Patulin
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| Category | Antibiotics |
| Catalog number | BBF-02671 |
| CAS | 149-29-1 |
| Molecular Weight | 154.12 |
| Molecular Formula | C7H6O4 |
| Purity | ≥98% |
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Description
It is produced by the strain of Pen. patulum. It has anti-bacterial and fungal effects.
Specification
| Synonyms | Clavacin; Expansin; Penicidin; Clavatin; Patuline; Clairformin; Gigantin; Leucopin; (2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone |
| Storage | Store at -20°C |
| IUPAC Name | 4-hydroxy-4,6-dihydrofuro[3,2-c]pyran-2-one |
| Canonical SMILES | C1C=C2C(=CC(=O)O2)C(O1)O |
| InChI | InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2 |
| InChI Key | ZRWPUFFVAOMMNM-UHFFFAOYSA-N |
| Source | Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. The major source of patulin contamination is in apples with brown rot, and in apple cider or apple juice. |
Properties
| Appearance | Colorless Flaky Crystal |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 513.7°C at 760 mmHg |
| Melting Point | 108-112°C |
| Density | 1.52 g/cm3 |
| Solubility | Soluble in Hydrochloric acid, Sodium hydroxide, Ethyl Acetate (50 mg/mL) |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | 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. |
| Toxicity | LD50: 29-48 mg/kg (Oral, Mouse); LD50: 10 mg/kg (Subcutaneous, Mosue); LD50: 5.7-8.17 mg/kg (Intraperitoneal, Mouse); LD50: 8.57 mg/kg (Intravenous, Mouse). |
Reference Reading
1.Cytotoxic effects induced by patulin, sterigmatocystin and beauvericin on CHO-K1 cells.
Zouaoui N1, Mallebrera B2, Berrada H2, Abid-Essefi S3, Bacha H3, Ruiz MJ4. Food Chem Toxicol. 2016 Mar;89:92-103. doi: 10.1016/j.fct.2016.01.010. Epub 2016 Jan 21.
Mycotoxins are produced by different genera of fungi; mainly Aspergillus, Penicillium and Fusarium. The natural co-occurrence of beauvericin (BEA), patulin (PAT) and sterigmatocystin (STE) has been proved in feed and food commodities. This study investigates the cytotoxicity of individual and combined mycotoxins BEA, PAT and STE. The cytotoxicity on immortalized ovarian cells (CHO-K1) was evaluated using the MTT assay. After 24, 48 and 72 h, the IC50 values were 2.9 μM for PAT and ranged from 10.7 to 2.2 μM and from 25.0 to 12.5 μM for BEA and STE, respectively. Cytotoxic interactions were assayed by the isobologram method, which provides a combination index (CI) value as a quantitative measure of the three mycotoxin interaction's degree. Binary and tertiary combinations showed a dose dependent effect. At low fraction affected, mycotoxin combinations were synergetic; whereas, at higher fraction affected, the combinations showed additive effect.
2.Regulation of the antioxidant system in cells of the fission yeast Schizosaccharomyces pombe after combined treatment with patulin and citrinin.
Papp G1, Máté G2, Mike N2, Gazdag Z3, Pesti M2. Toxicon. 2016 Mar 1;111:100-7. doi: 10.1016/j.toxicon.2015.12.021. Epub 2016 Jan 2.
The effects of combined treatment with patulin (PAT) and citrinin (CTN) on Schizosaccharomyces pombe cells were investigated in acute toxicity tests. In comparison with the controls the exposure of fission yeast cells (10(7) cells ml(-1)) to PAT + CTN (250 μM each) for 1 h at a survival rate of 66.6% significantly elevated the concentration of total reactive oxygen species (ROS) via increased levels of peroxides without affecting the concentrations of superoxides or the hydroxyl radical. This treatment induced a 3.08-fold increase in the specific concentration of glutathione and elevated specific activities of catalase and glutathione S-transferase, while at the same time the activity of glutathione reductase decreased. The pattern of the ROS was the same as that induced by CTN (Máté et al., 2014), while the presence of PAT in the PAT + CTN combination treatment modified the activities of the antioxidant system (Papp et al., 2012) in comparison with the individual PAT or CTN treatment, suggesting toxin-specific regulation of glutathione and the enzymes of the antioxidant system and the possibility that the transcription factor (pap1 and atf1) -regulated processes might be influenced directly by ROS.
3.Characterization of in vitro effects of patulin on intestinal epithelial and immune cells.
Assunção R1, Alvito P2, Kleiveland CR3, Lea TE4. Toxicol Lett. 2016 May 27;250-251:47-56. doi: 10.1016/j.toxlet.2016.04.007. Epub 2016 Apr 8.
The intestinal mucosa is the first biological barrier encountered by natural toxins, and could possibly be exposed to high amounts of dietary mycotoxins. Patulin (PAT), a mycotoxin produced by Penicillium spp. during fruit spoilage, is one of the best known enteropathogenic mycotoxins able to alter functions of the intestine (Maresca et al., 2008). This study evaluated the effects of PAT on barrier function of the gut mucosa utilizing the intestinal epithelial cell model Caco-2, and scrutinized immunomodulatory effects using human peripheral blood mononuclear cells (PBMC) and human blood monocyte-derived dendritic cells (moDCs) as test systems. PAT exposure reduced Caco-2 cell viability at concentrations above 12μM. As expected, the integrity of a polarized Caco-2 monolayer was affected by PAT exposure, as demonstrated by a decrease in TER values, becoming more pronounced at 50μM. No effects were detected on the expression levels of the tight junction proteins occludin, claudin-1 and claudin-3 at 50μM.
4.Crocin protects the liver and kidney from patulin-induced apoptosis in vivo.
Boussabbeh M1,2, Ben Salem I1,2, Belguesmi F1, Neffati F3, Najjar MF3, Abid-Essefi S4, Bacha H1. Environ Sci Pollut Res Int. 2016 Feb 9. [Epub ahead of print]
Patulin (PAT) is a mycotoxin mainly produced by Aspergillus, Penicillium, and Bissochlamys. Given the high risk associated with this mycotoxin, its potential effects have been investigated by many studies. It is known to be teratogenic, mutagenic, and genotoxic, and it has been shown to induce damages in several organs in experimental animals. Our aim was to investigate the preventive effect against PAT-induced apoptosis in vivo using natural carotenoid, Crocin (CRO). Mice were divided into six groups: a control group, a "PAT alone" group, a "CRO alone" group, and a "PAT plus CRO" groups (pre-treatment conditions). Our results showed that CRO restored the normal levels of biochemical parameters in the liver and kidney. The analysis of the protein expression in these organs revealed that PAT-induced toxicity promotes the induction of apoptosis via the increase in P53, Bax, and cytochrome C and the decrease in Bcl2 expressions. We also found that PAT triggered caspase 3 activation and DNA fragmentation.
Spectrum
LC-MS/MS Spectrum - 10V, Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
