Isolation, Bioactivity and Structural Studies of 6-acetyl-7-hydroxy-2,2-dimethylchoromene from Calea hispida

Autores

  • Agnes Thiane Pereira Machado Universidade Estadual de Ponta Grossa
  • Jorge Iulek Universidade Estadual de Ponta Grossa
  • Marcio Silva Universidade Tecnológica Federal do Paraná - Ponta Grossa
  • Lorna Hosoya Name Universidade Estadual de Ponta Grossa
  • Michele Aparecida Besten Universidade Estadual de Ponta Grossa
  • Domingos Sávio Nunes Universidade Estadual de Ponta Grossa

Palavras-chave:

6-acetyl-7-hydroxy-2, 2-dimethylchromene, Calea hispida, molecular dynamics, Helicobacter pylori activity.

Resumo

The volatiles from Calea hispida leaves were analyzed by GC-MS-FID and presented as the main components (E)-nerolidol, beta-cubebene, spathulenol, alfa-cadinol and 6-acetyl-7-hydroxy-2,2-dimethylchromene, the latter being the major component (54.46%), which was crystallized and analyzed by X ray diffraction. Microbiological assays indicated activity of this chromene against Helicobacter pylori (ATCC 26695), what prompts a deeper investigation on this concern. The crystal structure study showed no difference to that reported before for this compound while quantum mechanics optimization indicated that the crystal structure is close to a minimum energy conformation, what includes the relative position of the hydroxyl to the acetyl moiety. In fact, potential energy scan and molecular dynamics showed that the intramolecular hydrogen bond within these two moieties is quite stable, both in gas phase and in solution.

 

Publicado

18-11-2016

Edição

v. 8 n. 6 (2016): Revista Virtual de Química

Seção

Artigos

Licença

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