title: Synthesis and antimicrobial activity of (E) stilbene derivatives.
abstract: Plants use multiple defence mechanisms comprising both constitutive and inducible barriers to prevent entering of phytopathogenic micro-organisms. In many plant species one of the most efficient responses to combat attacking microbes is the rapid synthesis of antimicrobial low molecular weight phytoalexins, for example, resveratrol, 3,5,4'-trihydroxystilbene (1). Resveratrol and its natural derivatives, however, display only moderate antimicrobial effects. Nevertheless, resveratrol may be a useful lead structure for the chemical synthesis of antimicrobials. In this study, several series of stilbenes have been synthesized, starting from the aldehydes using Wittig reactions to access the corresponding styrenes that were subjected to Mizoroki-Heck reactions to yield the stilbenes in good yields. The stilbenes were tested in an agar diffusion assay against several bacteria and fungi. For some of these compounds the inhibiting zones for bacteria and fungi were comparable with those of the antibiotics tetracycline, streptomycin, ampicillin, or kanamycin, directed against prokaryotes, and nourseothricin or hygromycin controlling fungi, respectively.
authors.affiliation: Bereich Organische Chemie, Martin-Luther-Universität Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Sabrina
authors.initials: S
authors.lastname: Albert
authors.forename: Ralf
authors.initials: R
authors.lastname: Horbach
authors.forename: Holger B
authors.initials: HB
authors.lastname: Deising
authors.forename: Bianka
authors.initials: B
authors.lastname: Siewert
authors.forename: René
authors.initials: R
authors.lastname: Csuk
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002460:Cell Line; D052978:Disk Diffusion Antimicrobial Tests; D051379:Mice; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity
chemical_list: D000890:Anti-Infective Agents; D013267:Stilbenes; D000077185:Resveratrol