Diosgenin-induced physicochemical effects on phospholipid bilayers in comparison with cholesterol

College

College of Science

Department/Unit

Chemistry

Document Type

Article

Source Title

Bioorganic & Medicinal Chemistry Letters

Volume

36

First Page

1

Last Page

7

Publication Date

1-2021

Abstract

Diosgenin (DGN), which is a sterol occurring in plants of the Dioscorea family, has attracted increasing attention for its various pharmacological activities. DGN has a structural similarity to cholesterol (Cho). In this study we investigated the effects of the common tetracyclic cores and the different side chains on the physicochemical properties of lipid bilayer membranes. Differential scanning calorimetry showed that DGN and Cho reduce the phase transition enthalpy to a similar extent. In 2

H NMR, deuterated-DGN/Cho and POPC showed similar ordering in POPC bilayers, which revealed that DGN is oriented parallel to the membrane normal like Cho. It was suggested that the affinity of DGN-Cho in membrane is stronger than that of DGN-DGN or Cho-Cho interaction. 31P NMR of POPC in bilayers revealed that, unlike Cho, DGN altered the interactions of POPC headgroups at 30 mol%. These results suggest that DGN below 30 mol% has similar effects with Cho on basic biomembrane properties.

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Digitial Object Identifier (DOI)

https://doi.org/10.1016/j.bmcl.2021.127816

Disciplines

Biochemistry

Keywords

Diosgenin; Sapogenins; Cholesterol; Bilayer lipid membranes; Yams—Analysis

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