Computationally Assisted Assignment of the Kadsuraols, a Class of Chemopreventive Agents for the Control of Liver Cancer

Org Lett. 2018 Sep 21;20(18):5559-5563. doi: 10.1021/acs.orglett.8b02207. Epub 2018 Sep 7.

Abstract

Kadsuraols A-C (1-3), which are tetrahydrocyclobutaphenanthrofuranone-type lignans with a new carbon skeleton comprising a four-membered ring across C-1'-C-8, have been isolated from the roots of Kadsura longipedunculata. Their structures and absolute configurations were unambiguously determined using nuclear magnetic resonance, X-ray diffraction crystallography, DP4+ calculations, and computed and experimental electronic circular dichroism spectra. Kadsuraol C (3) exhibited hepatoprotective activity against N-acetyl- p-aminophenol (APAP)-induced toxicity. The compounds showed no cytotoxicity at 10 μM in a zone assay.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Chemoprevention
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • Kadsura / chemistry
  • Liver Neoplasms / drug therapy*
  • Liver Neoplasms / pathology
  • Models, Molecular
  • Plant Roots / chemistry
  • Quantum Theory

Substances

  • Antineoplastic Agents, Phytogenic