Isoquinoline alkaloids from Asimina triloba

Nat Prod Res. 2019 Oct;33(19):2823-2829. doi: 10.1080/14786419.2018.1504045. Epub 2018 Nov 20.

Abstract

A new aporphine glycoside, (-)-anolobine-9-O-β-D-glucopyranoside was isolated from the twigs of pawpaw (Asimina triloba) along with 7 known alkaloids including five aporphine alkaloids (anolobine, nornuciferine, norushinsunine, liriodenine, and lysicamine), a proaporhine alkaloid (stepharine), and a tetrahydrobenzylisoquinoline alkaloid (coclaurine). Among these compounds, nornuciferine, lysicamine, stepharine, and coclaurine are reported for the first time from this plant. The structure of the new compound was elucidated by spectroscopic methods, including 1 D, 2 D NMR, and HRESI-MS. The absolute configuration of compounds 1, 2, 7 and 8 was determined by CD experiment.

Keywords: Annonaceae; NMR; alkaloids; anolobine-9-O-β-D-glucopyranoside; aporphine.

Publication types

  • Video-Audio Media

MeSH terms

  • Alkaloids / chemistry*
  • Aporphines / chemistry
  • Asimina / chemistry*
  • Isoquinolines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Alkaloids
  • Aporphines
  • Isoquinolines
  • aporphine
  • lysicamine
  • stepharine
  • nornuciferine
  • liriodenine