Abstract
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.
Highlights
At lower temperature, the phase separation between the liquid-ordered (Lo ) phase and liquid-disordered (Ld ) phase are spontaneously formed in multicomponent lipid membranes consisting of saturated lipid, unsaturated lipid, and cholesterol
Further information regarding the interaction between DOPC and dor l-menthol was obtained mainly using 13 C-nuclear magnetic resonance (NMR) because its wide peak distribution aids analysis
According to previous reports [37], 1 H-NMR peaks characteristic of DOPC at 3.42, 1.30, and 0.895 ppm are assigned as choline methyl, methylene, and terminal methyl protons, respectively
Summary
The phase separation between the liquid-ordered (Lo ) phase and liquid-disordered (Ld ) phase are spontaneously formed in multicomponent lipid membranes consisting of saturated lipid, unsaturated lipid, and cholesterol. Lipid rafts are specialized membrane microdomains enriched in saturated lipids, sphingolipids, and cholesterol found in the plasma membrane [1,2,3,4,5,6,7]. Lipid rafts are believed to serve as a platform for the regulation of various cellular processes involved in signal transduction and membrane trafficking [8,9]. The fatty acid chains of phospholipids present in the lipid raft regions are rather tightly packed in the Lo phase, unlike the Ld phase present in the bulk of the membranes. Many studies have investigated the phase separation between Lo and Ld phases as a simple model for the raft domain
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