Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase

J Nat Prod. 2007 Sep;70(9):1458-61. doi: 10.1021/np0702077. Epub 2007 Sep 7.

Abstract

Five new benzylphenethylamine alkaloids, hostasine (1), 8-demethoxyhostasine, 8-demethoxy-10-O-methylhostasine, 10-O-methylhostasine, and 9-O-demethyl-7-O-methyllycorenine, along with 12 known compounds, were isolated from Hosta plantaginea by bioassay-guided fractionation. The structures of the new alkaloids were established by means of extensive spectroscopic methods, and the relative configuration of 1 was further confirmed by single-crystal X-ray diffraction. 7-Deoxy-trans-dihydronarciclasine (IC(50) = 1.80 microM), a known alkaloid, showed strong activity against tobacco mosaic virus by the half-leaf method. Some of these alkaloids were also evaluated for their inhibitory activity against acetylcholinesterase. 8-Demethoxy-10-O-methylhostasine was found to possess significant activity, with an IC(50) of 2.32 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / drug effects*
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / pharmacology*
  • Crystallography, X-Ray
  • Hosta / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Tobacco Mosaic Virus / drug effects*

Substances

  • Antiviral Agents
  • Cholinesterase Inhibitors
  • Acetylcholinesterase