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Issue 28, 2016
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Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

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Abstract

Two partially acylated oligorhamnoside derivatives 1 and 2 structurally related to the natural product mezzettiaside-6 were synthesized via a ‘2 + 1 + 1’ convergent strategy. The bioassay results showed that the introduction of the acetyl groups to the 2-position of the terminal L-rhamnose was helpful to improve in vitro cytotoxicity. Compound 1 showed both extensive in vitro cytotoxicity in tumor cell lines and potential antimultidrug resistance capability. Preliminary mechanistic studies demonstrated that compound 1 could inhibit cell growth by inducing apoptosis, arresting cell cycle progression at the S phase in K562 cells.

Graphical abstract: Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

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Supplementary files

Article information


Submitted
21 Apr 2016
Accepted
19 May 2016
First published
19 May 2016

Org. Biomol. Chem., 2016,14, 6691-6702
Article type
Paper

Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

G. Song, S. Li, Z. Lei, Y. Li, J. Li, Y. Liao and Z. Cui, Org. Biomol. Chem., 2016, 14, 6691
DOI: 10.1039/C6OB00862C

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