Pyrrole 2-carbaldehyde derived alkaloids from the roots of Angelica dahurica

J Nat Med. 2019 Sep;73(4):769-776. doi: 10.1007/s11418-019-01328-1. Epub 2019 Jun 17.

Abstract

Six new pyrrole 2-carbaldehyde derived alkaloids, dahurines A-F (1-6), along with five known ones (7-11) and butyl 2-pyrrolidone-5-carboxylate (12) were isolated from the roots of Angelica dahurica. Their structures were determined by extensive spectroscopic and spectrometric data (1D and 2D NMR, IR, and HRESIMS) and calculated electronic circular dichroism (ECD) methods. Although compounds 7 and 8 have been chemically synthesized, they were obtained from natural materials for the first time. Compounds 2, 3, 4, 10, and 11 exhibited acetylcholinesterase inhibitory activity with IC50 values in the range of 47.5-52.5 μM. Pyrrole 2-carbaldehyde derived alkaloids from the roots of Angelica dahurica.

Keywords: AChE inhibitory activity; Angelica dahurica; Dahurines A–F; Pyrrole 2-carbaldehyde alkaloid.

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alkaloids / chemistry*
  • Angelica / chemistry*
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Roots / chemistry*
  • Pyrroles / isolation & purification
  • Pyrroles / pharmacology*

Substances

  • Alkaloids
  • Cholinesterase Inhibitors
  • Pyrroles
  • pyrrole-2-carboxaldehyde
  • Acetylcholinesterase