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Membranes 2017, 7(4), 69; https://doi.org/10.3390/membranes7040069

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

1
School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1Asahidai, Nomi, Ishikawa 923-1292, Japan
2
Takasago International Corporation, 5-37-1, Kamata, Ota-ku, Tokyo 144-8721, Japan
*
Authors to whom correspondence should be addressed.
Received: 30 November 2017 / Revised: 13 December 2017 / Accepted: 14 December 2017 / Published: 15 December 2017
(This article belongs to the Section Membrane Preparation and Characterization)
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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. View Full-Text
Keywords: d- and l-menthol; phase separation; lipid rafts; liquid-ordered (Lo); liquid-disordered (Ld); solid-ordered (So) d- and l-menthol; phase separation; lipid rafts; liquid-ordered (Lo); liquid-disordered (Ld); solid-ordered (So)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Gusain, P.; Ohki, S.; Hoshino, K.; Tsujino, Y.; Shimokawa, N.; Takagi, M. Chirality-Dependent Interaction of d- and l-Menthol with Biomembrane Models. Membranes 2017, 7, 69.

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