Nematicidal Stemona Alkaloids from Stemona parviflora

J Nat Prod. 2016 Oct 28;79(10):2599-2605. doi: 10.1021/acs.jnatprod.6b00528. Epub 2016 Sep 29.

Abstract

Eight new alkaloids, 3β-n-butylstemonamine (1), 8-oxo-3β-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1-4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / isolation & purification*
  • Antinematodal Agents / pharmacology*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Heterocyclic Compounds, 4 or More Rings
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Stemonaceae / chemistry*

Substances

  • Alkaloids
  • Antinematodal Agents
  • Drugs, Chinese Herbal
  • Heterocyclic Compounds, 4 or More Rings
  • methoxystemofoline
  • stemofoline