Antibacterial Activity of Triterpene Acids and Semi-Synthetic Derivatives against Oral Pathogens

Abstract

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-α-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 μg/mL to 80 μg/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.

Maslinic acid suppresses osteoclastogenesis and prevents ovariectomy-induced bone loss by regulating RANKL-mediated NF-κB and MAPK signaling pathways

“…Maslinic acid (MA), a pentacyclic triterpene acid, is widely present in dietary plants, especially abundant in olive fruit skins and hawthorn. The compound has attracted much interest owing to its proven pharmacologic safety and its many biologic activities, such as anti-inflammatory, (2) antiviral, (3) antioxidant, (2,4) and antidiabetogenic activities (5,6) and anti-colon cancer (7) and antiastrocytoma (8) properties. In this study we examined the effects of MA on osteoclast differentiation and function in vitro and in vivo and then elucidated the underlying molecular mechanisms.…”

Effect of asiatic and ursolic acids on growth and virulence factors of uropathogenic Escherichia coli strains

“…As previously identified (Wojnicz et al, 2012), MIC values were high and ranged from 512 µg/mL to >1024 µg/mL. Cunha et al (2007) Garo et al (2007) noted that the MIC of AA against P. aeruginosa was 128 µg/mL. Djoukeng et al (2005) showed that the MICs of AA fractions obtained from the extract of Syzygium guineense were much higher for gram-negative Shigella sonnei and E. coli strains in comparison with gram-positive B. subtilis.…”

“…In our study we used AA, the therapeutic activity of which is poorly described, and UA, the antimicrobial action of which, mainly against gram-positive bacteria, has been described in several reports (Chandramu et al, 2003;Cunha et al, 2007;Fontanay et al, 2008;Kurek et al, 2010). Table 2 summarizes the in vitro susceptibilities of the 20 isolates of E. coli to AA and UA.…”

Bioactivity of the compounds isolated from Blepharocalyx salicifolius

“…al., 1987;Arisawa et al, 1993;Xu et al, 2009). By means of spectroscopic data and literature (Seebacher et al, 2003;Silva et al, 2008), it was possible to confirm the identity of the 5 as ursolic acid, (3β-hydroxy-urs-12-en-28-oic acid), an ursanic triterpene isolated from several species (Fu et al, 2005;Leite et al, 2006;Cunha et al, 2007).…”