Patulin

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Structural formula
Structural formula of patulin
General
Surname Patulin
other names
  • IUPAC name: 4-hydroxy-4H-furo [3,2-c] pyran-2 (6H) -one
  • 2-Hydroxy-3,7-dioxabicyclo [4.3.0] nona-5,9-dien-8-ones
  • Clavacin
  • Clavatine
  • Claviformin
  • Expansin
  • Giantess
  • Mycoin C 3
  • Leucopenine
  • Penicidin
  • Penantine
Molecular formula C 7 H 6 O 4
Brief description

colorless compact prisms or thick plates

External identifiers / databases
CAS number 149-29-1
EC number 205-735-2
ECHA InfoCard 100.005.215
PubChem 4696
Wikidata Q414526
properties
Molar mass 154.12 g mol −1
Physical state

firmly

Melting point

110-111 ° C

solubility

soluble in water and many organic solvents

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 300-315
P: 264-301 + 310
Toxicological data

17 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Patulin is a mycotoxin , i.e. a mold toxin. It can be classified in the substance groups of hydroxypyrofurans, toxic lactones or γ-pyrones. Patulin was first isolated from Penicillium griseofulvum and Penicillium expansum by Birkinshaw and co-workers in 1943.

Occurrence

Patulin is formed by molds of the species Penicillium , Aspergillus , Byssochlamys and Paecilomyces variotii . Patulin is mainly produced in rotten pome fruit, here by Penicillium expansum . Up to two grams of toxin per kilogram of rot can be found in apples or pears. In apples, patulin practically does not diffuse into the healthy tissue, so that the fruit can still be processed or consumed if the rotten areas are removed generously. In the case of core rot, patulin can be present in externally intact apples. B. get unnoticed in sweet must. In other types of fruit, the healthy part can also contain patulin.

When processing the fruit into juices, care must be taken that no fruit is used that has rotten spots. The pasteurization of fruit juices is ineffective as a rule, since patulin to short-acting heat is relatively stable. The fruit juices can, however, z. For example, by fermentation or sulphurisation be detoxified.

Properties and biological effect

Patulin is a white, crystalline powder. It has a hemorrhagic effect in the body . As a cell poison, it intervenes in the respiratory chain . Taken in higher doses, the mold toxin can cause nausea, inflammation of the stomach lining and damage to the liver . In animal experiments it has a carcinogenic effect ( sarcoma ) in rats when applied subcutaneously . No carcinogenic effects were found after oral administration.

Patulin is an effective antibiotic , but it cannot be used therapeutically because of its toxicity.

According to the WHO risk assessment , from a toxicological point of view, the amount of patulin consumed per day (PMTDI: provisional maximum tolerable daily intake) should not exceed 0.4 µg / kg body weight. In the EU there are limit values ​​for fruit juices (50 µg / kg), for solid apple products, e.g. B. applesauce (25 µg / kg), as well as for baby food (10 µg / kg).

biosynthesis

The Aspergillus species A. clavatus, A. giganteus and A. longivesica, the Penicillium species P. carneum, P. clavigerum, P. concentricum, P. coprobium, P. dipodomyicola, P. expansum have the ability to biosynthesize patulin , P. glandicola, P. gladioli, P. griseofulvum, P. marinum, P. paneum, P. sclerotigenum and P. vulpinum. Of the genera Paecilomyces and Byssochlamys , only Byssochlamys nivea and some strains of Paecilomyces saturatus produce patulin.

The biosynthesis takes place in about 10 stages. There are 15 genes involved in biosynthesis. The starting point is the formation of 6-MSA (6-methyl-salicylic acid) from acetyl-coenzyme A and three malonyl-CoA units by 6-MSAS . 6-methyl-salicylic acid synthethase (6-MSAS) is a multifunctional enzyme that performs the functions of acetyl transferase , malonyl transferase and ketoacyl synthetase . The enzyme 6-MSA decarboxylase produces m- cresol . Interaction with CYP 619C2 results in various intermediate products such as toluquinol , m- hydroxy-benzyl alcohol , gentisyl alcohol and gentisyl aldehyde . The further synthetic route leads via phyllostin , neopatulin and ascladiol .

literature

  • HK Frank: Mycotoxins in food and feed , in: Materials for environmental research, Volume 16. Verlag W. Kohlhammer GmbH, 1988

Individual evidence

  1. ↑ a b Entry on Patulin. In: Römpp Online . Georg Thieme Verlag, accessed on December 9, 2014.
  2. ↑ a b c d Datasheet Patulin from Sigma-Aldrich , accessed on April 18, 2011 ( PDF ).
  3. ^ JH Birkinshaw, SE Michael, A Bracken, H Raistrick: Patulin in the common cold collaborative research on a derivative of Penicillium patulum Bainier. II. Biochemistry and Chemistry. In: Lancet . tape 245 , 1943, pp. 625 .
  4. ↑ Complained juice withdrawn from the market. “Core rot” probably the reason for the increased value from Patulin / Diesdorfer manufacturer reacts immediately . In: Volksstimme Stendal . November 16, 2019, p. 16 .
  5. ↑ Frank, in: . Confructa - international Zeitschrift. for technology of fruit a. Vegetable processing , Frankfurt (Main), JV-Journal Verl.-Ges., 25 (1980) pp. 107-118.
  6. ↑ Osswald, u. a., in: Food and Cosmetics Toxicology , 16 (1978) pp. 243-247.
  7. ^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for Patulin , accessed December 9, 2014.
  8. ↑ Regulation (EC) No. 1881/2006 (PDF) of the Commission of December 19, 2006 setting the maximum levels for certain contaminants in food (OJ L 364/5), last amended by Regulation (EU) No. 594 / 2012 of 5 July 2012 (OJ L 176/43).
  9. ↑ J Varga, M Due, JC Frisvad, RA Samson: Taxonomic revision of Aspergillus section Clavati based on molecular, morphological and physiological data . In: Studies in Mycology . tape 59 , 2007, ISSN  0166-0616 , p. 89-106 , doi : 10.3114 / sim.2007.59.11 , PMID 18490946 , PMC 2275193 (free full text).
  10. ↑ JC Frisvad, J Smedsgaard, TO Larsen, RA Samson: Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium. In: Studies in Mycology . tape 49 , 2004, pp. 201-242 .
  11. ^ RA Samson, J Houbraken, J Varga, JC Frisvad: Polyphasic taxonomy of the heat resistant ascomycete genus Byssochlamys and its Paecilomyces anamorphs . In: Persoonia . tape 22 , 2009, ISSN  1878-9080 , p. 14-27 , doi : 10.3767 / 003158509X418925 , PMID 20198134 , PMC 2789542 (free full text).
  12. ↑ a b Olivier Puel, Pierre Galtier, Isabelle Oswald: Biosynthesis and Toxicological Effects of Patulin . In: Toxins . tape 2 , no. 4 , April 5, 2010, ISSN  2072-6651 , p. 613–631 , doi : 10.3390 / toxins2040613 , PMID 22069602 , PMC 3153204 (free full text) - ( mdpi.com [accessed November 24, 2019]).

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