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...
The control of body lice is an important issue for human health and welfare because lice act as vectors of disease such as typhus, relapsing fever, and trench fever. Body lice exhibit avoidance behavior to some essential oils, including clove essential oil. Therefore, odorants containing clove essential oil components may potentially be useful in the development of repellents to body lice. However, such odorants that induce avoidance behavior in body lice have not yet been identified from clove essential oil. Here, we established an analysis method to evaluate the avoidance behavior of body lice to specific odorants. The behavioral analysis of the body lice in response to clove essential oil and its constituents revealed that eugenol, a major component of clove essential oil, has strong repellent effect on body lice, whereas the other components failed to induce obvious avoidance behavior. A comparison of the repellent effects of eugenol with those of other structurally related odorants revealed possible moieties that are important for the avoidance effects to body lice. The repellent effect of eugenol to body lice was enhanced by combining it with the other major component of clove essential oil, β-caryophyllene. We conclude that a synthetic blend of eugenol and β-caryophyllene is the most effective repellent to body lice. This finding will be valuable as the potential use of eugenol as body lice repellent.
Trials of control of the cat fiea , Ctenocel) halides fetis (Bouch6) , by using candidate formulations containing pyriproxyfen, a juvenile hormone analogue , under semi − field conditions
Ovicidal effects of the juvenile hormone analogue , pyriproxyfen , a − gainst the cat flea , Ctenocephalides プ ' e lis , were evaluated by laboratory test . FLea eggs aged for く 2,4 − 6, 10 − 12, 22 − 24 , 0r 46 − 48 hrs after oviposition were ex −
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