PATULIN

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

Structure Search

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

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29302627

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29302627	Primary		Basic research	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29302627	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Patulin content in Polish apple juices].	2004	15732504
Influence of intrinsic factors of apples on the growth and patulin production of Penicillium expansum.	2004	15560184
Colds, international policy and inequalities.	2004 Apr	15127736
[Are mycotoxins in food a health hazard?].	2004 Aug	15469056
[Nutritional health aspects of mycotoxins].	2004 Aug 22	15493122
The isoepoxydon dehydrogenase gene of patulin biosynthesis in cultures and secondary metabolites as candidate PCR inhibitors.	2004 Dec	15757179
Development of liquid chromatography-electrospray mass spectrometry for the determination of patulin in apple juice: investigation of its contamination levels in Japan.	2004 Dec 15	15675789
Rational elimination of Aspergillus terreus sulochrin production.	2004 Mar 4	15129726
Patulin produced by an Aspergillus clavatus isolated from feed containing malting residues associated with a lethal neurotoxicosis in cattle.	2004 Nov	15702266
Antagonism against Rhizoctonia solani and fungitoxic metabolite production by some Penicillium isolates.	2004 Nov	15630556
Combined effects of selected Penicillium mycotoxins on in vitro proliferation of porcine lymphocytes.	2004 Nov	15630553
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 Oct	15702270
A quantification and confirmation method of patulin in apple juice by GC/MS.	2004 Oct	15678938
Characterization of molds from dry-cured meat products and their metabolites by micellar electrokinetic capillary electrophoresis and random amplified polymorphic DNA PCR.	2004 Oct	15508635
Micromycetes, producers of toxins, detected on stored vegetables.	2005	16457482
[Fungal spoilage of foods and its risk assessment].	2005	15711530
Chemical response of Picea glehnii seed-epiphytic Penicillium species to Pythium vexans under in vitro competitive conditions for mycelial growth.	2005 Apr	16124252
Patulin reduces glutathione level and enzyme activities in rat liver slices.	2005 Apr	15744717
Degradation of ochratoxin A and other mycotoxins by Rhizopus isolates.	2005 Apr 1	15808366
[Mycotoxin contamination and control in foods].	2005 Aug	16180695
Parallel synthesis: a new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry.	2005 Aug 24	16104779
Studies on the affinity chromatography purification of anti-patulin polyclonal antibodies by enzyme linked immunosorbent assay and electrophoresis.	2005 Dec	16356888
Fungal populations and mycotoxins in silage in Assiut and Sohag governorates in Egypt, with a special reference to characteristic Aspergilli toxins.	2005 Feb	15770455
Mutagenicity of the mycotoxin patulin in cultured Chinese hamster V79 cells, and its modulation by intracellular glutathione.	2005 Feb	15536543
Evaluation of several culture media for production of patulin by Penicillium species.	2005 Feb 15	15698685
Control of hepatitis C: a medicinal chemistry perspective.	2005 Jan 13	15633995
Estimated dietary exposure to principal food mycotoxins from the first French Total Diet Study.	2005 Jul	16019841
Production and stability of patulin, ochratoxin A, citrinin, and cyclopiazonic acid on dry cured ham.	2005 Jul	16013399
Detection of patulin in apple juices marketed in the Tohoku district, Japan.	2005 Mar	15771191
Mycological survey of ripped service tree fruits (Sorbus domestica L.) with an emphasis on toxinogenic fungi.	2005 Mar 15	15734569
Liquid chromatographic method for quantitation of patulin at 10 ng/mL in apple-based products intended for infants: interlaboratory study.	2005 Mar-Apr	15859080
Occurrence of patulin in conventional and organic fruit products in Italy and subsequent exposure assessment.	2005 May	16019815
Identity and effects of quorum-sensing inhibitors produced by Penicillium species.	2005 May	15870443
Inter-laboratory study for validation of a Japanese official analytical method for determination of patulin in apple juice.	2005 Oct	16305178
Activation of ERK mitogen-activated protein kinase in human cells by the mycotoxin patulin.	2005 Sep 1	16102563
Chemical and conformational study of the interactions involved in mycotoxin complexation with beta-D-glucans.	2006 Apr	16602732
In vitro investigation of individual and combined cytotoxic effects of ochratoxin A and other selected mycotoxins on renal cells.	2006 Apr	16140496
Cloning and molecular characterization of Penicillium expansum genes upregulated under conditions permissive for patulin biosynthesis.	2006 Feb	16436057
Mycotoxin patulin activates the p38 kinase and JNK signaling pathways in human embryonic kidney cells.	2006 Feb	16306151
Evaluation of different biological test systems to assess the toxicity of metabolites from fungal biocontrol agents.	2006 Feb 8	16139968
The isoepoxydon dehydrogenase gene of the patulin metabolic pathway differs for Penicillium griseofulvum and Penicillium expansum.	2006 Jan	16328863
Determination of patulin in apple juice by liquid chromatography.	2006 Jan-Feb	16512238
Recent advances in mycotoxin determination in food and feed by hyphenated chromatographic techniques/mass spectrometry.	2006 Jan-Feb	15892148
The genetic basis of thermal reaction norm evolution in lab and natural phage populations.	2006 Jul	16732695
Activity of trans-2-hexenal against Penicillium expansum in 'Conference' pears.	2006 Jun	16696666
Mechanisms of patulin toxicity under conditions that inhibit yeast growth.	2006 Mar 8	16506856
Monitoring the mycotoxins in food and their biomarkers in the Czech Republic.	2006 May	16676375
Aflatoxins, patulin and ergosterol contents of dried figs in Turkey.	2006 May	16644598
Survey and significance of filamentous fungi from tap water.	2006 May	16459143
Effects of patulin on thymus capillary of rats.	2006 Nov-Dec	16142687

Sample Use Guides

In Vivo Use Guide

risk assessment of patulin occurrence in fruit juices: revealed no health concern.

Route of Administration: Oral

In Vitro Use Guide

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 by `admin` on `Fri Dec 15 19:02:46 GMT 2023` Edited by `admin` on `Fri Dec 15 19:02:46 GMT 2023`
Record UNII	95X2BV4W8R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PATULIN

Common Name

English

PENICIDIN

Common Name

English

LEUCOPIN

Common Name

English

PATULIN [MI]

Common Name

English

DL-PATULIN

Common Name

English

CLAIRFORMIN

Common Name

English

CLAVACIN

Common Name

English

PATULIN [IARC]

Common Name

English

NSC-8120

Code

English

4H-FURO(3,2-C)PYRAN-2(6H)-ONE, 4-HYDROXY-

Systematic Name

English

EXPANSIN

Common Name

English

ACETIC ACID, (2,4-DIHYDROXY-2H-PYRAN-3(6H)-YLIDENE)-, 3,4-LACTONE

Common Name

English

4-HYDROXY-4H-FURO(3,2-C)PYRAN-2(6H)-ONE

Systematic Name

English

(±)-4-HYDROXY-4H-FURO(3,2-C)PYRAN-2(6H)-ONE

Systematic Name

English

MYCOIN

Common Name

English

CLAVIFORMIN

Common Name

English

PATULINE

Common Name

English

CLAVATIN

Common Name

English

NSC-32951

Code

English

PATULIN [HSDB]

Common Name

English

TERININ

Common Name

English

Code System Code Type Description

FDA UNII

95X2BV4W8R