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Chemical Compound Review:

Flavoglaucin 2-heptyl-3,6-dihydroxy-5-(3- methylbut-2...

Synonyms: CCRIS 6491, CHEMBL1813664, CHEBI:68188, AR-1H1779, NP-016137, ...

Kawai, K. et al., Li, Y. et al., Nazar, M. et al.

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Disease relevance of CCRIS 6491

Toxicity of flavoglaucin from Aspergillus chevalieri in rabbits [1].

High impact information on CCRIS 6491

A new anthracene glycoside, asperflavin ribofuranoside (1), and the previously described polyketides, flavoglaucin (2), isodihydroauroglaucin (3), and citrinin (4) have been isolated from the marine-derived fungus Microsporum sp. The structure and absolute stereochemistry of a new compound (1) was assigned on the basis of physicochemical data [2].
Flavoglaucin was toxic to isolated rat hepatocytes causing a karyoklasis, but did not show genotoxicity in hepatocyte primary culture (HPC)/DNA repair test [3].
It was found that flavoglaucin exhibited a strong uncoupling effect on oxidative phosphorylation, enhanced the latent ATPase activity, and elicited a drastic swelling of mitochondria [3].
The effects of flavoglaucin from Aspergillus chevalieri (Mangin) Thom et Church on mitochondrial reactions have been investigated to obtain insight into the mode of actions on biomembranes by means of isolated rat liver mitochondria [3].

References

Toxicity of flavoglaucin from Aspergillus chevalieri in rabbits. Nazar, M., Ali, M., Fatima, T., Gubler, C.J. Toxicol. Lett. (1984) [Pubmed]
A new radical scavenging anthracene glycoside, asperflavin ribofuranoside, and polyketides from a marine isolate of the fungus microsporum. Li, Y., Li, X., Lee, U., Kang, J.S., Choi, H.D., Sona, B.W. Chem. Pharm. Bull. (2006) [Pubmed]
The uncoupling effect of flavoglaucin, a quinol pigment from Aspergillus chevalieri (Mangin), on mitochondrial respiration. Kawai, K., Mori, H., Kitamura, J. Toxicol. Lett. (1983) [Pubmed]

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