Cytotoxic alkaloids from the bulbs of Fritillaria hupehensis

Chem Biodivers. 2008 Feb;5(2):259-66. doi: 10.1002/cbdv.200890023.

Abstract

Phytochemical investigation of the bulbs of Fritillaria hupehensis resulted in the isolation and structural elucidation of four new steroidal penta- and hexacyclic veratraman- and cevan-based alkaloids, respectively, compounds 1-4. They were obtained together with the known constituents ebeinine (5) and zhebeinine (6), which were isolated for the first time from this plant. The structures of the new isolates were established by spectroscopic and mass-spectrometric analyses, in combination with chemical methods. All compounds were assayed for their cytotoxic effects towards HeLa and HepG2 cell lines. Compounds 1 and 2 showed significant inhibitory effects against both types of tumor cells, with IC(50) values in the range 2.52-0.23 microM, similar as those for 5-fluorouracil used as positive control.

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*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cevanes / chemistry
  • Cevanes / isolation & purification
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fritillaria / chemistry*
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Plant Tubers / chemistry*
  • Reference Standards
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Spectrophotometry, Infrared / methods
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Cevanes
  • verticine