Larvicidal and Adulticidal Activity of Alkylphthalide Derivatives from Rhizome of Cnidium officinale against Drosophila melanogaster

The insecticidal activity of the chloroform extract of Cnidium officinale rhizomes and its constituents was investigated against larvae and adults of Drosophila melanogaster and compared with that of rotenone. Bioassay-guided isolation of the chloroform extract of C. officinale resulted in the isolation and characterization of four alkylphthalides, cnidilide (1), (Z)-ligustilide (2), (3S)-butylphthalide (3), and neocnidilide (4). The structures of these compounds were established by spectroscopic analysis. The isolated compounds 2, 3, and 4 exhibited LC50 values of 2.54, 4.99, and 9.90 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 3 showed the most potent activity of the compounds isolated with the LD50 value of 5.93 μg/adult, comparable to that of rotenone (LD50 = 3.68 μg/adult). Structure−activity relationships of phthalides isolated suggest that the presence of conjugation with the carbonyl group in the lactone ring appeared to play an important role in the larvicidal activity. Acetylcholinesterase (prepared from the adult heads of D. melanogaster) inhibitory activity was also investigated in vitro to determine the insecticide mode of action for the acute adulticidal activity. Keywords: Natural insecticide; Apiaceae; Cnidium officinale; Drosophila melanogaster; alkylphthalide; structure−activity relationship; acetylcholinesterase inhibition