The mode of action of allicin: its ready permeability through phospholipid membranes may contribute to its biological activity.
Allicin (diallyl thiosulfinate) is the main biologically active component of the freshly crushed garlic extracts. In the present work the ability of allicin to cross through membranes (artificial and biological) was studied. Partition coefficients of allicin in water/octanol, water/hexadecane and water/phospholipids mixtures were determined. Using phospholipid vesicles loaded with hydrophilic thiols (reduced glutathione or 2-nitro-5-thiobenzoate), we observed that allicin freely permeates through phospholipid bilayers and interacts with the SH groups. The reaction rate of allicin with SH containing molecules after crossing the membrane was the same as in solution. Fast diffusion and permeation of allicin across human red blood cell membranes was also demonstrated. Allicin does not induce leakage, fusion or aggregation of membrane. The high permeability of allicin through membranes may greatly enhance the intracellular interaction with thiols.
Miron
T
T
Department of Biological Chemistry, The Weizmann Institute of Science, Rehovot, Israel.
Rabinkov
A
A
Mirelman
D
D
Wilchek
M
M
Weiner
L
L
D002463:Cell Membrane Permeability / Q000187:drug effects; D004220:Disulfides; D004578:Electron Spin Resonance Spectroscopy; D004910:Erythrocyte Membrane / Q000187:drug effects / Q000378:metabolism; D005737:Garlic / Q000737:chemistry; D005978:Glutathione / Q000378:metabolism; D006801:Humans; D066298:In Vitro Techniques; D007700:Kinetics; D008081:Liposomes; D009682:Magnetic Resonance Spectroscopy; D008563:Membrane Lipids / Q000378:metabolism*; D009579:Nitrobenzoates / Q000378:metabolism; D010539:Permeability; D010743:Phospholipids / Q000378:metabolism*; D010946:Plants, Medicinal; D013438:Sulfhydryl Compounds; D013441:Sulfinic Acids / Q000378:metabolism / Q000493:pharmacokinetics* / Q000494:pharmacology*
D004220:Disulfides; D008081:Liposomes; D008563:Membrane Lipids; D009579:Nitrobenzoates; D010743:Phospholipids; D013438:Sulfhydryl Compounds; D013441:Sulfinic Acids; C011136:thionitrobenzoic acid; C006452:allicin; D005978:Glutathione