1.Two new protoberberine alkaloids from Stephania hernandifolia.
Wei-Hua DAI ; Xin-Tao CUI ; Yu-Jiao TU ; Lei JIANG ; Lin YUAN
China Journal of Chinese Materia Medica 2025;50(5):1231-1235
The 95% ethanol extract of Stephania hernandifolia was isolated and purified by column chromatography on silica gel and Sephadex LH-20, RP-18 medium-pressure liquid chromatography, and semi-preparative high performance liquid chromatography. The chemical structures of the compounds were identified by NMR and high-resolution mass spectrometry. Four alkaloids were isolated and identified as(-)-8-oxo-2,3,4,10,11-pentamethoxyberberine(1),(-)-8-oxo-11-hydroxy-2,3,4,10-tetramethoxyberberine(2), N-trans-feruloyl tyramine(3), and N-cis-feruloyl tyramine(4). Compounds 1 and 2 were new protoberberine alkaloids, while compounds 3 and 4 were amide alkaloids. All the four compounds were separated from this plant for the first time. The inhibitory activities of compounds 1, 3, and 4 against α-glycosidase were measured by the enzymatic reaction in vitro with 4-nitrophenyl-α-D-glucopyranoside(PNPG) as the substrate. Compounds 3 and 4 showed inhibitory activities against α-glucosidase, with median inhibition concentration(IC_(50)) values of(7.09±0.42) and(31.25±1.14) μmol·L~(-1), respectively.
Berberine Alkaloids/isolation & purification*
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Stephania/chemistry*
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Drugs, Chinese Herbal/isolation & purification*
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Molecular Structure
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alpha-Glucosidases/metabolism*
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Chromatography, High Pressure Liquid
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Alkaloids/isolation & purification*
2.In vitro transdermal delivery of the active fraction of xiangfusiwu decoction based on principal component analysis.
Zhen-Hao LI ; Pei LIU ; Da-Wei QIAN ; Wei LI ; Er-Xin SHANG ; Jin-Ao DUAN
Acta Pharmaceutica Sinica 2013;48(6):933-939
The objective of the present study was to establish a method based on principal component analysis (PCA) for the study of transdermal delivery of multiple components in Chinese medicine, and to choose the best penetration enhancers for the active fraction of Xiangfusiwu decoction (BW) with this method. Improved Franz diffusion cells with isolated rat abdomen skins were carried out to experiment on the transdermal delivery of six active components, including ferulic acid, paeoniflorin, albiflorin, protopine, tetrahydropalmatine and tetrahydrocolumbamine. The concentrations of these components were determined by LC-MS/MS, then the total factor scores of the concentrations at different times were calculated using PCA and were employed instead of the concentrations to compute the cumulative amounts and steady fluxes, the latter of which were considered as the indexes for optimizing penetration enhancers. The results showed that compared to the control group, the steady fluxes of the other groups increased significantly and furthermore, 4% azone with 1% propylene glycol manifested the best effect. The six components could penetrate through skin well under the action of penetration enhancers. The method established in this study has been proved to be suitable for the study of transdermal delivery of multiple components, and it provided a scientific basis for preparation research of Xiangfusiwu decoction and moreover, it could be a reference for Chinese medicine research.
Administration, Cutaneous
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Alkenes
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pharmacology
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Animals
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Azepines
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pharmacology
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Benzophenanthridines
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isolation & purification
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pharmacokinetics
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Berberine Alkaloids
;
isolation & purification
;
pharmacokinetics
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Bridged-Ring Compounds
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isolation & purification
;
pharmacokinetics
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Coumaric Acids
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isolation & purification
;
pharmacokinetics
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Drug Combinations
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Drug Synergism
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Drugs, Chinese Herbal
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administration & dosage
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chemistry
;
isolation & purification
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pharmacokinetics
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Glucosides
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isolation & purification
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pharmacokinetics
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In Vitro Techniques
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Male
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Monoterpenes
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isolation & purification
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pharmacokinetics
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Permeability
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Plants, Medicinal
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chemistry
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Principal Component Analysis
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Rats
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Rats, Sprague-Dawley
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Skin Absorption
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drug effects
3.Chemical constituents from Corydalis yanhusuo.
Ziming LU ; Wuxing SUN ; Xuhong DUAN ; Zhiyun YANG ; Yadong LIU ; Pengfei TU
China Journal of Chinese Materia Medica 2012;37(2):235-237
OBJECTIVETo investigate the chemical constituents of Corydalis yanhusuo.
METHODThe compounds were isolated and purified by column chromatography over macroporous absorption resin, silica gel, and Sephadex LH-20. Their structures were elucidated on the basis of physicochemical properties and spectral data.
RESULT22 compounds were isolated and identified as corydaline (1), tetrahydropalmatine (2), protopine (3), tetrahydrocorysamine (4), tetrahydrocoptisine (5) , tetrahydroberberine (6), tetrahydrocolumbamine (7), noroxyhydrastine (8), dehydrocorydaline (9), glaucine (10), columbamine (11), 8-oxocoptisine (12), 13-methyl-columbamine (13), coptisine (14), palmatine (15), herberine (16), oxoglaucine (17), 13-methyl-palmatrubine (18), dehydrocorybulbine (19), stepharanine (20), adenosine (21), and N5 -acetylornithine (22).
CONCLUSIONCompounds 13, 20, 21, and 22 were isolated from this plant for the first time.
Adenosine ; analysis ; isolation & purification ; Alkaloids ; analysis ; isolation & purification ; Apomorphine ; analogs & derivatives ; analysis ; isolation & purification ; Aporphines ; analysis ; isolation & purification ; Berberine ; analysis ; isolation & purification ; Berberine Alkaloids ; analysis ; isolation & purification ; Chromatography, Liquid ; methods ; Corydalis ; chemistry ; Plant Extracts ; analysis ; isolation & purification ; Spectrometry, Mass, Electrospray Ionization ; methods
4.Optimization of technology conditions from Ermiao Wan decoction by semi-bionic extraction method.
China Journal of Chinese Materia Medica 2012;37(16):2396-2399
OBJECTIVETo optimize the technology of Ermiao Wan decoction by SBE with uniform design.
METHODUniform design was used to optimize the efficient processing conditions of the SBE for Ermiao Wan decoction according to the content of the berberine, total alkaloids, volatile oil and the yield of the total extract.
RESULTThe extract condition for Ermiao Wan decoction was set up as follow: the pH value of the water was 6.00, 6.50 and 8.7, respectively,and the extract times were 2, 1 and 1 h,respectively.
CONCLUSIONThe optimized extraction condition of the SBE for Ermiao Wan decoction is reasonable.
Alkaloids ; chemistry ; isolation & purification ; Berberine ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Phellodendron ; chemistry ; Technology, Pharmaceutical ; methods
5.Intestinal absorption of different combinations of active compounds from Gegenqinlian decoction by rat single pass intestinal perfusion in situ.
Rui AN ; Hua ZHANG ; Yi-Zhu ZHANG ; Ran-Chi XU ; Xin-Hong WANG
Acta Pharmaceutica Sinica 2012;47(12):1696-1702
The aim is to study the intestinal absorption of different combinations of active compounds out of Gegenqinlian decoction. Rat single pass intestinal perfusion model with jugular vein cannulated was used. Samples were obtained continuously from the outlet perfusate and the mesenteric vein. The levels of puerarin, daidzin, liquilitin, baicalin, wogonoside, jatrorrhizine, berberine and palmatine were determined by LC-MS/MS and their permeability coefficients were calculated. The results showed that Glycyrrhiza could promote the absorption of the active ingredients in Pueraria which is the monarch herb; meanwhile, Pueraria also played a role in promoting the absorption of liquilitin. Based on the Gegenqinlian decoction and the different combinations experiments, the results concerning the absorption of baicalin and wogonoside were as follows. For baicalin, Pueraria and Glycyrrhiza could promote its absorption and the effect of Pueraria was more obvious. For wogonoside, Pueraria could also promote its absorption, while Glycyrrhiza played a opposite role. Pueraria and Glycyrrhiza both played a part in promoting the absorption of jateorhizine, berberine and palmatine, the effective compounds in Coptis.
Animals
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Berberine
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analogs & derivatives
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metabolism
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Berberine Alkaloids
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metabolism
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Coptis
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chemistry
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Drug Combinations
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Drugs, Chinese Herbal
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isolation & purification
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pharmacokinetics
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Flavanones
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metabolism
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Flavonoids
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metabolism
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Glucosides
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metabolism
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Glycyrrhiza
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chemistry
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Intestinal Absorption
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Intestines
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metabolism
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Isoflavones
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metabolism
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Male
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Plant Roots
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chemistry
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Plants, Medicinal
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chemistry
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Pueraria
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chemistry
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Rats
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Rats, Sprague-Dawley
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Rhizome
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chemistry
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Scutellaria baicalensis
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chemistry
6.Preliminary study to investigate dynamic extract process of Huanglian Jiedu Tang and the mechanism of subsidence produce.
Linmei PAN ; Jia FU ; Huaxu ZHU ; Liwei GUO
China Journal of Chinese Materia Medica 2010;35(1):40-43
OBJECTIVETo study the phenomenon of subsidence emergence in the process of Huanglian Jiedu Tang decoction extraction, and the mechanism of subsidence emergence.
METHODUV was applied to determine the concentration of total alkaloids and total flavones; Simultaneous determination of berberine, jatrorrhizine, palmatine, baicalin and geniposide were carried out by HPLC; The solid holdup and precipitation rate were calculated by the formula. The relativity among these parameters was analyzed by the SPSS software program.
RESULTThe contains of berberine, jatrorrhizine, palmatine in total alkaloids showed a good correlation with total alkaloids. The correlation between baicalin and total flavones was lower than that between geniposide and total flavones. Compared to precipitation rate, solided hold up shows a larger relevance with index component
CONCLUSIONWith the change of time, the total alkaloids represented by berberine alkaloids and baicalin at a certain concentration can be regarded as the equilibrium point, or one generated by the critical point of precipitation, the reaction can generate "sediments"; because "precipitation objects" generated, reducing the concentration of the above-mentioned components, destroy the" balance". The relevant components of herbal medicine increased dissolution rate, at the same time might partly dissolved sediment, reaching a new equilibrium state.
Alkaloids ; isolation & purification ; Berberine ; analogs & derivatives ; isolation & purification ; Berberine Alkaloids ; isolation & purification ; Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; chemistry ; Flavones ; isolation & purification ; Flavonoids ; isolation & purification ; Fractional Precipitation ; Iridoids ; isolation & purification ; Plants, Medicinal ; chemistry
7.Simultaneous determination of six alkaloids in Coptis chinensis of different regions by RP-HPLC.
Zhipeng GENG ; Haijie ZHENG ; Yi ZHANG ; Weizao LUO ; Xianyou QU
China Journal of Chinese Materia Medica 2010;35(19):2576-2580
A reversed-phase HPLC method for simultaneous determination of gatrorrhizine, columbamine, epiberberine, coptisine, palmatine and berberine in Coptis chinensis was developed. Analysis was carried out on an Xtimate C18 column (4.6 mm x 250 mm, 5 microm) eluted with acetonitrile-30 mmol x L(-1) ammonium bicarbonate solution (including 0.7% ammonia and 0.1% triethylamine) by gradient elution. The detective wavelength was 270 nm, the column temperature was 30 degrees C, and the flow rate was 1.0 mL x min(-1). By the above method, the linear ranges of gatrorrhizine, columbamine, epiberberine, coptisine, palmatine and berberine were 0.85-16.96 (r = 0.9997), 1.25-24.96 (r = 0.999 5), 2.05-40.96 (r = 0.999 9), 3.65-72.96 (r = 0.999 9), 2.88-57.60 (r = 0. 999 8),13.25-264.96 mg x L(-1) (r = 0.999 6), respectively. The average recoveries (n = 6) of the six alkaloids were 101.6% (RSD 1.3%),102.5% (RSD 1.5%), 100.8% (RSD 1.9%),102. 6% (RSD 1.2%), 97.80% (RSD 1.3%), 99.01% (RSD 1.5%), respectively. The determined results demonstrate that there is a significant difference in the contents of six alkaloids and total alkaloids among the tested samples. The method is accurate, reliable and repeatable for simultaneous determination of gatrorrhizine, columbamine, epiberberine, coptisine, palmatine and berberine in C. chinensis.
Alkaloids
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isolation & purification
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Berberine
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analogs & derivatives
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isolation & purification
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pharmacology
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therapeutic use
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Berberine Alkaloids
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isolation & purification
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Chromatography, High Pressure Liquid
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methods
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Coptis
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chemistry
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Drugs, Chinese Herbal
8.Pharmacokinetic studies of tetrahydropalmatine and dehydrocorydaline in rat after oral administration of yanhusuo extraction by LC-MS/MS method.
Li LIN ; Jian-Xun LIU ; Ying ZHANG ; Cheng-Ren LIN ; Chang-Ling DUAN
Acta Pharmaceutica Sinica 2008;43(11):1123-1127
A sensitive liquid chromatography-tandem mass spectrometric (LC-MS/MS) method was developed and validated for the quantification of tetrahydropalmatine (THP) and dehydrocorydaline (DHC) in rat plasma. The compounds were simply pretreated by protein precipitation using acetone. Chromatographic separation was achieved on a reversed-phase SB-C18 column with the mobile phase of acetonitrile-ammonium acetate (0. 1% acetic acid) and step gradient elution resulted at a flow rate of 0.80 mL x min(-1). A tandem mass spectrometer equipped with electrospray ionization source was used as detector and operated in the positive ion mode. Quantification was performed using multiple reaction monitoring (MRM) of the transitions m/z 356. 2 --> m/z 191.9 and m/z 366. 2 --> m/z 350.2 for THP and DHC respectively. The method showed excellent linearity over the concentration range 1-1 000 ng x mL(-1) of two components (r = 0.994 for THP and r = 0.992 for DHC). The low limits of quantification were both 1 ng x mL(-1). The extract recoveries of analytes were from 71.71% to 91.59% for THP and from 83.27% to 103.15% for DHC. The precisions, the accuracy and the stability of the analytes meet the requirements. The method was applied to a pharmacokinetic study of THP and DHC after oral administration of the total alkaloid extraction of Rhizoma Corydalis (Yanhusuo). The AUC were (1.90 +/- 0.04), (2.58 +/- 0.08) and (4.34 +/- 0.19) mg x L(-1) h for low, medium and high doses of THP, respectively. While the DHC concentrations in plasma of low dose and medium dose were too lower to be detected, the AUC of high dose was (0.0896 +/- 0.0002) mg x L(-1) h.
Administration, Oral
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Alkaloids
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administration & dosage
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blood
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isolation & purification
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metabolism
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pharmacokinetics
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Animals
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Area Under Curve
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Berberine Alkaloids
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blood
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pharmacokinetics
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Chromatography, Liquid
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Corydalis
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chemistry
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Male
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Plants, Medicinal
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chemistry
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Random Allocation
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Rats
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Rats, Wistar
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Spectrometry, Mass, Electrospray Ionization
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Tandem Mass Spectrometry
9.Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS.
Ya-Ting DENG ; Qiong-Feng LIAO ; Kai-Shun BI ; Mei-Cun YAO ; Xiao-fei JIANG ; Zhi-Yong XIE
Acta Pharmaceutica Sinica 2008;43(3):299-302
A comprehensive HPLC-DAD-MS method was developed to study the chemical components of semi-bionic extract of Coptis-Evodia herb couple. The extract was isolated on a Hypersil BDS C18 column (4.6 mm x 200 mm, 5 microm) using acetonitrile-ammonium formic buffer as mobile phase by gradient elution. Detection was performed on DAD and MS equipped with an electrospray ionization (ESI) source by full scan and product full scan on positive mode. The chromatogram of Coptis-Evodia showed seventeen main peaks, eight of which were from Evodia while the others were from Coptis. By comparison of the retention time, the on-line UV spectra and MS spectra, four peaks were identified as jatrorrhizine, hydroxevodiamine, palmatine and berberine, and three peaks were deduced as epiberberine, columbamine and coptisine. In addition, berberine and palmatine were quantitatively determined. No new component was created in the semi-bionic extract of the herb couple, yet the solubilities of berberine and palmatine decreased.
Berberine
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analogs & derivatives
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chemistry
;
isolation & purification
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Berberine Alkaloids
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chemistry
;
isolation & purification
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Chromatography, High Pressure Liquid
;
methods
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Coptis
;
chemistry
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Drugs, Chinese Herbal
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Evodia
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chemistry
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Plant Extracts
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chemistry
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Spectrometry, Mass, Electrospray Ionization
10.Optimal extraction of Dingxiang jiangqi granules.
Li-Hong ZHANG ; Yan FU ; Zhi-Rong ZHANG ; Jian-Xin WANG ; Shu-Ying MA ; Sheng-Liang ZHU
China Journal of Chinese Materia Medica 2007;32(21):2252-2255
OBJECTIVETo screen and optimize the extraction of Dingxiangjiangqi granules.
METHODThe extraction route was screened by using pharmacodynamic experiment and the extraction conditions were optimized by orthogonal design and taking extract yield, content of naringin and tetrahydropalmatine as indexes.
RESULTThe pharmacodynamic result showed that aqueous extract had the best effect to cure the esophagitis of rats and the optimized extraction technique was adding 12 times water, extracting 0. 5 hour for 3 times.
CONCLUSIONThe optimum extraction was simple, reasonable, stable and useful for further development.
Animals ; Berberine Alkaloids ; analysis ; Drug Combinations ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; Esophagitis, Peptic ; drug therapy ; pathology ; Esophagus ; drug effects ; pathology ; Flavanones ; analysis ; Male ; Phytotherapy ; Plants, Medicinal ; chemistry ; Random Allocation ; Rats ; Rats, Sprague-Dawley ; Syzygium ; chemistry ; Technology, Pharmaceutical ; methods

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