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At least 19 recordsLinked to original sources
PubMed1978

Comparison of the toxicities of patulin and patulin adducts formed with cysteine.

The toxicities of patulin and of the patulin adducts formed with cysteine were compared using the mutation-sensitive strain Escherichia coli W3110 thy polA1 and its polA1+ revertant. The acute toxicities of patulin and of the adduct mixture were also compared using NMRI mice. The adduct mixture was shown by thin-layer chromatography to consist of one ninhydrin-positive, one ninhydrin- and MBTH (3-methyl-2-benzothiazolinone hydrazone)-positive, three MBTH-positive, and two ninhydrin- and MBTH-negative components. The results showed that patulin was over 100 times more toxic to E. coli than the adduct complex. Neither patulin nor the adduct mixture was found to induce the repair effect in E. coli. In the mouse feeding tests, the oral 50% lethal dose for patulin was 29 mg/kg, while that of the adduct mixture was greater than 2,370 mg/kg.

Animals↗
PubMed1979

[Hygienic significance of patulin in food. 2. Occurrence of patulin in fruit and vegetables].

The analyses of more than 200 samples of various foods of plant origin showed that patulin was contained in 36% of the fresh and canned fruits infested with mould, and in 7% of the vegetables. Besides apples, pears, plums, peaches and tomatoes contained also patulin. In organoleptically impeccable fruit juices, the contamination rates were 40% (for apple juice) and 16% (for the other juices, such as sour cherry, currant, sea buckthorn juices). The patulin content varied from 20 to 200 microgram/l, the mean value being 80 microgram/l. It ranged from 0.1 to 5 microgram/g in apples and sterile apple preserves. The authors discuss the hygienic-toxicologic significance of these findings, and suggest to include patulin in the examination of foods for mycotoxins, stipulating a permissible value.

Food Analysis↗
PubMed1976

Teratogenicity of patulin and patulin adducts formed with cysteine.

The mean lethal dose of patulin for the chicken embryo injected in the air cell before incubation was determined to be 68.7 mug and that for the 4-day-old embryo was 2.35 mug. Both patulin (1 to 2 mug/egg) and the reaction mixture between patulin and cysteine (15 to 150 mug of patulin equivalents) were teratogenic to the chicken embryo. At least two ninhydrin-negative and four ninhydrin-positive products were formed during the latter reaction. Our explanation of the reaction mechanism remains to be elaborated.

Animals↗
PubMed1979

[Hygienic significance of patulin in foods. 1. Analytical detection of patulin].

The authors describe a thin-layer chromatographic method for determining patulin in fruit and vegetable products which is suited for routine work in hygiene practice. The samples are extracted with ethyl acetate, and the extracts are purified on a Florisil column. Separation is performed by means of a one-dimensional technique, using toluene/ehtyl acetate/formic acid (5 + 4 + 1), or, in the presence of interfering contaminants, by means of a two-dimensional technique, using benzene/methanol/glacial acetic acid (90 + 5 + 5) for the first run, and toluene/ethyl acetate/formic acid (5 + 4 + 1) for the second run. Patulin is detected by spraying with a benzidine solution, after chlorination. The limits of detection are 5 microgram/l of juice and 5 microgram/kg of fruit or vegetable. Derivatization with acetic anhydride/pyridine is used for corroborating the results obtained. The significance of 5-hydroxymethylfurfural as an interfering substance in apple juices is discussed.

Chromatography, Thin Layer↗
PubMed1977

[Determination of patulin in foodstuffs. Part I: Determination of patulin in apple juice (author's transl)].

For the determination of Patulin in apple juice a method of analysis was developed permitting the detection of 40 microng Patulin/kg apple juice. With additions between 120--200 microng Patulin/kg the recovery rates lie between 82 and 90%. After a pre-purification of the crude extract by liquid-liquid extraction and column-chromatography the Patulin is determined thinlayer chromatographically by reflectance measurement at 273 nm.

Beverages↗
PubMed1977

[Determination of patulin in foodstuffs Part II: Determination of patulin in tomatoes, pears, apples cucumbers and plums (author's transl)].

An analytical method for the determination of Patulin in tomatoes, pears, apples, cucumbers and plums is described. The determination limit of the method is 40 mug Patulin/kg. With additions between 100-500 mug Patulin/kg the recovery rates lie between 86--95%. After a pre-purification of the crude extract by column chromatography and liquid-liquid extraction the Patulin is determined thin-layer chromatographically by reflectance measurement at 273 nm.

Fruit↗
PubMed1992

Patulin-induced cellular toxicity: a vital fluorescence study.

The mechanisms of patulin-induced cellular toxicity in an immortalized rat granulosa cell line were examined using several vital fluorescence bioassays. Monochlorobimane and 5-chloromethylfluorescein diacetate were used to monitor cellular glutathione (GSH) levels and revealed dose- and time-dependent depletion of GSH by patulin. A significant reduction in the fluorescence of the monochlorobimane-GSH conjugate by 0.1 microM patulin was observed between 1 and 2 hr. Similar GSH depletion by the mycotoxin was also observed in parallel studies on a liver (Clone 9) and a renal (LLC-PK1) cell line, although reduction of fluorescence occurred within 1 hr at the same dosage. Analysis of the electrical potential-dependent partitioning of rhodamine 123 into mitochondria also revealed significant effects of patulin within 1 hr at 0.1 microM. An initial dose-dependent reduction in mitochondrial fluorescence was followed by loss of selective partitioning of the fluorophore into mitochondria at higher doses and/or a longer exposure of cells to patulin. The reduction in mitochondrial fluorescence was paralleled by a dose-dependent decrease in intracellular pH detected with 2',7'-bis-(2-carboxyethyl)-5(6)-carboxyfluorescein. Analysis of [Ca2+]i with indo-1 and fluo-3 revealed a significant dose-dependent influx of Ca2+ at 10 microM and an alteration of the pattern of ionomycin-induced Ca2+ influx at 1.0 microM following patulin treatment. A carboxyfluorescein fluorescence photobleaching assay was used to examine the effects of patulin on gap junction-mediated intercellular communication. Dose-dependent reduction in intercellular communication was observed within 2 hr with 1.0 microM patulin. These observations indicate that the fluorescence assays used in this study provide a sensitive index of toxicity caused by exposure to patulin. Further, the toxic effects of patulin may involve direct effects on cellular glutathione levels and mitochondrial function in addition to direct effects on the plasma membrane.

Animals↗
PubMed1979

[Determination and the hygienic-toxicologic significance of patulin in fruit and fruit products].

The combination of extracting, chromatographic and fluorescence densitometric steps permits to determine patulin in fruits and fruit products with great precision and sensitivity. The limit of detection is 10 microgram/kg; the recovery rates range from 86 to 92% with a variation coefficient lying between 5.6 and 13.6%. Interferences due to patulin-simulating substances are widely excluded. Patulin concentrations ranging from 0.3 to 42 mg/kg were found in the brown-rotten portions of apples. Juices domestically prepared from healthy fruits and fruits rid of rotten portions, respectively, contained no patulin. On the contrary, patulin concentrations ranging from 0.02 to 0.3 mg/l were observed in commercial apple juices. As to products with subsequent mould infection, patulin values up to 50 mg/l were found in apple juices, and up to 0.4 mg/kg in peach preserves. In a further 24 commercial fruit and vegetable juices, patulin was not detectable even not in cider, in cereals which had gone mouldy spontaneously, and in bread samples. The fruits and fruit products were analysed not only for patulin, but also for aflatoxin and ochratoxin; the latter two, however, were found in none of the samples examined. The possibilities of manufacturing patulin-free products are discussed.

Chromatography, Thin Layer↗
PubMed1991

Effect of the incubation conditions on the production of patulin by Penicillium griseofulvum isolated from wheat.

Sixty-four wheat samples from Spanish flour factories were screened for patulin and patulin-producing moulds. None of them was found to contain any patulin, whereas samples experimentally contaminated with this toxin proved it to be highly unstable. On the other hand, Penicillium griseofulvum was the only in vitro patulin-producing species found (19 samples). Mould growth in the samples was investigated by using yeast-sucrose medium (YES) and high-performance liquid chromatography (HPLC) to measure the amounts of toxin produced during 40 day's incubation at 20 and 28 degrees C. The highest yield rate of patulin was obtained between the 20th and 30th day of incubation; such a rate, however, was very low throughout the vigorous growth phase, during the first 20 days of incubation. The more appropriate temperature for incubation and patulin production was 28 degrees C. We also investigated the influence of other incubation conditions in the yield and found stationary dark cultures to be more efficient that shaken or fermentation cultures in YES medium. The best patulin yield achieved was 11.9 mg in the culture broth and 6.3 mg in the mycelium from 100 ml of medium.

Culture Media↗
PubMedDate not supplied

Physiological and biochemical effects of the mycotoxin patulin on Chang liver cell cultures.

Patulin exhibits both cytotoxic and cytopathic effects on cultured Chang liver cells. The LD50 found was 1.85 mug per ml of patulin. Effects on growth were observed with as little as 0.1 mug per ml of patulin; a 50% reduction in growth was observed at 0.38 mug per ml of patulin. Using a challenge dose of 2.5 mug per ml of patulin, the cytotoxic effect was reversible after an exposure of 10 min, but was not reversible after 20 min. Protein synthesis was depressed after 60 min and RNA synthesis after 20 min of contact with patulin. Neither protein nor RNA synthesis was completely inhibited after 260 min.

Cell Division↗
PubMed1978

Identification of phyllostine as an intermediate of the patulin pathway in Penicillium urticae.

A patulin negative mutant (J1) of Penicillium urticae (NRRL 2159A) was found to accumulate large quantities (greater than 128 mg/L culture) of a reactive, photosensitive compound, which was isolated and identified as (-)-phyllostine (5,6-epoxygentisylquinone). This epoxyquinone possessed an antibiotic activity against Bacillus subtilis which was approximately 80% of that exhibited by patulin. In separate in vivo feeding experiments, [2-14C]acetate and [G-3H]gentisaldehyde were readily incorporated into phyllostine by mutant J1 and [14C]phyllostine was incorporated into patulin by the parent strain (NRRL 2159A). When fed to a washed-cell suspension of a second patulin negative mutant (J2) which produced gentisaldehyde but not phyllostine, unlabeled phyllostine was efficiently converted to patulin in yields of 33, 56, and 92% after 30 min, 1 and 5 h, respectively. The role of phyllostine as an intermediate of a new post-gentisaldehyde portion of the patulin biosynthetic pathway is discussed.

Anti-Bacterial Agents↗
PubMed1979

Isoepoxydon, a new metabolite of the patulin pathway in Penicillium urticae.

A patulin-negative mutant (J1) of Penicillium urticae (N.R.R.L. 2159A) was known to accumulate about 100mg per litre quantities of the 5,6-epoxygentisyl quinone, (-)-phyllostine and another metabolite (UIII). Both were derived from acetate and hence were polyketides. Purified UIII (m.p. 53 degrees C, [alpha](32) (D)+206 degrees , lambda(methanol) (max.) 240nm; epsilon 3806 litre.mol(-1).cm(-1)) was characterized as a partially reduced derivative of (-)-phyllostine and was found to be a diastereoisomer of the known phytotoxin, (+)-epoxydon. Hence its designation as (+)-iso- or epi-epoxydon. From (1)H n.m.r. and c.d. data the stereochemistry of the epoxide ring in (+)-isoepoxydon was determined to be identical with that in (+)-epoxydon (i.e. R,R) but the configuration of the secondary alcohol at C-4 was S rather than R as in (+)-epoxydon. Isoepoxydon (compound UIII) is therefore (4S,5R,6R)-5,6-epoxy-4-hydroxy-2-hydroxymethylcyclohex-2-en-1-one. The boat conformation in which the C-4 hydroxy group is axial is preferred. In the range of 1mm to 5mm, the antibiotic activity of (+)-isoepoxydon against Bacillus subtilis sp. was 56% of that obtained with patulin. Over a period of 1 to 3h, [(14)C]isoepoxydon was efficiently converted into patulin by a shake culture of the parent strain of P. urticae. The precursor relationship of isoepoxydon to patulin was confirmed by feeding unlabelled isoepoxydon (1mm) to a washed-cell suspension of a mutant (J2) in which, over a period of 3 to 5h, a better than 60% conversion into patulin was attained. The enzymic relationship between isoepoxydon and phyllostine and their positions in the late portion of the patulin biosynthetic pathway are discussed.

Acetylation↗
PubMed1977

Intermediate-duration toxicity study of patulin in rats.

The toxicity of patulin was studied in two generations of Sprague-Dawley rats over a period of approximately 10 months. Patulin in 1 mM citrate buffer was administered by gavage to FO generation rats at a dose level of 0, 1.5, 7.5, or 15.0 mg/kg a body weight five times a week for 10-14 wk; females were treated seven times a week during pregnancy. High mortality and insufficient progeny in the groups given 7.5 and 15.0 mg/kg made it impossible to continue those two regimens into the second generation. The study was continued for 20-23 wk with F1A generation animals given 1.5 mg/kg and controls. The only lesion found at necropsy that could be attributed to patulin administration was gaseous distention of the gastrointestinal tract, which was probably the result of the antibiotic effect of this mycotoxin on the normal intestinal flora. A decreased weight gain in male rats of the FO generation was dose-related. An impairment in growth rates of F1A and F2A progeny of both sexes was statistically significant at the 1.5 mg/kg dose level. Fetuses taken from patulin-treated females on day 20 of pregnancy were noticeably smaller than controls fetuses and the difference was significant for F2A males. No other teratological abnormalities related to patulin dosing at the 1.5 mg/kg level were observed consistently in either F1A or F2A fetuses. Patulin did not appear to produce dominant lethal effects at dose levels up to 15.0 mg/kg when given by gavage to the males five times a week for 10 or 11 wk.

Animals↗
PubMed1976

Patulin inhibition of mycovirus replication in Penicillium stoloniferum.

Penicillium stoloniferum NRRL5267 contains two electrophoretically distinct viruses (PsV-F and PsV-S). An in vivo system was developed to test whether a number of fungal metabolites had antiviral properties on PsV-F replication in O.erties on PsV-F replication in P. stoloniferum. Preliminary results indicated that the mycotoxin patulin can block mycovirus replication. Portions of 48 h mycelium were incubated in the presence of varying levels of patulin, and after an additional 48 h incubation, PsV-F content was measured in E260 units by polyacrylamide gel electrophoresis. Patulin at 11, 16 and 20 mug/mg dry wt mycelia blocked PsV-F replication 26, 61 and 71%, respectively, compared with untreated controls. At these levels, host biomass RNA and protein synthesis were minimally affected. No-proliferating fungal mycelium is capable of continued support of PsV-F replication, which is sensitive to patulin. Apparently, inhibitory doses of patulin stimulated PsV-S replication during this 48 h incubation. The preferential action of patulin may arise from metabolite binding to functional enzymes required for virus replication.

Dose-Response Relationship, Drug↗
PubMed1976

Use of activated charcoal for the removal of patulin from cider.

Penicillium urticae (NRRL 2159A) was grown in culture broth containing 1 muCi of [1-14C-A1acetate to produce [14C]patulin. [14C]patulin was purified from the broth and added to apple cider. After the patulin concentration of the cider was adjusted to 30 mug/ml with unlabeled patulin, the cider was subjected to various charcoal treatments. [14C]patulin was completely removed by shaking the cider with 20 mg of activated charcoal per ml and by eluting the cider through a 40- to 60-mesh charcoal column. Activated charcola at 5 mg/ml reduced patulin in naturally contaminated cider to nondetectable levels.

Acetates↗
PubMed1975

Trimming as a means of removing patulin from fungus-rotted apples.

Penicillium expansum 1071, 1172, NRLL 973, and Penicillium patulum ATCC 24550 were inoculated into Red Delicious, Golden Delicious, and McIntosh apples. The decayed tissue was trimmed from the sound tissue, each fraction was weighed, and the patulin concentration in the juice was assayed by thin layer chromatography. The quantity of patulin in the whole apples and in decayed tissues was calculated and these values were used to determine the percentage of total patulin removed by trimming. The patulin content ranged from 140 to 4880 mug/apple. Trimming removed 93-99% of the total patulin, regardless of incubation temperature, fungus strain, or apple variety. Trimming of defective tissue from fungus-rotted apples could substantially reduce the patulin concentration.

Food Contamination↗
PubMed1978

Effects of patulin on the kinetics of substrate and cationic ligand activation of adenosine triphosphatase in mouse brain.

Patulin (4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one), a carcinogenic lactone produced as a major metabolite by several fungi, inhibited the Mg++-dependent Na+-K+ activated adenosine triphosphatase (ATPase) activity of mouse brain microsomal fractions with an estimated IC50 of 3.0 X 10(-4) M. Inhibition was concentration dependent. Hydrolysis of ATP was linear with both time and enzyme concentration either with or without patulin in reaction mixtures. Altered pH and activity curves for Na+-K+ ATPase demonstrated comparable inhibition by patulin in buffered acidic ranges through an optimum of 7.5, followed by a reduction of toxicity to this system at higher alkaline pH. Kinetic studies of cationic-substrate activation of Na+-K+ ATPase indicated noncompetitive inhibition with respect to ATP (at low affinity nucleotide-directed sites) and Na+ (in the presence of low, noninterfering concentrations of K+). Competitive inhibition with respect to activation of the Na+-k+-stimulated activity and K+-stimulated p-nitrophenyl phosphatase activity of the enzyme system was indicated by altered binding site parameters without change in apparent Vmax in the presence of patulin. Activity was partially restored by washing. Preincubation of patulin with dithiothreitol or glutathione protected the enzyme from inhibition. Results suggest that patulin exerted its effect on Na+-K+ ATPase either directly by interfering with K+ binding or indirectly by inducing a conformational change in the enzyme.

4-Nitrophenylphosphatase↗