Aflatoxin B1

Aflatoxin B1

Chemical structure of (−)-aflatoxin B1

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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.276 Edit this at Wikidata
UNII
  • 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
  • O=C5C=4C(=O)Oc3c1c(OC2O\C=C/C12)cc(OC)c3C=4CC5
Properties
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:
GHS06: ToxicGHS08: Health hazard
Danger
H300, H310, H330, H340, H350
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).
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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.[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 TC, Peerdeman AF (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. Bibcode:1970AcCrB..26.1940V. doi:10.1107/S0567740870005228.
  3. ^ "Aflatoxin B1". PubChem. U.S. National Library of Medicine.
  4. ^ "Summary Table by Chemical of Carcinogenicity Results in CPDB on 1547 Chemicals" (PDF). Toxnet.
  5. ^ McLean M, Dutton MF (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 (2005). "Mycotoxins in the human food chain.". In Diaz DE (ed.). The Mycotoxin Blue Book. Nottingham, UK: Nottingham University Press. pp. 187–224.
  8. ^ Azab RM, Tawakkol WM, Hamad AM, Abou-Elmagd MK, El-Agrab HM, Refai MK (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 (February 2022). "Burden of Disease Associated with Dietary Exposure to Aflatoxins in China in 2020". Nutrients. 14 (5): 1027. doi:10.3390/nu14051027. PMC 8912679. PMID 35268003.
  10. ^ Chen T, Heflich RH, Moore MM, Mei N (March 2010). "Differential mutagenicity of aflatoxin B1 in the liver of neonatal and adult mice". Environmental and Molecular Mutagenesis. 51 (2): 156–163. Bibcode:2010EnvMM..51..156C. doi:10.1002/em.20518. PMC 6359889. PMID 19642212.
  11. ^ Geissler F, Faustman EM (February 1988). "Developmental toxicity of aflatoxin B1 in the rodent embryo in vitro: contribution of exogenous biotransformation systems to toxicity". Teratology. 37 (2): 101–111. doi:10.1002/tera.1420370203. PMID 3127910.
  12. ^ Meissonnier GM, Pinton P, Laffitte J, Cossalter AM, Gong YY, Wild CP, et al. (September 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): 142–149. Bibcode:2008ToxAP.231..142M. doi:10.1016/j.taap.2008.04.004. PMID 18501398.
  13. ^ Wacoo AP, Wendiro D, Vuzi PC, Hawumba JF (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". Food and Agricultural Organization. United Nations.