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Synthesis and Antimicrobial Activity of Ursolic Acid Ester Derivatives
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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 (
1
H‐ and
13
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
(3
β‐
(3,4‐dimethoxybenzoyl)ursolic acid) and
15
(3
β
‐nicotinoylursolic acid) displayed promising antifungal activity, with inhibition of
C. albicans
growth of 93.1 and 95.9 %, respectively.
Title: Synthesis and Antimicrobial Activity of Ursolic Acid Ester Derivatives
Description:
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 (
1
H‐ and
13
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
(3
β‐
(3,4‐dimethoxybenzoyl)ursolic acid) and
15
(3
β
‐nicotinoylursolic acid) displayed promising antifungal activity, with inhibition of
C.
albicans
growth of 93.
1 and 95.
9 %, respectively.
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