Synthesis and Antimicrobial Activity of Ursolic Acid Ester Derivatives

• Published in: Chemistry & biodiversity Vol. 19; no. 1; pp. e202100566 - n/a
• Main Authors: Pereira, Vinicius Viana, Pereira, Nara Rúbia, Pereira, Rafael César Gonçalves, Duarte, Lucienir Pains, Takahashi, Jacqueline Aparecida, Silva, Roqueline Rodrigues
• Format: Journal Article
• Language: English
• Published: Switzerland Wiley Subscription Services, Inc 01-01-2022
• Subjects: Acids; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibacterial activity; Anticancer properties; Antifungal activity; Antimicrobial activity; Antimicrobial agents; Bignoniaceae - chemistry; Bignoniaceae - metabolism; Candida albicans; Candida albicans - drug effects; DIC/DMAP; E coli; Escherichia coli - drug effects; Esters; Esters - chemistry; Fungicides; Mass spectrometry; Mass spectroscopy; Microbial Sensitivity Tests; Microorganisms; Morbidity; Natural products; NMR; Nuclear magnetic resonance; Plant Extracts - chemistry; Public health; Salmonella; Staphylococcus aureus - drug effects; Structure-Activity Relationship; Triterpenes - chemical synthesis; Triterpenes - chemistry; Triterpenes - pharmacology; triterpenoid derivatives; Ursolic Acid; Yeasts; Candida albicans; antibacterial activity; DIC/DMAP; triterpenoid derivatives; ursolic acid
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.202100566

Infections caused by microorganisms are a major cause of morbidity and mortality worldwide, and natural products continue to be important sources for the discovery of new antimicrobial agents. Ursolic acid is a triterpene with known antibacterial action, being naturally found in plants, such as Jaracanda oxyphylla and Jacaranda caroba (Bignoniaceae). Ursolic acid derivative esters have revealed potential biological activities, such as antitumor, antiviral, and antibacterial activity. In this study, sixteen esters (1‐16) were synthesized from ursolic acid using DIC/DMAP and characterized by infrared (IR), nuclear magnetic resonance (1H‐ and 13C‐NMR) and mass spectrometry. All ursolic acid esters were evaluated against Bacillus cereus, Staphylococcus aureus, Escherichia coli, Salmonella typhimurium, and the yeast Candida albicans. Six compounds are herein described for the first time (3, 9, 11, 13, 14 and 16) with yields up to 91.6 %. Compounds 11 (3β‐(3,4‐dimethoxybenzoyl)ursolic acid) and 15 (3β‐nicotinoylursolic acid) displayed promising antifungal activity, with inhibition of C. albicans growth of 93.1 and 95.9 %, respectively.