Cytotoxic activity of some phenanthroindolizidine N-oxide alkaloids from Cynanchum vincetoxicum

Dan Stærk, Jette Christensen, Else Lemmich, Jens Øllgaard Duus, Carl Erik Olsen, Jerzy W. Jaroszewski

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Two previously known phenanthroindolizidine alkaloids, (-)-10 beta -antofine N-oxide (1) and (-)-10 beta ,13a alpha -14 beta -hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10 beta ,13a alpha -secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were established by means of NMR methods, including COSY, NOESY, HSQC, and HMBC experiments, as well as from their CD spectra. Cytotoxic activity of the alkaloids was assessed in vitro using both a drug-sensitive KB-3-1 and a multidrug-resistant KB-V1 cancer cell line. The antofine derivatives (1 and 2) showed pronounced cytotoxicity against the drug-sensitive cell line (IC50 values about 100 nM), whereas the secoantofine derivative (3) was considerably less active. The KB-V1 cell line showed a marginal resistance against all alkaloids, demonstrating that these compounds are poor substrates for the P-glycoprotein (P-170) efflux pump.
Original languageEnglish
JournalJournal of Natural Products
Volume63
Issue number11
Pages (from-to)1584-1586
ISSN0163-3864
DOIs
Publication statusPublished - 2000
Externally publishedYes

Keywords

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Circular Dichroism
  • Drug Screening Assays, Antitumor
  • Humans
  • Indolizines
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Phenanthrenes
  • Plant Leaves
  • Plants, Medicinal
  • Spectrophotometry, Ultraviolet
  • Tumor Cells, Cultured
  • 10,13a,14-hydroxyantofine N-oxide
  • 10,13a-secoantofine N-oxide
  • 10-antofine N-oxide
  • 10beta antofine n oxide
  • 10beta,13aalpha 14beta hydroxyantofine n oxide
  • phenanthroindolizidine derivative
  • plant extract
  • unclassified drug
  • article
  • cancer cell culture
  • controlled study
  • cytotoxicity
  • drug isolation
  • drug structure
  • human
  • human cell
  • nuclear magnetic resonance
  • squamous cell carcinoma
  • Cynanchum vincetoxicum
  • Vincetoxicum
  • PLANT
  • CHEMISTRY,
  • PHARMACOLOGY
  • MULTIDRUG-RESISTANCE
  • TYLOPHORA-TANAKAE
  • CARCINOMA-CELLS

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