Synthesis and Evaluation of Four Hederagenin Glycosides as α‐Glucosidase Inhibitor

Abstract

The four hederagenin glycosides 1–4 were efficiently synthesized through one‐pot sequential glycosylations with glycose 1‐(trichloroacetimidate)s as donors, resulting in a significantly simplified synthetic procedure without isolation of glycosylation intermediates. The activity of the synthetic hederagenin glycosides 1–4 against α‐glucosidase type IV was evaluated; hederagenin glycoside 4 containing an α‐L‐rhamnopyranosyl unit showed the best activity with an IC50 value of 47.9 μM.

Comprehensive profiling of phenolic compounds and triterpenoid saponins from Acanthopanax senticosus and their antioxidant, α-glucosidase inhibitory activities

“…The hydroxylation at C-23 position affected to reduce in the α-glucosidase activity, which was supported by previous studies 80,81 . Additionally, the presence of rhamnose at C-3 position was assumed to be an important point in α-glucosidase inhibition, and Wang, et al 19 and Liu, et al 82 also reported similar results. Meanwhile, several compounds exhibited moderate inhibitory activities against ONOO − .…”

Pharmacological overview of hederagenin and its derivatives

“…Liu et al 94 efficiently synthesized four hederagenin glycosides 303–306 by glycosylation and evaluated the activity of compounds 303–306 against α-glucosidase type IV (Fig. 17).…”

Generalising a Simple Methodology for the Regioselective Anomeric Deacetylation of Carbohydrates

“…Methylamine has advantages over other alkali‐type materials in that it has a low boiling point (‐6.3 °C, but is readily available as a solution) and the by‐products of the deacetylation reaction are water soluble, which means they can be removed easily during the workup of the reaction. The use of methylamine has been reported previously but only in isolated situations (See refs . for examples) using varying conditions.…”

“…The use of methylamine has been reported previously but only in isolated situations (See refs. [18][19][20][21][22] for examples) using varying conditions. Thus we felt that the development of a general methodology, utilising methylamine, that is amenable to a variety of different substrates would be useful for scientists preparing hemiacetals for various purposes.…”