JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 3 (2016): Journal of the Chilean Chemical Society
Original Research Papers

SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES

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  • Mauricio E. Osorio,
  • Karol A. Quiroz,
  • Marcela A. Carvajal,
  • Alejandra P. Vergara,
  • Elizabeth Y. Sánchez,
  • Cesar E. González,
  • Karen S. Catalán
Mauricio E. Osorio
Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María
Karol A. Quiroz
Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María
Marcela A. Carvajal
Centro de Biotecnología CB-DAL, Universidad Técnica Federico Santa María
Alejandra P. Vergara
Centro de Biotecnología CB-DAL, Universidad Técnica Federico Santa María
Elizabeth Y. Sánchez
Centro de Biotecnología CB-DAL, Universidad Técnica Federico Santa María
Cesar E. González
Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María
Karen S. Catalán
Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María
Published September 10, 2016
Keywords
  • C-prenylation,
  • Prenylated acetophenone,
  • Prenylated benzaldehyde,
  • Electrophilic aromatic substitution,
  • Anti-phytopathogenic,
  • DPPH radical scav¬enging activity
    • ...More
    Less
How to Cite
Osorio, M. E., Quiroz, K. A., Carvajal, M. A., Vergara, A. P., Sánchez, E. Y., González, C. E., & Catalán, K. S. (2016). SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES. Journal of the Chilean Chemical Society, 61(3). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/100

Copyright (c) 2017 Mauricio E. Osorio, Karol A. Quiroz, Marcela A. Carvajal, Alejandra P. Vergara, Elizabeth Y. Sánchez, Cesar E. González, Karen S. Catalán

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Abstract

The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These com­pounds were obtained by electrophilic aromatic substitution (SEAr) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scav­enging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μM concentrations. The antioxidant activity went from 27.20 μM to >100 μM. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and <3.9 μM.

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