Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis

Phytochemistry. 2011 Apr;72(6):523-32. doi: 10.1016/j.phytochem.2010.12.015.

Abstract

Six aporphine alkaloids, (+)-(S)-N-butyrylcaaverine (1), (+)-(S)-N-propionylcaaverine (2), (+)-(S)-N-acetylcaaverine (3), (+)-(6aR,7R)-N-butyrylnorushinsunine (4), (+)-(6aR,7R,E)-N-(but-2-enoyl)norushinsunine (5), and N-formyldehydrocaaverine (6) were isolated from the roots of Illigera luzonensis, together with 16 known compounds. Their structures were determined through spectroscopic and MS analyses. Among the isolates, (-)-deoxypodophyllotoxin (13) was the most cytotoxic, with IC(50) values of 0.0057, 0.0067, 0.00004, and 0.0035μg/mL, respectively, against DLD-1, CCRF-CEM, HL-60, and IMR-32 cell lines. In addition, (-)-yatein (12) exhibited cytotoxic effects, with IC(50) values of 0.81, 0.20, and 0.59μg/mL, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Aporphines / chemistry*
  • Aporphines / isolation & purification*
  • Aporphines / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Hernandiaceae / chemistry*
  • Humans
  • Lignans / chemistry*
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Models, Molecular
  • Molecular Conformation
  • Plant Roots / chemistry*
  • Plants, Medicinal / chemistry
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Aporphines
  • Cytotoxins
  • Lignans