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Patulin

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Patulin

Patulin[1]
Names
IUPAC name
4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
Other names
2-Hydroxy-3,7-dioxabicyclo[4.3.0]nona-5,9-dien-8-one
Clairformin
Claviform
Expansine
Clavacin
Clavatin
Expansin
Gigantin
Leucopin
Patuline
Identifiers
 YesY
ChEBI  N
ChEMBL  YesY
ChemSpider  YesY
EC number 205-735-2
Jmol-3D images Image
KEGG  N
PubChem
UNII  YesY
Properties
C7H6O4
Molar mass 154.12 g/mol
Appearance Compact prisms
Density 1.52 g/ml
Melting point 110 °C (230 °F; 383 K)
Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

Patulin is a

  • http://www.foodsafetywatch.org/factsheets/patulin/

External links

  1. ^ a b Merck Index, 11th Edition, 7002
  2. ^ "Patulin: a Mycotoxin in Apples". Perishables Handling Quarterly (91): 5. August 1997
  3. ^ a b "Foodborne hazards (World Health Organization". Retrieved 2007-01-22.
  4. ^ Patulin information leaf from Fermentek
  5. ^ a b http://www.sigmaaldrich.com/catalog/product/sigma/p1639?lang=en®ion=US
  6. ^ a b c d e f g h i j k http://www.fda.gov/food/foodborneillnesscontaminants/naturaltoxins/ucm212520.htm
  7. ^ a b c d e f g
  8. ^ a b c d Llewellyn, G.C.; McCay, J.A.; Brown, R.D.; Musgrove, D.L.; Butterworth, L.F.; Munson, A.E.; White, K.L., Jr. Immunological evaluation of the mycotoxin patulin in female B6C3F1 mice. Food Chem. Toxicol. 1998, 36, 1107–1111.
  9. ^ a b c Medical Research Council. Clinical trial of patulin in the common cold. Lancet1944; ii: 373-5.
  10. ^
  11. ^ a b http://www.orangepippin.com/resources/general/patulin
  12. ^ a b Pouchous et all. Shellfish
  13. ^ a b Wouters, FA, and Speijers, GJA.. JECFA Monograph on Patulin . World Health Organization Food Additives Series 35( http://www.inchem.org/documents/jecfa/jecmono/v26je10.htm)
  14. ^ Pique, E., et al. Occurrence of patulin in organic and conventional apple juice. Risk Assessment. Recent Advances in Pharmacuetical Sciences, III, 2013: 131–144.
  15. ^ http://www.foodsafetynews.com/2013/04/recall-of-organic-juices-a-lesson-in-mycotoxins/#.Uk3Ld9LksnE
  16. ^ Beark et al 2007
  17. ^ Selmanoglu, G. Evaluation of the reproductive toxicity of patulin in growing male rats. Food Chem. Toxicol. 2006, 44, 2019–2024.
  18. ^ Variability and uncertainty assessment of patulin exposure for preschool children in Flanders
return p

end

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function p._hatnote(s, options) checkType('_hatnote', 1, s, 'string') checkType('_hatnote', 2, options, 'table', true) local classes = {'hatnote'} local extraclasses = options.extraclasses local selfref = options.selfref if type(extraclasses) == 'string' then classes[#classes + 1] = extraclasses end if selfref then classes[#classes + 1] = 'selfref' end return string.format( '

function p.hatnote(frame) local args = getArgs(frame) local s = args[1] local options = {} if not s then return p.makeWikitextError( 'no text specified', 'Template:Hatnote#Errors', args.category ) end options.extraclasses = args.extraclasses options.selfref = args.selfref return p._hatnote(s, options) end


-- Hatnote -- -- Produces standard hatnote text. Implements the template.


function p._formatLink(link, display) -- Find whether we need to use the colon trick or not. We need to use the -- colon trick for categories and files, as otherwise category links -- categorise the page and file links display the file. checkType('_formatLink', 1, link, 'string') checkType('_formatLink', 2, display, 'string', true) link = removeInitialColon(link) local namespace = p.findNamespaceId(link, false) local colon if namespace == 6 or namespace == 14 then colon = ':' else colon = end -- Find whether a faux display value has been added with the | magic -- word. if not display then local prePipe, postPipe = link:match('^(.-)|(.*)$') link = prePipe or link display = postPipe end -- Find the display value. if not display then local page, section = link:match('^(.-)#(.*)$') if page then display = page .. ' § ' .. section end end -- Assemble the link. if display then return string.format('%s', colon, link, display) else return string.format('%s%s', colon, link) end end

function p.formatLink(frame) local args = getArgs(frame) local link = args[1] local display = args[2] if not link then return p.makeWikitextError( 'no link specified', 'Template:Format hatnote link#Errors', args.category ) end return p._formatLink(link, display) end


-- Format link -- -- Makes a wikilink from the given link and display values. Links are escaped -- with colons if necessary, and links to sections are detected and displayed -- with " § " as a separator rather than the standard MediaWiki "#". Used in -- the template.


function p.makeWikitextError(msg, helpLink, addTrackingCategory) -- Formats an error message to be returned to wikitext. If -- addTrackingCategory is not false after being returned from -- Module:Yesno, and if we are not on a talk page, a tracking category -- is added. checkType('makeWikitextError', 1, msg, 'string') checkType('makeWikitextError', 2, helpLink, 'string', true) yesno = require('Module:Yesno') local title = mw.title.getCurrentTitle() -- Make the help link text. local helpText if helpLink then helpText = ' (help)' else helpText = end -- Make the category text. local category if not title.isTalkPage and yesno(addTrackingCategory) ~= false then category = 'Hatnote templates with errors' category = string.format( '%s:%s', mw.site.namespaces[14].name, category ) else category = end return string.format( '%s', msg, helpText, category ) end

function p.formatPageTables(...) -- Takes a list of page/display tables and returns it as a list of -- formatted links. Nil values are not allowed. local pages = {...} local links = {} for i, t in ipairs(pages) do checkType('formatPageTables', i, t, 'table') local link = t[1] local display = t[2] links[i] = p._formatLink(link, display) end return links end

function p.formatPages(...) -- Formats a list of pages using formatLink and returns it as an array. Nil -- values are not allowed. local pages = {...} local ret = {} for i, page in ipairs(pages) do ret[i] = p._formatLink(page) end return ret end

function p.findNamespaceId(link, removeColon) -- Finds the namespace id (namespace number) of a link or a pagename. This -- function will not work if the link is enclosed in double brackets. Colons -- are trimmed from the start of the link by default. To skip colon -- trimming, set the removeColon parameter to true. checkType('findNamespaceId', 1, link, 'string') checkType('findNamespaceId', 2, removeColon, 'boolean', true) if removeColon ~= false then link = removeInitialColon(link) end local namespace = link:match('^(.-):') if namespace then local nsTable = mw.site.namespaces[namespace] if nsTable then return nsTable.id end end return 0 end

local function removeInitialColon(s) -- Removes the initial colon from a string, if present. return s:match('^:?(.*)') end

local function getArgs(frame) -- Fetches the arguments from the parent frame. Whitespace is trimmed and -- blanks are removed. mArguments = require('Module:Arguments') return mArguments.getArgs(frame, {parentOnly = true}) end


-- Helper functions


local p = {}

local libraryUtil = require('libraryUtil') local checkType = libraryUtil.checkType local mArguments -- lazily initialise Module:Arguments local yesno -- lazily initialise Module:Yesno


return p-------------------------------------------------------------------------------- -- Module:Hatnote -- -- -- -- This module produces hatnote links and links to related articles. It -- -- implements the and meta-templates and includes -- -- helper functions for other Lua hatnote modules. --

end

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function p._hatnote(s, options) checkType('_hatnote', 1, s, 'string') checkType('_hatnote', 2, options, 'table', true) local classes = {'hatnote'} local extraclasses = options.extraclasses local selfref = options.selfref if type(extraclasses) == 'string' then classes[#classes + 1] = extraclasses end if selfref then classes[#classes + 1] = 'selfref' end return string.format( '

function p.hatnote(frame) local args = getArgs(frame) local s = args[1] local options = {} if not s then return p.makeWikitextError( 'no text specified', 'Template:Hatnote#Errors', args.category ) end options.extraclasses = args.extraclasses options.selfref = args.selfref return p._hatnote(s, options) end


-- Hatnote -- -- Produces standard hatnote text. Implements the template.


function p._formatLink(link, display) -- Find whether we need to use the colon trick or not. We need to use the -- colon trick for categories and files, as otherwise category links -- categorise the page and file links display the file. checkType('_formatLink', 1, link, 'string') checkType('_formatLink', 2, display, 'string', true) link = removeInitialColon(link) local namespace = p.findNamespaceId(link, false) local colon if namespace == 6 or namespace == 14 then colon = ':' else colon = end -- Find whether a faux display value has been added with the | magic -- word. if not display then local prePipe, postPipe = link:match('^(.-)|(.*)$') link = prePipe or link display = postPipe end -- Find the display value. if not display then local page, section = link:match('^(.-)#(.*)$') if page then display = page .. ' § ' .. section end end -- Assemble the link. if display then return string.format('%s', colon, link, display) else return string.format('%s%s', colon, link) end end

function p.formatLink(frame) local args = getArgs(frame) local link = args[1] local display = args[2] if not link then return p.makeWikitextError( 'no link specified', 'Template:Format hatnote link#Errors', args.category ) end return p._formatLink(link, display) end


-- Format link -- -- Makes a wikilink from the given link and display values. Links are escaped -- with colons if necessary, and links to sections are detected and displayed -- with " § " as a separator rather than the standard MediaWiki "#". Used in -- the template.


function p.makeWikitextError(msg, helpLink, addTrackingCategory) -- Formats an error message to be returned to wikitext. If -- addTrackingCategory is not false after being returned from -- Module:Yesno, and if we are not on a talk page, a tracking category -- is added. checkType('makeWikitextError', 1, msg, 'string') checkType('makeWikitextError', 2, helpLink, 'string', true) yesno = require('Module:Yesno') local title = mw.title.getCurrentTitle() -- Make the help link text. local helpText if helpLink then helpText = ' (help)' else helpText = end -- Make the category text. local category if not title.isTalkPage and yesno(addTrackingCategory) ~= false then category = 'Hatnote templates with errors' category = string.format( '%s:%s', mw.site.namespaces[14].name, category ) else category = end return string.format( '%s', msg, helpText, category ) end

function p.formatPageTables(...) -- Takes a list of page/display tables and returns it as a list of -- formatted links. Nil values are not allowed. local pages = {...} local links = {} for i, t in ipairs(pages) do checkType('formatPageTables', i, t, 'table') local link = t[1] local display = t[2] links[i] = p._formatLink(link, display) end return links end

function p.formatPages(...) -- Formats a list of pages using formatLink and returns it as an array. Nil -- values are not allowed. local pages = {...} local ret = {} for i, page in ipairs(pages) do ret[i] = p._formatLink(page) end return ret end

function p.findNamespaceId(link, removeColon) -- Finds the namespace id (namespace number) of a link or a pagename. This -- function will not work if the link is enclosed in double brackets. Colons -- are trimmed from the start of the link by default. To skip colon -- trimming, set the removeColon parameter to true. checkType('findNamespaceId', 1, link, 'string') checkType('findNamespaceId', 2, removeColon, 'boolean', true) if removeColon ~= false then link = removeInitialColon(link) end local namespace = link:match('^(.-):') if namespace then local nsTable = mw.site.namespaces[namespace] if nsTable then return nsTable.id end end return 0 end

local function removeInitialColon(s) -- Removes the initial colon from a string, if present. return s:match('^:?(.*)') end

local function getArgs(frame) -- Fetches the arguments from the parent frame. Whitespace is trimmed and -- blanks are removed. mArguments = require('Module:Arguments') return mArguments.getArgs(frame, {parentOnly = true}) end


-- Helper functions


local p = {}

local libraryUtil = require('libraryUtil') local checkType = libraryUtil.checkType local mArguments -- lazily initialise Module:Arguments local yesno -- lazily initialise Module:Yesno


-- Module:Hatnote -- -- -- -- This module produces hatnote links and links to related articles. It -- -- implements the and meta-templates and includes -- -- helper functions for other Lua hatnote modules. --


References

To test for patulin contamination, a variety of methods and sample preparation methods have been employed including thin layer chromatography (TLC), gas chromatography (GC), high-performance liquid chromatography (HPLC), capillary electrophoresis.[18]

The European Union (EU) has set a maximum limits of 50μg/kg pertaining to fruit juices and drinks, while solid apple products have a limit of 25μg/kg. For certain foods intended for infants, and even lower limit of 10μg/kg is observed.

EU

[3] The

WHO

The provisional tolerable daily intake (PTDI) for patulin was set at 0.43 µg/kg bw by the FDA[6] based on a NOAEL of 0.3 mg/kg bw per week.[6] Monte Carlo analysis was done on apple juice to compare exposure and the PTDI. Without controls or an action limit, 90th percentile of consumers would not be above the PTDI. However, the concentration in children 1–2 years old would be 3 times higher than the PDTI. Hence, an action limit of 50 µg/kg was set.[6]

US


Patulin exposure can be successfully managed by following good agricultural practices such as removing mold, washing, and not using rotten or damaged apples for baking, canning, or juice production.[11][6]

Risk Management and Regulations

Although there are only very few reported cases and epidemiological data, the FDA has set an action limit of 50 ppb in cider due to its potential carcinogenicity and other reported adverse effects.[6] In humans, it was tested as an antibiotic intranasally for use against the common cold with few significant adverse effects, yet also had negligible or no beneficial effect.[9]

Human health

Patulin was found to be immunotoxic in a number of animal and even human studies. Reduced cytokine secretion, oxidative burst in macrophages, increased splenic T lymphocytes, and increased neutrophil numbers are a few endpoints noticed.[7] However, dietary relevant exposure would not be likely to alter immune response.[8]

Immunotoxicity

Patulin decreased sperm count and altered sperm morphology in the rat.[17] Also, it resulted in abortion of F1 litters in rats and mice after i.p. injection.[7] Embryotoxicity and teratogenicity were also reported in chick eggs.[7]

Reproduction studies

WHO concluded that patulin is genotoxic based on variable genotoxicity data, however it is considered a group 3 carcinogen by the International Agency for Research on Cancer (IARC), since data was inconclusive.[6]

Genotoxicity

Studies in rats showed decreased weight, and gastric, intestinal, and renal function changes, while repetitive doses lead to neurotoxicity. Reproductive toxicity in males were also reported.[7] A NOAEL in rodents was observed at 43μg/kg bw.[6]

Subacute

Patulin is toxic primarily through affinity to sulfhydryl groups (SH), which results in inhibition of enzymes. Oral LD50 in rodent models have ranged between 20 and 100 mg/kg.[6] In poultry, the oral LD50 range was reported between 50–170 mg/kg.[7] Other routes of exposure are more toxic, yet less likely to occur. Major acute toxicity findings include gastrointestinal problems, neurotoxicity (i.e., convulsions), pulmonary congestion, and edema.[6]

Acute


A subacute rodent NOAEL of 43 μg/kg body weight as well as genotoxicity studies were primarily the cause for setting limits for patulin exposure, although a range of other types of toxicity also exist.[6]

Toxicity

Frequently, patulin is found in apples and apple products such as juices, jams, and ciders. It has also been detected in other fruits including cherries, blueberries, plums, bananas, strawberries, and grapes.[8] Fungal growth leading to patulin production is most common on damaged fruits.[11] Patulin has also been detected in grains like barley, wheat, corn and their processed products as well as in shellfish.,[8][12] Dietary intake of patulin from apple juice has been estimated at between 0.03 and 0.26 μg/kg bw/day in various age groups and populations.[13] Content of patulin in apple juice is estimated to be less than 10–15μg/L.[13] A number of studies have looked into comparisons of organic vs conventional harvest of apples and levels of patulin contamination.,[14][15] For example, one study showed 0.9% of children drinking organic apple juice exceeded the tolerable daily intake (TDI) for patulin.[16] A recent article described detection of patulin in marine strains of Penicillium, indicating a potential risk in shellfish consumption.[12]

Sources of Exposure

Patulin was originally used as an antibiotic against Gram-positive and Gram-negative bacteria, but after several toxicity reports, it is no longer used for that purpose.[9] It was specifically trialed to be used against the common cold.[9] Patulin is used as a potassium-uptake inhibitor in laboratory applications.[5] Kashif Jilani and co-workers reported that patulin stimulates suicidal erythrocyte death under physiological concentrations.[10]

Uses

Patulin is a white powder soluble in low-pH water and polyketide lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation.[5] However, stability following fermentation is lessened.[6] Isoepoxydon dehydrogenase (IDH) is an important enzyme in the multi-step biosynthesis of patulin, and its gene is present in other fungi that may potentially produce the toxin.[7] It is reactive with sulfur dioxide, so antioxidant and antimicrobial agents may be useful to destroy it.[8] Levels of nitrogen, manganese, and pH as well as abundance of necessary enzymes regulate the biosynthetic pathway of patulin.[7]

Chemistry

Contents

  • Chemistry 1
  • Uses 2
  • Sources of Exposure 3
  • Toxicity 4
  • Risk Management and Regulations 5
  • References 6
    • External links 6.1

[4] In the European Union, the limit is set to 50 micrograms per kilogram (µg/kg) in both apple juice and cider, and to half of that concentration, 25 µg/kg, in solid apple products and 10 µg/kg in products for infants and young children. These limits came into force on 1 November 2003.[3]

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