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PubMed1956

Will Cook Spain.

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Cooking↗
PubMed1993

Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food.

Sixty-four flavonoids were tested for their antimutagenic potencies with respect to IQ in Salmonella typhimurium TA98 and in part also towards MeIQ, MeIQx, Trp-P-2, and Glu-P-1 and in S. typhimurium TA100. Antimutagenic potencies were quantified by the inhibitory dose for 50% reduction of mutagenic activity (ID50). A carbonyl function at C-4 of the flavane nucleus seems to be essential for antimutagenicity: two flavanols and four anthocyanidines were inactive. Again, five isoflavons, except biochanin A, were inactive. Within the other groups of 21 flavones, 16 flavonols and 16 flavanones the parent compounds flavone, flavonol, and flavanone possessed the highest antimutagenic potencies (ID50: 4.1, 2.5, 5.5 nmoles). Increasing polarity by introduction of hydroxyl functions reduced antimutagenic potency. Reducing polarity of hydroxy flavonoids by methyl etherification, however, increased antimutagenic potency again. 6-Hydroxy- and 2'-hydroxy substituted flavonoids were considerably less potent antimutagens. Of 11 flavonoid glycosides tested all compounds except apigenin- and luteolin-7-glucoside (ID50:74, 115 nmoles) were inactive or only weakly antimutagenic. Rings C and A of the nucleus were not essential for antimutagenicity: chalcone and three derivatives were nearly as active as comparable flavones while antimutagenicity of benzylidenacetone was considerably reduced (ID50: 95 nmoles). Cinnamylaldehyde and cinnamoates, however, were inactive. A planar structure in the vicinity of the carbonyl group may also be important for antimutagenicity. Flavanones were less potent antimutagens than the corresponding flavones, but dihydrochalcones and 14 structurally related saturated aromatic carbonyl compounds were inactive. Fisetin and 6-hydroxyflavone were competitive inhibitors, but luteolin was a mixed type inhibitor. The inhibition mechanisms of flavone, kaempferol, morin, flavanone, and 2'-hydroxyflavanone were concentration dependent, being competitive at low concentrations and mixed or non-competitive (2'-hydroxyflavanone) at concentrations about the ID50 value. No fundamental differences between the two tester strains and no clear influence of mutagen structure on antimutagenic potency could be detected.

Animals↗
PubMed1991

Effect of emodin on cooked-food mutagen activation.

The herbs Rheum palmatum B and Polygonum cuspidatum S are frequently used as laxatives and anticancer drugs in Chinese medicine. The antimutagenic activity of these herbs as well as their active component emodin was examined in Salmonella typhimurium TA98. The crude extracts and emodin induced a dose-dependent decrease in the mutagenicity of benzo[a]pyrene (B[a]P), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2). Furthermore, emodin reduced the mutagenicity of IQ by direct inhibition of the hepatic microsomal activation and not by interaction with proximate metabolites of IQ and/or by modification of DNA repair processes in the bacterial cell.

Animals↗
PubMed1987

Identification of the cooked food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and its N-acetylated and 3-N-demethylated metabolites in rat urine.

The extractable unconjugated metabolites of 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ) were identified in the urine of rats which had received a single dose of [3H]IQ by gavage. The dichloromethane and ethylacetate extracts prepared from the alkalinized 0-24 h urines were analyzed by radio-TLC and radio-HPLC. The 3 major HPLC fractions were submitted to DCI-MS analysis. Unchanged IQ, N-acetylIQ and 3-N-demethylIQ have been identified. Extractable unconjugated metabolites represent only about 0.85% of the total radioactivity excreted in the urine.

Animals↗
PubMed1980

Formation of mutagens in cooked foods. III. Isolation of a potent mutagen from beef.

The major mutagenic component of fried beef has been isolated using a series of chromatographic steps. The pure compound has been analyzed by low and high resolution mass spectroscopy and nuclear magnetic resonance spectroscopy. The results indicate that the molecular weight of this extremely mutagenic compound is 198, with an elemental composition of C11H10N4. The compound is different from the known mutagenic pyrolysis products of amino acids or proteins.

Animals↗