Protection against the bacterial mutagenicity of heterocyclic amines by purpurin, a natural anthraquinone pigment

Timothy H. Marczylo, Toshiko Hayatsu, Sakae Arimoto, Mikio Tada, Ken Ichi Fujita, Tetsuya Kamataki, Kazuo Nakayama, Hikoya Hayatsu

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Purpurin (1,2,4-trihydroxy-9,10-anthraquinone) is a naturally occurring anthraquinone pigment found in species of madder root. We have found that the presence of purpurin in bacterial mutagenicity assays is responsible for a marked inhibition of mutagenicity induced by food-derived heterocyclic amines. Purpurin was found to be a better inhibitor of Trp-P-2-dependent mutagenicity than either epigallocatechin gallate or chlorophyllin both of which are well-established anti-mutagenic components of diet. Inhibition of Trp-P-2(NHOH) mutagenicity by purpurin was dependent upon pH. It was a better inhibitor in neutral than acidic conditions. Purpurin was protective against the direct mutagen Trp-P-2(NHOH) in both the presence and the absence of hepatic S9 but required pre-incubation. Finally, purpurin was responsible for the inhibition of human CYP1A2 and human NADPH-cytochrome P450 reductase and a decrease in the bioactivation of Trp-P-2 by these enzymes when they were expressed in Salmonella typhimurium TA1538ARO. However, inhibition of Trp-P-2(NHOH)-dependent mutations suggests purpurin also has a direct effect on this mutagen in addition to inhibiting its formation by CYP1A2. Copyright (C) 1999 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)451-461
Number of pages11
JournalMutation Research - Genetic Toxicology and Environmental Mutagenesis
Volume444
Issue number2
DOIs
Publication statusPublished - Aug 18 1999

Fingerprint

Anthraquinones
Amines
Cytochrome P-450 CYP1A2
Mutagens
Cytochromes a
NADPH-Ferrihemoprotein Reductase
Salmonella typhimurium
purpurin
3-amino-1-methyl-5H-pyrido(4,3-b)indole
Diet
Food
Mutation
Liver
Enzymes

Keywords

  • Anti-mutagenesis
  • CYP
  • Heterocyclic amine
  • Purpurin
  • Trp-P-2

ASJC Scopus subject areas

  • Health, Toxicology and Mutagenesis
  • Genetics

Cite this

Protection against the bacterial mutagenicity of heterocyclic amines by purpurin, a natural anthraquinone pigment. / Marczylo, Timothy H.; Hayatsu, Toshiko; Arimoto, Sakae; Tada, Mikio; Fujita, Ken Ichi; Kamataki, Tetsuya; Nakayama, Kazuo; Hayatsu, Hikoya.

In: Mutation Research - Genetic Toxicology and Environmental Mutagenesis, Vol. 444, No. 2, 18.08.1999, p. 451-461.

Research output: Contribution to journalArticle

Marczylo, Timothy H. ; Hayatsu, Toshiko ; Arimoto, Sakae ; Tada, Mikio ; Fujita, Ken Ichi ; Kamataki, Tetsuya ; Nakayama, Kazuo ; Hayatsu, Hikoya. / Protection against the bacterial mutagenicity of heterocyclic amines by purpurin, a natural anthraquinone pigment. In: Mutation Research - Genetic Toxicology and Environmental Mutagenesis. 1999 ; Vol. 444, No. 2. pp. 451-461.
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