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Several synthetic 7-hydroxyflavylium salts related to apigeninidin, a natural 3-deoxyanthocyanidin, have been studied in the Ames mutagenicity test using strain TA1537 of Salmonella typhimurium. Under the neutral pH conditions of the test, these flavylium salts are deprotonated through ionization of the C7-OH (pK'a = 4.2-4.4) to form quinone methides. Only the quinone methides of 4-methyl-7-hydroxyflavylium chloride and 4'-methoxy-4-methyl-7-hydroxy-flavylium chloride showed mutagenicity. Responses of 4-8 times the background were observed at the higher doses (1000 micrograms/plate), both with and without metabolic activation. It was concluded that the induction of frameshift mutagenicity by this group of compounds is caused by those quinone methides that have non-ionic, stable polycyclic structures at neutral pH.
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
February 1984,
Mutation research,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
January 2001,
Advances in experimental medicine and biology,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
March 1989,
Mutagenesis,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
January 1985,
Chemico-biological interactions,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
January 1982,
Environmental mutagenesis,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
August 1985,
Mutation research,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
February 1982,
International journal of cosmetic science,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
April 1993,
Mutation research,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
July 1990,
Mutation research,
J G Sweeny, and
G A Iacobucci, and
D Brusick, and
D R Jagannath
July 1987,
Research communications in chemical pathology and pharmacology,
