Journal
CARBOHYDRATE RESEARCH
Volume 423, Issue -, Pages 49-69Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2016.01.010
Keywords
OSW-1 disaccharide; Glycosylation; Lupane saponins; SAR; Hydrogen bond network
Funding
- National Science Centre, Poland [2012/07/B/ST5/00823]
- Czech Ministry of Education grant from the National Program for Sustainability I [LO1204]
- Czech Grant Agency [14-19590S]
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A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1 -> 4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds. (C) 2016 Elsevier Ltd. All rights reserved.
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