Effect of the number of sugar units on the interaction between diosgenyl saponin and membrane lipids

Abstract

Saponin is the main bioactive component of the Dioscorea species, which are traditionally used for treating chronic diseases. An understanding of the interaction process of bioactive saponins with biomembranes provides insights into their development as therapeutic agents. The biological effects of saponins have been thought to be associated with membrane cholesterol (Chol). To shed light on the exact mechanisms of their interactions, we investigated the effects of diosgenyl saponins trillin (TRL) and dioscin (DSN) on the dynamic behavior of lipids and membrane properties in palmitoyloleolylphosphatidylcholine (POPC) bilayers using solid-state NMR and fluorescence spectroscopy. The membrane effects of diosgenin, a sapogenin of TRL and DSN, are similar to those of Chol, suggesting that diosgenin plays a major role in membrane binding and POPC chain ordering. The amphiphilicity of TRL and DSN enabled them to interact with POPC bilayers, regardless of Chol. In the presence of Chol, the sugar residues more prominently influenced the membrane-disrupting effects of saponins. The activity of DSN, which bears three sugar units, led to perturbation and further disruption of the membrane in the presence of Chol. However, TRL, which bears one sugar residue, increased the ordering of POPC chains while maintaining the integrity of the bilayer. This effect on the phospholipid bilayers is similar to that of cholesteryl glucoside. The influence of the number of sugars in saponin is discussed in more detail.