Study On Structural Modification And Pharmacological Activity Of Shikimic Acid Derivatives From The Flower Of Trachycarpus Fortunei

Trachycarpus fortunei(Hook.)H.Wendl.(Arecaceae)is a common evergreen tree,widely distributed in the areas south of the Yangtze River and Qinling Mountains in China.The flower of Trachycarpus fortune is a kind of vegetable fruit used for both medicine and food.It is rich in 24 amino acids and has the effect of reducing blood pressure and clearing heat.According to literature reports,the flowers of Trachycarpus fortune contain a large amount of shikimic acid derivatives.Shikimic acid is an important industrial raw material,which often used as a raw material or synthetic intermediate in synthesis and modification.In this study,the chemical components of Trachycarpus fortune flowers were studied.HPLC-DAD-MS technology and TLC color development technology were used to quickly identify,isolate,and identify shikimic acid from the flowers of Trachycarpus fortune.After systematic separation and purification,16 shikimic acid derivatives(1-16)were isolated and identified from the flowers of Trachycarpus fortune.Compounds 1 and 2 were new compounds,and their absolute configurations were determined by hydrolysis and optical rotation.All compounds except compound 3 were isolated from the genus Trachycarpus for the first time.The amount of shikimic acid derivatives 3,15,and 16 isolated reached the gram level.α-Glucosidase inhibitory activity showed that shikimic acid derivatives had certainα-glucosidase inhibitory activity.The activities of compounds 2,5,6,7,10 and 12 were stronger than those of the positive control drug acarbose.In addition,this study is the first time to construct oxime ester bonds and modify the structure of the 3-hydroxyl group of shikimic acid.Jones reagent was used to oxidize the3-hydroxy group of shikimic acid to ketone,and a hydroxime bond was formed by reacting with hydroxylamine,and then the active hydroxime bond was modified.A series of 20(4a-4t)shikimic acid derivatives with oxime ester bonds were obtained by condensation with carboxyl groups using EDCl condensation agent,with yields ranging from 37 to 68%.Anti-fungi against plant pathogenic bacteria showed that the constructed shikimic acid derivatives with oxime ester bonds had the activity.Among these derivatives,shikimic acid derivatives substituted with chlorine had the best activity,and their activity was stronger or equivalent to that of the positive control prochloraz.In addition,bromo substituted and alkoxy substituted benzoyl oxime ester shikimic acid also has broad spectrum antibacterial activity.