Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay

Kamal A. Rashid, Christopher A. Mullin, Ralph O. Mumma

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4′) substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch π parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.

Original languageEnglish (US)
Pages (from-to)71-79
Number of pages9
JournalMutation Research/Genetic Toxicology
Volume169
Issue number3
DOIs
StatePublished - Mar 1986

All Science Journal Classification (ASJC) codes

  • Toxicology
  • Genetics

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