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Components from Sri Lankan Piper betle L. leaf oil and their analogues showing toxicity against the housefly, Musca domestica
Author(s) -
Mohottalage Susantha,
Tabacchi Raffaele,
Guerin Patrick M.
Publication year - 2006
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1770
Subject(s) - safrole , eugenol , chemistry , housefly , isoeugenol , bioassay , essential oil , piper , fractionation , estragole , citronellal , methyl eugenol , steam distillation , chromatography , traditional medicine , toxicology , botany , organic chemistry , musca , larva , biology , medicine , genetics , pest analysis , tephritidae
Abstract The essential oil extracted from Piper betle L . leaf using pilot plant steam distillation was tested against the adult housefly, Musca domestica , for insecticidal activity. LC 50 values at the end of 24 and 48 h exposure periods were 10.3 and 8.7 mg/dm 3 , respectively. Ceylon citronella oil ( Cymbopogon nardus ) used as a standard showed LC 50 s of 26.5 and 24.2 mg/dm 3 for the same exposure periods. Bioassay‐guided fractionation of P. betle leaf oil revealed safrole and eugenol as the active principles against M. domestica , safrole showing LC 50 values of 4.8 and 4.7 mg/dm 3 , and eugenol 7.3 and 6.2 mg/dm 3 for the 24 and 48 h exposure periods, respectively, while citronellal (synthetic standard) showed equal LC 50 values of 14.3 mg/dm 3 for the same exposure periods. Using safrole as the starting compound, eight analogues were prepared to study structure–activity relationships. Among the eight analogues, dihydrosafrole gave almost equal mortality at LC 50 4.7 mg/dm 3 as that of the parent compound safrole after 24 and 48 h exposure, but isosafrole was twice as active as safrole, showing LC 50 values of 2.3 and 2.2 mg/dm 3 for the 24 and 48 h exposure periods. Our GC–MS studies on Sri Lankan P. betle leaf oil show that it contains safrole (52.7%), allylpyrocatechol diacetate (15.4%), eugenol (6.4%) and eugenyl acetate (5.8%) as the major components. Here we also present the GC–MS profile of fractions of Sri Lankan P. betle leaf oil. Copyright © 2006 John Wiley & Sons, Ltd.