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15 July 2010, Volume 19 Issue 4

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Journal of Chinese Pharmaceutical Sciences

2010, 19(4):  239-242. 

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Full Papers

HPLC fingerprinting and quantification of gentiopicroside and loganic acid in Gentianae Macrophyllae Radix crude drugs

Xiao-Qing Ma, Wei-Feng Deng, Dong-Hui Yang^*, Guang-Xue Liu, Hao Hong,
Kuang-Nam Paek, Shao-Qing Cai

2010, 19(4):  243-250. 

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HPLC fingerprinting and quantification of gentiopicroside (GPS) and loganic acid (LA) in Gentianae Macrophyllae Radix (GMR) crude drugs were developed in this study. The samples were separated on Zorbax SB-C18 column (250 mm×4.6 mm, 5 μm) with a linear gradient of acetonitrile and 0.04% phosphoric acid. The HPLC flow rate was 1.0 mL/min and a UV absorption was measured at 230 nm. An orthogonal L9 (3⁴) test was applied for the optimization of sample extraction conditions, and an aliquot of GMR sample (g) was extracted with 15-fold of 50% ethanol (mL) for 30 min by sonication. Quantitative analysis showed that the content of GPS (14.05 mg/g-74.61 mg/g) in all samples was obviously higher than that of LA (1.13 mg/g-40.46 mg/g). Based on the content ratio of GPS over LA (1.8-11.4), samples originated from Gentiana macrophylla (with content ratio of GPS over LA ≤4.3) could be distinguished from those from G. dahurica and G. dahurica var. gracilipes (with content ratio of GPS over LA ≥4.8). The principle components analysis of the HPLC fingerprints showed that samples originated from G. macrophylla and G. dahurica (including G. dahurica var. gracilipes) could be divided into two groups. This established HPLC-DAD method could be efficiently used for the species identification and quality control of GMR crude drugs.

Butyrolactones, inhibitors of 5-lipoxygenase from fungal metabolites

Fu-Sheng Wang, Ai-Bing Ke, Jing-Tong Zhu, Ye-Ying Li, Xin-Hua Lu, Zhi-Hui Zheng, Hua Zhang, Ying Ma, Xiao Ren, Ya-Ting Wang, Bao-Hua Zhao^*

2010, 19(4):  251-255. 

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In our ongoing search for new inhibitors of 5-lipoxygenase (5-LOX) from microbial resources, Aspergillus F06Z-509 was found to produce active components. Three active compounds named F06Z-509-A, B and C were obtained and identified as butyrolactone II, I and III by NMR and MS data analyses. They showed inhibitory activity against 5-LOX with IC50 of 21.43, 22.51 and 11.83 μg/mL, respectively. Butyrolactones are shown to be inhibitors of 5-LOX for the first time.

Phenolic glucopyranosides from the Chinese mangrove plant Excoecaria agallocha L.

Yong-Xin Li, Xia Yu, Shan-Jiang Yu, Ai-Ying Ma, Zhi-Wei Deng, Wen-Han Lin^*

2010, 19(4):  256-259. 

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Chemical examination of a Chinese mangrove plant Excoecaria agallocha L. led to the isolations of a new glucoside named 1-(3,5-dimethoxy-4-hydroxybenzyl)-6-O-galloyl-1-O-β-D-glucopyranoside (1), together with 10 known glycosides including 3,5-dimethoxy-4-hydroxybenzyl-1-O-β-D-glucopyranoside (2), hydrangeifolin I (3), (2-methoxy-5-hydroxymethyl-phenyl)-1-O-β-D-(6-O-galloyl) glucopyranoside (4), (3,5-dimethoxy-4-hydroxyphenyl)-1-O-β-D-(6-O-galloyl) glucopyranoside (5), 3-methoxy-4-hydroxyphenyl 1-O-β-D-(6-O-galloyl) glucopyranoside (6), 3,4,5-trimethoxyphenyl-(6-O-galloyl)-O-β-D-glucopyranoside (7), koaburaside (8), koaburaside monomethyl ether (9), cuneatasides D (10), and (E)-isosyringin (11). Their structures were determined through the extensive spectroscopic analysis and comparison with the reported data in literature. Compounds 2-6, 8-11 were isolated from the genus Excoecaria for the first time.

Enantiomers separation using avidin-liposome complex as a chiral selector in capillary electrophoresis

Yiming·Gahafu, Xin Chen, Li-Ying Zheng, Qi-Lei Yin, Rui-Rui He, Xian-Wang Zhan, Yao-Xin Wang, Xi-Hui He, Nan-Yin Han^*

2010, 19(4):  260-270. 

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Avidin-liposome complex is a specific chiral selector used to separate the enantiomers of D,L-tryptophan, D,L-phenylthiohydantoin-serine (D,L-PTH-Ser), D,L-phenylthiohydantoin-threonine (D,L-PTH-Thr) and R,S-pioglitazone hydrochloride in capillary electrochromatography (CEC). The avidin is immobilized on the phospholipids coated in the capillary. The liposome used for the phospholipid coating contains 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-(Cap biotinyl) (sodium salt) (Biotinyl-cap-DPPE) (16:0) and different proportions of L-α-phosphatidylserine (PS) in Tris (hydroxymethyl) aminomethane (Tris) buffer at pH 7.4. A good resolution and reproducibility was obtained by coating the capillary with Biotinyl-cap-DPPE/PS (80:20, mol%) followed by immobilization of 1 mg/mL of avidin solution in N-(2-hydroxyethyl) piperazine-N'-(2-ethanesulfonic acid) (HEPES) buffer at pH 7.4. A comparative study of chiral separation efficiency with different capillary coating methods and preconditioning conditions was conducted. Finally, the electrochromatographic method was successfully used to separate enantiomers of pioglitazone hydrochloride. Therefore, coated CEC will be a promising tool for pharmaceutical enantiomers separation in new drug development.

Simultaneous determination of five bioactive phenolic acids in Salvia yunnanensis and Salvia miltiorrhiza by HPLC

Zheng-Fu Zhang, Hong-Shan Chen, Zhuo-Rong Li*

2010, 19(4):  271-278. 

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A reverse-phase HPLC method was developed for the simultaneous separation and determination of five bioactive phenolic acids, yunnaneic acid E, rosmarinic acid, lithospermic acid, salvianolic acid B and salvianolic acid A in eight different samples of Salvia yunnanensis collected in Yunnan Province. For comparison, the sample of Salvia miltiorrhiza was included. All the samples were extracted for 60 min with 50% methanol in an ultrasonic bath. The optimal separation was achieved on a YMC-Pack Pro C18 column, with a gradient of 0.1% (v/v) phosphoric acid and acetonitrile, at a flow rate of 1.0 mL/min and at a detection wavelength of 280 nm. The separation was obtained within 65 min for five bioactive phenolic acids. All calibration curves showed good linearity (r²>0.999) within test ranges. The relative standard deviation of the method was less than 5% for intra- and inter-day assays. The mean recovery of the method was in the range from 97% to 104%, with RSD less than 5%. This assay was successfully applied to the quantitative determination of five bioactive phenolic acids in nine resource samples. The results showed that the developed HPLC assay was suitable for the quality control of S. yunnanensis and it can be used to differentiate S. yunnanensis from S. miltiorrhiza.

Quantitative determination of nizatidine in human plasma and urine by high performance liquid chromatography and its pharmacokinetic study in humans

Ling Zhang, Yan-Ping Zhao, Hua Qiao, Ting Wang^*, Li Liang, Wei Chang, Dan Li, Pei-Han Xu

2010, 19(4):  279-284. 

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A validated simple and sensitive high performance liquid chromatographic (HPLC) method for the quantitative determination of nizatidine (NIZ) in human plasma and urine is reported. Reverse phase chromatographic separation of NIZ and salicylic acid (internal standard) was achieved on Diamonsil C18 column, using acetonitrile-0.05 mol/L K2HPO4-triethylamine (17:83:1, v/v/v, pH 6.5) as the mobile phase. Flow rate was 0.9 mL/min and the ultraviolet detector was set at a wavelength of 320 nm. The assay was linear over the range of 0.0117-6 mg/mL for plasma samples and 0.029-50 µg/mL for urine samples. The limit of quantification was 0.0117 μg/mL. The intra- and inter-day RSD values were lower than 5.12% and 8.03%, respectively, in plasma, and 6.2% and 6.9%, respectively, in urine. A single dose of 100 mg NIZ and multiple doses of 100 mg NIZ were administered to 10 healthy volunteers through intravenous infusions. The multiple dose regimens were administered every 8 h for 6 consecutive days. The pharmacokinetic parameters were obtained as following: for single-dose, Cmax (2.7±0.6) µg/mL, t1/2 (1.4±0.4) h, AUC0-12h (2.45±0.33) μg·h/mL, AUC_0-∞ (2.46±0.33) μg·h/mL, and the accumulated urine excretion rate in 12 h was 61.2%±9.46%; for multiple doses, Cmax (2.9±0.8) µg/mL, t1/2 (1.3±0.2) h, AUC0-12h (2.56±0.52) μg·h/mL, AUC_0-∞ (2.56±0.52) μg·h/mL, and the accumulated urine excretion rate in 12 h was 51.3%±9.42%. The statistical analysis of the pharmacokinetic parameters in males and females after single-dose and multiple-dose intravenous infusion of NIZ showed no differences. No drug accumulation after multiple-dose intravenous infusion of 100 mg NIZ was observed. The validated HPLC method was suitable for the pharmacokinetic study of NIZ.

Optimal mode of capillary electrophoresis for the impurity analysis of β-lactam antibiotics

Jian-Ping Zhu, Hui-Wen Zhang, Chang-Qin Hu^*

2010, 19(4):  285-292. 

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In order to determine the optimal mode of capillary electrophoresis for the impurity control of β-lactam antibiotics, different modes and various electrophoresis conditions for the separation of impurities were compared. The results showed that micellar electrokinetic capillary chromatography (MEKC) was the optimal separation mode for the impurity profiling of β-lactam antibiotics. In MEKC, not only the common R and S isomers, Δ-2 and Δ-3 isomers, and Z and E isomers, but also the impurities of β-lactam antibiotics could be well separated compared with the capillary zone electrophoresis. Therefore, MECK is the first choice for the separation of impurities of β-lactam antibiotics with capillary electrophoresis (CE). The optimal separation could be achieved in MEKC by optimizing the pH and the concentrations of buffered saline, micelles and organic solvent (methanol) in running buffer.

Comparison of different polysaccharide-based chiral stationary phases for enantioselective resolution of Naftopidil and its derivatives by HPLC

Xia-Wen Liu, Mu Yuan^*, Hong Ji

2010, 19(4):  293-299. 

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Effective enantioseparation of Naftopidil and its derivatives by HPLC was accomplished using several different polysaccharide-based chiral stationary phases (CSPs). In normal-phase mode, the compounds were eluted on four coated- and two immobilized-columns with the mixture of n-hexane, isopropanol and diethylamine (DEA). Polysaccharide tris(3,5-dimethylphenyl carbamate) was shown to be the best enantiomer selector. In addition, the immobilized column packed with Chiralpak IA or IB was applied under polar-organic and reversed-phase conditions, both of which exhibited excellent enantioselectivity for Naftopidil and its derivatives. Furthermore, the underlying possible chiral recognition mechanisms were discussed.

Development of an HPLC-UV method for the simultaneous determination of epirubicin, amlodipine and dequalinium in anti-resistant liposomes

Ying Men, Xiao-Xing Wang, Rui-Jun Ju, Wei Tian, Xue Ying, Hong-Juan Yao, Yan Zhang, Ruo-Jing Li, Wan-Liang Lu^*

2010, 19(4):  300-306. 

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Novel anti-resistant liposomes have been developed to overcome intrinsic resistance in leukemia. Anticancer agent epirubicin and apoptotic inducer amlodipine were encapsulated into the liposome aqueous core, and the surface of the liposome was modified using dequalinium. The objective of the present study was to establish a high performance liquid chromatography (HPLC) method for the determination of epirubicin, amlodipine and dequalinium in the liposomes. Analysis was performed on an ODS column with an isocratic elution at ambient temperature. Mobile phase was consisted of acetonitrile, 0.02 M NaH2PO4 and triethylamine (34:66:0.3, v/v/v, pH 4.0). The detection wavelength was set at 240 nm and the flow rate was 1.0 mL/min. The results showed that the calibration curves of epirubicin, amlodipine and dequalinium were linear in the range of (1-50) µg/mL (r² = 0.9999), respectively. The mean recoveries of epirubicin, amlodipine, and dequalinium were in the range of 95.86%-97.52%, 97.17%-98.92% and 98.04%-101.13%, respectively. The contents of epirubicin, amlodipine and dequalinium in the liposomes were in the range of (564.2-606.1) µg/mL, (641.0-704.0) µg/mL, and (816.0-898.0) µg/mL, respectively. The encapsulation efficiencies of epirubicin and amlodipine were around 90%, and the modification rate of dequalinium was approximate 70 µg/µmol lipids. The proposed HPLC method was simple and accurate for the simultaneous determination of epirubicin, amlodipine and dequalinium in newly developed anti-resistant liposomes.

Synthesis of two metabolites of edaravone

Xin-Rong Zhu, Yi Zheng, Peng Wang, Shi-Bao Yang, Rong Chen, Yong-Qiang Zhu^*

2010, 19(4):  307-311. 

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Edaravone glucuronate and edaravone sulfate, two metabolites of edaravone, were synthesized in improved yields. Edaravone glucuronate was synthesized by conjugation of edaravone with glucuronolactone through a series of reactions. Edaravone sulfate was synthesized through sulfonation of edaravone. Compared with the reported methods in the literature, the yields of both metabolites with the improved methods were much higher.

Synthesis and biological evaluation of novel 1-aryl-5-iodo-6-benzyluracils as potent HIV-1 non-nucleoside reverse transcriptase inhibitors

Wei Wang, Li Li, Chang Liu, Liang Zhang, Han Yan, Zhi-Li Zhang, Xiao-Wei Wang, Jun-Yi Liu^*

2010, 19(4):  312-317. 

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We have synthesized the novel compounds 1a-1i, which are a series of hybrid analogues to 6-benzyl-1-(benzyloxymethyl)-5-iodouracil, a compound showing strong activity against HIV-1. We also evaluated the activity of these compounds as the inhibitors of HIV-1 reverse transcriptase (HIV-1 RT), and they have demonstrated moderate activity.

Note

Microwave synthesis and pharmacological activity of Mannich base cyclohexanone derivatives

Ch. Rajveer^*, B. Stephenrathinaraj, Naveen Kumar Bimal, S. Sudharshini, Ch. Swarnalatha, Prasanta Kumar Choudhury

2010, 19(4):  318-322. 

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We have synthesized mannich base cyclohexanone using microwave irradiation method, and studied their pharmacological activity. Based on analytical and spectral (IR, NMR and Mass) data, a number of mono as well as double mannich base cyclohexanones have been synthesized from primary and secondary amines and formaldehyde, and then purified and characterized. The required 3-aryl-2,4-diacetyl-5-hydroxy-5-methylcyclohexanone was prepared from appropriate aldehyde and acetylacetone. The synthesized compounds were screened for analgesic activity via standard approaches, and they have shown positive analgesic activity.