title: Garlic allyl derivatives interact with membrane lipids to modify the membrane fluidity.
abstract: As a novel approach to the mode of medicinal action of garlic, its constituents were comparatively studied with respect to their interactions with membrane lipids to modify the membrane fluidity. Allyl derivatives rigidified tumor cell and platelet model membranes consisting of unsaturated phospholipids and cholesterol at 20-500 muM with the potency being diallyl trisulfide (DATS) > diallyl disulfide (DADS) by preferentially acting on the hydrocarbon cores of lipid bilayers. They were also effective in rigidifying candida cell model membranes prepared with ergosterol and phospholipids at 100-500 microM with the potency being DADS > DATS > diallyl sulfide (DAS), but not bacteria cell model membranes without ergosterol. Alliin, a precursor of these DASs, was not active on any membranes at 500 microM. Both relative intensity and selectivity in membrane effects correlated with those in antiproliferative, antiplatelet and antimicrobial effects. In cell culture experiments, membrane-active DASs inhibited the growth of tumor cells cultured for 24 and 48 h at 20-500 muM to show the potency being DATS > DADS, together with rigidifying cell membranes by acting on their deeper regions more intensively. However, membrane-inactive allyl derivatives were not growth-inhibitory on tumor cells. The membrane lipid interactions of DASs appear to be one of possible mechanisms underlying different effects of garlic.
authors.affiliation: Department of Dental Basic Education, Asahi University School of Dentistry, Building 3, 1851 Hozumi, Mizuho, Gifu 501-0296, Japan. hiro@dent.asahi-u.ac.jp
authors.forename: Hironori
authors.initials: H
authors.lastname: Tsuchiya
authors.forename: Motohiko
authors.initials: M
authors.lastname: Nagayama
mesh_terms: D000498:Allyl Compounds / Q000494:pharmacology*; D001419:Bacteria; D045744:Cell Line, Tumor; D004220:Disulfides / Q000494:pharmacology; D004912:Erythrocytes; D005737:Garlic / Q000737:chemistry*; D006801:Humans; D008560:Membrane Fluidity / Q000187:drug effects*; D008563:Membrane Lipids / Q000378:metabolism*; D008954:Models, Biological; D009369:Neoplasms / Q000473:pathology; D013440:Sulfides / Q000494:pharmacology
chemical_list: D000498:Allyl Compounds; D004220:Disulfides; D008563:Membrane Lipids; D013440:Sulfides; C042577:diallyl trisulfide; C028009:diallyl disulfide