Isolation of 2-Amino-3-methyl-imidazo- [4,5-<i>f</i>]quinoline as Mutagen from the Heated Product of a Mixture of Creatine and Proline

Yoshida, Daisuke; Saito, Yutaka; Mizusaki, Shigenobu

doi:10.1080/00021369.1984.10866128

Cited by 5 publications

(5 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additionally, it is known that amino acids also play an important role in the formation of IQ‐type HCAs . The studies performed in the model system show that alanine amino acid is a precursor of MeIQ and proline amino acid is a precursor of IQ . In the present study, while MeIQ was detected in the control group meatballs, but its quantity could not be determined, MeIQ was detected in all the meatballs containing onion‐water extract.…”

Section: Resultscontrasting

confidence: 63%

The effect of using different types and rates of onion‐water extract in meatball production on the formation of heterocyclic aromatic amines

Nuray

Öz

2019

J Sci Food Agric

View full text Add to dashboard Cite

BACKGROUND The effect of using different types (yellow, white and purple) and rates (0.25%, 0.50% and 0.75%) of onion‐water extract in meatball production on the various quality criteria of meatballs and the formation of heterocyclic aromatic amines (HCAs) was investigated. RESULTS It was determined that cooking process caused a reduction in the water content of meatballs as well as an increase in pH values. MeIQx, 7,8‐DiMeIQx, 4,8‐DiMeIQx, PhIP, AαC and MeAαC could not be detected in any of the analyzed meatballs, while IQx, IQ and MeIQ were determined in some of the samples. CONCLUSION The use of 0.25% and 0.50% white onion‐water extract in meatball preparation inhibited the formation of IQx and IQ that were identified in the control group, but their quantities could not be determined. However, the use of water extract of varying types of onions in meatball preparation increased the total HCA content due to the increase of the MeIQ formation. In addition, it was determined that as the rate of onion‐water extract for varying types of onions increased, the total HCA amount also increased. The total HCA amount of the meatballs varied between 0.05 and 0.1 ng g−1. © 2019 Society of Chemical Industry

show abstract

Section: Resultscontrasting

confidence: 63%

The effect of using different types and rates of onion‐water extract in meatball production on the formation of heterocyclic aromatic amines

Nuray

Öz

2019

J Sci Food Agric

View full text Add to dashboard Cite

show abstract

“…In addition, it is also known that amino acids play an important role in the formation of IQ-type HAAs (J€ agerstad et al, 1983). Studies performed in model system shows that alanine is a precursor of MeIQ, and proline is a precursor of IQ (J€ agerstad et al, 1983;Yoshida et al, 1984;Skog et al, 1998). In the present study, it is thought that while IQ was not detected in any of the cooked control group meatballs for all the cooking temperatures, it was detected in all the meatballs containing dry breadcrumb.…”

Section: Dry Breadcrumbmentioning

confidence: 41%

Effect of the use of dry breadcrumb in meatball production on the formation of heterocyclic aromatic amines

Korkmaz

Öz

2020

BFJ

View full text Add to dashboard Cite

PurposeHeterocyclic aromatic amines are mutagenic and/or carcinogenic compounds formed during cooking of meat. Therefore, the formation levels of them should be reduced. For this aim, the purpose of the present study was to determine the effect of dry breadcrumb in meatball production on the formation of heterocyclic aromatic amines. In addition, the effect of dry breadcrumb on some quality parameters of the meatballs was also investigated.Design/methodology/approachMeatball dough with 15 percent fat was divided into four parts, where one group was selected as the control group (without dry breadcrumb). In the other three groups, dry breadcrumb was added in various ratios of 5 percent, 10 percent and 15 percent (w/w). Then, meatball dough was stored at 4 °C for 3 h and shaped into meatballs with a metal shaping device (7 × 1 cm). For some of the quality parameters, water, pH, cooking loss and TBARS analyses were done in the samples. Heterocyclic aromatic amine analysis was done in only cooked samples according to solid phase extraction.FindingsThe use of dry breadcrumb in meatball production decreased water content and cooking loss. As cooking temperature increased, water contents and cooking loss of meatball decreased. PhIP, AαC and MeAαC were not detected in any of the samples analyzed. As cooking temperature increased, total amount of HCAs increased and ranged between 0.05 and 0.51 ng/g. While the use of dry breadcrumb in the meatball production increased IQ content of the meatballs, the use of 5 percent dry breadcrumb caused a decrease in the total HAA content (28.57–66.67 percent) for all cooking temperatures.Originality/valueMany research studies including our study in the literature were conducted on formation and reduction of HAAs in meat and meat products. However, although dry breadcrumb is frequently used both in domestic and commercial meatball formulations; to the best of our knowledge, effect of using dry breadcrumb in meatball production on HAAs formation has not been investigated in the literature. Therefore, in the present study, the effects of the use of dry breadcrumb in meatball production on some quality parameters and formation of HAAs in meatballs cooked at 150 °C, 200 °C and 250 °C were determined.

show abstract

“…Interestingly, these values bracket the IQ contents that were estimated for Difco beef extract, 20 to 40 ng/g (26) and 41 to 142 ng/g (25). Yoshida et al recently isolated several micrograms of IQ after dryheating 14 g of creatine and 11.5 g of Pro for 1 hr at 180°C (42). Finding that CP doubles the formation of IQ from boiled S2 ( Table 5, Fig.…”

Section: Discussionmentioning

confidence: 99%

“…However, both boiled ( Table 5) and dry-heated S2 (discussed above) and boiled-dehydrated beef extracts (24-26) contain many parts per million of IQ. And some IQ can be formed without a reducing sugar, from dry-heated Cre + Pro (42). Moreover, it is not obvious how Maillard amino acid-sugar products might be involved in the formation of the Trp-P mutagens from boiled S2 mixtures (Table 5).…”

Section: Discussionmentioning

confidence: 99%

Mutagen formation in a model beef supernatant fraction. IV. Properties of the system.

Taylor¹,

Fultz²,

Knize³

1986

Environ Health Perspect

View full text Add to dashboard Cite

To identify the precursors and elucidate the reaction conditions that yield heterocyclic amine mutagens in cooked meat products and fish, we have used a supernatant 2 (S2) fraction prepared from H2O-homogenized lean round steak. Compounds (MW less than 500) in S2 are the sources of the microsomal-dependent, Salmonella TA 1538 mutagenic activity in open boiled (aqueous), 200 degrees C pressure-heated (aqueous), or 200 to 300 degrees C oven-baked (freeze-dried) homogenates. Combined incorporation-HPLC experiments show that they are also the precursors for frameshift mutagen formation in the outer surfaces of 200 degrees C griddle-fried ground beef. Maximal stimulations of boiled S2 mutagenic activity are given by 10 mM Trp, 2.5 mM creatine phosphate (CP), and synergistically by 10 mM Trp + 2.5 mM CP + 1.0 mM FeSO4 (a mixture abbreviated as S2*). Boiling S2 for 30 hr at the acidic optimum pH of 4.0----600 TA 1538 revertants (no additions) and 1,400 revertants (+CP), while S2*----24,000 revertants/10(8) bacteria/g of dry beef. By the criteria of HPLC, paper electrophoresis, and resistance of the active HPLC fractions to acid-nitrite inactivation, boiled S2 contains 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) and a minor amount of 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ). Boiling S2 with CP doubles the IQ, halves the Trp-P-2, produced traces of MeIQ, and generates an unknown nitrite-resistant mutagen. Boiled S2* contains these same four mutagens, but both the IQ and Trp-P-2 are increased and large amounts of Trp-P-1 also are generated. The identities of IQ, Trp-P-2, and Trp-P-1 were verified by purification and by light-absorption and mass spectra. Their increments in stimulated S2 indicate that Trp (or its degradation products) and CP (or its degradation products) are the beef juice precursors for the indole ring in Trp-P type mutagens and the NH2-imidazole ring in IQ-type mutagens, respectively. Aqueous (pressure) heating or oven-baking S2 for 2 hr at 200 degrees C greatly elevates its TA 1538 activity----45,000 revertants/10(8) bacteria/g of dry beef; dry heating at 300 degrees C----approximately 180,000 revertants/g of dry beef. Along with the increases in total TA 1538 activity at 200 to 300 degrees C, the number of mutagens formed from the less than 500 MW S2 precursors also multiplies.(ABSTRACT TRUNCATED AT 400 WORDS)

show abstract

Isolation of 2-Amino-3-methyl-imidazo- [4,5-f]quinoline as Mutagen from the Heated Product of a Mixture of Creatine and Proline

Cited by 5 publications

References 1 publication

The effect of using different types and rates of onion‐water extract in meatball production on the formation of heterocyclic aromatic amines

The effect of using different types and rates of onion‐water extract in meatball production on the formation of heterocyclic aromatic amines

Effect of the use of dry breadcrumb in meatball production on the formation of heterocyclic aromatic amines

Mutagen formation in a model beef supernatant fraction. IV. Properties of the system.

Contact Info

Product

Resources

About