Chirality-Dependent Interaction of d- and l-Menthol with Biomembrane Models

Chirality plays a vital role in biological membranes and has a significant effect depending on the type and arrangement of the isomer. Menthol has two typical chiral forms, d- and l-, which exhibit different behaviours. l-Menthol is known for its physiological effect on sensitivity (i.e. a cooling e...

Full description

Bibliographic Details
Main Authors: Pooja Gusain, Shinya Ohki, Kunihide Hoshino, Yoshio Tsujino, Naofumi Shimokawa, Masahiro Takagi
Format: Article
Language:English
Published: MDPI AG 2017-12-01
Series:Membranes
Subjects:
Online Access:https://www.mdpi.com/2077-0375/7/4/69
Description
Summary:Chirality plays a vital role in biological membranes and has a significant effect depending on the type and arrangement of the isomer. Menthol has two typical chiral forms, d- and l-, which exhibit different behaviours. l-Menthol is known for its physiological effect on sensitivity (i.e. a cooling effect), whereas d-menthol causes skin irritation. Menthol molecules may affect not only the thermoreceptors on biomembranes, but also the membrane itself. Membrane heterogeneity (lipid rafts, phase separation) depends on lipid packing and acyl chain ordering. Our interest is to elaborate the chirality dependence of d- and l-menthol on membrane heterogeneity. We revealed physical differences between the two optical isomers of menthol on membrane heterogeneity by studying model membranes using nuclear magnetic resonance and microscopic observation.
ISSN:2077-0375