New jacaranone glucoside from Jacaranda oxyphylla leaves

Nat Prod Res. 2016 Nov;30(21):2421-8. doi: 10.1080/14786419.2016.1195378. Epub 2016 Jun 13.

Abstract

Jacaranda oxyphylla Cham. is popularly known as 'caroba-de-São-Paulo' and it is used in traditional medicine for microbial infections. A new phytoquinoid (α/β-glucoside-4-phenylacetate-6-(1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetate) (1) was isolated from J. oxyphylla leaves, together with three known compounds: quercetin-3-O-β-d-galactoside (2), verbascoside (3) and polystyrene (4). Their chemical structures were elucidated using spectroscopic techniques and by comparison with the related known compounds. In addition, it was found a pronounced acetylcholinesterase inhibitory activity for the quinoid 1 (100.0 ± 0.8%) and phenolic compounds 2 and 3 (99.9 ± 0.7 and 99.3 ± 0.5%, respectively), if compared to the standard eserine (92.7 ± 0.4%), that was analysed by a microplate spectrophotometer.

Keywords: Bignoniaceae; Jacaranda oxyphylla; antiacetylcholinesterase activity; quinoid.

MeSH terms

  • Anti-Infective Agents / pharmacology
  • Benzoquinones / chemistry
  • Benzoquinones / isolation & purification*
  • Benzoquinones / pharmacology
  • Bignoniaceae / chemistry*
  • Cholinesterase Inhibitors / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Plant Leaves / chemistry

Substances

  • Anti-Infective Agents
  • Benzoquinones
  • Cholinesterase Inhibitors
  • Glucosides
  • jacaranone