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Chemistry of Natural Compounds

, Volume 55, Issue 4, pp 677–684 | Cite as

Hemisynthesis and Bactericidal Activity of Several Substituted Benzoic Acid Esters of 13(S)-Labdan-8α,15-Diol, a Diterpene from Oxylobus glanduliferus

  • Pablo A. Chacon-MoralesEmail author
  • Juan M. Amaro-Luis
  • Luis B. Rojas Fermin
  • Nurby N. Rios Tesch
  • Maria E. Lucena Escalona
  • Miguel A. Rodriguez Pena
  • Philippe A. Peixoto
  • Remi Jacquet
  • Denis Deffieux
  • Laurent Pouysegu
  • Stephane Quideau
Article
  • 6 Downloads

The diterpene 13(S)-labdan-8α,15-diol (1) was isolated in high yield from Oxylobus glanduliferus, a native species of Venezuelan Andean moorlands. Using this compound (1) as a starting material, it was possible to prepare 12 aromatic esters, which were structurally characterized by analysis of their spectroscopic data (IR, 1D and 2D NMR and MS). The bactericidal activity of these diterpene derivatives was evaluated against four bacterial strains [two Gram-positive and two Gram-negative]: Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa.

Keywords

labdanes substituted benzoic acids esterifications NMR bactericidal activity 

Notes

Acknowledgment

This work was financially supported by the National Fund of Science, Technology and Innovation (FONACIT) (Grant No. 201300288) within the framework of the Project PCP France-Venezuela and by the CDCHTA-ULA (Grant No. C-1935-15-08-ED). Thanks are due to Eng. Juan Carmona Arzola, Department of Pharmacognosy and Organic Medicaments, Faculty of Pharmacy and Bioanalysis, University of Los Andes (ULA) for identification of plant material.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Pablo A. Chacon-Morales
    • 1
    • 2
    Email author
  • Juan M. Amaro-Luis
    • 2
  • Luis B. Rojas Fermin
    • 3
  • Nurby N. Rios Tesch
    • 3
  • Maria E. Lucena Escalona
    • 4
  • Miguel A. Rodriguez Pena
    • 5
  • Philippe A. Peixoto
    • 6
  • Remi Jacquet
    • 6
  • Denis Deffieux
    • 6
  • Laurent Pouysegu
    • 6
  • Stephane Quideau
    • 6
  1. 1.Natural Products Laboratory, Department of Chemistry, Faculty of ScienceUniversity of Los AndesMeridaVenezuela
  2. 2.Faculty of Chemical SciencesUniversity of GuayaquilGuayaquilEcuador
  3. 3.Research Institute, Faculty of Pharmacy and BioanalysisUniversity of Los AndesMeridaVenezuela
  4. 4.Facultad de Ciencias de la Salud, Laboratorio Clinico e HistopatologicoUniversidad Nacional de Chimborazo, UNACHRiobambaEcuador
  5. 5.Faculty of Pharmacy, Central University of Venezuela (UCV)CaracasVenezuela
  6. 6.Univ. Bordeaux, ISM (CNRS-UMR 5255) 351 cours de la LiberationTalence CedexFrance

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