Synthesis of 13-amino telekin derivatives and their cytotoxic activity

Nat Prod Res. 2015;29(8):756-63. doi: 10.1080/14786419.2014.987143. Epub 2014 Dec 11.

Abstract

Telekin is a eudesmane sesquiterpene-lactone naturally occurring in many medicinal plants with antitumour and anti-inflammatory activity. In this study, a series of 13-amino derivatives of telekin have been synthesised through Michael addition reaction, and their relative configurations were exemplified by the single crystal X-ray diffraction of the dimethylamine adduct. The in vitro cytotoxicity against three tumour cell lines of these amine derivatives was evaluated. The piperidine and 4-hydroxypiperidine adducts displayed stronger cytotoxic activity than telekin.

Keywords: Michael addition reaction; cytotoxicity; eudesmane; sesquiterpene lactone; telekin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plants, Medicinal / chemistry
  • Sesquiterpenes, Eudesmane / chemical synthesis*
  • Sesquiterpenes, Eudesmane / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Sesquiterpenes, Eudesmane
  • telekin