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Pimarane-type Diterpenes: Antimicrobial Activity against Oral Pathogens
Núcleo de Pesquisa em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca, SP, Brazil
Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
* Authors to whom correspondence should be addressed.
Received: 24 November 2008; in revised form: 16 December 2008 / Accepted: 26 December 2008 / Published: 4 January 2009
Abstract: Seven pimarane type-diterpenes re-isolated from Viguiera arenaria Baker and two semi-synthetic pimarane derivatives were evaluated in vitro against the following main microorganisms responsible for dental caries: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis and Lactobacillus casei. The compounds ent-pimara-8(14),15-dien-19-oic acid (PA); ent-8(14),15-pimaradien-3b-ol; ent-15-pimarene-8b,19-diol; ent-8(14),15-pimaradien-3b-acetoxy and the sodium salt derivative of PA were the most active compounds, displaying MIC values ranging from 2 to 8 μg∙mL-1. Thus, this class of compounds seems promising as a class of new effective anticariogenic agents. Furthermore, our results also allow us to conclude that minor structural differences among these diterpenes significantly influence their antimicrobial activity, bringing new perspectives to the discovery of new natural compounds that could be employed in the development of oral care products.
Keywords: Antimicrobial activity; Pimarane-type diterpenes; Oral pathogens; Viguiera arenaria; Structural requirements
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Porto, T.S.; Rangel, R.; Furtado, N.A.J.C.; De Carvalho, T.C.; Martins, C.H.G.; Veneziani, R.C.S.; Da Costa, F.B.; Vinholis, A.H.C.; Cunha, W.R.; Heleno, V.C.G.; Ambrosio, S.R. Pimarane-type Diterpenes: Antimicrobial Activity against Oral Pathogens. Molecules 2009, 14, 191-199.
Porto TS, Rangel R, Furtado NAJC, De Carvalho TC, Martins CHG, Veneziani RCS, Da Costa FB, Vinholis AHC, Cunha WR, Heleno VCG, Ambrosio SR. Pimarane-type Diterpenes: Antimicrobial Activity against Oral Pathogens. Molecules. 2009; 14(1):191-199.
Porto, Thiago S.; Rangel, Rander; Furtado, Niege A.J.C.; De Carvalho, Tatiane C.; Martins, Carlos H.G.; Veneziani, Rodrigo C.S.; Da Costa, Fernando B.; Vinholis, Adriana H.C.; Cunha, Wilson R.; Heleno, Vladimir C.G.; Ambrosio, Sergio R. 2009. "Pimarane-type Diterpenes: Antimicrobial Activity against Oral Pathogens." Molecules 14, no. 1: 191-199.