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Synthesis and Antimicrobial Activity of Ursolic Acid Ester Derivatives.
- Source :
-
Chemistry & biodiversity [Chem Biodivers] 2022 Jan; Vol. 19 (1), pp. e202100566. Date of Electronic Publication: 2021 Dec 06. - Publication Year :
- 2022
-
Abstract
- 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 ( <superscript>1</superscript> H- and <superscript>13</superscript> C-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.<br /> (© 2021 Wiley-VHCA AG, Zurich, Switzerland.)
- Subjects :
- Anti-Infective Agents chemistry
Anti-Infective Agents pharmacology
Bignoniaceae chemistry
Bignoniaceae metabolism
Candida albicans drug effects
Escherichia coli drug effects
Microbial Sensitivity Tests
Plant Extracts chemistry
Staphylococcus aureus drug effects
Structure-Activity Relationship
Triterpenes chemical synthesis
Triterpenes pharmacology
Ursolic Acid
Anti-Infective Agents chemical synthesis
Esters chemistry
Triterpenes chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1612-1880
- Volume :
- 19
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Chemistry & biodiversity
- Publication Type :
- Academic Journal
- Accession number :
- 34793623
- Full Text :
- https://doi.org/10.1002/cbdv.202100566