11-oxygenated cytotoxic 8,9-secokauranes from a New Zealand liverwort, Lepidolaena taylorii

Phytochemistry. 1999 Feb;50(3):423-33. doi: 10.1016/s0031-9422(98)00602-5.

Abstract

Four new cytotoxic 8,9-secokauranes have been identified from the liverwort Lepidolaena taylorii. The 11-oxygenation found in three of these has not been encountered in the 8,9-secokauranes known from higher plants. NMR studies were combined with molecular modelling to determine the preferred conformations. Six structurally related kauren-15-ones were also found, including three new compounds. Some of these compounds showed differential cytotoxic activity against human tumor cell lines. The probable mode of cytotoxic action was supported by Michael addition of a thiol. Two 8,9-secokauranes were the main cytotoxins in another New Zealand liverwort. L. palpebrifolia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Division / drug effects
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry / methods
  • Mice
  • Molecular Structure
  • Oxygen / chemistry
  • Plants / chemistry*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes
  • Oxygen