Influence of plant terpenoids on the permeability of mitochondria and lipid bilayers

Five sesquiterpene alcohol esters of the carotane series, from plants of the genus Ferula, were investigated with regard to their capacity to modify the ion permeability of both planar lipid bilayers and mitochondria. These compounds are subdivided into two structural groups that differ in their eff...

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Published in:Biochimica et biophysica acta 2001-05, Vol.1512 (1), p.98-110
Main Authors: Abramov, Andrey Y, Zamaraeva, Maria V, Hagelgans, Albert I, Azimov, Rustam R, Krasilnikov, Oleg V
Format: Article
Language:English
Subjects:
Animals
Benzoates - pharmacology
Bridged Bicyclo Compounds
Carrier
Cycloheptanes
Divalent cation
Electrochemistry
Intracellular Membranes - chemistry
Intracellular Membranes - drug effects
Ion Transport
Ionophores - pharmacology
Lipid bilayer
Lipid Bilayers - chemistry
Mitochondria
Mitochondria, Liver - drug effects
Models, Molecular
Molecular Structure
Permeability
Plants - chemistry
Rats
Sesquiterpenes - pharmacology
Structure-Activity Relationship
Terpenes - chemistry
Terpenes - pharmacology
Terpenoid
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Summary:Five sesquiterpene alcohol esters of the carotane series, from plants of the genus Ferula, were investigated with regard to their capacity to modify the ion permeability of both planar lipid bilayers and mitochondria. These compounds are subdivided into two structural groups that differ in their effects on membrane permeability. Complex esters of sesquiterpene alcohols with aliphatic acids, which constituted the first group (lapidin and lapiferin), do not possess ionophoric properties. The second group comprised complex esters of sesquiterpene alcohols with aromatic acids (ferutinin, tenuferidin and ferutidin), all of which increase cation permeability of lipid bilayers and mitochondria in a dose-dependent manner. A pronounced selectivity of the terpenoid-modified membranes for divalent cations versus monovalent cations was found. Evidence of a carrier mechanism for terpenoid-induced ion transport is demonstrated. A tentative complex composed of a divalent cation with two molecules of membrane-active terpenoid is proposed.
ISSN:0005-2736
0006-3002
1879-2642
DOI:10.1016/S0005-2736(01)00307-8