Action of Amino Reductones on Nucleic Acids

Shinohara, Kazuki; Fukumoto, Yuji; Tseng, Yaw-Kun; Inoue, Yuzuru; Ômura, Hirohisa

doi:10.1271/nogeikagaku1924.48.499

Cited by 7 publications

(11 citation statements)

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“…To achieve the practical application of the XTT assay in food industries including dairy products, it was essential to demonstrate the presence of aminoreductone in milk. Because of this background, we attempted to isolate aminoreductone from milk proteins using 2,4-dinitrophenylhydrazine (DNP), a common labeling reagent for the carbonyl group, and Cu 2+ [16]. A mechanism of derivatization of aminoreductone in milk is shown in Figure 10.…”

Section: In Milk [15]mentioning

confidence: 99%

Maillard Reaction in Milk - Effect of Heat Treatment

Shimamura¹,

Ukeda²

2012

Milk Protein

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Section: In Milk [15]mentioning

confidence: 99%

Maillard Reaction in Milk - Effect of Heat Treatment

Shimamura¹,

Ukeda²

2012

Milk Protein

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Section: Discussionmentioning

confidence: 99%

“…Previous papers by our group reported that antitumoric reductones (AsA , DAsA, MDT, EA and TR) depolymerized nucleic acids (1)(2)(3)(4)(5)(6), and AsA altered the priming activity of DNA for DNA polymerase (7). Furthermore, it has been deduced that the enediol group of them is the functional group responsible for de polymerization.…”

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confidence: 94%

“…These reductones are concerned with the change of color , flavor, and taste during processing, storage and cooking. In spite of their importance in food science and biochemistry, very little has been known about the physiological action of amino and thiol reductones (6,8).In this paper, we examined the action of amino and thiol reductones on nucleic acids from the points of intensity and base specificity, and their action is discussed in comparison with that of AsA, a typical enediol reductone.Abbreviations: AsA, ascorbic acid; ScA, scorbamic acid; MHC , 3-mercapto-4-hydroxycoumarin monohydrate;MDT, 5-methyl-3,4-dihydroxytetrone; EA, erythorbic acid; TR , triose reductone; Apu, apurinic acid; Apy, apyrimidinic acid; SSC , standard saline citrate (0.15M sodium chloride +0.015M sodium citrate). …”

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confidence: 99%

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Breaking action of reductones related to ascorbic acid on nucleic acids.

Ômura

Tomita

Fujiki

et al. 1978

Journal of Nutritional Science and Vitaminology, J Nutr Sci Vit

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SummaryThe action of two types of ascorbate-related reductones on nucleic acids was investigated by comparison with that of ascorbic acid (AsA). Amino reductone (ScA) and thiol reductone (MHC) caused strand scissions in nucleic acids. This was confirmed by the fact that reductones lowered the viscosity of DNA solution and shifted the peaks of DNA and RNA to the low molecular side in centrifugal profile . Cue2+ strengthened their action as in the case of enediol reductones . The breaking activity of thiol reductone is relatively weak compared with those of amino and enediol reductones, The preferential degradation of apurinic acid was caused with amino and thiol reductones, suggesting that pyrimidine clusters in nucleic acids were susceptible to breakage .Previous papers by our group reported that antitumoric reductones (AsA , DAsA, MDT, EA and TR) depolymerized nucleic acids (1-6), and AsA altered the priming activity of DNA for DNA polymerase (7). Furthermore, it has been deduced that the enediol group of them is the functional group responsible for de polymerization. These substances are classified into the group enediol reductone. Besides enediol reductones, structually related amino and thiol reductones are contained in foods. These reductones are concerned with the change of color , flavor, and taste during processing, storage and cooking. In spite of their importance in food science and biochemistry, very little has been known about the physiological action of amino and thiol reductones (6,8).In this paper, we examined the action of amino and thiol reductones on nucleic acids from the points of intensity and base specificity, and their action is discussed in comparison with that of AsA, a typical enediol reductone.Abbreviations: AsA, ascorbic acid; ScA, scorbamic acid; MHC , 3-mercapto-4-hydroxycoumarin monohydrate;MDT, 5-methyl-3,4-dihydroxytetrone; EA, erythorbic acid; TR , triose reductone; Apu, apurinic acid; Apy, apyrimidinic acid; SSC , standard saline citrate (0.15M sodium chloride +0.015M sodium citrate).

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“…2) The nucleic acid-depolymerizing potenciality was detected not only with aromatic reductones but also with triose reductone and its derivatives, 3) suggesting that their enediol groups take part in the degradation.…”

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Breakage of chromosomal DNA with aromatic reductones.

Murakami

Miyoshi

Koga

et al. 1975

Agricultural and Biological Chemistry

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Strand breakages of mammalian cellular chromosomal DNA with aromatic reductones were ascertained by use of a cultured cell strain of the rat fetal lung (RFL). The mode of the breakages was investigated by ultracentrifugal analyses. The reductones induced the breakages of the cellular DNA in two different fashions; one is single strand breaks and another double strand breaks. Although the single strand breaks were rapidly repaired, double strand breaks were only partially repaired. Both breaks were not cytocidal. Some physiological alterations were observed to follow the strand breaks.The DNA and RNA strand breaking abi lities and the anticancer activity of aromatic reductones were first discovered by Yamafuji and Murakami.1) Enhanced transcription of the DNA which had been treated with the reductones were discussed also by them.2) The nucleic acid-depolymerizing potenciality was detected not only with aromatic reductones but also with triose reductone and its derivatives,3) suggesting that their enediol groups take part in the degradation.

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Action of Amino Reductones on Nucleic Acids

Cited by 7 publications

References 0 publications

Maillard Reaction in Milk - Effect of Heat Treatment

Maillard Reaction in Milk - Effect of Heat Treatment

Breaking action of reductones related to ascorbic acid on nucleic acids.

Breakage of chromosomal DNA with aromatic reductones.

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