Comparison of Larvicidal, Adulticidal and Acaricidal Activity of Two Geometrical Butylidenephthalide Isomers

Abstract

Butylidenephthalide, the components of Angelica acutiloba var. sugiyamae HIKINO (Apiaceae) has the biological activities, such as centrally acting muscle relaxant 1) and antispasmodic effects 2) with characteristic odor. In our previous work,3) (Z)-butylidenephthalide was isolated as the potent insecticidal compound against adults and larvae of Drosophila melanogaster. Recently, Ahn et al. reported that butylidenephthalide was active constituent of Cnidium officinale against Dermatophagoides farinae and Tyrophagus putrescentiae, and more effective than acaricide, N,N-diethyl-mtoluamide (DEET). 4,5) Therefore, butylidenephthalide is the potential candidate for new natural pesticide. However, above report was unclear on stereochemistry of butylidenephthalide even though both (E)-and (Z)-butylidenephthalide were found from natural resources, and (E)-butylidenephthalide has not been tested against insects and mites.Geometrical stereoselectivity is often crucial on biological activities. Asahina et al. reported that synthetic fluoroquinolone derivatives were tested for antibacterial activity, and (Z)-isomers exhibited 2-to 32-fold more potent than corresponding (E)-isomers. 6) Against insects, the importance of geometry was discussed that binding affinity of juvenile hormone carrier protein from the hemolymph of Manduca sexta was decreased as (Z)-double bond are substituted for (E)-double bond in synthetic juvenile hormone analogues. 7)Therefore, evaluation of biological activity for geometrical isomers is required.Biological activity of (E)-butylidenephthalide against insects and mites has not been previously reported. In this paper, we investigated biological activities of (E)-butylidenephthalide against larvae and adults of D. melanogaster, adults of Ctenocephalides felis and two house dust mites, D. farinae and T. putrescentiae, and compared with (Z)-butylidenephthalide to investigate geometrical stereoselectivity. Rotenone (positive control for insecticidal activity) and DEET (positive control for acaricidal activity) were also tested. MATERIALS AND METHODSGC and GC-MS Analysis GC was performed on a Hewlett-Packard 5890A gas chromatograph equipped with a flame ionization detector (FID). The column was a fused silica capillary column (DB-5, 30 m length, 0.25 mm i.d.). Chromatographic conditions were as follows: oven temperature was programmed from 80 to 250°C at 4°C/min and held at 250°C for 15 min; injector and detector temperature were 270 and 280°C, respectively; carrier gas, helium at a flow rate of 40 cm/s. GC-MS was performed on a HewlettPackard 5972A mass selective detector interfaced with a Hewlett-Packard 5890A gas chromatograph fitted with a capillary column (HP-5MS, 30 m length, 0.25 i.d.). Chromatographic conditions were the same for the GC analysis.Chemicals (Z)-Butylidenephthalide was previously isolated from Angelica acutiloba.3) (E)-Butylidenephthalide was isolated from chloroform extract of A. acutiloba by SiO 2 (200 mesh) column chromatography (hexane : ethyl acetate ϭ93 : 7), repeatedly. The pu...

Bioactivities of 3-Butylidenephthalide and <i>n</i>-Butylbenzene from the Essential Oil of<i>Ligusticum jeholense</i> against Stored-product Insects

“…It was potently toxic to the adults of fruit fly, Drosophila melanogaster, and the effective performance of its E-and Z-two isomers make no difference in the bioassays. This compound also showed acaricidal activity against two house dust mites, Dermatophagoides farinae and Tyrophagus putrescentiae 24 . Additionally, a published article reported that 3-butylidenephthalide was toxic to B-and Q-biotypes females of Bemisia tabaci in leaf-dip bioassay LC 50 254.2 and 586.3 ppm, respectively .…”

Antimicrobial activity of extracts and phthalides occurring in Apiaceae plants

“…There are studies concerning antiproliferation and antitumor potential of this group of compounds. Furthermore, the authors also report their insecticidal properties (Chu, Jiang, & Liu, ; Kan, Cho, Rudd, & Lin, ; Tsai et al, ; Tsukamoto et al, ). Another significant bioactivities of phthalides involve antifungal and antibacterial effects (Sim & Shin, ).…”