Synthesis and anti-cancer activity of a glycosyl library of \varvec{N}-acetylglucosamine-bearing oleanolic acid |
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Authors: | Yi-Bing Zeng Hsin-Min Hsiao She-Hung Chan Ying-Hsin Wang You-Yu Lin Yu-Hsuan Kuo Jih-Hwa Guh Pi-Hui Liang |
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Institution: | 1. School of Pharmacy, College of Medicine, National Taiwan University, 1 Jen-Ai Road, Section 1, Taipei, 100, Taiwan
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Abstract: | N-Acetylglucosamine-bearing triterpenoid saponins (GNTS) were reported to be a unique type of saponins with potent anti-tumor activity. In order to study the structure–activity relationship of GNTS, 24 oleanolic acid saponins with ( $1 \rightarrow 3$ )-linked, ( $1\rightarrow 4$ )-linked, ( $1\rightarrow 6$ )-linked $N$ -acetylglucosamine oligosaccharide residues were synthesized in a combinatorial and concise method. The cytotoxicity of these compounds toward the leukemia cell line HL-60 and the colorectal cancer cell line HT-29 could not be improved. Half maximal inhibition below $10\,\upmu \hbox {M}$ was achieved in one single case. The study revealed that the activity decreased following the order of $3^{\prime }>4^{\prime }>6^{\prime }$ glycosyl modifications. GNTS that incorporated (d/l)-xylose and l-arabinose at positions $3^{\prime }$ and $4^{\prime }$ were more potent than those bearing other sugars. |
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