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 ; Berberine ; Berberine Alkaloids ; Biotransformation ; Coptis

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 ; Berberine ; Berberine Alkaloids ; Coptis ; Drugs, Chinese Herbal ; Isoquinolines ; Rhizome

One of the constituents of the oriental traditional pill named Balok was Tuber Stephaniae rotundae, the active principle of which was rotundine. The test solutions used for the analysis of rotundine were standardized after ISO/IEC 17027 and GLP, the equipment was adjusted after ISO/IEC 17025. The proposed HPLC technique was proved to be appropriate and stable for the quantitative determination of rotundine. The examined concentration showed the linear correlation between the rotundine concentration and the pic surface. The reproducibility of the method was high, with RSD = 0.98%. The accuracy rate of the method was 100.01%, with RSD = 2.0%.
Chromatography, High Pressure Liquid ; Berberine Alkaloids

An HPLC method has been established to determine l-tetrahydropalmatine (rotundine) extracted by chloroform from powders of Stephania viridiflavens, S. dielsiana and Stephania sp. (Menispermaceae). The technique was carried out on an RP-18 (250 x 4.0 mm; 5 m) column with a diode array detector or UV detector at  = 283 nm, using a mixture of 0.05 M potassium dihydrogen phosphate, acetonitrile and triethylamine (62.5 : 37.5 : 0.5) adjusted to pH 4.0 by concentrated phosphoric acid as a mobile phase. The HPLC method proved accurate, specise and sensitive. The results show that differences exist in the content of l-tetrahydropalmatine between species.
Chromatography, High Pressure Liquid ; Berberine Alkaloids

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

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

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

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 ; Medicine, Traditional ; Chromatography, High Pressure Liquid ; Biochemistry ; Berberine Alkaloids

OBJECTIVETo study the absorption characteristics of alkaloids in Coptis chinensis in rat intestinal.

METHODIn situ single-pass perfused rat intestinal model was used and the concentrations of berberine and palmatine were determined by HPLC, the drug absorption rate constant (K(a)) and apparent absorption coefficient (P(app)) were tested to evaluate their absorption characteristics.

RESULTThe absorption of berberine and palmatine in different regions of rat intestinals was significantly different. From bigness to smallness, the P(app) value of berberine at 50 mg x L(-1) were ileum, duodenum, jejunum and colon, of palmatine at 50 mg x L(-1) were ileum, colon, jejunum and duodenum. The concentration of berberine and palmatine had distinctive effect on the K(a) value of berberine and palmatine were ordered from larger to little as in Wujiwan compatibility, Coptis chinensis extractive and single compound.

CONCLUSIONThe berberine and palmatine were absroped at all regions of rat intestinal. The absorption characteristics of 2 alkaloids were not passive diffusion. The other ingredients in Wujiwan compatibility and Coptis chinensis extractive could promote the absorption of alkaloids.

Alkaloids ; pharmacokinetics ; Animals ; Berberine ; pharmacokinetics ; Berberine Alkaloids ; pharmacokinetics ; Coptis ; Intestinal Absorption ; Male ; Perfusion ; Rats ; Rats, Wistar

According to the records of Chinese materia medica,Coptis chinensis var. brevisepala is an authentic Chinese medicinal plant highly recommended by ancient physicians since its rhizome is like a string of beads and has a good medicinal value. However,its medicinal components and values remain to be studied as it is endangered because of overexploitation. Therefore,this study aims to quantitatively determine its effective components based on UPLC-QTOF-MS,and to compare the contents of isoquinoline alkaloids in C.chinensis var. brevisepala with those in other Coptis species. Meanwhile,molecular methods accurately identified 12 batches of C. chinensis var. brevisepala,9 batches of C. chinensis,4 batches of C. deltoidea,and 1 batch of C. teeta. Gradient elution was performed with Waters CORTECS C18 column( 4. 6 mm× 150 mm,2. 7 μm) and the mobile phase acetonitrile-water with 0. 4% formic acid. Mass spectrometry was conducted in ESI positive mode. The quantitative results showed that 8 main alkaloids had a good linear relationship within the concentration range( R~2>0. 996),with the recovery rate of 95. 18%-105. 0% and the RSD of 0. 28%-3. 7%. Compared with that of other Coptis species,the rhizome of C. chinensis var. brevisepala had the highest contents of berberine and columbamine. The total content of the 8 alkaloids in C. chinensis var. brevisepala was similar to that in C. chinensis but higher than that of the other two species. PCA was performed to compare the alkaloids among the 4 species. Besides,the 8 alkaloids were evaluated in different parts of C. chinensis var. brevisepala. The results indicate that this method is reliable and efficient and can provide a reference for the quality research.
Alkaloids ; Berberine Alkaloids ; China ; Coptis ; Drugs, Chinese Herbal/analysis* ; Plants, Medicinal