1038536-92-3Relevant academic research and scientific papers
Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity
Miyashita, Hiroyuki,Kai, Yuuki,Nohara, Toshihiro,Ikeda, Tsuyoshi
, p. 1309 - 1315 (2008)
Natural steroidal glycosides containing α-l-rhamnopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that α-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while β-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring β-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding α-chacotriosyl glycosides.
