Dissertation
Dissertation > Medicine, health > Chinese Medicine > Of Pharmacy > Traditional Chinese medicine chemical

Study on Synthesis and Antitumor Activities of Derivatives of Ursolic Acid

Author WangHui
Tutor ZhangHong
School Sichuan Normal University
Course Organic Chemistry
Keywords ursolic acid saponins 3-carbonyl ursolic acid synthesis antitumor activities
CLC R284
Type Master's thesis
Year 2012
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Abstract:Ursolic acid, which has pharmacological properties of antibacterial, anti-inflammatory, hepatoprotective, anti-tumor, anti-HIV, belongs to triterpenes. It exists in many plants and has a rich resource. It is quite efficient to gain highly bioactive compounds by modifying structure of ursolic acid dervatives and screening its biological activities.The first five different ursolic acid glucosides with different yields (73.6%、75.1%、59.4%、66.6%、52.5%) have been synthesized by using ursolic acid and five sugars (D-glucose, D-galactose, D-mannose, D-lactose, D-maltose) as raw materials reacting at the C-3hydroxyl groups of ursolic acid.And the second seven different3-carbonyl ursolic acid esters also have been prepared by oxiziding C-3hydroxyl group of ursolic acid to carbonyl and esterifying C-17carboxyl of it. And it can produce seven different kinds of compounds (UA-3-UA-9) with the yields of90.2%、91.5%、93.1%、90.4%、92.1%、87.5%、89.1%.Human myeloma cells also called U266as experimental subjects were studied to explore the antitumor activities of13kinds of compounds synthesized. The IC50values of compounds (7a-7e) are8.5μg/ml、15.4μg/ml、12.6μg/ml、43.0μg/ml、41.8μg/ml、6.4μg/m. The IC50value results of the compounds (7a-7c) show that: increasing the number of hydroxyl group in molecule can improve its hydrophilicity, while the antitumor activities may be reduced. BELE7402, A549 and HT-29are chosen as the experimental subjects for UA-3-UA-9. According to the IC50value results, increasing the lipid solubility of UA is to help improve the activities of A549and HT-29. And too many alkyl side chains at C-28alkyl chain can increase the inhibitory activity.The result provides a certain reference for both further modifying the molecule structure of ursolic acid and investigating higher activity of the target molecule.

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