title: Antibacterial activity of a virgatusin-related compound.
abstract: The relationship between antibacterial activity of tetra-substituted tetrahydrofuran lignans (1-4) and their absolute configurations was tested. Only compound 4 among two virgatusins and two related compounds exhibited growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis, Staphylococcus aureus and Listeria denitrificans. Compound 4 affected the growth of B. subtilis in a bactericidic manner, and its ability to dissipate the cytoplasmic membrane potential was investigated using the fluorescence probe 3,3'-dipropylthiadicarbocyanine iodide. These results suggested that compound 4 damages cells by causing the loss of the proton motive force and disruption of the cellular integrity of the membrane, leading to cell death. In addition, it was shown that the antibacterial activity of a lignan was closely related to its absolute configuration and functional groups.
authors.affiliation: Faculty of Agriculture, Ehime University, Matsuyama, Ehime, Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Maruyama
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
authors.forename: Koichi
authors.initials: K
authors.lastname: Akiyama
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugahara
authors.forename: Taro
authors.initials: T
authors.lastname: Kishida
authors.forename: Yojiro
authors.initials: Y
authors.lastname: Koba
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D052160:Benzothiazoles / Q000737:chemistry; D002232:Carbocyanines / Q000737:chemistry; D002462:Cell Membrane / Q000187:drug effects*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005663:Furans / Q000494:pharmacology*; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000254:growth & development*; D008564:Membrane Potentials / Q000187:drug effects*; D050296:Microbial Viability / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D052160:Benzothiazoles; D002232:Carbocyanines; D005456:Fluorescent Dyes; D005663:Furans; C511226:virgatusin; C012944:3,3'-dipropyl-2,2'-thiadicarbocyanine