Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract.
Three active components were identified by bioassay-guided fractionation of bitter orange ( Citrus aurantium L.) fruit peel petroleum ether extract. Silica gel fractionation of the extract yielded a fraction that inflicted up to 96% mortality to adults of the olive fruit fly Bactrocera oleae (Gmelin) three days post-treatment. Subsequent HPLC purification of the active fraction resulted in the isolation of three components, eluted in fractions F 222, F 224, and F 226, that induced adult mortality. Considering the data obtained from UV, FTIR, MS, and (1)H NMR spectra, they were identified as 7-methoxy-8-(3'-methyl-2'-butenyl)-2 H-1-benzopyran-2-one (osthol), 4-methoxy-7 H-furo[3,2- g]benzopyran-7-one (bergapten), and 4-(( E)-3'-methyl-5'-(3'',3''-dimethyloxiran-2''-yl)pent-2'-enyloxy)-7 H-furo[3,2- g][1]benzopyran-7-one (6',7'-epoxybergamottin). Our results are in concordance with those reported in the literature and were further verified by direct comparison to authentic components. 6',7'-Epoxybergamottin was toxic when tested individually, while bergapten and osthol were found to act synergistically to 6',7'-epoxybergamottin.
Siskos
Elias P
EP
Chemical Ecology and Natural Products Laboratory, NCSR Demokritos, 150 13 Aghia Paraskevi, Attikis, Greece.
Mazomenos
Basilis E
BE
Konstantopoulou
Maria A
MA
D000078223:5-Methoxypsoralen; D000818:Animals; D005591:Chemical Fractionation; D002957:Citrus / Q000737:chemistry*; D003374:Coumarins / Q000032:analysis; D005638:Fruit / Q000737:chemistry*; D011564:Furocoumarins / Q000032:analysis; D007306:Insecticides / Q000032:analysis / Q000302:isolation & purification*; D008730:Methoxsalen / Q000031:analogs & derivatives / Q000032:analysis; D033621:Tephritidae
D003374:Coumarins; D011564:Furocoumarins; D007306:Insecticides; C475527:epoxybergamottin; D000078223:5-Methoxypsoralen; D008730:Methoxsalen; C046627:osthol