Citrinin
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| Category | Bioactive by-products |
| Catalog number | BBF-00644 |
| CAS | 518-75-2 |
| Molecular Weight | 250.25 |
| Molecular Formula | C13H14O5 |
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Description
It is produced by the strain of Penicillum citrinum. Citrinin has the ability of anti-gram positive bacteria, negative bacteria (weak) and mycobacterium (10-100 μg/mL), and can inhibit vaginal trichomonas when diluted with 1:25600 ratio. It can also induce the differentiation of mouse leukemia cells.
Specification
| Synonyms | (-)-Citrinin; UNII-3S697X6SNZ |
| Storage | Store at -20°C |
| IUPAC Name | (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid |
| Canonical SMILES | CC1C(OC=C2C1=C(C(=C(C2=O)C(=O)O)O)C)C |
| InChI | InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,14H,1-3H3,(H,16,17)/t5-,7-/m1/s1 |
| InChI Key | CBGDIJWINPWWJW-IYSWYEEDSA-N |
| Source | Citrinin is a mycotoxin originally isolated from Penicillium citrinum. Citrinin is also produced by a variety of other fungi including Aspergillus niveus, Aspergillus ochraceus, Aspergillus oryzae, Aspergillus terreus, Monascus ruber, Monascus purpureus, and Penicillium camemberti. |
Properties
| Appearance | Light Yellow to Orange Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria; parasites |
| Boiling Point | 440.6°C at 760 mmHg |
| Melting Point | 173-174°C |
| Density | 1.37 g/cm3 |
| Solubility | Soluble in DMSO |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Citrinin produces proximal tubular necrosis, but only after transport into proximal tubular cells. It utilizes the organic anion transporter for entry into the cells, a transporter probably important physiologically for moving metabolic substrates into cells. Citrinin is also cytotoxic and increases formation of reactive oxygen species by stimulating the production of superoxide anion in the respiratory chain. It further potentiates this oxidative stress by modifying antioxidative enzymatic defences by inhibiting GSSG-reductase and transhydrogenase. Citrinin also alters mitochondrial function and permeability, decreasing Ca2+ accumulation in the matrix by inhibiting its influx and increasing its efflux. Citrinin inhibits respiration by interfering with the NADH oxidase and NADH cytochrome c reductase involved with complex I of the respiratory chain. 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: 112 mg/kg (Oral, Mouse); LD50: 50 mg/kg (Oral, Rat); LD50: 67 mg/kg (Subcutaneous, Rat). |
Reference Reading
1. Citrinin biomarkers: a review of recent data and application to human exposure assessment
Nurshad Ali, Gisela H Degen Arch Toxicol . 2019 Nov;93(11):3057-3066. doi: 10.1007/s00204-019-02570-y.
The mycotoxin citrinin (CIT) deserves attention due to its known toxic effects in mammalian species and a widespread occurrence in food commodities, often along with ochratoxin A, another nephrotoxic mycotoxin. Human exposure, a key element in assessing risks related to these food contaminants, depends upon mycotoxin levels in food and on food consumption. Yet, data available for CIT levels in food are insufficient for reliable intake estimates. Now biomonitoring, i.e., analysis of parent compound and/or metabolites in human specimen (blood, urine, breast milk), is increasingly used to investigate mycotoxin exposure. Biomonitoring requires sensitive methods for determining biomarkers of exposure, combined with kinetic data to conclude on the absorbed internal dose in an individual. Recent advances in LC-MS/MS-based analytical techniques have facilitated biomonitoring studies on the occurrence of CIT biomarkers in body fluids, mainly in urine samples. This review compiles evidence on human exposure to CIT in different countries, on CIT kinetics in humans, and on biomarker-based CIT intake estimates. Human CIT exposures are discussed in light of an intake value defined as 'level of no concern for nephrotoxicity' by the European Food Safety Agency, and some uncertainties in the toxicological data base. Further studies on CIT, including biomarker-based studies are warranted along with regular food surveys for this mycotoxin to protect consumers against undesirable health effects.
2. Co-occurrence of citrinin and ochratoxin A in rice in Asia and its implications for human health
Nurshad Ali J Sci Food Agric . 2018 Apr;98(6):2055-2059. doi: 10.1002/jsfa.8667.
Citrinin (CIT) and ochratoxin A (OTA) are nephrotoxic mycotoxins, produced by several Aspergillus and Penicillium species and their co-occurrence in rice may cause health effects in humans. Rice is an important food crop worldwide and is a major staple food in Asia which may be invaded by CIT and OTA producing fungal spores in the field, during harvest and storage. Humans are exposed to these mycotoxins through ingestion of contaminated rice and other food commodities. Yet, data on the combined presence to these food contaminants are still insufficient to estimate human exposure in Asia. This review describes the prevalence of CIT and OTA in rice in Asia and its implications on human health, which may help in establishing and carrying out proper management strategies against mould development on rice. From the health point of view, combined exposition of CIT and OTA should be a public concern as both are nephrotoxic and long-term exposure can pose detrimental health effects. Thus, it is necessary for local farmers and food factories to implement strict measures and to improve methods for rice preservation during the distribution to consumers, particularly in the markets. Moreover, regular surveys for CIT and OTA occurrence in rice and human biomonitoring are recommended to reduce the health effects in Asian population. © 2017 Society of Chemical Industry.
3. Citrinin
H K Frank Z Ernahrungswiss . 1992 Sep;31(3):164-77. doi: 10.1007/BF01611139.
Citrinin, a nephrotoxic mycotoxin, has been of growing importance also for the "International Agency for Research on Cancer", ever since its presumable role in the occurrence of Balcan endemic nephropathy (BEN) was discussed at the congress on "Mycotoxins, Endemic Nepthropathy and Urinary Tract Tumours" held in Lyon in June 1991 (12). In late 1991, citrinin was therefore also included in the list of toxins to be examined by the screening subcommittees on natural toxins of the International Live Science Institute, European Branch.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C13H14O5
Molecular Weight (Monoisotopic Mass): 250.0841 Da
Molecular Weight (Avergae Mass): 250.2473 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C13H14O5
Molecular Weight (Monoisotopic Mass): 250.0841 Da
Molecular Weight (Avergae Mass): 250.2473 Da
LC-MS/MS Spectrum - LC-ESI-qToF , Positive
Experimental Conditions
Instrument Type: LC-ESI-qToF
Ionization Mode: Positive
Ionization Mode: 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
Molecular Formula: C13H14O5
Molecular Weight (Monoisotopic Mass): 250.0841 Da
Molecular Weight (Avergae Mass): 250.2473 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C13H14O5
Molecular Weight (Monoisotopic Mass): 250.0841 Da
Molecular Weight (Avergae Mass): 250.2473 Da
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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
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