1.Five alkaloids from vine stems of Diploclisia affinis.
En-Jun WANG ; Yun-Bao MA ; Xue-Mei ZHANG ; Zhi-Yong JIANG ; Ji-Jun CHEN
China Journal of Chinese Materia Medica 2008;33(21):2503-2505
OBJECTIVETo study alkaloid constituents of Diploclisia affinis.
METHODThe air-dried vine stems of D. affinis were extracted with 90% EtOH three times at room temperature. The EtOH extract was suspended in H2 O and adjusted to pH 2 with 5% HCl solution. After extracted with petroleum ether and CHCl3 successively, the aqueous fraction was adjusted to pH 9 with 10% NH3 x H2O and extracted with CHCl3 again to afford the total alkaloids fraction. The compounds were isolated through column chromatography from the total alkaloids fraction. Their structures were determined on the basis of spectral analysis (MS, 1H-NMR, 13C-NMR).
RESULTFive alkaloids was identified as reticuline (1), asimilobine (2), acutumine (3), dihydroxyprotoberberine (4), stepholidine (5), were isolated from the vine stems of D. affinis.
CONCLUSIONAll the compounds were obtained from D. affinis for the first time.
Alkaloids ; chemistry ; Aporphines ; chemistry ; Benzylisoquinolines ; chemistry ; Berberine ; analogs & derivatives ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Ethanol ; chemistry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Menispermaceae ; chemistry ; Plant Stems ; chemistry ; Spiro Compounds ; chemistry
2.Determination of four alkaloids in Berberis plants by HPLC.
Duo-long DI ; Ye-wei LIU ; Zhi-gang MA ; Sheng-xiang JIANG
China Journal of Chinese Materia Medica 2003;28(12):1132-1134
OBJECTIVEIn order to assess Berberis, a simple and effective high-performance liquid chromatographic (HPLC) method was established.
METHODBy applying HPLC with gradiation elution, this method was developed for determination of four kinds of alkaloids including berbamine, Jatrorrhizine, berberine and palmatine in methanolic extracts from root bark, root, stem bark and stem of Berberis.
RESULTThe alkaloids berbamine, jatrorrhizine, berberine and palmatine shown good linear correlations in the range of 0.028-4.74 microg (r = 0.9998); 0.012-2.0 microg (r = 0.9996); 0.026-0.52 microg (r = 0.9999); 0.015-2.56 microg (r = 0.9998), respectively. The correlation coefficients of the calibration curve for the analytes exceeded 0.9998.
CONCLUSIONThe optimized HPLC method was applied to analyze various samples, and the results shown that the content of alkaloids were obvious difference in Berberis from different area, different species and different parts.
Alkaloids ; analysis ; Benzylisoquinolines ; analysis ; Berberine ; analogs & derivatives ; analysis ; Berberine Alkaloids ; analysis ; Berberis ; chemistry ; classification ; China ; Chromatography, High Pressure Liquid ; methods ; Ecosystem ; Plant Bark ; chemistry ; Plant Roots ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; classification ; Species Specificity
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.The interference in correlated molecular mechanism obtained multi-drug resistance of mouse S180's tumour cell for different alkaloid.
Gui-hai LI ; Cheng-ye PAN ; Fu-jun SUN ; Ge-ping YIN ; Xue-rong WANG
China Journal of Chinese Materia Medica 2005;30(23):1844-1848
OBJECTIVETo observe the base of the interference in correlated biotic active matter obtained multi-drug resistance induced by chemotherapy for different alkaloid, and to supervise the use in clinic to restrain the multi-drug resistant of chemotherapy, and thereby to improve the curative effect.
METHODAfter bestowing subter-dosage unite chemotherapeutant to ascites S180 mouse to set up the mouse models of multi-drug resistance of S180 tumour cell, and giving the mouse matrine, terandrine, oxymatrine and berberine hydrooh loride for 4 weeks, the P170, LRP, TOPOII, Fas and apoposis were determined by flow cytometry.
RESULTMatrine and terandrine could obviously reduce the express of P170, LRP and the activation of TOPOII, and increase the ratio of the express of Fas and the apoposis of drug resistant tumour cell. And at the same time it could obviously reduce the express of intercellular adhesion molecule(CD54).
CONCLUSIONMatrine and terandrine can interfere in MDR which results from chemotherapeutics by the adjustment of correlated biotic active matter, besides, the different degree of alkaloid effect with different configuration.
ATP-Binding Cassette, Sub-Family B, Member 1 ; metabolism ; Alkaloids ; isolation & purification ; pharmacology ; Animals ; Apoptosis ; drug effects ; Benzylisoquinolines ; isolation & purification ; pharmacology ; Berberine Alkaloids ; isolation & purification ; pharmacology ; DNA Topoisomerases, Type II ; metabolism ; Drug Resistance, Multiple ; Drug Resistance, Neoplasm ; Female ; Male ; Mice ; Plants, Medicinal ; chemistry ; Quinolizines ; isolation & purification ; pharmacology ; Random Allocation ; Sarcoma 180 ; metabolism ; pathology ; Tumor Cells, Cultured ; Vault Ribonucleoprotein Particles ; metabolism ; fas Receptor ; metabolism
5.Resource investigation and quality evaluation on wild Corydalis yanhusuo.
Xiang-hong XU ; Guo-dian YU ; Zheng-tao WANG
China Journal of Chinese Materia Medica 2004;29(5):399-401
OBJECTIVETo study the resource and the quality of wild Corydalis yanhusuo distributed in China.
METHODDistribution was observed and samples of wild C. yanhusuo were collected and qualities were evaluated by determining six main alkaloids contained in the samples.
RESULTThe main distribution of wild Corydalis yanhusuo was in the hills around middle and lower reaches of Yangtze River. Its distributive areas were continuously decreasing. The alkaloids contents in the samples varied among different populations.
CONCLUSIONThe alkaloids contents in wild populations of C. yanhusuo are diverse. The main kinds of alkaloids in some wild populations are higher than cultivated ones, which are valuable for breeding. The wild C. yanhusuo propagate well, however they are endangered due to environment problem, and should be protected.
Aporphines ; analysis ; Berberine Alkaloids ; analysis ; China ; Conservation of Natural Resources ; Corydalis ; chemistry ; Ecosystem ; Pharmacognosy ; Plants, Medicinal ; chemistry ; Quality Control ; Rhizome ; chemistry
6.Determination of protopine and isocorydine in root of Dactylicapnos scandens by HPLC.
Tian-qing YAN ; Yan-fang YANG ; Tie-min AI
China Journal of Chinese Materia Medica 2004;29(10):961-963
OBJECTIVETo establish a HPLC method for determination of protopine and isocorydine in root of Dactylicapnos scandens.
METHODThe separation was performed in a PHENOMENEX-C18 column with a mobile phase of methanol-0.2% phosphoric acid (adjusted to pH 7.0 with triethylamine)(50:50), The detection wavelength was at 254 nm and the flow rate was 0.8 mL x min(-1).
RESULTThe average recovery of Protopine and Isocorydine was 97.9%, 98.6% respectively, and RSD 1.3%, 1.4%.
CONCLUSIONThis method is accurate, simple and reliable. It can be used for quality control of D. scandens.
Aporphines ; analysis ; Benzophenanthridines ; Berberine Alkaloids ; analysis ; Chromatography, High Pressure Liquid ; Papaveraceae ; chemistry ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Quality Control
7.Biotransformation and enzymatic mechanism of protoberberine alkaloids.
Shou-Hao ZHENG ; Guo-Jian LIAO ; Chang-Hua HU
China Journal of Chinese Materia Medica 2020;45(24):5884-5889
Protoberberine alkaloids belong to the quaternary ammonium isoquinoline alkaloids, and are the main active ingredients in traditional Chinese herbal medicines, like Coptis chinensis. They have been widely used to treat such diseases as gastroenteritis, intestinal infections, and conjunctivitis. Studies have shown that structural modification of the protoberberine alkaloids could produce derivative compounds with new pharmacological effects and biological activities, but the transformation mechanism is not clear yet. This article mainly summarizes the researches on the biotransformation and structure modification of protoberberine alkaloids mainly based on berberine, so as to provide background basis and new ideas for studies relating to the mechanism of protoberberine alkaloids and the pharmacological activity and application of new compounds.
Alkaloids
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Berberine
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Berberine Alkaloids
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Biotransformation
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Coptis
8.Research progress on medicinal resources of Coptis and its isoquinoline alkaloids.
An-Qi WANG ; Qing-Jun YUAN ; Ning GUO ; Bin YANG ; Yi SUN
China Journal of Chinese Materia Medica 2021;46(14):3504-3513
Coptidis Rhizoma is a common Chinese medicinal in clinical practice,with the effects of clearing heat,drying dampness,purging fire,and removing toxin. All the medicinal plants of Coptis can be used for clinical treatment,but some species are endangered due to resource destruction and difficulty in planting. The dominant medicinal components in Coptidis Rhizoma are isoquinoline alkaloids. There are various methods for the analysis and detection of alkaloids,such as LC-MS,HPLC,and TLC,among which LC-MS is the most widely applied. Different plants of Coptis vary in the kind and content of alkaloids. C. chinensis,C. deltoidea,C. teeta,C. chinensis var. brevisepala,C. omeiensis,C. quinquefolia,and C. quinquesecta mainly contain berberine,palmatine,coptisine,jatrorrhizine,and columbamine,five effective alkaloid components. Plant isoquinoline alkaloids( PIAs) have strong pharmacological activity but are difficult to prepare. The application of synthetic biology of PIAs will be helpful for the clinical application of PIAs. This paper reviews the research progress on biological resources of Coptis species and structures of alkaloids as well as analysis methods and synthetic biology for isoquinoline alkaloids in the medicinal plants of Coptis in recent years,which will facilitate the protection of Coptis medicinal resources and the application and development of alkaloids.
Alkaloids
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Berberine
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Berberine Alkaloids
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Coptis
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Drugs, Chinese Herbal
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Isoquinolines
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Rhizome
9.Absorption of papaverine, laudanosine and cepharanthine across human intestine by using human Caco-2 cells monolayers model.
Acta Pharmaceutica Sinica 2008;43(2):202-207
Absorption of papaverine (PAP), laudanosine (LAU) and cepharanthine (CEP) as some chemical constituents of traditional Chinese medicines in human intestine were studied. By using Caco-2 (the human colonic adenocarcinoma cell lines) cell monolayers as an intestinal epithelial cell model, the permeability of PAP, LAU and CEP were studied from apical side (AP side) to basolateral side (BL side) or from BL side to AP side. The three alkaloids were measured by reversed-phase high-performance liquid chromatography coupled with UV detector. Transport parameters and apparent permeability coefficients (Papp) were then calculated and compared with those of propranolol as a control substance of high permeability and atenolol as a control substance of poor permeability. The Papp values of PAP, LAU and CEP were (3.524+/-0.223) x 10(-5), (2.821+/-0.050) x 10(-5) and (6.524+/-0.052) x 10(-5) cm s(-1) from AP side to BL side, and (5.095+/-0.508) x 10(-5), (2.646+/-0.146) x 10(-5) and (5.495+/-0.036) x 10(-5) cm s(-1) from BL side to AP side, respectively. Their Papp values were identical with those of propranolol, which is a transcellular transport marker. On the other hand, the efflux transport of PAP was 1.45 times higher than its influx transport with 0.69 rate of P(app A-->B)/P(app B-->A). But P(app A-->B)/P(app B-->A) values of LAU and CEP were 1.07 and 1.19, respectively, which suggested that the efflux transport have not been involved in their absorbed mechanism in Caco-2 cells monolayers. There is a good correlation between the Papp value and apparent distribution coefficient (Log D) at pH 7.35 for the three alkaloids. PAP, LAU and CEP can be absorbed across intestinal epithelial cells, and they are completely absorbed compounds. PAP may have been involved in efflux mechanism in Caco-2 cells monolayers model from the basolateral-to-apical direction. The O/W (oil/water) partition coefficient plays key role in their transmembrane permeation.
Benzylisoquinolines
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analysis
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isolation & purification
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pharmacokinetics
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Biological Transport
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Caco-2 Cells
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Cell Membrane Permeability
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Chromatography, High Pressure Liquid
;
methods
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Epithelial Cells
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metabolism
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Humans
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Intestinal Absorption
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Isoquinolines
;
analysis
;
isolation & purification
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pharmacokinetics
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Papaverine
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analysis
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isolation & purification
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pharmacokinetics
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Plants, Medicinal
;
chemistry
10.Simultaneous Determination of Berberine and Palmatine in “Huong Lien Hoan” by HPLC
Journal of Medicinal Materials - Hanoi 2003;8(2):45-49
Berberine and Palmatine were extracted from the powdered Huong Lien pills with a mixture of methanol and hydrochloric acid (100:1) and subjected to HPLC to simultaneously determine the alkaloids. The HPLC technique was carried out on a Lichrosorb RP-8 (10 m, 250x4 mm) column using a UV detector at =345 nm and a mixture of 3,4g potassium dihydrogen phosphate and 1,7g sodium lauryl sulfate dissolved in 1000 ml of water-acetonitrile (1:1) as a mobile phase. The experimental results proved that the proposed HPLC method was rapid, specific, accurate and precise.
Berberine
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Medicine, Traditional
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Chromatography, High Pressure Liquid
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Biochemistry
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Berberine Alkaloids