Transforming technology for semi-synthesized isocorydione from the natural product ofisocorydine was studied. The factors affecting on the reaction yield were investigated. UV spectrophotometry was used to indicate the semi-synthesized yield of isocorydione. The optimum reaction conditions were determined as following: reacting for 12 h in the solution of sodium dihydrogen phosphate at pH 10, the temperature was 25 degrees C and the ratio of isocorydine to Fremy's radical was 1 : 2. Under the optimum conditions, the yield could reach up to 50.0%. The molecular structure of isocorydione was elucidated by X-ray single-crystal diffraction analysis for the first time.
Antineoplastic Agents, Phytogenic ; chemical synthesis ; chemistry ; isolation & purification ; Aporphines ; chemical synthesis ; chemistry ; isolation & purification ; Crystallography, X-Ray ; Hydrogen-Ion Concentration ; Molecular Structure ; Nitroso Compounds ; Oxidation-Reduction ; Papaveraceae ; chemistry ; Plants, Medicinal ; chemistry ; Spectrophotometry, Ultraviolet ; Temperature ; X-Ray Diffraction

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

Isocorydine and its analogs were extracted from Dicranostigma leptopodum and Stephania yunnanensis through the method of natural products chemistry. Its derivatives were prepared by chemical structure modifications from isocorydine. MTT method was used to study the inhibitory effect of those compounds on the growth of HepG2, HeLa and MGC-803 cancer cell lines in vitro. The results showed that isocorydine and its analogs all have the growth inhibition for those cancer cell lines. This paper investigated the structure-activity relationship of isocorydine and its derivatives with anticancer activity in the aspect of stereochemical structure, functional groups positions of the compounds and the electron density of aromatic rings based on the single crystal diffraction structure and the molecular docking of EGFR and isocorydine.