New amide alkaloids from Delphinium brunonianum

Fitoterapia. 2019 Jul:136:104186. doi: 10.1016/j.fitote.2019.104186. Epub 2019 May 28.

Abstract

Five new amide alkaloids, named delamide A-E (1-5), along with five known ones, methyl-N-(3-carboxy-2-methylpropanoyl) anthranilate (6), benzoic acid, 2-[(1-oxodecyl) amino]-methylester (7), puberline (8), benzoic acid, 2-[(4-methoxy-2-methyl-1, 4-dioxobutyl) amino]-methylester (9) and benzoic acid, 2-[(4-methoxy-3-methyl-1, 4-dioxobutyl) amino]-methylester (10) were isolated from the extract of Delphinium brunonianum. Their structures were elucidated by extensive spectroscopic analyses (including 1D-, 2D-NMR, and HR-ESI-MS). 1-10 were also evaluated for their acetylcholinesterase (AChE) inhibiting activity by the Ellman's method. Delamide A (1) showed highly selective AChE inhibition activity. The kinetic analysis revealed that 1 was a mixed-type reversible inhibitor of AChE.

Keywords: Acetylcholinesterase; Amide alkaloids; Butyrylcholinesterase; Delphinium brunonianum.

MeSH terms

  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Delphinium / chemistry*
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Components, Aerial / chemistry*
  • Tibet

Substances

  • Alkaloids
  • Cholinesterase Inhibitors
  • Phytochemicals