Gymnasterkoreaynes A-F, cytotoxic polyacetylenes from Gymnaster koraiensis

J Nat Prod. 2002 Jun;65(6):897-901. doi: 10.1021/np0104018.

Abstract

Six new polyacetylenes, gymnasterkoreaynes A-F (1-6), were isolated from the roots of Gymnaster koraiensis, together with 2,9,16-heptadecatrien-4,6-diyn-8-ol (7) and 1,9,16-heptadecatriene-4,6-diyn-3,8-diol (8), by bioassay-guided fractionation using the L1210 tumor cell line as a model for cytotoxicity. The structures of compounds 1-6 were established spectroscopically, which included 2D NMR experiments. Gymnasterkoreaynes A-F (1-6) are linear diacetylenes and are structurally related to falcarinol, panaxynol, panaxydiol, and panaxytriol. Of the compounds isolated, gymnasterkoreaynes B (2), C (3), F (6), and 1,9,16-heptadecatrien-4,6-diyn-3,8-diol (8) exhibited significant cytotoxicity against L1210 tumor cells with ED(50) values of 0.12-3.3 microg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry
  • Acetylene / isolation & purification*
  • Acetylene / pharmacology
  • Alkynes
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Asteraceae / chemistry*
  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / isolation & purification*
  • Bridged-Ring Compounds / pharmacology
  • Diynes
  • Drug Screening Assays, Antitumor
  • Fatty Alcohols / chemistry
  • Korea
  • Leukemia
  • Mice
  • Models, Biological
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Polymers / chemistry
  • Polymers / isolation & purification*
  • Polymers / pharmacology
  • Polyynes
  • Triterpenes / chemistry
  • Tumor Cells, Cultured / drug effects

Substances

  • Alkynes
  • Antineoplastic Agents, Phytogenic
  • Bridged-Ring Compounds
  • Diynes
  • Fatty Alcohols
  • Polymers
  • Triterpenes
  • gymnastatin F
  • falcarinol
  • Polyynes
  • Acetylene