Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogens
Triterpene acids (ursolic, oleanoic, gypsogenic, and sumaresinolic acids) isolated from Miconia species, along with a mixture of ursolic and oleanolic acids and a mixture of maslinic and 2-a-hydroxyursolic acids, as well as ursolic acid derivatives were evaluated against the following microorganisms: Streptococcus mutans, Streptococcus mitis, Streptococcus sanguinis, Streptococcus salivarius, Streptococcus sobrinus, and Enterococcus faecalis, which are potentially responsible for the formation of dental caries in humans. The microdilution method was used for the determination of the minimum inhibitory concentration (MIC) during the evaluation of the antibacterial activity. All the isolated compounds, mixtures, and semi-synthetic derivatives displayed activity against all the tested bacteria, showing that they are promising antiplaque and anticaries agents. Ursolic and oleanolic acids displayed the most intense antibacterial effect, with MIC values ranging from 30 microg/mL to 80 microg/mL. The MIC values of ursolic acid derivatives, as well as those obtained for the mixture of ursolic and oleanolic acids showed that these compounds do not have higher antibacterial activity when compared with the activity observed with either ursolic acid or oleanolic acid alone. With regard to the structure-activity relationship of triterpene acids and derivatives, it is suggested that both hydroxy and carboxy groups present in the triterpenes are important for their antibacterial activity against oral pathogens.
Scalon Cunha
Luis C
LC
Universidade de Franca, Av. Dr. Armando Salles de Oliveira, 201 Parque Universitário, Franca-SP, CEP 14404-600, Brazil.
Andrade e Silva
Márcio L
ML
Cardoso Furtado
Niege A J
NA
Vinhólis
Adriana H C
AH
Martins
Carlos H
CH
da Silva Filho
Ademar A
AA
Cunha
Wilson R
WR
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D016983:Enterococcus / Q000187:drug effects; D006801:Humans; D035322:Melastomataceae / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D009055:Mouth / Q000382:microbiology; D009828:Oleanolic Acid / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013291:Streptococcus / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000097245:Ursolic Acid
D000900:Anti-Bacterial Agents; D009828:Oleanolic Acid; D014315:Triterpenes; D000097245:Ursolic Acid