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Yeast Luminometric and Xenopus Oocyte Electrophysiological Examinations of the Molecular Mechanosensitivity of TRPV4

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Umbellulone modulates TRP channels.

Jian Zhong¹, Alberto Minassi, Jean Prenen

¹Department of Molecular Cell Biology, Laboratory Ion Channel Research, Campus Gasthuisberg, Katholieke Universiteit Leuven, Herestraat 49, 3000 Leuven, Belgium.

Pflugers Archiv : European Journal of Physiology

|November 1, 2011

Summary

Umbellulone (UMB) from California bay laurel activates cold-sensing TRPA1 and TRPM8 channels. Derivatives show altered activity, with non-electrophilic forms acting as potent TRPM8 activators and TRPA1/TRPM8 blockers.

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Area of Science:

Molecular pharmacology
Neuroscience
Chemical senses

Background:

Umbellulone (UMB), a compound from California bay laurel, induces a cold sensation upon inhalation.
This sensation is linked to the activation of cold-sensing transient receptor potential (TRP) channels, specifically TRPA1 and TRPM8.

Purpose of the Study:

To investigate the action of umbellulone and its derivatives on TRPA1 and TRPM8 channels.
To determine the role of umbellulone's electrophilic properties in channel activation and blocking.

Main Methods:

Electrophysiological studies using TRPA1 and TRPM8 channels expressed in cell systems.
Utilized umbellulone derivatives with modified thiol-trapping (electrophilic) properties.
Investigated dose-dependent activation, channel block, and effects of specific mutations (e.g., TRPA1 C622S).

Main Results:

Umbellulone dose-dependently activated TRPA1, acting as a partial electrophilic agonist.
Umbellulone also activated TRPM8, though less potently than TRPA1.
Non-electrophilic UMB derivatives showed increased TRPM8 activation and potent TRPA1/TRPM8 blocking, while acetylated analogs lost activity, suggesting steric hindrance.

Conclusions:

Umbellulone is a bimodal activator of TRPA1 and a weak activator of TRPM8.
Non-electrophilic UMB derivatives are superior TRPM8 activators and effective blockers of both TRPA1 and TRPM8.
Steric factors likely influence the binding of the UMB pharmacophore to TRPA1 and TRPM8.