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Synthesis of Coptisine from Alkaloids in Coptids Rhizoma with the Similar Structure of Isoquinoline

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Tutor: WangDaoWu
School: Changchun University of
Course: Biochemical Engineering
Keywords: Coptids Rhizoma,coptisine,the structure of isoquinoline,alkaloids in Coptids Rhi
CLC: R284
Type: Master's thesis
Year:  2011
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Abstract:
Coptisine in overall yield of 16% was synthesized from the alkaloids with the same main structure of isoquinoline included berberine, berberurine, palmatine and jatrorrhizine by a four-step reaction of hydro genati on, demethylation or demethylene-dioxy, cyclization, dehydrogenation and so on.Through the single-factor experimental design, the synthetic conditions of Coptisine were studied. The conditions were compared with the two process. The optimum process conditions were obtianed. Candida albicans, Staphylococcus aureus, Candida krusei and Cryptococcus were for the experimental bacterium.The value of minimum inhibitory concentration is tested.The optimal conditions for the experiment are as follows:alkaloids first were hydrogenated and then demethoxy and demethylenedioxy to obtain the monomer coptisine after the final dehydrogenation of the hydroxyl ring. The conditions for synthesis tetrahydroberberine alkaloids:the most appropriate molar ratio of the sodium borohydride and raw materials is 4:1 and the reaction time is 4 h, using anhydrous potassium carbonate as catalyst and the appropriate methanol solution concentration was 80%.. The conditions for the synthesis of tetrahydrotetrahydroxy coptisine is that the most appropriate molar ratio of borontribromide and the intermediates is 6:1, reaction time is 14 h. The temperature of the tetrahydrocoptisine synthesis is 120¡æand the reaction time is 30 h; the most appropriate molar ratio of bromochloromethane and the intermediates is 6:1. The molar ratio of catalys and the intermediates is 10:1.And the reaction time of coptisine synthesis is 10 h. the most appropriate catalys is sodium acetate.The results of the antibacterial show that:the prepared coptisine monomer maintain or even improve the antibacterial properties. The prepared monomer coptisine has, a high antibacterial activity for Staphylococcus aureus, the value of MIC is 8¦Ì/mL. The mechanism of their antibacterial may due to that the prepared product has higher lipophilic and enhance the permeability of the drug on the cell membrane.The method which used in this article compared with the conventional method of prepareing coptisine eliminated the purification of the raw materials used for the drugs synthesis, and at the same time it contraved the mixture of bases into monomer coptisine which has higher antimicrobial specificity and activity.This method was simple and easy to operate.The cost was low and suitable for coptisine¡¯s mass production.The transformation of the main components to one component would provide useful ideas for the Chinese herbal medicine¡¯s value and good guide for the development of new medicine.
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