Nematicidal alkylene resorcinols from Lithraea molleoides.
Four new alkylene resorcinols, (Z,Z)-5-(trideca-4,7-dienyl)resorcinol (1), (Z,Z,Z)-5-(trideca-4,7,10-trienyl)resorcinol (2), (Z,Z,E)-5-(trideca-4,7,10-trienyl)resorcinol (3), and (Z)-5-(trideca-4-enyl)resorcinol (4), were isolated from the MeOH-CH(2)Cl(2) extract of Lithraea molleoides. The structures of these compounds were determined by one- and two-dimensional NMR including selective decoupling experiments. In vitro all four compounds showed strong paralyzing effects on the nematode Caenorhabditis elegans at concentrations between 6 and 50 microg/mL, whereas the activity of compounds 1 and 2 against the nematode Trichostrongylus colubriformis was less pronounced and no activity against this nematode was observed for compounds 1-4 in a rodent model.
D000475:Alkenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D027926:Anacardiaceae / Q000737:chemistry*; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001118:Argentina; D017173:Caenorhabditis elegans / Q000187:drug effects*; D002175:Candida / Q000187:drug effects / Q000254:growth & development; D002851:Chromatography, High Pressure Liquid; D007814:Larva / Q000187:drug effects; D000432:Methanol; D008968:Molecular Conformation; D015394:Molecular Structure; D009348:Nematoda / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D014254:Trichostrongylus / Q000187:drug effects*
D000475:Alkenes; D000969:Antinematodal Agents; D010936:Plant Extracts; D012118:Resorcinols; D000432:Methanol