The Isolation and Characterization of Two Phototoxic Furanocoumarins (Psoralens) from Diseased Celery

Scheel, Lester D.; Perone, Vernon B.; Larkin, Robert L.; Kupel, Richard E.

doi:10.1021/bi00905a038

Cited by 94 publications

(41 citation statements)

References 5 publications

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“…The photochemistry of furocoumarins (psoralens) has received considerable attention from several groups of workers (2,10,11,19). The parent compound, psoralen, and some of its derivatives have a photosensitizing action on viruses (3,12), bacterial cells, and mammalian cultures (2,13) and produce lethal and mutagenic effects.…”

Section: Methodsmentioning

confidence: 99%

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Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Hadwiger

1972

Plant Physiol.

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Section: Methodsmentioning

confidence: 99%

“…Psoralen compounds such as xanthotoxin have been found in an array of plants (17,19,22,23) including the family Leguminosae (to date, these compounds have not been isolated from peas) (1 2The term "inducer" in this paper will refer to an agent which can cause an increase in extractable PAL and pisatin.…”

Section: Methodsmentioning

confidence: 99%

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Hadwiger

1972

Plant Physiol.

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“…The toxic potential of both psoralens [24] and to a lesser extent marmesin [25] has long been recognized, leading, for example, to such colloquial plant names as 'blisterweed' [26] and causing severe problems in celery harvesting [27] and storage [28]. Psoralens may intercalate with DNA in the dark [29] and may, upon irradiation (320-400 nm), form photocycloaddition products, most frequently with thymidine in the cis-syn orientation [30].…”

Section: Discussionmentioning

confidence: 99%

Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. Microsomal conversion of (+)marmesin into psoralen

Wendorff

Matern

1986

Eur J Biochem

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Microsomal fractions isolated from parsley cell suspension cultures, which had been challenged with an elicitor from either Alternaria carthami or PI1 ~~tlrophthora megasperma f. sp. glycinea, catalyzed the formation of psoralen from synthetic [3-'4C](+)marmesin. Whereas psoralen was the only product formed in incubations with Alternaria-induced microsomes, another unidentified product was isolated from incubations with Phythophthorainduced microsomes. The latter product is neither a precursor nor a product of psoralen. In contrast, microsomes isolated from non-induced parsley cells lacked both of these catalytic activities. The formation of psoralen depends on NADPH as a cofactor and molecular oxygen. Blue-light-reversible CO inhibition and inhibition by various synthetic chemicals known to bind to cytochromes P450 indicated that the reaction is catalyzed by an elicitorinducible cytochrome P,,,-dependent psoralen synthase. Fractionation of microsomal preparations by centrifugation revealed that psoralen synthase is associated with the endoplasmic reticulum. Our results suggest that the endoplasmic reticulum of cultured parsley cells is the primary target in the previously reported differential induction by elicitors from these two non-pathogenic strains of fungi.Continuously dark-cultured parsley cells accumulate and excrete various linear furanocoumarin and a pyronocoumarin phytoalexins in response to elicitor challenge, as was shown previously using crude cell-wall fractions from two nonpathogenic fungi (Alternaria carthami and Phythophthora megasperma f. sp. glycinea) [I, 21. The relative composition of the coumarins induced varied significantly in response to the two elicitors. Furthermore, the increase in fresh weight of A. carthami (Ac) elicitor-induced parsley cells was comparable to that of untreated controls [3], suggesting that the primary metabolism of the cells was not severely altered, whereas comparable amounts of P. megasperma (Pmg) elicitor inhibited the growth of the cells. Since massive synthesis of the coumarins was observed within a few hours of addition of either one of the elicitors, parsley cells appeared to represent Correspondence to U. Matern, Lehrstuhl fiir Biochemie der

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“…These are difficult to remove, particularly in crops like sunflower where the sclerotia are of similar size to the seeds. S. sclerotiorum also causes 'pink rot' of celery, and many years ago (Scheel et al 1963) it was recorded that celery pickers coming in contact with affected celery and exposed to sunlight developed a severe dermatitis due to psoralens. Mung bean screenings containing high concentrations of sclerotia were obtained from central Queensland and fed to pigs at the Biloela Research Station.…”

Section: Sclerotinia Sclerotiorium Toxicitymentioning

confidence: 99%

Effective use in livestock feeds of mouldy and weather-damaged grain containing mycotoxins—case histories and economic assessments pertaining to pig and poultry industries of Queensland

Blaney¹,

Williams²

1991

Aust. J. Agric. Res.

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Mould growth in field crops or stored grain reduces starch and lipid content, with consequent increases in fibre, and an overall reduction in digestible energy; palatability is often adversely affected. If these factors are allowed for, and mycotoxin concentrations are low, there are sound economic reasons for using this cheaper grain.Mycotoxins are common in stock feed but their effects on animal productivity are usually slight because either the concentration is too low or the animal is tolerant to the toxin. In Australia, aflatoxins occur in peanut by-products and in maize and sorghum if the grain is moist when stored. Zearalenone is found in maize and in sorghum and wheat in wetter regions. Nivalenol and deoxynivalenol are found in maize and wheat but at concentrations that rarely affect pigs, with chickens and cattle being even more tolerant. Other mycotoxins including cyclopiazonic acid, T-2 toxin, cytochalasins and tenuazonic acid are produced by Australian fungi in culture but are not found to be significant grain contaminants.Extremely mouldy sorghum containing Alternaria and Fusarium mycotoxins decreased feed conversion in pigs and chickens by up to 14%. However, E moniliforme-and Diplodia maydis-infected maize produced only slight reductions in feed intake by pigs and Ustilagoinfected barley produced no ill effects. Use of these grains would substantially increase profits if the grain can be purchased cheaply.

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The Isolation and Characterization of Two Phototoxic Furanocoumarins (Psoralens) from Diseased Celery

Cited by 94 publications

References 5 publications

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. Microsomal conversion of (+)marmesin into psoralen

Effective use in livestock feeds of mouldy and weather-damaged grain containing mycotoxins—case histories and economic assessments pertaining to pig and poultry industries of Queensland

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