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Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and Their Derivatives.

Journal of agricultural and food chemistry (2015-07-16)
Monika Stompor, Katarzyna Dancewicz, Beata Gabryś, Mirosław Anioł
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).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
trans-Chalcone, 97%
Sigma-Aldrich
Flavone, ≥99.0%
Sigma-Aldrich
1,3-Diphenyl-2-propenone, ≥98.0% (GC)
Sigma-Aldrich
4-Chromanone, 97%
Sigma-Aldrich
Flavanone, 98%
Sigma-Aldrich
Chromone, 99%
Sigma-Aldrich
7-Aminoflavone, 97%