Lignans from the Australian Endemic Plant Austrobaileya scandens

J Nat Prod. 2016 Jun 24;79(6):1514-23. doi: 10.1021/acs.jnatprod.5b00988. Epub 2016 May 23.

Abstract

The sole species of the vascular plant family Austrobaileyaceae, Austrobaileya scandens, is endemic to the tropical rainforest of northeastern Queensland, Australia. A single lead-like enhanced fraction of A. scandens showed potent inhibition against human prostate cancer PC3 cells. Chemical investigation of this plant resulted in the isolation of two new aryltetralin lignans, austrobailignans 8 and 9 (1 and 2), and the synthetic compound nicotlactone B (3), newly identified as a natural product together with nine known lignans (4-12). Their structures were established on the basis of spectroscopic analyses. Absolute configurations of the new compounds were determined by quantum chemical electronic circular dichroism (ECD) calculations employing time-dependent density functional theory. The ECD calculations were also used to assign the absolute configuration of marphenol K (4) and revise the absolute configuration of kadsurindutin C (20). Ten out of the 12 isolated compounds inhibited the growth of PC3 cells with IC50 values ranging from micromolar to nanomolar. Marphenol A (5) was found for the first time to induce apoptosis and arrest the S cell cycle phase of PC3 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Australia
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Magnoliopsida / chemistry*
  • Male
  • Molecular Structure
  • Prostatic Neoplasms / drug therapy*
  • S Phase / drug effects

Substances

  • Antineoplastic Agents, Phytogenic
  • Lignans