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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 10 (1984), S. 893-911 
    ISSN: 1573-1561
    Keywords: Xanthotoxin ; psoralen ; isopsoralen ; furanocoumarin ; Papilio polyxenes ; Lepidoptera ; Papilionidae ; Spodoptera frugiperda ; Noctuidae ; metabolism ; detoxification ; tolerance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The fate of [14C]xanthotoxin (8-methoxypsoralen) was studied in larvae of insect species that are tolerant (Papilio polyxenes Stoll) or sensitive (Spodoptera frugiperda J.E. Smith) to the phototoxic effects of photosensitizing psoralens. Both insects metabolize xanthotoxin by oxidative cleavage of the furan ring, but the detoxification occurs at a much more rapid rate inP. polyxenes in which 〉95% of an oral 5 μg/g xanthotoxin dose is metabolized within 1.5 hr after treatment. The detoxification of psoralens byP. polyxenes appears to occur primarily in the midgut tissue prior to absorption, with the result that the intact phototoxin does not reach appreciable levels in body tissues. Studies with an angular furanocoumarin indicated that isopsoralens are metabolized byP. polyxenes at a somewhat slower rate than observed for psoralens; however, a reduced rate of metabolic detoxification of isopsoralens probably does not explain the fact that psoralen tolerance inP. polyxenes does not extend to the isopsoralen series.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1573-1561
    Keywords: Psoralen ; isopsoralen ; furanocoumarin ; Papilio polyxenes ; Lepidoptera ; Papilionidae ; metabolism ; detoxification
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The comparative fate of tritiated preparations of a linear furanocoumarin (psoralen) and an angular furanocoumarin (isopsoralen) was determined in last-instar caterpillars of the black swallowtail butterfly (Papilio polyxenes Fabr.). Oral administration of either furanocoumarin at 5 μg/g is followed by rapid metabolism, primarily through oxidative cleavage of the furan ring, and the metabolites are rapidly excreted. Isopsoralen is, however, metabolized at a somewhat slower rate than is psoralen, and levels of unmetabolized isopsoralen in body tissues of the treated caterpillars are about three-fold higher. These data are compatible with the hypothesis that a reduced detoxification rate accounts at least in part for the susceptibility ofP. polyxenes caterpillars to the deleterious effect of isopsoralens.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1573-1561
    Keywords: Xanthotoxin ; 8-methoxypsoralen ; furanocoumarin ; metabolism ; detoxification ; chicken ; goat ; egg ; milk14C radiolabel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The metabolism of xanthotoxin, a naturally occurring furanocoumarin photosensitizer, was studied in laying hens and a lactating goat treated with single oral doses equivalent to 10 mg xanthotoxin/kg of body weight. Within 48 h, essentially all of the administered radiocarbon was eliminated in the excreta of the laying hens, while in the goat 92% and 3% were excreted in the urine and feces, respectively. Radiocarbon residues in the milk, egg white, and egg yolk were low. Xanthotoxin, 8-hydroxypsoralen (xanthotoxol), 6-(7-hydroxy-8-methoxycoumaryl)-acetic acid (HCA) and 6-(7-hydroxy-8-methoxycoumaryl)-hydroxyacetic acid (HCHA) were identified in the excreta of laying hens. In the goat, xanthotoxin was metabolized to HCA, HCHA, xanthotoxol, 5,8-dihydroxypsoralen, psoralenquinone, 5-hydroxy-8-methoxy-psoralen and 3[5-(6-hydroxy-7-methoxybenzofuryl)]-propanoic acid. Thus, identified metabolites in one or both of these species arose throughO-demethylation, oxidative cleavage of the furan ring, hydroxylation, reduction, oxidation, and hydrolysis of the lactone ring.
    Type of Medium: Electronic Resource
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