Cephalocyclidin A, a novel pentacyclic alkaloid from Cephalotaxus harringtonia var. nana

J Org Chem. 2002 Apr 5;67(7):2283-6. doi: 10.1021/jo016327f.

Abstract

A novel alkaloid with an unprecedented fused-pentacyclic skeleton and six-consecutive asymmetric centers, cephalocyclidin A (1), has been isolated from the fruits of Cephalotaxus harringtonia var. nana, and the structure was elucidated on the basis of spectroscopic data. The relative and absolute stereochemistry of 1 was determined by a combination of NOESY correlations, X-ray crystallographic data, and the exciton chirality method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Japan
  • KB Cells / drug effects
  • Lymphoma
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • cephalocyclidin A