title: Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and Their Derivatives.
abstract: Xanthohumol (14) and isoxanthohumol (6) derived from hop (Humulus lupulus L., Cannabaceae) and selected chalcone and chromene derivatives, obtained by chemical synthesis, were studied for antifeedant activity against the peach-potato aphid (Myzus persicae [Sulz.]). The study used also commercially available 4-chromanone (1), flavanone (4), naringenin (5), chromone (7), flavone (8), 7-aminoflavone (9), trans-chalcone (10), and 4-methoxychalcone (12). For chromone derivatives it was observed that the presence of a phenyl substituent at C-2 in the chromone (7) skeleton increased the insect antifeedant activity, and this activity was observed for a longer time. Also, the introduction of an amino group at C-7 of flavone (8) considerably increased the insect antifeedant activity, which was observed for the whole test time. Among the compounds examined, the strongest deterrents were isoxanthohumol (6), 7-methoxy-2,2-dimethylchroman-4-one (3), 7-aminoflavone (9), and 4-ethyl-4'-methoxychalcone (13).
authors.affiliation: †Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Monika
authors.initials: M
authors.lastname: Stompor
authors.affiliation: §Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Dancewicz
authors.affiliation: §Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland.
authors.forename: Beata
authors.initials: B
authors.lastname: Gabryś
authors.affiliation: †Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Mirosław
authors.initials: M
authors.lastname: Anioł
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects* / Q000502:physiology; D005247:Feeding Behavior / Q000187:drug effects*; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D027582:Humulus / Q000737:chemistry*; D007306:Insecticides / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D011427:Propiophenones / Q000737:chemistry / Q000494:pharmacology*; D044004:Xanthones / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D005419:Flavonoids; D007306:Insecticides; D010936:Plant Extracts; D011427:Propiophenones; D044004:Xanthones; C512910:isoxanthohumol; C104536:xanthohumol
keywords: M. persicae (Sulz.); antifeedants; chalcones; isoxanthohumol; xanthohumol