• YAKHAK HOEJI
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• v.45 no.4
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• pp.321-327
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• 2001

The synthesis of novel taxol analogues with an amine moiety at the 7- and 10-positions to examine the BBB penetration was described. The analogues were synthesized from 2'-O-(tert-butyldim-ethylsilyl)taxol and 2'-0-(tert-butyldimethylsilyl) -7-O-(triethylsilyl)-10-deacetyltaxol, the key intermediates, in 2 steps via the esterification with heterocyclic amino acids and the subsequent desilylation reaction.

• Journal of the Korean Chemical Society
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• v.57 no.3
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• pp.361-364
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• 2013

A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.

• Food Science and Biotechnology
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• v.14 no.5
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• pp.572-575
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• 2005

The effects of cooking method, cooking time and various food ingredients on the formation/ inhibition of heterocyclic aromatic amines (HAAs) in pork products were investigated. Three HAAs, 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline ($MeIQ_x$), 2-amino-3,4,8-trimethylimidazo [4,5-f] quinoxaline ($DiMeIQ_x$) and 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) were measured in pork products using solid-phase extraction and HPLC. Pork patties were boiled, oven-broiled and pan-fried to internal temperatures of 71, 77 and $88^{\circ}C$. Generally, HAA concentrations increased with increasing internal temperature, and HAA formation was greatest with pan-fried. Selected food ingredients (vitamin E, sodium nitrite, sodium tripolyphosphate, sodium ascorbate, Nanking cherry tissue and cherry tissue extract) inhibited HAA formation in pork patties fried at $225^{\circ}C$ for 10 min/side, with the greater inhibition provided by cherry tissue and its methanolic extract.

• Food Science of Animal Resources
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• v.31 no.4
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• pp.563-569
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• 2011

Heterocyclic amines (HCAs) are food mutagens and carcinogens that are found in cooked fish, meat, and protein-rich foods. This study examined the inhibitory effect of marinades containing a Nelumbo nucifera leaf fraction on HCA formation in cooked beef steak. As a result of the Ames assay, cooked beef marinated with the N. nucifera leaf butanol fraction (2.0 g) cooked at $190^{\circ}C$ showed a 61.5% reduction in overall mutagenicity. However, these data revealed no significant difference in mutagenicity in the ethanol, ethyl acetate, or water fractions. Formation of MeIQx (2-amino-3,8 dimethylimidazo[4,5-f]-quinoxalin) and PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine) was inhibited 60.7-63.5%. Cooked beef marinated with the water fraction of the N. nucifera leaf significantly (p<0.05) reduced the formation of MeIQx, PhIP, and DiMeIQx (2-amino-3,4,8 trimethylimidazo[4,5-f]-quinoxaline) by 65.3, 67.6, and 73.9%, respectively. These results show that marinades containing the N. nucifera leaf fraction could be an alternative method for reducing HCA formation in cooked beef steak.

• Proceedings of the Korean Society of Toxicology Conference
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• 2002.05a
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• pp.100-100
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• 2002

2-amino-3-methylimidazo[4,5-f]quinoline (IQ), a heterocyclic amine, significantly inhibits nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophages. The decrease in NO production was found to correlate well with a decrease in iNOS mRNA expression as demonstrated by Northern blot analysis.(omitted)

• Food Science of Animal Resources
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• v.29 no.6
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• pp.719-725
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• 2009

Heterocyclic aromatic amines (HCAs) are potent mutagens and possible human carcinogens that are formed during the heating of protein-rich foods. The effects of preheating treatment of beef patties using a microwave prior to frying at $220^{\circ}C$ for 10 min on each side on the reduction of HCAs (amino-carbolines and amino-imidazo-azaarenes) were evaluated. The amount of HCAs was then evaluated by solid-phase extraction and high pressure liquid chromatography (HPLC) analysis. The beef patties were treated by microwaving for various times (0, 1, 1.5, 2, or 3 min) before pan-frying. The results revealed the presence of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2), 3-amino-1,4-dimethyl-5H-pyrido-[4,3-b] indole (Trp-P-1), 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1), 2-aminodipyrido[1,2-a:3',2'-d]imidazole (Glu-P-2), 9H-pyrido[3,4-b]indole (Norharman), 1-methyl-9H-pyrido[3,4-b]indole (Harman), 2-amino-9H-pyrido[2,3-b] indole ($A{\alpha}C$), 2-amino-3,8 dimethylimidazo[4,5-f]-quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine (PhIP) in all samples. However, microwave pretreatment for 1 min inhibited the formation of these HCAs by up to 90% when compared to the control.

• Proceedings of the Korea Environmental Mutagen Society Conference
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• 2002.05a
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• pp.100-100
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• 2002

• Korean Journal of Microbiology
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• v.50 no.1
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• pp.73-83
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• 2014

The objective of the this study was to investigate the binding capacity and removal ability of lactic acid bacterial strains obtained from Korean soybean paste for mutagenic heterocyclic amines (HCAs) formed during cooking of protein-rich food at high temperature. Among 19 strains identified by carbohydrate fermentation and 16S rRNA sequencing, the live cell or cell-free culture supernatant of Lactobacillus acidophilus D11, Enterococcus faecium D12, Pediococcus acidilactici D19, L. acidophilus D38, Lactobacillus sakei D44, Enterococcus faecalis D66, and Lactobacillus plantarum D70 inhibited the mutagenesis caused by either 3-amino-1,4-dimethyl-5H-pyrido[4,3-b] indole (Trp-P-1) or 3-amino-1-methyl-5H-pyrido[4,3-b] indole (Trp-P-2) in Salmonella typhimurium TA98 and TA100. The bacterial cells of the isolated strains showed greater binding activity than the pure cell wall, exopolysaccharide, and pepetidoglycan. The carbohydrate moieties of the cell wall or protein molecules on the cell surface have a significant role in binding Trp-P-1 and Trp-P-2, since protease, heating, sodium metaperiodate, or acidic pH treatments significantly (P<0.05) reduced the binding efficacy of the tested bacteria. Addition of metal ions or sodium dodecyl sulfate decreased the binding ability of E. faecium D12, L. acidophilus D38, and E. faecalis D66. Therefore, the binding mechanisms of these strains may consist of ion-exchange and hydrophobic bonds. Especially, the high mutagen binding by L. acidophilus D38 and L. plantarum D70 may reduce the accumulation or absorption of Trp-P-1 and Trp-P-2 in the small intestine via increased excretion of a mutagen-bacteria complex.

• Bulletin of the Korean Chemical Society
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• v.13 no.3
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• pp.343-344
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• 1992

• Food Science and Biotechnology
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• v.16 no.4
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• pp.576-579
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• 2007

The effects of temperature and Korean bramble (Rubus coreanum Miquel) tissue concentrate on heterocyclic aromatic amine (HAA) formation in fried ground beef patties were investigated. Various amounts of Korean bramble tissue (4.0, 7.0, and 11.0%, w/w) were added to ground beef patties were fried at 2 different temperatures (190 and $225^{\circ}C$) for 10 min/side. It was observed in the fried ground beef patties fried at $190^{\circ}C$ with the addition of 11.0%(w/w) Korean bramble that the mutagenicity decreased by 64%, and formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-I-methyl-6-phenylimidazo[4,5-b]-pyridine(PhIP) reduced by 55 and 86%, respectively. Although no difference in total mutagenicity was shown in patties fried at $225^{\circ}C$ with the addition of 4.0, 7.0, and 11.0%(w/w), different levels of reduction of PhIP formation in patties fried at $225^{\circ}C$ with the addition of 4.0, 7.0, and 11.0%(w/w) were shown 49, 63, and 75%, respectively.