1989
DOI: 10.1007/bf02027792
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Myristicin, safrole, and fagaramide as phytosynergists of xanthotoxin

Abstract: The methylenedioxyphenyl-containing (MDP) inhibitors of mixed-function oxidase detoxification enzymes, myristicin, safrole, fagaramide, and isosafrole, occur with xanthotoxin or other toxic furanocoumarins in plants of the families Umbelliferae and Rutaceae. All four MDP compounds have a synergistic effect on the toxicity of xanthotoxin toHeliothis zea. Myristicin also increased the phototoxicity of xanthotoxin in the presence of UV light. The term phytosynergist is used to describe plant compounds that are pr… Show more

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Cited by 29 publications
(11 citation statements)
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“…Structure-activity relationships indicate that the substituents in the amino group and in the aromatic ring might play a crucial role in the insecticidal activity. Although, we have verified a low to moderate toxicity effect for amides 1Ð9 and 11 (Table I), Neal (1989) has described that fagaramide, a natural isomer of amide 1, is a phytosynergist, a plant compound that is present at concentrations producing no toxic effect by itself but has a synergistic effect on co-occurring toxins. Fagaramide has shown a synergistic effect on the toxic-ity of xanthotoxin to Heliothis zea (Lepidoptera: Noctuidae).…”
Section: ð1mentioning
confidence: 66%
“…Structure-activity relationships indicate that the substituents in the amino group and in the aromatic ring might play a crucial role in the insecticidal activity. Although, we have verified a low to moderate toxicity effect for amides 1Ð9 and 11 (Table I), Neal (1989) has described that fagaramide, a natural isomer of amide 1, is a phytosynergist, a plant compound that is present at concentrations producing no toxic effect by itself but has a synergistic effect on co-occurring toxins. Fagaramide has shown a synergistic effect on the toxic-ity of xanthotoxin to Heliothis zea (Lepidoptera: Noctuidae).…”
Section: ð1mentioning
confidence: 66%
“…Moreover, the enzyme CYP6AB11 from navel orangeworm, expressed heterologously in a baculovirus system, is capable in vitro of metabolizing imperatorin, a furanocoumarin related to xanthotoxin that is found in some species in the Rutaceae, a family that contains some of the reported hosts of this species (Niu et al 2011). Myristicin also synergizes furanocoumarin toxicity in several other lepidopteran species (Berenbaum and Neal 1985, Neal 1989, Neal and Berenbaum 1989, Yu and Hsu 1993, Mao et al 2008. There are few approved insecticides for sustainable management of navel orangeworm in organic orchards, and myristicin may be of potential utility as a Þeld treatment to increase the toxicity of naturally occurring phytochemicals to navel orangeworm as well as reduce aßatoxin contamination in the orchard.…”
Section: Discussionmentioning
confidence: 99%
“…Myristicin is a known synergist for synthetic insecticides (Lichtenstein and Casida 1963) and phytochemicals (Berenbaum and Neal 1985, Neal 1989, Neal and Berenbaum 1989. In this study, we compared myristicin activity with that of piperonyl butoxide, a commonly used synthetic inhibitor of P450 enzymes and synergist for pyrethroids (Ishaaya 1993) that has structural similarities to myristicin.…”
mentioning
confidence: 99%
“…Myristicin (1-allyl-5-methoxy-2,3-methylenedioxybenzene) is an MDP-containing compound found in the essential oil of many plants of economic value, including nutmeg, dill, parsley, parsnip and carrot (Lichtenstein and Casida, 1963;Salzer, 1977). Biochemical analyses in insect systems have shown that myristicin is a strong synergist of some synthetic insecticides, including allethrin (Lichtenstein and Casida, 1963), and some plant secondary metabolites (Berenbaum and Neal, 1985;Neal, 1989;Neal and Berenbaum, 1989). When incorporated into the artificial diet, both myristicin and safrole increased the toxicity of xanthotoxin, a furanocoumarin, toward the corn earworm, Helicoverpa zea (Berenbaum and Neal, 1985;Neal, 1989) and the black swallowtail, Papilio polyxenes (Neal and Berenbaum, 1989).…”
Section: Introductionmentioning
confidence: 99%
“…Biochemical analyses in insect systems have shown that myristicin is a strong synergist of some synthetic insecticides, including allethrin (Lichtenstein and Casida, 1963), and some plant secondary metabolites (Berenbaum and Neal, 1985;Neal, 1989;Neal and Berenbaum, 1989). When incorporated into the artificial diet, both myristicin and safrole increased the toxicity of xanthotoxin, a furanocoumarin, toward the corn earworm, Helicoverpa zea (Berenbaum and Neal, 1985;Neal, 1989) and the black swallowtail, Papilio polyxenes (Neal and Berenbaum, 1989). Piperonyl butoxide (PBO), a synthetic analogue of the natural MDP compounds, is an effective inhibitor of many cytochrome P450 monooxygenases (Murray, 2000;Correia and Ortiz deMontellano, 2005) and a leading insecticide synergist also in commercial use (Casida, 1970).…”
Section: Introductionmentioning
confidence: 99%