Oleanoic Acid (OA) is a pentacyclic triterpenoid widely found in food and medicinal plants, which exerts a broad range of bioactivities, such as anti-microbial activity. However, the biological activities and pharmacological effects of OA are undermined by its poor water solubility. Therefore, it is necessary to modify the OA’s structure to improve its biological activity. There are 3 major schemes in this study featuring the structural modifications of OA on its positions at C-3, C-11 and C-28. Herein, we report the synthesis of fifty OA derivatives and the evaluation of their anti-bacterial activity. Data showed that when the C-3 position was oxidized to carbonyl and link with a benzoindoles ring, OA derivatives showed improved water solubility and displayed a higher level of antimicrobial activity against Gram-positive strains. Further studies on the structural and activity relationship of the anti-bacterial activity of novel OA derivatives are being pursued in our laboratory.

Design, synthesis and evaluation of oleanolic acid derivatives at C-3 position as antibacterial agents

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.