Synthesis of 13-amino telekin derivatives and their cytotoxic activity

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::

• telekin
• Michael addition reaction
• sesquiterpene lactone
• cytotoxicity
• eudesmane

Additional information

Funding

This work was partly supported by the Basic Science Research Program of National Research Foundation from the Ministry of Education, Science and Technology of Korea [grant number 2014-002046]. Dr Xie also thanks for the support of the International Scholar Exchange Fellowship Program [grant number ISEF 2014-2015] from the Korea Foundation for Advanced Studies.