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Molecules 2010, 15(12), 8553-8566; doi:10.3390/molecules15128553
Article

Anticariogenic Properties of ent-Pimarane Diterpenes Obtained by Microbial Transformation

1,†, 1,†, 1, 1, 1, 2, 3, 2, 3, 1, 2 and 2,*
1 Nucleus of Research in Sciences and Technology, University of Franca, Franca, SP, Brazil 2 Faculty of Pharmaceutical Sciences of Ribeirao Preto, University of Sao Paulo, Ribeirao Preto, SP, Brazil 3 Institute of Research and Development, Vale do Paraiba University, Sao Jose dos Campos, SP, Brazil These authors contributed equally to this paper.
* Author to whom correspondence should be addressed.
Received: 28 October 2010 / Revised: 12 November 2010 / Accepted: 16 November 2010 / Published: 25 November 2010
(This article belongs to the Section Metabolites)
Download PDF [135 KB, 18 June 2014; original version 18 June 2014]

Abstract

In the present work, the anticariogenic activities of three pimarane-type diterpenes obtained by fungal biotransformation were investigated. Among these metabolites, ent-8(14),15-pimaradien-19-ol was the most active compound, displaying very promising MIC values (ranging from 1.5 to 4.0 μg mL-1) against the main microorganisms responsible for dental caries: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis, and Lactobacillus casei. Time kill assays performed with ent-8(14),15-pimaradien-19-ol against the primary causative agent S. mutans revealed that this compound only avoids growth of the inoculum in the first 12 h (bacteriostatic effect). However, its bactericidal effect is clearly noted thereafter (between 12 and 24 h). The curve profile obtained by combining ent-8(14),15-pimaradien-19-ol and chlorhexidine revealed a significant reduction in the time necessary for killing S. mutans compared with each of these two chemicals alone. However, no synergistic effect was observed using the same combination in the checkerboard assays against this microorganism. In conclusion, our results point out that ent-8(14),15-pimaradien-19-ol is an important metabolite in the search for new effective anticariogenic agents.
Keywords: Ent-pimara-8(14),15-dien-19-oic acid; microbial transformation; diterpenes; anticariogenic properties; antimicrobial activity Ent-pimara-8(14),15-dien-19-oic acid; microbial transformation; diterpenes; anticariogenic properties; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Severiano, M.E.; Simao, M.R.; Porto, T.S.; Martins, C.H.G.; Veneziani, R.C.S.; Furtado, N.A.J.C.; Arakawa, N.S.; Said, S.; Oliveira, D.C.R.; Cunha, W.R.; Gregorio, L.E.; Ambrosio, S.R. Anticariogenic Properties of ent-Pimarane Diterpenes Obtained by Microbial Transformation. Molecules 2010, 15, 8553-8566.

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