Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C7H6O4 |
| Molecular Weight | 154.1201 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1OCC=C2OC(=O)C=C12
InChI
InChIKey=ZRWPUFFVAOMMNM-UHFFFAOYSA-N
InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
| Molecular Formula | C7H6O4 |
| Molecular Weight | 154.1201 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Patulin is a toxic secondary metabolite produced by molds, especially Penicillium and Aspergillus, and is usually found in apples and apple-derived products including juice and compote. Several reports have demonstrated that exposure to different levels of this polyketide metabolite is associated with immunotoxicity, genotoxicity, embryotoxicity, and teratogenicity in animals and some microorganisms. Recently was shown, that patulin possesses the antitumor activity against cervical and colorectal cancer cell lines.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The genetic basis of thermal reaction norm evolution in lab and natural phage populations. | 2006-07 |
|
| Activity of trans-2-hexenal against Penicillium expansum in 'Conference' pears. | 2006-06 |
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| Monitoring the mycotoxins in food and their biomarkers in the Czech Republic. | 2006-05 |
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| Aflatoxins, patulin and ergosterol contents of dried figs in Turkey. | 2006-05 |
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| Survey and significance of filamentous fungi from tap water. | 2006-05 |
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| Chemical and conformational study of the interactions involved in mycotoxin complexation with beta-D-glucans. | 2006-04 |
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| In vitro investigation of individual and combined cytotoxic effects of ochratoxin A and other selected mycotoxins on renal cells. | 2006-04 |
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| Mechanisms of patulin toxicity under conditions that inhibit yeast growth. | 2006-03-08 |
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| Determination of patulin in apple juice by liquid chromatography. | 2006-03-04 |
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| Evaluation of different biological test systems to assess the toxicity of metabolites from fungal biocontrol agents. | 2006-02-08 |
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| Cloning and molecular characterization of Penicillium expansum genes upregulated under conditions permissive for patulin biosynthesis. | 2006-02 |
|
| Mycotoxin patulin activates the p38 kinase and JNK signaling pathways in human embryonic kidney cells. | 2006-02 |
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| The isoepoxydon dehydrogenase gene of the patulin metabolic pathway differs for Penicillium griseofulvum and Penicillium expansum. | 2006-01 |
|
| Studies on the affinity chromatography purification of anti-patulin polyclonal antibodies by enzyme linked immunosorbent assay and electrophoresis. | 2005-12 |
|
| [Inter-laboratory study for validation of a Japanese official analytical method for determination of patulin in apple juice]. | 2005-10 |
|
| Effects of patulin on thymus capillary of rats. | 2005-09-06 |
|
| Activation of ERK mitogen-activated protein kinase in human cells by the mycotoxin patulin. | 2005-09-01 |
|
| Parallel synthesis: a new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry. | 2005-08-24 |
|
| [Mycotoxin contamination and control in foods]. | 2005-08 |
|
| Estimated dietary exposure to principal food mycotoxins from the first French Total Diet Study. | 2005-07 |
|
| Production and stability of patulin, ochratoxin A, citrinin, and cyclopiazonic acid on dry cured ham. | 2005-07 |
|
| Recent advances in mycotoxin determination in food and feed by hyphenated chromatographic techniques/mass spectrometry. | 2005-05-14 |
|
| Occurrence of patulin in conventional and organic fruit products in Italy and subsequent exposure assessment. | 2005-05 |
|
| Identity and effects of quorum-sensing inhibitors produced by Penicillium species. | 2005-05 |
|
| Liquid chromatographic method for quantitation of patulin at 10 ng/mL in apple-based products intended for infants: interlaboratory study. | 2005-04-30 |
|
| Degradation of ochratoxin A and other mycotoxins by Rhizopus isolates. | 2005-04-01 |
|
| Chemical response of Picea glehnii seed-epiphytic Penicillium species to Pythium vexans under in vitro competitive conditions for mycelial growth. | 2005-04 |
|
| Patulin reduces glutathione level and enzyme activities in rat liver slices. | 2005-04 |
|
| Mycological survey of ripped service tree fruits (Sorbus domestica L.) with an emphasis on toxinogenic fungi. | 2005-03-15 |
|
| Detection of patulin in apple juices marketed in the Tohoku district, Japan. | 2005-03 |
|
| Evaluation of several culture media for production of patulin by Penicillium species. | 2005-02-15 |
|
| Fungal populations and mycotoxins in silage in Assiut and Sohag governorates in Egypt, with a special reference to characteristic Aspergilli toxins. | 2005-02 |
|
| Mutagenicity of the mycotoxin patulin in cultured Chinese hamster V79 cells, and its modulation by intracellular glutathione. | 2005-02 |
|
| Control of hepatitis C: a medicinal chemistry perspective. | 2005-01-13 |
|
| Micromycetes, producers of toxins, detected on stored vegetables. | 2005 |
|
| [Fungal spoilage of foods and its risk assessment]. | 2005 |
|
| Development of liquid chromatography-electrospray mass spectrometry for the determination of patulin in apple juice: investigation of its contamination levels in Japan. | 2004-12-15 |
|
| The isoepoxydon dehydrogenase gene of patulin biosynthesis in cultures and secondary metabolites as candidate PCR inhibitors. | 2004-12 |
|
| Patulin produced by an Aspergillus clavatus isolated from feed containing malting residues associated with a lethal neurotoxicosis in cattle. | 2004-11 |
|
| Antagonism against Rhizoctonia solani and fungitoxic metabolite production by some Penicillium isolates. | 2004-11 |
|
| Combined effects of selected Penicillium mycotoxins on in vitro proliferation of porcine lymphocytes. | 2004-11 |
|
| The effects of the Penicillium mycotoxins citrinin, cyclopiazonic acid, ochratoxin A, patulin, penicillic acid, and roquefortine C on in vitro proliferation of porcine lymphocytes. | 2004-10 |
|
| A quantification and confirmation method of patulin in apple juice by GC/MS. | 2004-10 |
|
| Characterization of molds from dry-cured meat products and their metabolites by micellar electrokinetic capillary electrophoresis and random amplified polymorphic DNA PCR. | 2004-10 |
|
| [Nutritional health aspects of mycotoxins]. | 2004-08-22 |
|
| [Are mycotoxins in food a health hazard?]. | 2004-08 |
|
| Colds, international policy and inequalities. | 2004-04 |
|
| Rational elimination of Aspergillus terreus sulochrin production. | 2004-03-04 |
|
| [Patulin content in Polish apple juices]. | 2004 |
|
| Influence of intrinsic factors of apples on the growth and patulin production of Penicillium expansum. | 2004 |
Sample Use Guides
risk assessment of patulin occurrence in fruit juices: revealed no health concern.
Route of Administration:
Oral
To determine the efficacy of patulin as a therapeutic strategy for cervical and colorectal cancers, there were investigated its effects on HeLa,SW-48, and MRC-5 cell lines. Cell lines were exposed to various concentrations of patulin (i.e., 0.5, 1, 2, and 4 µM), then using methyl thiazolyl tetrazolium (MTT) and bromo-2'-deoxyuridine (BrdU) assays, the rates of apoptosis and cell viability were determined.
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
95X2BV4W8R
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| Record Status |
Validated (UNII)
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| Record Version |
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