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Authors: Jianbo Li, Yujie Hu, Yajin Wu, Tiantian Feng, Congcong Wen and Xiajuan Jiang

[ 1–3 ]. One example is palmatine, which is a compound with good water solubility, extracted from Coptis chinensis, Fibraurea recisa Pierre, Cortex Phellodendri, Chinensis [ 4–7 ]. Palmatine has good antibacterial activity and is mainly used for the

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Authors: Yumei Han, Dan Yan, Yanling Zhao, Cheng Peng and Xiaohe Xiao

toxicants [ 14 , 18 , 19 ]. Rhizoma Coptidis contains protoberberine alkaloids (PAs, e.g., berberine, coptisine, palmatine, and jateorhizine), and has been used for thousands of years for the treatment of dysentery, arrhythmia, diabetes

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Abstract  

The inhibitory effects of three berberine alkaloids (BAs) from Coptis chinensis Franch on Bifidobacterium adolescentis growth were investigated by microcalorimetry. The growth rate constant (k) and maximum heat-output power (Pmax) decreased and peak time of maximum heat-output power (tp) prolonged with the increase of BAs concentration. Half inhibitory ratios (IC50) BAs were respectively 790.3 (berberine), 339.6 (coptisine) and 229.8 μL−1 (palmatine), which indicated the sequence of their antimicrobial activity: berberine<coptisine<palmatine. Combined with previous findings, the sequence which could show the bioactivity of Bacillus shigae and Escherichia coli was: berberine>coptisine>palmatine. The structure-function relationship of BAs indicated that the functional group methylenedioxy or methoxyl at C2 and C3 might be the major group inducing the activities of BAs on E. coli and B. adolescentis. Meanwhile, the substituent groups at C2, C3, C9 and C10 almost had equal effect on B. shigae.

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A simple and inexpensive two-dimensional thin-layer chromatography (2D-TLC) method was applied with mobile phase containing ionic liquid (IL) for the separation of ten components of a mixture of isoquinoline alkaloids such as allocryptopine (A), berberine (Be), boldine (Bo), chelidonine (Ch), papaverine (Pa), emetine (E), columbamine (Col), magnoflorine (M), palmatine (Pal), and coptisine (Cop). Separation of the alkaloid mixture was achieved by 2D-TLC using an aqueous mobile phase (RP) in the first dimension (80% methanol—water–0.05 M L−1 diethylamine) and a normal phase (NP) in the second dimension (75% methanol [MeOH], 24.75% ethyl methyl ketone–0.25% IL (1-butyl-3-methylimidazolium tetrafluoroborate) (v/v) on bilayer Multi-K CS5 plates. The procedure was evaluated in terms of natural samples analysis. Coptisine, palmatine, and berberine were identified in Rhizoma Coptidis (Huang Lian) extract. Additionally, the alkaloids in the extract sample were confirmed by high-performance liquid chromatography–diode-array detection (HPLC—DAD) method with application of a Synergi Polar RP column and a mobile phase consisting of a mixture of 25% acetonitrile (MeCN), 0.25% IL (1-butyl-3-methylimidazolium tetrafluoroborate), and 74.75% water (v/v). The composition of the mobile phases was optimized in terms of retention, separation selectivity, spots symmetry, and system efficiency. Limits of detection (LODs) were from 0.10 and 0.13 μg mL−1 and limits of quantification (LOQs) between 0.31 and 0.41 μg mL−1.

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Summary

As a new form of traditional Chinese medicine (TCM), Zuojin pill extract is made containing Coptidis rhizoma (the rhizome of Coptis chinesis Franch. [Ranunculaceae]) and Euodiae fructus (the unripe fruit of Euodia rutaecarpa [Juss.] Benth. [Rutaceae]) at the ratio of 6:1 (w/w) and has been most widely used in TCM to treat gastro-intestinal disorders. However, the quality control is insufficient. For establishing an analysis method for the effective quality control of Zuojin pill extract, the active components of three protoberberine alkaloids (coptisine, palmatine, berberine, components from C. rhizoma) and two indolequinoline alkaloids (evodiamine, rutaecarpine, components from E. fructus) in Zuojin pill extract were determined simultaneously by high-performance liquid chromatography. Chromatographic separations were performed on an Inertsil ODS-3 column (4.6 mm × 250 mm, 5 μm). Elution was carried out at 25°C under isocratic conditions by using 25 mmol L−1 KH2PO4-25 mmol L−1 SDS-acetonitrile (1:1:2, v/v/v, adjusted pH to 3.0 using phosphoric acid) as a mobile phase with a flow rate of 0.5 mL min−1. Detection wavelength was set at 264 nm. Good linearity was obtained with correlation coefficient higher than 0.999 for all the analytes over the investigated concentration ranges. Three batches of Zuojin pill extract were successfully analyzed. The average percentages of coptisine, palmatine, berberine, evodiamine, and rutaecarpine in Zuojin pill extract were 5.35%, 3.92%, 16.64%, 0.03%, and 0.03%, respectively. Consequently, these protoberberine and indolequinoline alkaloids could be identified and determined easily by the established high-performance liquid chromatography (HPLC) method which can be used to evaluate and control the quality of Zuojin pill extract.

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In this study, authors propose a simple and cost-effective two-dimensional thin-layer chromatography (2D-TLC) method for the simultaneous determination of eleven standards alkaloids: allocryptopine (A), berberine (Be), boldine (Bo), chelidonine (Ch), glaucine (G), papaverine (Pa), emetine (E), columbamine (Col), magnoflorine (M), palmatine (Pal), and coptisine (Cop). Separation of the alkaloid mixture was achieved by 2D-TLC using an aqueous mobile phase (RP) in the first dimension (80% methanol + water + 0.05 mL−1 diethylamine) and a normal phase (NP) in the second dimension (18% methanol, 18% acetone in 63% diisopropyl ether containing 1% ammonia, v/v) on bilayer Multi-K CS5 plates. The composition of the mobile phases was optimized in terms of retention, separation selectivity, spots symmetry, and system efficiency. The procedure was evaluated in terms of natural samples analysis. Magnoflorine and berberine were identified in Thalictrum foetidum root extract. Additionally, the alkaloids in the extract sample were confirmed by high-performance liquid chromatography—diode-array detection method.

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Authors: Gui-Hua Gu, Da-Jian Yang, Shi-Yun Wang, Wei Zeng, Wei Wang and Jing-Song Yuan

A high-performance liquid chromatography—diode-array detection method was developed and validated to determine simultaneously eleven major alkaloids in Corydalis decumbens (Thunb.) Pers. The alkaloids detected were corlumidine, protopine, coptisine, tetrahydrojatrorrhizine, palmatine, berberine, sanguinarine, papaverine hydrochloride, tetrahydropalmatine, bicuculline, and corydaline. Chromatographic separation was achieved using a C-18 column with a mobile phase composed of A (0.2% acetic acid solution, adjusted with triethylamine to pH 5.0) and B (acetonitrile), with stepwise gradient elution. Ultraviolet diode-array detection was used; chromatograms were examined at the wavelength of 280 nm. The regression equations showed a good linear relationship between the peak area of each marker and concentration (r = 0.9994–0.9999). The recovery values ranged between 93.66% and 100.54%. The method was fully validated with respect to detection and quantification limits, precision, reproducibility, and accuracy. The described high-performance liquid chromatography (HPLC) method was successfully used for the differentiation and quantification of the eleven major alkaloids in C. decumbens (Thunb.) Pers. and can be considered an effective procedure for the analyses of this important class of natural compounds.

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alkaloids, e.g., fangchinoline and tetrandrine in Stephania tetrandra [ 9 ], jatrorrhizine, palmatine, and berberine in Huangbo, the dried bark of Chinese Corktree [ 10 ]. ILs were also applied for analysis of some basic drugs such as β-blockers [ 11 ] and

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