Synthesis And Antibacterial Activity Of 13 Derivatives Of Berberine And Berberis Red Alkali

In this paper,four berberine's and berberrubine's derivatives were synthesized as follow:13-benzyl berberine (P2),13-(3',5'-dinitro)benzyl berberine (P3),13-benzyl berberrubine (P6) and 13-(3',5'-dinitro) benzyl berberrubine (P7).And their purity, structure and antibacterial activity were studied.Through the single-factor experimental design,the synthetic conditions of derivatives were studied to get the optimal process conditions. This article focuses on the antibacterial activity of berberine and berberrubine and their derivatives.Staphylococcus aureus, Candida albicans, Luxi Te Candida, Candida krusei, and Cryptococcus neoformans were for the experimental bacterium. The value of the minimum inhibitory concentration is tested.The optimal synthetid conditions for the experiment are as follows:acetone berberine's synthetic conditions:the appropriate NaOH solution concentration was 5mol/L, the reactional time was 4h,and the reactional temperature was room temperature; 13-benzyl berberine's synthesis conditions:the reactional temperature was 80℃, the reactional time was 4h, the catalyst used for was the sodium bromide; 13-(3',5'-dinitro) benzyl berberine's synthesis conditions:the reactional temperature was 80℃, the reactional time was 4h; Berberrubine's synthesis conditions:the reaction temperature was 110℃, the reactional time was 7h, berberine: anhydrous AICl3 was 1:3; acetone berberrubine's synthesis conditions:the appropriate NaOH solution concentration was 5mol/L, the reactional time was 4h, the reactional temperature was room temperature; 13-Benzyl berberrubine's synthesis conditions:the reactional temperature was 80℃, the reactional time was 4h, the catalyst used was sodium bromide; 13-(3',5'-dinitro) benzyl berberrubine's synthesis conditions:the reactional temperature was 80℃, the reactional time was 4h.The antibacterial results showed that:13-benzyl berberine,13-(3',5'-dinitro)benzyl berberine,13-benzyl berberrubine and 13-(3',5'-dinitro) benzyl berberrubine had maintained and even increased the antibacterial properties of berberine and berberrubine, which greatly broadens the applicational scope of berberine. Among them,13-(3',5'-dinitro) benzyl berberine showed the highest antibacterial activity, the MIC value was 4μg/mL. Its antibacterial mechanism may be due to the modified product has a higher lipophilic and enhanced the permeability to cell membranes.