Antimicrobial evaluation of diterpenes from copaifera langsdorffii oleoresin against periodontal anaerobic bacteria

Molecules

Volumn 16, Issue 11, 2011, Pages 9611-9619

  Souza, Ariana B ^a   De Souza, Maria G M ^a   Moreira, Maísa A ^a   Moreira, Monique R ^a   Furtado, Niege A J C ^b   Martins, Carlos H G ^a   Bastos, Jairo K ^b   Dos Santos, Raquel A ^a   Heleno, Vladimir C G ^a   Ambrosio, Sergio Ricardo ^a   Veneziani, Rodrigo C S ^a  

^a UNIVERSIDADE DE FRANCA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Copaiba oleoresin; Copaifera langsdorffii; Copalic acid; Periodontitis; Porphyromonas gingivalis

Indexed keywords

ANTIINFECTIVE AGENT; COPALIC ACID; DITERPENE; MANOOL; OLEORESINS; PLANT EXTRACT; SCLAREOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; EVALUATION; FABACEAE; HUMAN; MICROBIOLOGICAL EXAMINATION; MICROBIOLOGY; PERIODONTITIS; PORPHYROMONAS GINGIVALIS;

ANTI-INFECTIVE AGENTS; DITERPENES; FABACEAE; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PERIODONTITIS; PLANT EXTRACTS; PORPHYROMONAS GINGIVALIS;

EID: 82255184151     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16119611     Document Type: Article

References (30)

1. Gursoy, U.K.; Gursoy, M.; Gursoy, O.V.; Cakmakci, L.; Kononen, E.; Uitto, V.J. Anti-biofilm properties of Satureja hortensis L. essential oil against periodontal pathogens. Anaerobe 2009, 15, 164-167.
2. Milazzo, I.; Blandino, G.; Musumeci, R.; Nicoletti, G.; Lo Bue, A.M.; Speciale, A. Antibacterial activity of moxifloxacin against periodontal anaerobic pathogens involved in systemic infections. Int. J. Antimicrob. Agents 2002, 20, 451-456. (Pubitemid 35379986)
3. Newman, D.J. Natural products as leads to potential drugs: An old process or the new hope for drug discovery? J. Med. Chem. 2008, 51, 2589-2599. (Pubitemid 351620778)
4. Kuzma, L.; Rozalski, M.; Walencka, E.; Rozalska, B.; Wysokinska, H. Antimicrobial activity of diterpenoids from hairy roots of Salvia sclarea L.: Salvipisone as a potential anti-biofilm agent active against antibiotic resistant Staphylococci. Phytomedicine 2007, 14, 31-35. (Pubitemid 46019787)
5. Almeida, L.S.B.; Murata, R.M.; Yatsuda, R.; Dos Santos, M.H.; Nagem, T.J.; Alencar, S.M.; Koo, H.; Rosalen, P.L. Antimicrobial activity of Rheedia brasiliensis and 7-epiclusianone against Streptococcus mutans. Phytomedicine 2008, 15, 886-891.
6. Porto, T.S.; Furtado, N.A.J.C.; Heleno, V.C.G.; Martins, C.H.G.; da Costa, F.B.; Severiano, M.E.; Silva, A.N.; Veneziani, R.C.S.; Ambrosio, S.R. Antimicrobial ent-pimarane diterpenes from Viguiera arenaria against Gram-positive bacteria. Fitoterapia 2009, 80, 432-436.
7. Porto, T.S.; Rangel, R.; Furtado, N.; 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.; et al. Pimarane-type diterpenes: Antimicrobial activity against oral pathogens. Molecules 2009, 14, 191-199.
8. Stavri, M.; Paton, A.; Skelton, B.W.; Gibbons, S. Antibacterial diterpenes from Plectranthus ernstii. J. Nat. Prod. 2009, 72, 1191-1194.
9. Habtemariam, S. In vitro antileishmanial effects of antibacterial diterpenes from two Ethiopian Premna species: P. schimperi and P. oligotricha. BMC Pharmacol. 2003, 3, 1-6.
10. Wiart, C.; Au, T.S.; Mohd, Y.; Hamimah, H.; Sulaiman, M. 16 Alpha hydroxy-(-)-kauran-19-oic: An antibacterial diterpene from sweet apple (Annona squamosa L., Annonaceae). Int. J. Pharmacol. 2005, 1, 296-298.
11. Radulovic, N.; Denic, M.; Stojanovic-Radic, Z. Antimicrobial phenolic abietane diterpene from Lycopus europaeus L. (Lamiaceae). Bioorg. Med. Chem. Lett. 2010, 20, 4988-4991.
12. Woldemichael, G.M.; Wächter, G.; Singh, M.P.; Maiese, W.M.; Timmermann, B.N. Antibacterial diterpenes from Calceolaria pinifolia. J. Nat. Prod. 2003, 66, 242-246. (Pubitemid 36278237)
13. Kalpoutzakis, E.; Chinou, I.; Mitaku, S.; Skaitsounis, A.L.; Hervala, C. Antibacterial labdane-type diterpenes from the resin "Ladano" of Cistus creticus Subsp. creticus. Nat. Prod. Lett. 1998, 11, 173-179. (Pubitemid 28176924)
14. Carvalho, T.C.; Simao, M.R.; Ambrosio, S.R.; Furtado, N.A.; Veneziani, R.C.; Heleno, V.C.; Da Costa, F.B.; Gomes, B.P.; Souza, M.G.; Borges dos Reis, E.; et al. Antimicrobial activity of diterpenes from Viguiera arenaria against endodontic bacteria. Molecules 2011, 16, 543-51.
15. Souza, A.B.; Martins, C.H.G.; Souza, M.G.M.; Furtado, N.A.J.C.; Heleno, V.C.G.; Sousa, J.P.B.D.; Rocha, E.M.P.; Bastos, J.K.; Cunha, W.R.; Veneziani, R.C.S.; et al. Antimicrobial activity of terpenoids from Copaifera langsdorffii Desf. against cariogenic bacteria. Phytother. Res. 2011, 25, 215-220.
16. Ohsaki, A.; Yan, L.T.; Ito, S.; Edatsugi, H.; Iwata, D.; Komoda, Y. The isolation and in-vivo potent antitumor-activity of clerodane diterpenoid from the oleoresin of the Brazilian medicinal plant, Copaiferalangsdorfii Desfon. Bioorg. Med. Chem. 1994, 4, 2889-2892.
17. Braun, S.; Breitenbach, H. Strukturaufklärung einer neuen Diterpensäure aus Metasequoia glyptostroboides mit hilfe der 13C-NMR-spektroskopie. Tetrahedron 1977, 33, 145-150.
18. Romero, A.L.; Baptistella, L.H.B.; Imamura, P.M. Absolute configuration of some dinorlabdanes from copaiba oil. J. Brazil Chem. Soc. 2009, 20, 1036-1040.
19. Zdero, C.; Bohlmann, F.; King, R.M. Diterpenes and norditerpenes from the aristeguetia group. Phytochemistry 1991, 30, 2991-3000.
20. Clinical Laboratory Standards Institute (CLSI). Methods for Antimicrobial Susceptibility Testing of Anaerobic Bacteria, Approved standard; CLSI: Wayne, PA, USA, 2007.
21. Rios, J.L.; Recio, M.C. Medicinal plants and antimicrobial activity. J. Ethnopharmacol. 2005, 100, 80-84. (Pubitemid 41073526)
22. Gibbons, S. Phytochemicals for bacterial resistance-Strengths, weaknesses and opportunities. Planta. Med. 2008, 74, 594-602. (Pubitemid 351846775)
23. Greenberg, M.; Dodds, M.; Tian, M. Naturally occurring phenolic antibacterial compounds show effectiveness against oral bacteria by a quantitative structure-activity relationship study. J. Agric. Food. Chem. 2008, 56, 11151-11156.
24. Urzúa, A.; Rezende, M.C.; Mascayano, C.; Vasquez, L. A structure-activity study of antibacterial diterpenoids. Molecules 2008, 13, 882-891.
25. Park, M.; Bae, J.; Lee, D.S. Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria. Phytother. Res. 2008, 22, 1446-1449. (Pubitemid 352789611)
26. Tsui, V.W.K.; Wong, R.W.K.; Rabie, A.B.M. The inhibitory effects of naringrin on the growth of periodontal pathogens in vitro. Phytother. Res. 2008, 22, 401-406. (Pubitemid 351397446)
27. More, G.; Tshikalange, T.E.; Lall, N.; Botha, F.; Meyer, J.J.M. Antimicrobial activity of medicinal plants against oral microorganisms. J. Ethnopharmacol. 2008, 119, 473-477.
28. Katsura, H.; Tsukiyama, R.I.; Suzuki, A.; Kobayashi, M. In vitro antimicrobial activities of bakuchiol against oral microorganisms. Antimicrob. Agents Chemother. 2001, 45, 3009-3013. (Pubitemid 32988821)
29. Sarker, S.D.; Nahar, L.; Kumarasamy, Y. Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods 2007, 42, 321-324. (Pubitemid 46856865)
30. D'Arrigo, M.; Ginestra, G.; Mandalari, G.; Furneri, P.M.; Bisignano, G. Synergism and postantibiotic effect of tobramycin and Melaleuca alternifolia (tea tree) oil against Staphylococcus aureus and Escherichia coli. Phytomedicine 2010, 17, 317-322.