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.

Lignans: Chemical and Biological Properties

“…Secoisolariciresinol gives the presumably common precursor of all dibenzylbutyrolactol lignans and, through the formation of matairesinol and yatein, also forms the aryltetralin lignans. These subclasses of lignans includes some important bioactive compounds such as cubebin (1) and podophyllotoxin (Canel et al, 2000;de Souza et al, 2005;Gordaliza et al, 2004;Saraiva et al, 2007;Silva et al, 2007;Silva et al, 2009;Srivastava et al, 2005;You, 2005;Yousefzadi et al, 2010).…”

“…Considering this fact, our research group also decided to investigate the potential of some natural and semi-synthetic lignans against mycobateria and oral pathogens (Silva et al, 2007;Silva et al, 2009). …”

“…Thus, our research group tested compounds 1, 4, 5, and 6 (Figure 11) and another semisynthetic derivative (O-benzyl cubebin, 8, Figure 12)using the broth microdilution method (Andrews, 2001) (Silva et al 2007). Table 7.…”

Green Oxidation Reactions of Drugs Catalyzed by Bio-inspired Complexes as an Efficient Methodology to Obtain New Active Molecules

“…Considering its promising biological activities, as well as its potential use as trypanocidal drug, large quantities of (-)-hinokinin are needed. (-)-Hinokinin and (-)-cubebin co-occur in P. cubeba, where they are among the major components of the biomass (Souza et al, 2004;Silva et al, 2007). In a traditional process, the oxidation of (-)-cubebin, catalyzed by pyridinium chlorochromate, PCC, can produce additional quantities of (-)-hinokinin.…”

Antimicrobial activity of Aegiphila sellowiana Cham., Lamiaceae, against oral pathogens

“…As part of our ongoing research on the antimicrobial activities of Brazilian plants and bioactive natural compounds (Oliveira et al, 2007;Silva et al, 2007;Cunha et al, 2007), and because previous reports documenting the antimicrobial activity of Verbenaceae species against oral pathogens (Chung et al, 2004;Botelho et al, 2007), we have investigated the in vitro antimicrobial potential of Aegiphila sellowiana Cham., Lamiaceae, popularly known as "tamanqueira". This species is an arboreous (or sometimes arbustive) species, which naturally occurs in the tropical and subtropical regions of America, mainly in Brazil.…”