Synthesis of Aflatoxin

B2
Presenter: Akmaral Kudaibergen
General information

● Potent mycotoxin
● Food contaminant produced by Aspergillus flavus, a common soil fungus.
● The minor analogue of the blue fluorescent family of bisfuranocoumarin mycotoxins produced by
Aspergillus flavus and related species.
● Found widely in nature in trace amounts, particularly in grains and nuts.
● 1950s: first recognition of the toxicity of these metabolites.
● 1963: structures elucidated.
● Extensively reviewed.
● In fact they are "pre-toxins", requiring metabolic activation to the toxic principle.
MSDS

Acute toxic

Health hazards

Hepatocarcinogen.

Hepatotoxic, teratogenic and carcinogenic risks for humans and livestock.

Miscible in ethanol, methanol, DMF or DMSO. Not highly miscible in water.

Yield of the synthesis is not likely to exceed 3%.

Aflatoxin B2 synthesis

Figure 1. Retrieved from https://en.wikipedia.org/wiki/Aflatoxin.

Detailed mechanism
Detailed mechanism
Detailed mechanism
Detailed mechanism
Applications

Very important for quality control of food, especially for nuts and grains.

Used as a standard in a study to find out aflatoxins in various foods, spices and feedstuffs by high
performance liquid chromatography (HPLC).

Used as a standard to determine aflatoxins in honey by HPLC.

Aflatoxins are densely fluorescent

Exhibits blue fluorescence

Conclusions

Very hazardous compound during preparation and quality control

Very useful for prevention fungal diseases by quality control

References

Aflatoxin B2. https://pubchem.ncbi.nlm.nih.gov/compound/Aflatoxin-B2.

Aflatoxin B2. https://www.bioaustralis.com/product/aflatoxin-b2/.

Aflatoxin B2. https://www.sigmaaldrich.com/KZ/en/product/sigma/a9887.

Aflatoxin total synthesis. https://en.wikipedia.org/wiki/Aflatoxin_total_synthesis#:~:text=The%20total%20synthesis%20of%20Aflatoxin,2%20in%20a%20Duff%20reaction.

Aflatoxin. https://en.wikipedia.org/wiki/Aflatoxin.

File:aflatoxin B2 total synthesis.svg. https://commons.m.wikimedia.org/wiki/File:Aflatoxin_B2_total_synthesis.svg.

Gurav NP, Medhe S. Analysis of Aflatoxins B1, B2, G1 and G2 in Peanuts: Validation Study. Anal Chem Ind J. 2018;17(2):126

Kumar, P.; Mahato, D. K.; Kamle, M.; Mohanta, T. K.; Kang, S. G. Aflatoxins: A Global Concern for Food Safety, Human Health and Their Management. Frontiers in Microbiology 2017, 07.

Yang, L.; Wang, Z. Advances in the Total Synthesis of Aflatoxins. Frontiers in Chemistry 2021, 9.