title: Evaluation of piper cubeba extract, (-)-cubebin and its semi-synthetic derivatives against oral pathogens.
abstract: The activities of the crude ethanol extract from Piper cubeba seeds, (-)-cubebin and its semi-synthetic derivatives were evaluated against oral pathogens. The crude ethanol extract was more active against Streptococcus salivarius (MIC value of 80 microg/mL). (-)-Cubebin displayed MIC values ranging from 0.20 mm for Streptococcus mitis to 0.35 mm for Enterococcus faecalis. The natural product (-)-cubebin and its semi-synthetic derivative (-)-hinokinin displayed bacteriostatic activity at all evaluated concentrations, as well as fungicidal activity against Candida albicans at 0.28 mm. The O-benzyl cubebin derivative showed fungistatic and fungicidal effects against C. albicans at 0.28 mm and 0.35 mm, respectively. Also, the other dibenzylbutyrolactone derivatives [(-)-6,6'-dinitrohinokinin and (-)-O-(N,N-dimethylaminoethyl)-cubebin] displayed bacteriostatic and fungistatic effects at the evaluated concentrations. Moreover, the semi-synthetic derivative (-)-6,6'-dinitrohinokinin was the most active compound against all the evaluated microorganisms. Therefore, it may be suggested that the presence of the carbonyl group at C-9 plus the introduction of polar groups in the aromatic rings improve the antimicrobial activity of dibenzylbutyrolactone compounds.
authors.affiliation: Núcleo de Pesquisa em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca, SP 14404-600, Brazil. mlasliva@unifran.br
authors.forename: M L A
authors.initials: ML
authors.lastname: Silva
authors.forename: H S
authors.initials: HS
authors.lastname: Coímbra
authors.forename: A C
authors.initials: AC
authors.lastname: Pereira
authors.forename: V A
authors.initials: VA
authors.lastname: Almeida
authors.forename: T C
authors.initials: TC
authors.lastname: Lima
authors.forename: E S
authors.initials: ES
authors.lastname: Costa
authors.forename: A H C
authors.initials: AH
authors.lastname: Vinhólis
authors.forename: V A
authors.initials: VA
authors.lastname: Royo
authors.forename: R
authors.initials: R
authors.lastname: Silva
authors.forename: A A S
authors.initials: AA
authors.lastname: Filho
authors.forename: W R
authors.initials: WR
authors.lastname: Cunha
authors.forename: N A J C
authors.initials: NA
authors.lastname: Furtado
authors.forename: Carlos H G
authors.initials: CH
authors.lastname: Martins
authors.forename: T C
authors.initials: TC
authors.lastname: Carvalho
authors.forename: J K
authors.initials: JK
authors.lastname: Bastos
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D052117:Benzodioxoles; D002176:Candida albicans / Q000187:drug effects*; D004149:Dioxoles / Q000737:chemistry / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D031701:Piper / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D013291:Streptococcus / Q000187:drug effects*
chemical_list: D000890:Anti-Infective Agents; D052117:Benzodioxoles; D004149:Dioxoles; D017705:Lignans; D010936:Plant Extracts; C475934:hinokinin; C433065:cubebin; D015107:4-Butyrolactone