Natural terpenes: Self-assembly and membrane partitioning

Monoterpenes (MTs) are highly hydrophobic substances present in essential oils. They cover a wide spectrum of biological effects with a membrane interaction as a common point. Here we studied the surface activity of camphor, cineole, thymol, menthol and geraniol, and their ability to reach and incor...

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Bibliographic Details
Published in:	Biophysical chemistry Vol. 122; no. 2; pp. 101 - 113
Main Authors:	Turina, A.del V., Nolan, M.V., Zygadlo, J.A., Perillo, M.A.
Format:	Journal Article
Language:	English
Published:	Netherlands Elsevier B.V 20-07-2006
Subjects:	Air Bromthymol Blue - chemistry Camphor Cineole Critical micellar concentration Diffusion Geraniol Langmuir films penetration Membranes, Artificial Menthol Micelles Molecular Structure Monoterpene-bilayer interaction Octanols - chemistry Octoxynol - chemistry Particle Size Permeability Phosphatidylcholines - chemistry Principal Component Analysis Pyrimidinones - chemistry Self-assembling Surface Properties Terpenes - chemistry Thymol Water - chemistry π A D poPC π i Δ π 0 Thymol K d SA dpPC Langmuir films penetration Critical micellar concentration GABA A-R [ 3H] FNZ ANOVA CMC MLVs Menthol Self-assembling λ max Geraniol P m / w PCs THY MT sPC Cineole CIN π cut-off TX-100 CAM PCA BTB B max GER Camphor MEN SEM MER Monoterpene-bilayer interaction μ P o / w Principal component analysis
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Summary:	Monoterpenes (MTs) are highly hydrophobic substances present in essential oils. They cover a wide spectrum of biological effects with a membrane interaction as a common point. Here we studied the surface activity of camphor, cineole, thymol, menthol and geraniol, and their ability to reach and incorporate into model membranes affecting some features of their dynamic organization. All the MTs studied self-aggregated in water with critical micellar concentrations (CMC) between 3 and 8 μM. Their octanol–water and membrane–water partition coefficients were correlated with one another. They all penetrated in monomolecular layers of dipalmitoyl-phosphatildylcholine at the air–water interface, even at surface pressures ( π) above the equilibrium lateral pressure of bilayers; thymol exhibited the highest (61.3 mN/m) and camphor the lowest (37 mN/m) π cut-off value. They affected the self-aggregation of Triton X-100, increasing its CMC from 0.16 mM in the absence of MTs up to 0.68 mM (e.g. for geraniol), and the topology of sPC vesicles, increasing its surface curvature, suggesting their location at the polar head group region of the membrane. The latter was supported by their ability to increase differentially the polarity of the membrane environment sensed by two electrochromic dyes. Dipole moment values (between 1.224 and 2.523 D) and solvation areas (between 80 and 97 Å 2) were calculated from their energy-minimized structures. The relative contribution of each experimental, theoretical and structural property to determine MTs' effects on membrane dynamics were evaluated by a principal component analysis.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0301-4622 1873-4200
DOI:	10.1016/j.bpc.2006.02.007