A zwitterionic alkaloid, containing a rare cyclopentadienyl anion unit, from the stem barks of Daphniphyllum macropodum Miq

Chem Biodivers. 2006 Nov;3(11):1255-9. doi: 10.1002/cbdv.200690127.

Abstract

A new Daphniphyllum alkaloid daphnicyclidin L (1), containing a rare cyclopentadienyl anion, which is stabilized as a zwitterion by an internal iminium counterion, was isolated from the stem barks of Daphniphyllum macropodum Miq., together with four known alkaloids: daphnicyclidin D (2), daphnicyclidin H (3), deoxyyuzurimine (4), and yuzurimine (5). The structures were elucidated on the basis of spectroscopic data. The configuration of 1 was elucidated by single-crystal X-ray diffraction crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Anions
  • Crystallography, X-Ray
  • Cyclopentanes / chemistry*
  • Ethanol / chemistry
  • Magnetic Resonance Spectroscopy
  • Magnoliopsida / metabolism*
  • Models, Chemical
  • Models, Molecular
  • Nitrogen / chemistry
  • Plant Extracts / chemistry*
  • Plants, Medicinal / metabolism
  • Polycyclic Compounds / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry
  • Temperature
  • X-Ray Diffraction

Substances

  • Alkaloids
  • Anions
  • Cyclopentanes
  • Plant Extracts
  • Polycyclic Compounds
  • daphnicyclidin L
  • Ethanol
  • Nitrogen