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Aflatoxin B1 information


Aflatoxin B1

Chemical structure of (–)-aflatoxin B1

Ball-and-stick model of aflatoxin B1[1][2]
Names
Preferred IUPAC name
(6aR,9aS)-4-Methoxy-2,3,6a,9a-tetrahydrocyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione
Other names
NSC 529592
Identifiers
CAS Number
  • 1162-65-8 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1697694 ☒N
ChemSpider
  • 13758 checkY
ECHA InfoCard 100.013.276 Edit this at Wikidata
PubChem CID
  • 14403
UNII
  • 9N2N2Y55MH checkY
CompTox Dashboard (EPA)
  • DTXSID00873175 DTXSID9020035, DTXSID00873175 Edit this at Wikidata
InChI
  • InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3 checkY
    Key: OQIQSTLJSLGHID-UHFFFAOYSA-N checkY
SMILES
  • O=C5C=4C(=O)Oc3c1c(OC2O\C=C/C12)cc(OC)c3C=4CC5
Properties
Chemical formula
C17H12O6
Molar mass 312.277 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Carcinogen – Mutagen – Acute toxicity / Poison[3]
GHS labelling:
Pictograms
GHS06: ToxicGHS08: Health hazard
Signal word
Danger
Hazard statements
H300, H310, H330, H340, H350
Precautionary statements
P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P330+P331, P302+P350, P304+P340, P308+P313, P310, P311, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Aflatoxin B1 is an aflatoxin produced by Aspergillus flavus and A. parasiticus. It is a very potent carcinogen with a TD50 3.2 μg/kg/day in rats.[4] This carcinogenic potency varies across species with some, such as rats and monkeys, seemingly much more susceptible than others.[5][6] Aflatoxin B1 is a common contaminant in a variety of foods including peanuts, cottonseed meal, corn, and other grains;[7] as well as animal feeds.[8] Aflatoxin B1 is considered the most toxic aflatoxin and it is highly implicated in hepatocellular carcinoma (HCC) in humans.[9] In animals, aflatoxin B1 has also been shown to be mutagenic,[10] teratogenic,[11] and to cause immunosuppression.[12] Several sampling and analytical methods including thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), mass spectrometry, and enzyme-linked immunosorbent assay (ELISA), among others, have been used to test for aflatoxin B1 contamination in foods.[13] According to the Food and Agriculture Organization (FAO), a division of the United Nations, the worldwide maximum tolerated levels of aflatoxin B1 was reported to be in the range of 1–20 μg/kg (or .001 ppm - 1 part-per-billion) in food, and 5–50 μg/kg (.005 ppm) in dietary cattle feed in 2003.[14]

  1. ^ "AFLATC : Aflatoxin B1 chloroform solvate". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. Retrieved 2021-03-23.
  2. ^ van Soest, T. C.; Peerdeman, A. F. (1970). "The crystal structures of aflatoxin B1. I. The structure of the chloroform solvate of aflatoxin B1 and the absolute configuration of aflatoxin B1". Acta Crystallogr. B. 26 (12): 1940–1947. doi:10.1107/S0567740870005228.
  3. ^ PubChem
  4. ^ "Summary Table by Chemical of Carcinogenicity Results in CPDB on 1547 Chemicals" (PDF). Toxnet.
  5. ^ McLean, M (February 1995). "Cellular interactions and metabolism of aflatoxin: an update". Pharmacology & Therapeutics. 65 (2): 163–192. doi:10.1016/0163-7258(94)00054-7. PMID 7540767.
  6. ^ Aflatoxin B1 (CAS 1162-65-8) The Carcinogenic Potency Project.
  7. ^ Galvano F., Ritieni A., Piva G., Pietri A. Mycotoxins in the human food chain. In: Diaz D.E., editor. The Mycotoxin Blue Book. Nottingham University Press; Nottingham, UK: 2005. pp. 187–224.
  8. ^ Azab Rania M.; Tawakkol Wael M.; Abdel-Rahman M. Hamad; Abou-Elmagd Mohamed K.; El-Agrab Hassan M.; Refai Mohamed K. (2005). "Detection and estimation of aflatoxin B1 in feeds and its biodegradation by bacteria and fungi". Egyptian Journal of Natural Toxins. 2: 39–56.
  9. ^ Chen T; Liu J; Li Y; Wei S (2022). "Burden of disease associated with dietary exposure to aflatoxins in China in 2020". Nutrients. 14: 1027.
  10. ^ Chen, Tao; Heflich, Robert H; Moore, Martha M; Mei, Nan (2009). "Differential mutagenicity of aflatoxin B1in the liver of neonatal and adult mice". Environmental and Molecular Mutagenesis. 51 (2): 156–63. doi:10.1002/em.20518. PMC 6359889. PMID 19642212.
  11. ^ Geissler, Francis; Faustman, Elaine M (1988). "Developmental toxicity of aflatoxin B1 in the rodent embryo in vitro: Contribution of exogenous biotransformation systems to toxicity". Teratology. 37 (2): 101–11. doi:10.1002/tera.1420370203. PMID 3127910.
  12. ^ Meissonnier GM, Pinton P, Laffitte J, Cossalter AM, Gong YY, Wild CP, Bertin G, Galtier P, Oswald IP (2008). "Immunotoxicity of aflatoxin B1: Impairment of the cell-mediated response to vaccine antigen and modulation of cytokine expression". Toxicology and Applied Pharmacology. 231 (2): 142–9. doi:10.1016/j.taap.2008.04.004. PMID 18501398.
  13. ^ Wacoo Alex P.; Wendiro Deborah; Vuzi Peter C.; Hawumba Joseph F. (2014). "Methods for Detection of Aflatoxins in Agricultural Food Crops". Journal of Applied Chemistry. 2014: 1–15. doi:10.1155/2014/706291.
  14. ^ "Worldwide regulations for mycotoxins in food and feed in 2003".

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Aflatoxin B1

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Aflatoxin B1 is an aflatoxin produced by Aspergillus flavus and A. parasiticus. It is a very potent carcinogen with a TD50 3.2 μg/kg/day in rats. This...

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Aflatoxin

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parasiticus, but it and aflatoxin M2 are also produced when an infected liver metabolizes aflatoxin B1 and B2. Aflatoxin B1 and B2 (AFB), produced by...

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Aflatoxin M1

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Aspergillus flavus produces only B-type aflatoxins. Aflatoxin M1 is the hydroxylated metabolite of aflatoxin B1 and can be found in milk or milk products...

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Aflatoxin total synthesis

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program. The synthesis of racemic aflatoxin B1 has been reported by Buechi et al. in 1967 and that of racemic aflatoxin B2 by Roberts et al. in 1968 The...

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Copra

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December 2019. Tosun, Halil; Arslan, Recep (2013). "Determination of Aflatoxin B1 Levels in Organic Spices and Herbs". The Scientific World Journal. 2013:...

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Linaria purpurea

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reduced the production of aflatoxin B1 in Aspergillus flavus Link., making it a potential natural and 'green' anti-aflatoxin B1 agent suitable for use in...

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2013 European aflatoxin contamination

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Alert System for Food and Feed (RASFF) has reported 10 notifications of aflatoxin B1 in maize of European origin since the last maize harvest in autumn 2012...

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Sterigmatocystin

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metabolite structurally closely related to the aflatoxins as it is the penultimate precursor of aflatoxins B1 and G1. It contains a xanthone nucleus attached...

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Aspergillus flavus

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strains can produce the two most common aflatoxins (B1 and B2). Unique to the S strains is the production of aflatoxin G1 and G2 which typically are not produced...

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Sugarcane juice

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pose health risks due to contamination with the mycotoxins, aflatoxin B1 and fumonisin B1. Sugarcane juice, known locally as caldo de cana, is commonly...

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Liver cancer

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S2CID 20842446. Dai Y, Huang K, Zhang B, Zhu L, Xu W (November 2017). "Aflatoxin B1-induced epigenetic alterations: An overview". Food and Chemical Toxicology...

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Butylated hydroxytoluene

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Egner, PA; Trush, MA; Bueding, E; Groopman, JD (1985). "Modification of aflatoxin B1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin...

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Cytochrome P450

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in terms of their kinetic properties as well as in the metabolism of aflatoxin B1. CYPs have also been extensively studied in insects, often to understand...

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AKR7A2

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Aflatoxin B1 aldehyde reductase member 2 is an enzyme that in humans is encoded by the AKR7A2 gene. Aldo-keto reductases, such as AKR7A2, are involved...

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Almond

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Retrieved 23 August 2012. Rushing, Blake R.; Selim, Mustafa I. (2019). "Aflatoxin B1: A review on metabolism, toxicity, occurrence in food, occupational exposure...

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Mycotoxin

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to four different types of mycotoxins produced, which are B1, B2, G1, and G2. Aflatoxin B1, the most toxic, is a potent carcinogen and has been directly...

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Biliary atresia

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aflatoxin in its blood and liver. Moreover, the baby feeds aflatoxin M1 from its mom, as aflatoxin M1 is the detoxification product of aflatoxin B1....

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Median lethal dose

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Meister Pub Co. p. 664. ISBN 978-1892829269. "Safety (MSDS) data for aflatoxin B1". ox.ac.uk. Archived from the original on 2010-08-11. Voelz GL, Buican...

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Polyketide

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inhibitors) The cholesterol lowering agent lovastatin Discodermolide Aflatoxin Usnic acid Anthracimycin Anthramycin Olivetolic acid (intermediate in...

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Peanut

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ISBN 978-1-84826-368-0. Hirano, S; Shima, T; Shimada, T (August 2001). "[Proportion of aflatoxin B1 contaminated kernels and its concentration in imported peanut samples]"...

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Aspergillus parvisclerotigenus

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isolated in Nigeria and has been found to produce aflatoxin B1, aflatoxin B2, aflatoxin G1, aflatoxin G2, aflatrem, aflavarin, aspirochlorin, cyclopiazonic...

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C17H12O7

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C17H12O7 may refer to: Aflatoxin B1 exo-8,9-epoxide, a toxic metabolite of aflatoxin B1 Aflatoxin M1, a chemical compound of the aflatoxin class This set index...

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CYP1A2

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intermediates. Other xenobiotic substrates for this enzyme include caffeine, aflatoxin B1, and paracetamol (acetaminophen). The transcript from this gene contains...

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Carcinogen

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causes cancer as a "myth". Several biologic agents are known carcinogens. Aflatoxin B1, a toxin produced by the fungus Aspergillus flavus which is a common...

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Aspergillus minisclerotigenes

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described in 2008. It has been reported to produce aflatoxin B1, aflatoxin B2, aflatoxin G1, aflatoxin G2, aflavarins, aflatrems, aflavinins, aspergillic...

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Tempeh

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Aspergillus parasiticus by interfering with the accumulation of aflatoxin (especially aflatoxin B1), the mycotoxin of greatest concern. R. oligosporus has also...

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Cancer

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linked to specific cancers. A high-salt diet is linked to gastric cancer. Aflatoxin B1, a frequent food contaminant, causes liver cancer. Betel nut chewing...

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Aspergillus nomius

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described in 1987. It has been reported to produce aflatoxin B1, aflatoxin B2, aflatoxin G1, aflatoxin G2, aspergillic acid, kojic acid, nominine, paspaline...

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