Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity

Can Side-Chain Conformation and Glycosylation Selectivity of Hexopyranosyl Donors Be Controlled with a Dummy Ligand?

“…Glycosylation reactions were carried out by stirring 0.15 M CH 2 Cl 2 solutions of donors 7a – d (1.0 equiv) with the acceptor (1.2 equiv) and 4 Å AWMS for 1 h, followed by cooling to −78 °C and stirring for another 0.5 h. TMSOTf (0.2 equiv) then was added to the mixture as a 10% solution in CH 2 Cl 2 . ,− All glycosylations were maintained at −78 °C and quenched with 0.2 mL of triethylamine at that temperature before the mixtures were warmed to room temperature, filtered through celite, diluted with CH 2 Cl 2 , and washed with saturated aqueous NaHCO 3 . The resulting glycosides were then isolated by silica gel chromatography, leading to the results presented in Tables and .…”

“…HRMS (ESI) m/z: [M + Na] + calcd for C 16 H 28 O 10 Na 403.1574; found 403.1567. (32). Obtained from the deprotection of compound 11β (15 mg) using the general procedure for desulfurization eluting from silica gel with 10% MeOH in CH 2 Cl 2 to give 6.5 mg for a 91% yield.…”

Characterization of Seven New Steroidal Saponins from Korean Oat Cultivars by UPLC-QTOF-MS and UPLC-MS/MS

“…Similar results were confirmed in reports by Okubo et al, Beit-Yannai et al, Dai et al (furospirostane < furostane < spirostane saponin). In addition, structures containing two or more sugar chains at the C-3 position (especially the additional rhamnose units), ,, and the 25­( R / S )-configuration (25 R > 25 S : A549, Caski, HepG2, and MCF-7; , 25 S > 25 R : BEL-7402, HT-29, Hela, MDA-MB-468, BT549, and SW620 cell lines , ) were considered important for cytotoxicity. Moreover, the aforementioned factors also influenced anti-inflammatory, − antiatherosclerotic, antidiabetic, and antiosteosarcoma activities.…”