were exchanged when the rotation direction was reversed. The two purified alkaloids (purity over 98% as determined by HPLC) were identified by ESI-MS, (1)H-NMR and (13)C-NMR.
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Cytotoxic tirucallane C26 triterpenoids from the stem barks of Aphanamixis grandifolia.
Phytochemistry
PUBLISHED: 03-26-2010
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Five tirucallane type C(26) triterpenoids, accompanied by two known compounds, 3?-hydroxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone and 3-oxo-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, were isolated from the stem barks of Aphanamixis grandifolia. Their structures were established mainly by means of a combination of 1D and 2D NMR spectroscopic and mass spectrometry techniques as 3?-hydroxyl-21?-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3?-hydroxy-21?-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3-oxo-21?-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3-oxo-21?-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, and 3-oxo-21?-ethoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone. All isolates were in vitro evaluated for their cytotoxic activities against five tumor cell lines (MCF-7, HeLa, HepG2, SGC-7901 and BGC-823).
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(+/-)-Praeruptorin A enantiomers exert distinct relaxant effects on isolated rat aorta rings dependent on endothelium and nitric oxide synthesis.
Chem. Biol. Interact.
PUBLISHED: 02-06-2010
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Praeruptorin A is a coumarin compound naturally occurring in the roots of Peucedanum praeruptorum Dunn., a commonly used traditional Chinese medicine for the treatment of certain respiratory diseases and hypertension. Although previous studies indicated the relaxant effects of (+/-)-praeruptorin A on tracheal and arterial preparations, little is known about the functional characteristics of the enantiomers. In the present study, the two enantiomers were successfully isolated and identified by using a preparative Daicel Chiralpak AD-H column, and their relaxant effects on aorta rings were observed and compared. (+)-Praeruptorin A showed more potent relaxation than (-)-praeruptorin A against KCl- and phenylephrine-induced contraction of rat isolated aortic rings with intact endothelium. Removal of the endothelium remarkably reduced the relaxant effect of (+)-praeruptorin A but not that of (-)-praeruptorin A. Pretreatment of aortic rings with N(omega)-nitro-L-arginine methyl ester (L-NAME, an inhibitor of nitric oxide synthase) or methylene blue (MB, a soluble guanylyl cyclase inhibitor) resulted in similar changes of the relaxant effects of the two enantiomers to endothelium removal. Molecular docking studies also demonstrated that (+)-praeruptorin A was in more agreement to nitric oxide synthase pharmacophores than (-)-praeruptorin A. On the other hand, the two enantiomers of praeruptorin A could slightly attenuate the contraction of rat aortic rings induced by internal Ca(2+) release from sarcoplasmic reticulum (SR). These findings indicated that (+)-praeruptorin A and (-)-praeruptorin A exerted distinct relaxant effects on isolated rat aorta rings, which might be mainly attributed to nitric oxide synthesis catalyzed by endothelial nitric oxide synthase.
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[HPLC-ESI-MS(n) analysis of chemical constituents in Semen Ziziphi Spinosae].
Zhongguo Zhong Yao Za Zhi
PUBLISHED: 12-03-2009
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To study on the chemical constituents of effective part of Semen Ziziphi Spinosae.
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Inhibition of human gastric carcinoma cell growth in vitro and in vivo by cladosporol isolated from the paclitaxel-producing strain Alternaria alternata var. monosporus.
Biol. Pharm. Bull.
PUBLISHED: 12-03-2009
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Cladosporol was isolated from the fermentation broth of Alternaria alternata var. monosporus obtained from the inner bark of the yew tree and mutated for many generations. We investigated the antitumor effects of cladosporol in vitro and in vivo. The growth-inhibitory effects of cladosporol in vitro against six human cancer cell lines were examined using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The results showed that cladosporol selectively killed cancer cells and had a significant inhibitory effect on the human gastric carcinoma cell line MGC-803 in a concentration- and time-dependent manner. In vivo, cladosporol also showed antitumor activity in nude mice bearing MGC-803 gastric cancer xenografts. These findings suggest that cladosporol has potentially useful growth inhibitory effects on human gastric carcinoma cell lines.
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[Chemical constituents in the introduced Coleus forskohlii].
Zhongguo Zhong Yao Za Zhi
PUBLISHED: 11-27-2009
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To study the chemical constituents in the introduced Coleus forskohlii.
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Rapid identification of two species of Peucedanum by high-performance liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry.
Nat Prod Commun
PUBLISHED: 09-23-2009
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The fragmentation behaviors of the angular- and linear-type coumarins from Peucedanum praeruptorum Dunn and P. decursivum (Miq.) Maxim were simultaneously investigated by HPLC-DAD/ESI-MS(n). For more structural identification, the fragment ions were analyzed and some possible fragmentation pathways were proposed. Different positions and numbers of the substituent also led to different fragment behaviors. Two types of coumarins from P. praeruptorum and P. decursivum were structurally elucidated by these techniques. In addition, UV spectra were applied to support the MS analysis. This is the first time that the two types of coumarins from herbal extracts have been differentiated by HPLC-DAD/ESI-MS(n). The method further illustrated the importance of the ESI-MS(n) technique in the identification of different types of coumarins and was applied for the rapid differentiation of the two herbs.
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A new steroidal saponin from the dried stems of Asparagus officinalis L.
Fitoterapia
PUBLISHED: 06-24-2009
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Yamogenin II (1), a new steroidal saponin with a unique aglycone moiety, and (25S)-spirostan-5-ene-3beta-ol-3-O-alpha-L-rhamnopyranosyl-(1,2)-[alpha-L-rhamnopyranosyl-(1,4)]-beta-D-glucopyranoside (2), were isolated from the dried stems of Asparagus officinalis L. The structure of 1 was assessed by spectroscopial analysis as (25S)-spirostan-5-ene-3beta,21-diol-3-O-alpha-L-rhamnopyranosyl-(1,2)-[alpha-L-rhamnopyranosyl-(1,4)]-beta-D-glucopyranoside.
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Structure elucidation and complete NMR spectral assignments of new furostanol glycosides from Solanum torvum.
Magn Reson Chem
PUBLISHED: 06-23-2009
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Two new furostanol glycosides, torvosides O (1) and P (2), were isolated from leaves of Solanum torvum. Their structures were completely and unambiguously assigned by one- and two-dimensional NMR techniques ((1)H NMR, (13)C NMR, TOCSY, HSQC, ROESY and HMBC), ESI-MS spectrometry and chemical methods.
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Preparative isolation and purification of anthocyanins from purple sweet potato by high-speed counter-current chromatography.
J Sep Sci
PUBLISHED: 05-30-2009
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High-speed counter-current chromatography (HSCCC) was applied to the preparative isolation and purification of peonidin 3-O-(6-O-(E)-caffeoyl-2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside)-5-O-beta-D-glucoside (1), cyanidin 3-O-(6-O-p-coumaroyl)-beta-D-glucopyranoside (2), peonidin 3-O-(2-O-(6-O-(E)-caffeoyl-beta-D-glucopyranosyl)-6-O-(E)-caffeoyl-beta-D-glucopyranoside)-5-O-beta-D-glucopyranoside (3), peonidin 3-O-(2-O-(6-O-(E)-feruloyl-beta-D-glucopyranosyl)-6-O-(E)-caffeoyl-beta-D-glucopyranoside)-5-O-beta-D-glucopyranoside (4) from purple sweet potato. Separation of crude extracts (200 mg) from the roots of purple sweet potato using methyl tert-butyl ether/n-butanol/acetonitrile/water/trifluoroacetic acid (1:4:1:5:0.01, v/v) as the two-phase solvent system yielded 1 (15 mg), 2 (7 mg), 3 (10 mg), and 4 (12 mg). The purities of 1-4 were 95.5%, 95.0%, 97.8%, and 96.3%, respectively, as determined by HPLC. Compound 2 was isolated from purple sweet potato for the first time. The chemical structures of these components were identified by 1H NMR, 13C NMR and ESI-MS(n).
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Four new steroidal glycosides from Solanum torvum and their cytotoxic activities.
Steroids
PUBLISHED: 03-04-2009
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Two novel C-22 steroidal lactone saponins, namely solanolactosides A, B (1, 2) and two new spirostanol glycosides, namely torvosides M, N (3, 4) were isolated from ethanol extract of aerial parts of Solanum torvum. Their structures were characterized as solanolide 6-O-[alpha-l-rhamnopyranosyl-(1-->3)-O-beta-d-quinovopyranoside] (1), solanolide 6-O-[beta-d-xylopyranosyl-(1-->3)-O-beta-d-quinovopyranoside] (2), yamogenin 3-O-[beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranoside] (3) and neochlorogenin 3-O-[beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranoside] (4) on the basis of spectroscopic analysis. The cytotoxicities of the saponins (1-4) were evaluated in vitro against a panel of human cancer cell lines. Compounds 3 and 4 showed significant cytotoxic activity with the cell lines.
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An application of high-speed counter-current chromatography coupled with electrospray ionization mass spectrometry for separation and online identification of coumarins from Peucedanum praeruptorum Dunn.
J. Chromatogr. B Analyt. Technol. Biomed. Life Sci.
PUBLISHED: 01-16-2009
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A new and systematic application for separation and online identification of coumarins from Peucedanum praeruptorum Dunn by preparative high-speed counter-current chromatography coupled with electrospray ionization multi-stage mass spectrometry (prep-HSCCC/ESI-MS(n)) was established. The procedure of separation was guided by the chromatogram of ion current. The structures of acquisitions were deduced by MS information. The hyphenation between prep-HSCCC/ESI-MS(n) was designed to keep the split ratio from 1:20 to 1:200 exactly. Seven compounds were obtained and two new compounds were detected. It was proved that prep-HSCCC/ESI-MS(n) was an effective method for sensitive detection, rapid identification and separation of natural products.
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Chiral separation, configurational identification and antihypertensive evaluation of (±)-7,8-dihydroxy-3-methyl-isochromanone-4.
Bioorg. Med. Chem. Lett.
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(±)-7,8-Dihydroxy-3-methyl-isochromanone-4 [(±)-XJP] is a natural antihypertensive product contained in banana (Musa sapientum L.) peel. (-)-XJP and (+)-XJP were first obtained by chiral resolution, meanwhile circular dichroism (CD) calculations and chiral synthesis were employed to investigate the absolute configuration. The results indicated that the absolute configuration of (+)-XJP is S-configured and the absolute configuration of (-)-XJP is R-configured. Furthermore, the evaluation of antihypertensive effects in vivo proved that R-(-)-XJP was more potent than S-(+)-XJP and [(±)-XJP].
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Determination of 10 ginsenosides in Panax ginseng of different harvest times based on HPLC fingerprints and principal component analysis.
Nat. Prod. Res.
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A combinative method of HPLC fingerprinting and quantitative determination was successfully applied to monitor dynamic accumulation of ginsenosides in five-year-old Panax ginseng roots from different harvest times. The optimal chromatographic conditions were achieved on a C18 column with gradient elution using acetonitrile and 1?mmol?·?L(-1) KH2PO4 buffer solution at 203?nm. The result indicated that the contents of total ginsenosides showed significant variations, and a decrease tendency appeared in the growth period of the fifth year.
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Screening of radical scavengers in Scutellaria baicalensis using HPLC with diode array and chemiluminescence detection.
J Sep Sci
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Scutellaria baicalensis Georgi is a well-known medical plant widely used as a famous traditional Chinese medicine. It has been reported that S. baicalensis can protect against oxidative stress and possess anti-inflammatory effect. In the present paper, an HPLC-diode array-chemiluminescence detection method for on-line detection was successfully developed to screen antioxidants in complex S. baicalensis extracts. Using the proposed approach, eight compounds in the S. baicalensis extracts were found to possess a potential antioxidant activity. Furthermore, the effects of purified compounds on protecting RAW 264.7 cells from hydrogen peroxide injury were also investigated in vitro to confirm the established method, which were consistent with the results of HPLC-diode array-chemiluminescence detection method. These results demonstrated that this method was a useful technique for rapidly screening and identifying bioactive components from complex herbal medicines.
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Quantitative analysis of four major diterpenoids in Andrographis paniculata by 1H NMR and its application for quality control of commercial preparations.
J Pharm Biomed Anal
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A quantitative proton nuclear magnetic resonance technique (qHNMR) has been successfully introduced to quantify andrographolide, dehydroandrographolide, deoxyandrographolide and neoandrographolide in Andrographis paniculata, a commonly used important traditional Chinese medicine. Creative use of trifluoroacetic acid-d, which satisfactorily resolved the overlapping signals of these compounds in crowded regions of ? 4.5-5.6 ppm in (1)H NMR spectrum, made their quantification possible. Optimization of other experimental conditions, including internal standard, NMR pulse sequence, and NMR relaxation delay time, finally established the (1)H NMR based quantification approach, which was validated with satisfactory accuracy, precision, repeatability, and recovery. Except for deoxyandrographolide and neoandrographolide in two compound recipes, this method was successfully applied to quantify the four major components in fourteen raw herb materials and five commercial preparations, providing quantification results in good agreement with those determined by HPLC. The inherent advantages of qHNMR, such as its rapidity and simplicity, make itself a feasible alternative to HPLC for the quality control of A. paniculata raw material and herbal preparations.
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Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents.
Bioorg. Med. Chem. Lett.
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Ticagrelor (1) is the first reversible P2Y12 receptor antagonist blocking adenine diphosphate (ADP)-induced platelet aggregation with rapid onset and offset of effects. In this study, synthesis of ticagrelor and its derivatives has been accomplished in a convergent way. The compound design was based on modifications of ticagrelor and its major metabolite (33) in order to ameliorate their pharmacokinetic properties and dosing profile. The final compounds (1a-g, 35a-g) were evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats. The assay results showed that some compounds (e.g., 1b, 1d, 33, 35b, 35f) exhibited comparable potency with that of ticagrelor.
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Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor.
Bioorg. Med. Chem. Lett.
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Naftidrofuryl oxalate (Praxilene®, 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (5-HT(2)) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT(2A)) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT(2A) receptor, and the C-2 configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT(2A) receptor that have clinical significance as vasodilators and CNS agents.
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Effects of (±)-praeruptorin A on airway inflammation, airway hyperresponsiveness and NF-?B signaling pathway in a mouse model of allergic airway disease.
Eur. J. Pharmacol.
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The root of Peucedanum praeruptorum Dunn is a traditional Chinese medicine commonly used to treat asthma in China. (±)-praeruptorin A (PA) is the most abundant constituent of P. praeruptorum Dunn, the effects of which on asthma were investigated using a murine model of allergic airway disease. BALB/c mice were sensitized and challenged by ovalbumin to induce airway inflammation. PA was administered intragastrically before every OVA challenge. Airway responsiveness was measured by a lung function analysis system. The number of total leukocytes in bronchoalveolar lavage fluid was counted using a hemocytometer, and differential cell counts were determined using Diff-Quick-stained smears. Histopathology of lung tissue was analyzed by hematoxylin-eosin and Congo red staining. Levels of inflammatory mediators in bronchoalveolar lavage fluid and immunoglobulins in serum were measured by enzyme-linked immunosorbent assay. The expression of pulmonary eotaxin was detected by immunohistochemistry and reverse transcription polymerase chain reaction. The activation of NF-?B was evaluated by electrophoretic mobility shift assay and western blot analysis. Compared with model group, PA significantly reduced airway hyperresponsiveness and airway eosinophilic inflammation, improved pathologic lesion of the lungs, reduced levels of interleukin (IL)-4, IL-5, IL-13 and LTC? in bronchoalveolar lavage fluid and immunoglobulin (Ig) E in serum, and inhibited eotaxin protein and mRNA expression, I?B? degradation, NF-?B nuclear translocation, NF-?B DNA-binding activity and RelA/p65 phosphorylation in lung, which suggested that PA can significantly suppress OVA-induced airway inflammation and airway hyperresponsiveness in mice, showing great therapeutic potential for the treatment of allergic asthma.
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Danggui-Shaoyao-San ameliorates cognition deficits and attenuates oxidative stress-related neuronal apoptosis in d-galactose-induced senescent mice.
J Ethnopharmacol
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Danggui-Shaoyao-San (DSS), a famous traditional Chinese medicine formula consisting of six herbal medicines, has been used to treat gynecological disorders and neural dysfunctions.
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Pd(II)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage.
Chem. Commun. (Camb.)
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The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C-H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance.
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