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

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Chemistry of Natural Compounds Aims and scope

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.

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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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Authors and Affiliations

  1. Natural Products Laboratory, Department of Chemistry, Faculty of Science, University of Los Andes, Merida, 5101, Venezuela

    Pablo A. Chacon-Morales

  2. Faculty of Chemical Sciences, University of Guayaquil, 090112, Guayaquil, Ecuador

    Pablo A. Chacon-Morales & Juan M. Amaro-Luis

  3. Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Merida, 5101, Venezuela

    Luis B. Rojas Fermin & Nurby N. Rios Tesch

  4. Facultad de Ciencias de la Salud, Laboratorio Clinico e Histopatologico, Universidad Nacional de Chimborazo, UNACH, Riobamba, Ecuador

    Maria E. Lucena Escalona

  5. Faculty of Pharmacy, Central University of Venezuela (UCV), Caracas, 1051, Venezuela

    Miguel A. Rodriguez Pena

  6. Univ. Bordeaux, ISM (CNRS-UMR 5255) 351 cours de la Liberation, 33405, Talence Cedex, France

    Philippe A. Peixoto, Remi Jacquet, Denis Deffieux, Laurent Pouysegu & Stephane Quideau

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  1. Pablo A. Chacon-Morales
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  2. Juan M. Amaro-Luis
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  11. Stephane Quideau
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Correspondence to Pablo A. Chacon-Morales.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2019, pp. 580–585.

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Chacon-Morales, P.A., Amaro-Luis, J.M., Rojas Fermin, L.B. et al. Hemisynthesis and Bactericidal Activity of Several Substituted Benzoic Acid Esters of 13(S)-Labdan-8α,15-Diol, a Diterpene from Oxylobus glanduliferus. Chem Nat Compd 55, 677–684 (2019). https://doi.org/10.1007/s10600-019-02777-6

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  • DOI: https://doi.org/10.1007/s10600-019-02777-6

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