Insecticidal Effect of Phthalides and Furanocoumarins from Angelica acutiloba against Drosophila melanogaster

• Published in: Journal of agricultural and food chemistry Vol. 52; no. 14; pp. 4401 - 4405
• Main Authors: Miyazawa, Mitsuo, Tsukamoto, Toshihiko, Anzai, Jun, Ishikawa, Yukio
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 14.07.2004
• Subjects: adult insects; Angelica - chemistry; Angelica acutiloba; Animals; Benzofurans - chemistry; Benzofurans - isolation & purification; bioassays; Biological and medical sciences; Biological control; botanical insecticides; Cholinesterase Inhibitors; Control; coumarins; Drosophila melanogaster; Female; Fundamental and applied biological sciences. Psychology; Furocoumarins - chemistry; Furocoumarins - isolation & purification; insecticidal properties; Insecticides - chemistry; Insecticides - isolation & purification; Larva; larvae; Male; pesticidal plants; phthalides; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; Structure-Activity Relationship; structure-activity relationships; Insecticide; Insecta; phthalides; Esterases; Acetylcholinesterase; Natural; Structure activity relation; Dicotyledones; Angiospermae; furanocoumarins; Angelica; Inhibition; structure-activity relationship; Enzyme; Pesticides; Coumarin; Carboxylic ester hydrolases; Drosophilidae; natural Insecticide; Arthropoda; Angelica acutiloba; Hydrolases; acetylcholinesterase inhibition; Spermatophyta; Umbelliferae; Invertebrata; Drosophila melanogaster; Diptera
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf0497049

Insecticidal activity of Angelica acutiloba extract and its constituents was investigated and compared with that of rotenone. Bioassay-guided isolation of the chloroform extract of A. acutiloba against larvae of Drosophila melanogaster afforded two phthalides, (Z)-butylidenephthalide (1) and (Z)-ligustilide (2), and two furanocoumarins, xanthotoxin (3) and isopimpinellin (4). The structures of these compounds were established by spectroscopic analysis. The isolated compounds 1, 2, 3, and 4 exhibited LC50 values of 0.94, 2.54, 3.35, and 0.82 μmol/mL of diet concentration against larvae of D. melanogaster, respectively. Against both sexes (males/females, 1:1) of adults (5−7 days old), compound 1 showed the most potent activity with a LD50 value of 0.84 μg/adult. Compound 1 is a more active insecticide than rotenone (LD50 = 3.68 μg/adult) and has potential as a novel insect control agent. However, compound 2 was inactive against adults. The structure−activity relationship of phthalides isolated indicated that the aromaticity appeared to play an important role in the activity of both larvae and adults. To determine the insecticide mode of action for acute adulticidal activity, acetylcholinesterase (AChE) inhibitory activity was also investigated in vitro, and the result indicated that the acute adulticidal activity of compounds 3 and 4 was due to the inhibition of AChE. Keywords: Angelica acutiloba; natural insecticide; structure−activity relationship; phthalides; furanocoumarins; Drosophila melanogaster; acetylcholinesterase inhibition