Antimicrobial Evaluation of Diterpenes from Copaifera langsdorffii Oleoresin Against Periodontal Anaerobic Bacteria

Abstract

The antimicrobial activity of four labdane-type diterpenes isolated from the oleoresin of Copaifera langsdorffii as well as of two commercially available diterpenes (sclareol and manool) was investigated against a representative panel of microorganisms responsible for periodontitis. Among all the evaluated compounds, (−)-copalic acid (CA) was the most active, displaying a very promising MIC value (3.1 µg mL−1; 10.2 µM) against the key pathogen (Porphyromonas gingivalis) involved in this infectious disease. Moreover, CA did not exhibit cytotoxicity when tested in human fibroblasts. Time-kill curve assays performed with CA against P. gingivalis revealed that this compound only inhibited the growth of the inoculums in the first 12 h (bacteriostatic effect). However, its bactericidal effect was clearly noted thereafter (between 12 and 24 h). It was also possible to verify an additive effect when CA and chlorhexidine dihydrochloride (CHD, positive control) were associated at their MBC values. The time curve profile resulting from this combination showed that this association needed only six hours for the bactericidal effect to be noted. In summary, CA has shown to be an important metabolite for the control of periodontal diseases. Moreover, the use of standardized extracts based on copaiba oleoresin with high CA contents can be an important strategy in the development of novel oral care products.

Influence of abiotic factors on the chemical composition of copaiba oil (Copaifera multijuga Hayne): soil composition, seasonality and diameter at breast height

“…Pinifolic acid was the major diterpenic constituent in two other samples (M09-C1 and M21-C1). The 3b-hydroxy-copalic acid and 3b-acetoxy-copalic acid, both with antimicrobial activities already described, 81 were detected in thirteen and eleven samples, respectively.The results obtained by chromatographic analysis were submitted to HCA and PCA methods for the classification of sixteen samples. HCA was used to determine the similarities between the samples, based on DBH, clay content and amount of each compound detected by GC-FID and GC-MS.…”

Diterpenes of the pimarane type isolated from Viguiera arenaria: Promising in vitro biological potential as therapeutic agents for endodontics

“…This bacterial sensitivity to diterpene III is relevant because microbial arrangement in the biofilm mode provides higher bacterial resistance to the root canal chemicalmechanical preparation, especially because the biofilm is located in inaccessible areas of the necrotic pulp in root surfaces and cement gaps (Lomçali et al, 1996;Stewart and Costerton, 2001;Siqueira Jr et al, 2010). Souza et al (2011) examined the bactericidal kinetics of copalic acid, a diterpene of the labdane type isolated from the oleoresin of Copaifera langsdorffii, against P. gingivalis (ATCC 33277). Copalic acid at 3.1 µg/mL presented bactericidal action within 24 h of incubation.…”

“…Moreti et al (2017) evaluated ent-kaurenoic acid against endodontic pathogens, to find MIC and MBC values ranging from 3.12 to 400 g/mL. Souza et al (2011) investigated copalic acid, a labdane-type diterpene isolated from the Copaifera langsdorffii oleoresin, against anaerobic bacteria, to obtain MIC values spanning from 3.1 to 200 µg/mL. In our study, diterpenes I, II, and III afforded MIC values between 0.5 and 10 µg/mL, which agreed with the claim by Rios and Recio (2005) that compounds that can inhibit microorganisms at concentrations close to 10 μg/mL are promising antimicrobials.…”

Manool, a Salvia officinalis diterpene, induces selective cytotoxicity in cancer cells

“…1) is one of the most abundant components found in its essential oils and extracts (Farhat et al 2009). Among other biological properties, manool has shown activity against Staphylococcus aureus (Ulubelen et al 1994) and exhibited promising minimal inhibitory concentration (MIC) values against several bacteria associated with periodontitis (Souza et al 2011).…”