Synthesis and antitumor activity evaluation of a novel series of xanthone derivatives

Abstract

A natural xanthone, 1,3,6-trihydroxy-5-methoxyxanthone, was totally synthesized for the first time by six steps in 31% overall yield. The xanthone skeleton was formed by a one-step synthesis in 80% yield, and five of its novel derivatives were also obtained by this approach. This synthetic strategy and all the derivatives could be further used for the preparation of other natural xanthones. All the xanthones were characterized by NMR and ESI-MS, and the cytotoxicity of these xanthones was evaluated against HepG2 and HT-29 cells, and the preliminary structure–activity relationship was evaluated from the results. It was proved that the presence of 3-OH group in the molecule is crucial for its biological activity, while the presence of substituents at C-5 and C-6 may also be beneficial.

Keywords::

• xanthones
• 1,3,6-trihydroxy-5-methoxyxanthone
• cytotoxicity of xanthones
• xanthone synthesis

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by the National Natural Science Foundation of China [grant number 81302649], Tianjin Municipal Science and Technology Commission [grant number 14JCQNJC13200], and Scientific Research Program of Tianjin University of Science and Technology [grant number 20120116].