Synthesis And Characterization Of Derivatives Of Oleanolic Acid And The Study On The Antibacterial Activity

Oleanolic acid is an oleanane-type compound of pentacyclic triterpenoids, and it is the main functional components of various natural products. Oleanolic acid distributes in nature widely, such as swertia mileenis, oldenlandia diffusa, fruit of glossy privet and other plants, with free form existence or with sugar to combine into the glucoside exist. It shows a variety of biological activities such as anti-inflammatory, antitumor, hypoglycemic, anti-high blood cholesterol, and many other kinds of pharmacological effects. Oleanolic acid is a perfect drug to treat acute icterohepatitis and chronic viral hepatitis, and it is in the nature of low toxicity and fewer side effects. Due to its superior pharmacological activities, fewer side effects and lower toxicity, a lot of research work about the extraction, content determination and pharmacological activity of oleanolic acid has been done at home and abroad in recent years. Some of the research teams have studied the derivatives of oieanolic acid on anti-tumor and anti-AIDS activity, but researches on antibacterial activity are very little.In order to study the structure activity relationship of oleanolic acid and its derivatives in depth, this dissertation use oleanolic acid as a lead compound and combine the achievements of biological activity test to modified its structure based on the theories of organic chemistry and pharmaceutical synthesis and the methods of organic synthesis technology. Some derivatives of oleanolic acid were synthesized, and their antibacterial activities were tested in order to obtain high efficiency and low toxicity derivatives of oleanolic acid.Three parts are included in this dissertation.The first part described the pharmacological effects of oleanolic acid and introduced the progress, clinical application and development prospects of oleanolic acid.The second part synthesized and characterized the derivatives of oleanolic acid. By exploring the synthesis, separation and purification conditions,35 kinds of oleanolic acid derivatives were designed and synthesized.32 kinds of the compounds have not been reported. All the structures were characterized by the methods of IR and 1HNMR.The third part tested the antibacterial activity of the oleanolic acid and its derivatives.