Naturally occurring diallyl disulfide inhibits the formation of carcinogenic heterocyclic aromatic amines in boiled pork juice

Shun Jen Tsai, Shinn Nen Jenq, Huei Lee

研究成果: 雜誌貢獻文章

50 引文 (Scopus)

摘要

Three heterocyclic aromatic amines, 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), 2-amino-3,4- dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,4-dimethylimidazo[4-5-f]quinoline, have been found in boiled pork juice. We have investigated the effect of naturally occurring organosulfur compounds, which are present in garlic and onion, on mutagen formation in boiled pork juice. Six organosulfur compounds - diallyl disulfide (DAD), dipropyl disulfide (DPD), diallyl sulfide (DAS), allyl methyl sulfide (AMS), allyl mercaptan (AM) and cysteine - were added separately to the pork juice before reflux boiling and then the mutagenicity of each sample was examined with the Salmonella typhimurium strain TA98 in the presence of S9 mix. All six compounds were found to inhibit the mutagenicity of boiled pork juice. The greatest inhibitory effect was observed with DAD and DPD, and this was 111-fold higher than that of the lowest, cysteine. To elucidate the inhibitory effect of DAD on mutagen formation in boiled pork juice, the major mutagenic fractions were monitored after HPLC separation by their mutagenicity with S.typhimurium TA98. By comparing the retention times of authentic IQ compounds from boiled pork juice with those following the addition of DAD, we showed that the mutagenicity of three major fractions was significantly inhibited compared with those same fractions in boiled pork juice alone. In addition, the Maillard reaction products (MRPs) in the boiled pork juice with and without the addition of DAD were quantified and identified by capillary gas chromatography and gas chromatography-mass spectrometry. The results show that the reduction in the total amount of MRPs (pyridines, pyrazines, thiophenes and thiazoles) in boiled pork juice after boiling for 12 h is correlated with their mutagenicity. Among the MRPs, tetrahydrothiophene-3-one exhibited the strongest correlation. These data suggest that the inhibition of IQ mutagen formation by DAD is mediated through the reduction of MRPs production.
原文英語
頁(從 - 到)235-240
頁數6
期刊Mutagenesis
11
發行號3
DOIs
出版狀態已發佈 - 五月 1996
對外發佈Yes

指紋

Amines
Reaction products
Maillard Reaction
Mutagens
2-amino-3-methylimidazo(4,5-f)quinoline
Gas chromatography
Boiling liquids
Cysteine
Pyridines
Pyrazines
Thiazoles
Thiophenes
Quinoxalines
Salmonella
Sulfhydryl Compounds
Mass spectrometry
diallyl disulfide
Red Meat
Garlic
Onions

ASJC Scopus subject areas

  • Genetics
  • Genetics(clinical)
  • Toxicology
  • Health, Toxicology and Mutagenesis

引用此文

Naturally occurring diallyl disulfide inhibits the formation of carcinogenic heterocyclic aromatic amines in boiled pork juice. / Tsai, Shun Jen; Jenq, Shinn Nen; Lee, Huei.

於: Mutagenesis, 卷 11, 編號 3, 05.1996, p. 235-240.

研究成果: 雜誌貢獻文章

Tsai, Shun Jen ; Jenq, Shinn Nen ; Lee, Huei. / Naturally occurring diallyl disulfide inhibits the formation of carcinogenic heterocyclic aromatic amines in boiled pork juice. 於: Mutagenesis. 1996 ; 卷 11, 編號 3. 頁 235-240.
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N2 - Three heterocyclic aromatic amines, 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), 2-amino-3,4- dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,4-dimethylimidazo[4-5-f]quinoline, have been found in boiled pork juice. We have investigated the effect of naturally occurring organosulfur compounds, which are present in garlic and onion, on mutagen formation in boiled pork juice. Six organosulfur compounds - diallyl disulfide (DAD), dipropyl disulfide (DPD), diallyl sulfide (DAS), allyl methyl sulfide (AMS), allyl mercaptan (AM) and cysteine - were added separately to the pork juice before reflux boiling and then the mutagenicity of each sample was examined with the Salmonella typhimurium strain TA98 in the presence of S9 mix. All six compounds were found to inhibit the mutagenicity of boiled pork juice. The greatest inhibitory effect was observed with DAD and DPD, and this was 111-fold higher than that of the lowest, cysteine. To elucidate the inhibitory effect of DAD on mutagen formation in boiled pork juice, the major mutagenic fractions were monitored after HPLC separation by their mutagenicity with S.typhimurium TA98. By comparing the retention times of authentic IQ compounds from boiled pork juice with those following the addition of DAD, we showed that the mutagenicity of three major fractions was significantly inhibited compared with those same fractions in boiled pork juice alone. In addition, the Maillard reaction products (MRPs) in the boiled pork juice with and without the addition of DAD were quantified and identified by capillary gas chromatography and gas chromatography-mass spectrometry. The results show that the reduction in the total amount of MRPs (pyridines, pyrazines, thiophenes and thiazoles) in boiled pork juice after boiling for 12 h is correlated with their mutagenicity. Among the MRPs, tetrahydrothiophene-3-one exhibited the strongest correlation. These data suggest that the inhibition of IQ mutagen formation by DAD is mediated through the reduction of MRPs production.

AB - Three heterocyclic aromatic amines, 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), 2-amino-3,4- dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,4-dimethylimidazo[4-5-f]quinoline, have been found in boiled pork juice. We have investigated the effect of naturally occurring organosulfur compounds, which are present in garlic and onion, on mutagen formation in boiled pork juice. Six organosulfur compounds - diallyl disulfide (DAD), dipropyl disulfide (DPD), diallyl sulfide (DAS), allyl methyl sulfide (AMS), allyl mercaptan (AM) and cysteine - were added separately to the pork juice before reflux boiling and then the mutagenicity of each sample was examined with the Salmonella typhimurium strain TA98 in the presence of S9 mix. All six compounds were found to inhibit the mutagenicity of boiled pork juice. The greatest inhibitory effect was observed with DAD and DPD, and this was 111-fold higher than that of the lowest, cysteine. To elucidate the inhibitory effect of DAD on mutagen formation in boiled pork juice, the major mutagenic fractions were monitored after HPLC separation by their mutagenicity with S.typhimurium TA98. By comparing the retention times of authentic IQ compounds from boiled pork juice with those following the addition of DAD, we showed that the mutagenicity of three major fractions was significantly inhibited compared with those same fractions in boiled pork juice alone. In addition, the Maillard reaction products (MRPs) in the boiled pork juice with and without the addition of DAD were quantified and identified by capillary gas chromatography and gas chromatography-mass spectrometry. The results show that the reduction in the total amount of MRPs (pyridines, pyrazines, thiophenes and thiazoles) in boiled pork juice after boiling for 12 h is correlated with their mutagenicity. Among the MRPs, tetrahydrothiophene-3-one exhibited the strongest correlation. These data suggest that the inhibition of IQ mutagen formation by DAD is mediated through the reduction of MRPs production.

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