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Chemical Compound Review:

AC1NUNZZ 5-hydroxy-6-oxo-1,2- dihydroindole-2...

Synonyms: ACMC-20mxcg, 138230-21-4, Quinone methide

Miller, J.R. et al., Niampoka, C. et al., Douglas, I.S. et al., Ngassapa, O. et al.

Douglas, Diaz del Valle, Winn, Voelkel,

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Disease relevance of Quinone methide

The quinone-methide triterpenes 1-3 exhibited strong but non-specific in vitro cytotoxicity against P-388 murine lymphocytic leukemia cells and a panel of human cancer cell lines [1].

High impact information on Quinone methide

MAO A partially purified from yeast grown on 8-nor-8-chlororiboflavin exhibited an absorption spectrum indicating the covalent flavin is an 8-nor-8-S-thioflavin, suggesting a nucleophilic displacement mechanism that supports the quinone-methide mechanism previously suggested as a general mechanism for covalent flavin attachment [2].
Proliferation of murine lung epithelial-12 cells in vitro after 8 h of treatment with BHT quinone-methide and hyperoxia and 48 h of normoxic recovery was enhanced 2.7-fold compared with vehicle-treated control mice at the same time point [3].
A new oleanane-triterpene, 3beta-acetoxy-11alpha-benzoyloxy-13beta-hydroxyolean-12-one (1), was isolated along with a known quinone-methide triterpene, pristimerin (2), from the root bark of Siphonodon celastrineus Griff., a Thai medicinal plant of the family Celastraceae [4].

References

Quinone-methide triterpenes and salaspermic acid from Kokoona ochracea. Ngassapa, O., Soejarto, D.D., Pezzuto, J.M., Farnsworth, N.R. J. Nat. Prod. (1994) [Pubmed]
Influence of flavin analogue structure on the catalytic activities and flavinylation reactions of recombinant human liver monoamine oxidases A and B. Miller, J.R., Edmondson, D.E. J. Biol. Chem. (1999) [Pubmed]
Beta-catenin in the fibroproliferative response to acute lung injury. Douglas, I.S., Diaz del Valle, F., Winn, R.A., Voelkel, N.F. Am. J. Respir. Cell Mol. Biol. (2006) [Pubmed]
Potentially cytotoxic triterpenoids from the root bark of Siphonodon celastrineus Griff. Niampoka, C., Suttisri, R., Bavovada, R., Takayama, H., Aimi, N. Arch. Pharm. Res. (2005) [Pubmed]

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