Patulin

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

The following techniques were tested for the degradation of patulin /in laboratory wastes/: treatment with ammonia, treatment with ascorbic acid, and treatment with potassium permanganate in acidic or in alkaline conditions... Complete disappearance of patulin was not achieved after 92 hr of treatment with ascorbic acid. All the other methods tested led to complete removal of the molecule. However, the technique using potassium permanganate in acidic conditions produced residues which were mutagenic without activation to Salmonella typhimurium strains TA 100 and TA 102, which was attributed later to Mn2+. The two other techniques gave satisfactory results and were selected for further validation studies.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Enhancement of patulin toxicity by penicillic acid was indicated by the occurrence of deaths in dogs exposed simultaneously to sublethal doses of both mycotoxins, and by the presence in these dogs of toxic signs and lesions resembling those elicited by a single lethal dose of patulin given alone. Enhancement was also indicated by the presence of pulmonary histopathology in dogs receiving both toxins at levels that, given alone, produced no such lesions.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that patulin is expected to have very high mobility in soil(SRC). Volatilization of patulin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Patulin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradatation data were not available(SRC, 2009). However, Gluconobacter oxydans, isolated from patulin-contaminated apples, was capable of degrading patulin up to 96% to a less-toxic compound, ascladiol(5).

TERRESTRIAL FATE: Patulin was applied to Holdrege silt loam, Sharpsburg silty clay loam, Peorian loess subsoil, and fine quartz sand in concentrations of 200, 400, and 800 ug/g of soil or sand. Patulin disappearance was determined by chemical analysis and bioassay techniques using winter and spring wheat (Triticum aestivum L.). After application of 400 ug of patulin per gram of soil, only 27-69 percent of the patulin was immediately extractable using ethyl acetate. The inability to extract patulin from soil or sand was related to physical and chemical properties. Patulin seemed to be inactivated biologically and nonbiologically in the soil. After 192 hours, patulin was detected in only one of the autoclaved soils treated with 400 ug of patulin(1).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that patulin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from an estimated log Kow of -2.4(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradatation data were not available(SRC, 2009). However, Gluconobacter oxydans, isolated from patulin-contaminated apples, was capable of degrading patulin up to 96% to a less-toxic compound, ascladiol(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), patulin, which has an estimated vapor pressure of 6.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase patulin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1 hour(SRC), calculated from its rate constant of 1.38X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3) Particulate-phase patulin may be removed from the air by wet or dry deposition(SRC). Patulin does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

/Patulin/ ...found...in one sample of commercial 'sweet apple cider'. ...up to 45 mg/L /was found/ in cider made in mills using rotten apples which had been stored for long periods before use.

A number of studies have detected the presence of patulin in apples, apple juice, apple products as well as moldy bread and other fruits. In the United States, patulin was detected in commercial apple concentrate at 0.054 ug/g. In France, from 1976-1981, patulin was detected at concentrations of 1-4.8 ug/g in pureed apple samples, 0.001-1.2 ug/g in commercial apple concentrate, and 0.01-0.1 ug/g in apple baby food. In Germany from 1978-1982 patulin was detected in rotten apple samples and at concentrations of 0.002-0.052 ug/g in apple juice, 0.1-0.3 ug/g in moldy bread, and 0.024 ug/g in pear juice. The highest range of values reported were from Portugal at concentrations of 0.8-100 ug/g in rotten apples. The USSR reported the presence of patulin at concentrations of 0.021-0.031 ug/g in apples, 0.062 ug/g in cherry juice, 0.054 ug/g in commercial apple concentrate, 0.032 ug/g in mandarins, 0.030 ug/g in peach juice, 0.031 ug/g in pear juice, and 0.021-0.04 ug/g in plum juice. In Norway patulin was detected at concentrations of 0.009-0.22 ug/g in commercial apple concentrate and in Sweden 0.005-0.054 ug/g, and Mexico 0.009-0.04 ug/g. In the Poland patulin was detected in moldy beetroots at concentrations ranging from 0.12 to 3.7 ug/g. In Finland patulin was detected at a concentration of 0.02-0.16 ug/g in moldy bread.

Twenty-seven isolates of patulin-producing Penicillium expansum were obtained from Europe, Australia, and North America originating from apples, grapes, pears, apricots, and persimmon. The concentrations ranged from 7-100 ug/g fresh weight in apples, 15-80 ug/g fresh weight in grapes, 3-80 ug/g fresh weight in pears, 18 ug/g fresh weight in apricots, and 50 ug/g fresh weight in persimmon. Pure cultures derived from these isolates produced much higher titers(1).

In cider produced in Athens, GA, patulin was detected at concentrations of 244-3993 ug/L in pasteurized apple cider samples. Eight high-temperature, short-time treatments of the cider indicated a reduced patulin level, but not complete degradation(1).

For more Food Survey Values (Complete) data for PATULIN (7 total), please visit the HSDB record page.

Patulin's strong affinity to sulfhydryl groups enables to to inhibit a number of enzymes, including succinate dehydrogenase, alcohol dehydrogenases, ATPases, acetylcholinesterase, aldolases, protein tyrosine phosphatases, RNA polymerases, aminoacyl-tRNA synthetase, ribonuclease H, and lactate dehydrogenase. This widespread enzyme inhibition has a number of effects, including inhibition of aerobic respiration, inhibition of RNA synthesis, and inhibition of protein synthesis. Patulin also affects some aspects of membrane permeability and causes DNA-strand breakage and chromosomal aberrations, likely contributing to it's genotoxicity. Patulin may also cause the development of allergies by inhibiting interferon-gamma production. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (L1943, A2952, A3014)

/AQUATIC SPECIES/ Patulin was the most toxic mycotoxin for rana temporaria and triturus alpestris tadpoles. The obviously high toxicity to the tadpoles could be explained by an interaction of this mycotoxin with essential sulfhydryl-containing enzymes.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of patulin can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that patulin is expected to have low mobility in soil.

...FOUND IN APPLES AND THEIR BY-PRODUCTS...

/Patulin/ ...identified in rotten apples contaminated by Penicillium expansum; up to 18 mg/apple were detected.

... Patulin is one of several mycotoxins produced by certain fungi on fruit, grains and other foods. The fungal species include Penicillium claviforme, P. chrysogenum, P. cyclopium, P. divergens, P. equinum, P. expansum, P. griseofulvum, P. lapidosum, P. leucopus, P. melinii, P. novaezielandiae, P. patulum, P. roqueforti, P. rugulosum, P. urticae, P. variabile, Aspergillus clavatus, A. giganteus, A. terreus and Byssochlamys nivea. Patulin has been detected in numerous mouldy fruits, vegetables, cereals and animal feeds. It has been found following natural infection or inoculation with Penicillium species or Byssochlamys nivea in apples, peaches, pears, tomatoes, apricots, bananas, pineapples, grapes, greengages, strawberries, honeydew melons, red and green paprika, cucumbers and carrots. A number of other vegetables, including aubergines, cauliflower, celeriac, courgettes, kohlrabi, horseradish, radish, red cabbage, onions and potatoes, did not support the growth of patulin-producing molds...

Mycotoxin metabolite of many molds that possesses antibacterial, antiviral, and antiprotozoal properties but is toxic to plants and animals; One of the most common sources of contamination is from the blue mold (Penicillium expansum) that causes soft rot of apples, cherries, and other fruit; Also found often in unfermented apple juice; [Reference #1] Antibiotic metabolites derived from various fungi in the Aspergillus, Penicillium, and Gymnoascus species; [Merck Index] Mycotoxin produced by Aspergillus and Penicillium species found in unfermented apple juice and grape juice and field crops; [ChemIDplus] Mycotoxin found on fruits, vegetables, grains, and other foods; Also produced by the fungi Byssochlamys nivea; Purified form included in analytical reagent kit used as a standard for mycotoxins; Formerly used as a topical antibiotic cream; [HSDB]

... Purified patulin /is included/ in an analytical reagent kit for use as a standard for mycotoxins.

Medication: Patulin was also used at one time as an antibiotic cream for topical application, but was found to cause dermal irritation. /Former/

Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. Although patulin can occur in many molding fruits, grains and other foods, the major source of patulin contamination is in apples with brown rot, and in apple cider or apple juice. Patulin is also an antibiotic. (L1942, L1943)

An antibiotic derived from the metabolism of a number of fungi... Birkinshaw et al Lancet 245, 625 (1943); Birkinshaw, Michael, US Pat 2,417,584 (1947 To Therap Res Corp Of Great Britain)...Norstadt, McCalla, Appl Microbiol 17, 193 (1969).

Patulin is not produced commercially, but it is available from one company in the US for experimental purposes only and is also available in Israel. This chemical is not authorized for use as a drug by the US Food and Drug Administration.

Stable in grape and apple juice and dry corn, but not in orange juice, flour, baked bread, cheese, wet corn, or apple juice fermented with saccharomyces species.

The aim of this study was to evaluate different species of Penicillium to identify those which have the potential to produce the greatest amount of the mycotoxin, patulin. ... Eleven different strains ... included Penicillium expansum, Penicillium griseofulvum (formerly Penicillium urticae), Penicillium clavigerum, and Penicillium coprobium and a recent Penicillium sp. isolated from an apple. Cultures were grown in duplicate in three different liquid media: potato dextrose, malt extract, and glucose/yeast extract/peptone, both with and without manganese supplementation. Patulin production was compared at 24, 48, 72, and 96 hr. Variability in patulin production occurred among the different species, growth media used, and time of incubation. All three of the P. griseofulvum isolates were the highest producers of patulin at 96 hr. For most of the strains, potato dextrose broth supplemented with manganese was optimal for maximum production of patulin. Although P. expansum is frequently cited as the most likely source of patulin in apple juice, certain other Penicillium species are capable of producing more patulin than strains of P. expansum. The apple juice industry should be alert to the possibility that Penicillium species other than P. expansum can be responsible for the occurrence of patulin.

Activated charcoal at 5 mg/mL reduced patulin in naturally contaminated cider to nondetectable levels.

Trimming removed 93-99% of the total patulin, regardless of incubation temperature, fungus strain or apple variety.

For more General Manufacturing Information (Complete) data for PATULIN (6 total), please visit the HSDB record page.