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全文: "Maillard"
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  • MUNETADA OIMOMI, NAOYA IGAKI, TSUYOSHI OHARA, MAKOTO SAKAI, TSUNEO NAKAMICHI, FUMIHIKO HATA, YUICHIRO MAEDA, SHIGEAKI BABA
    臨床化学
    1988年 17 巻 3 号 125-127
    発行日: 1988/12/30
    公開日: 2012/11/27
    ジャーナル フリー
    3-Deoxyglucosone, which is formed as an intermediate compound in the Maillard reaction, acts on lysozyme to increase its fluorescence and to increase the level of peak L1 compound which we identified previously as an advanced Maillard product. This finding suggests the possibility that 3-deoxyglucosone may act on various types of protein in the body to accelerate the production of advanced Maillard products.
  • 老籾 宗忠, 中道 恒雄, 坂井 誠, 大原 毅, 井垣 直哉, 秦 文彦, 馬場 茂明
    臨床化学
    1989年 18 巻 1 号 29-31
    発行日: 1989/06/30
    公開日: 2012/11/27
    ジャーナル フリー
    We investigated the in vitro effect of fructose on the formation of advanced Maillard reaction products which have fluorescence and cross-links.
    Bovine serum albumin was incubated at 37°C for 14days. added various concentrations of glucose or fructose The fluorescence intensity increased with increasing concentrations of both sugars and with increasing incubation time. The fluorescence intensity was higher after incubation with fructose than after incubation with glucose.
    These results suggest that fructose in polyol pathway plays an important role in the formation of advanced Maillard products.
  • MUNETADA OIMOMI, NAOYA IGAKI, SHOGO MASUTA, FUMIHIKO HATA, YUICHIRO MAEDA, SHIGEKI NISHIMOTO, YOSHIAKI KITAMURA, SHINICHIRO MATSUMOTO, SHIGEAKI BABA
    臨床化学
    1988年 17 巻 3 号 121-124
    発行日: 1988/12/30
    公開日: 2012/11/27
    ジャーナル フリー
    Since lens protein is a long-lived protein, the levels of advanced-stage products of the Maillard reaction are considered to reflect the sum of accumulated glycation. We nvestigated the relationship between the level of advanced product in cataractous lens nucleus and the motor nerve conduction velocity (MCV) of the peroneal nerve, and the sensory nerve conduction velocity (SCV) of the sural nerve, in diabetic patients. There were significant correlations between the product level and both of these parameters. However, there was no significant relationship between the levels of fasting plasma glucose and hemoglobin Alc immediately prior to surgery and the MCV and the SCV.
    These results suggest that glycation measured by advanced Maillard product plays an important role in the etiology of diabetic neuropathy.
  • 柳本 卓, 田中 宗彦, 長島 裕二, 田口 武
    日本水産学会誌
    1992年 58 巻 11 号 2153-2158
    発行日: 1992年
    公開日: 2008/02/29
    ジャーナル フリー
    The influence of the Maillard reaction on the antibacterial activity of salmine was determined. A model system consisting of salmine sulfate (1g) and xylose (1.5g) in 10ml of distilled water (pH 5, 7, 9, or 11) was prepared and heated at 100°C for up to 60h to accelerate the Maillard reaction. The development of brown color was more pronounced in model systems with a higher initial pH value. It was revealed that the antibacterial activity of salmine increased at the beginning of the Maillard reaction. The minimum inhibitory concentration of salmine against Bacillus subtilis (IAM 1026) decreased to 75μg per ml of medium from 250μg as a result of the Maillard reaction. However, Gram-negative bacteria were not sensitive to either salmine or browned salmine. Browned salmine was bactericidal against B. subtilis, while salmine before the reaction seemed to be bacteri-ostatic. The addition of browned salmine to kamaboko at the level of 1% resulted in the elongation of its shelf-life at 5°C.
  • Tomoko SHIMAMURA, Hiroyuki UKEDA, Masayoshi SAWAMURA
    Food Science and Technology Research
    2004年 10 巻 1 号 6-9
    発行日: 2004年
    公開日: 2007/05/18
    ジャーナル フリー
    The XTT (3′-[1-(phenylamino)-carbonyl]-3,4-tetrazolium)-bis(4-methoxy-6-nitro)benzenesulfonic acid hydrate) reducibility of practical milk sample enables evaluation of the heat-treatment and storage conditions such as temperature and period. Based on the appearance of absorption maximum at 320 nm in a model heated solution, we suggested that aminoreductone formed during the Maillard reaction of lactose is involved in the reduction of XTT. In this report, the relationship between the XTT reducibility and the formation of aminoreductone was investigated more specifically using HPLC equipped with a photodiode array detector. Lactose and butylamine were heated at 100°C for 15 min, and then analyzed by HPLC. A main peak with absorption maximum at 324 nm, which is thought to be aminoreductone, was recognized in the chromatogram of the heated reaction mixture. The peak corresponding to aminoreductone showed the XTT reducibility. After the addition of Cu2, the main peak and its ability to reduce XTT completely disappeared. Moreover, the formation of aminoreductone under various kinds of heating conditions linearly related with the XTT reducibility of the reaction mixture. These findings strongly suggested that the XTT-reducing substance formed during the Maillard reaction of lactose was aminoreductone.
  • 田中 宗彦, 黄 俊儒, 邱 文貴, 石崎 松一郎, 田口 武
    日本水産学会誌
    1993年 59 巻 11 号 1915-1921
    発行日: 1993/11/25
    公開日: 2008/02/29
    ジャーナル フリー
    In order to elucidate the possible participation of chitosan in the Maillard reaction, model systems consisting of chitosan and glucose (1:0.1, 1:0.5, and 1:1, w/w) with different water activity (Aw 0.33, 0.51, and 0.84) were prepared. By heating the model systems at 65°C, it was discovered that chitosan took part in the Maillard browning reaction and its rate was faster with a higher ratio of glucose and water activity. Furthermore, it was disclosed that some of the unique functional properties of chitosan were altered as a result of the Maillard reaction with glucose. Water binding capacity and antibacterial activity of chitosan decreased to some extent at the initial stage of the Maillard reaction, while acidic dye binding capacity increased considerably with the progress of the reaction. Most of the changes due to the Maillard reaction became significant when more than 80% of amino groups of chitosan were lost by the reaction. On the contrary, the fat binding capacity and iron chelating properties were not affected by the reaction.
  • MUNETAD OIMOMI, NAOYA IGAKI, TSUNEO NAKAMICHI, SHOGO MASUDA, FUMIHIKO HATA, YUICHIRO MAEDA, SHIGEKI NISHIMOTO, YOSHIAKI KITAMURA, SHINICHIRO MATSUMOTO, HIROSHI HATANAKA, SHIGEAKI BABA
    臨床化学
    1988年 17 巻 1 号 20-24
    発行日: 1988/08/31
    公開日: 2012/11/27
    ジャーナル フリー
    An advanced-stage product in the Maillard reaction was determined by fluorometry using high-performance liquid chromatography (HPLC). A peak which could be determined by fluorescence HPLC appeared with a retention time of 12min, increased in height with increasing glucose concentration and incubation time when albumin and glucose were incubated for 4 weeks at 37°C, and did not disappear on pretreatment with NaBH4 before acid-hydrolysis. Therefore, this peak was considered as an advanced-stage product of the Maillard reaction.
  • Tsukasa Matsuda, Hiroshi Ishiguro, Iwao Ohkubo, Makoto Sasaki, Ryo Nakamura
    The Journal of Biochemistry
    1992年 111 巻 3 号 383-387
    発行日: 1992年
    公開日: 2008/11/18
    ジャーナル フリー
    Three hybridoma antibodies (L101, L104, and L117) specific for lactose-protein amino carbonyl products (Maillard adducts) were obtained by immunizing mice with the lactoseovalbumin Maillard adduct and by screening with the lactose-bovine serum albumin (BSA) adduct. They reacted with the Maillard adducts of lactose with several different proteins, but not with the adducts of several other reducing sugars. L101 reacted well with the lactose-BSA adducts formed by 2- to 16-day incubation, whereas L104 and L117 reacted with the advanced stage reaction products but not with the adducts of 2-day incubation. The competitive inhibition of the antibody binding by several mono- and disaccharides showed that lactulose (4-O-β-D-galactopylanosyl-D-fructose) was the best inhibitor for all three antibodies, and that L104 and L117 were inhibited by methyl-β-D-galactoside more effectively than L101. These results suggested that different components produced during the progress of the Maillard reaction could be antigenic determinants, and that the carbohydrate moiety including the terminal galactosyl residue played an important role in the antibody binding to the lactose-protein Maillard adducts.
  • Fumitaka HAYASE
    Food Science and Technology Research
    2000年 6 巻 2 号 79-86
    発行日: 2007/05/25
    公開日: 2008/08/28
    ジャーナル フリー
    Maillard reaction occurs extensively in food systems and in vivo. In an intermediate Maillard reaction of proteins with glucose, 3-deoxyglucosone (3DG) was generated from Amadori compounds in an early stage, leading to generation of advanced glycation endproducts (AGEs). 3DG modified lysine residues to form pyrrole aldehydes (lysyl-pyrraline), and arginine residues to form imidazolone compounds, and is speculated to be a cross-linker responsible for the polymerization of proteins. 3DG is also thought to be related to the evolution of fluorescence during Maillard reaction. The fluorescent compound has been identified as lysyl-pyrropyridine which is formed by the loss of five molecules of water from the reaction between 2 molecules of lysine residues and 2 molecules of 3DG. In the protein-glucose and pentose reaction systems, crossline and pentosidine have reportedly been formed as fluorescent and crosslinking compound, respectively, as well as pyrropyridine. Immunochemical and chemical methods have clearly indicated the progressive accumulation of AGEs in tissue proteins in aging. In diabetes, AGE accumulation in general is accelerated and linked to arteriosclerosis, nephropathy, neuropathy, retinopathy, and cataract. 3DG, which has weaker mutagenicity, reacted readily with 2′-deoxyguanosine in nucleosides. Two major products (G-A and G-B) were isolated, and G-A was identified as N-(1-oxo-2,4,5,6-hydroxyhexyl)-2′-deoxyguanosine. G-B was identified as a diastereomer of G-A. Blue pigment was isolated from the reaction between D-xylose and glycine. Blue pigment which was designated Blue-M1 (blue Maillard reaction intermediate-1) was identified as novel pyrrolopyrrolylium compound and is assumed to be a dimer of yellow colored pyrrolopyrrole-2-carboxaldehyde compounds. Blue-M1 that reacts readily to yellow compounds has a polymerizing activity, suggesting that it is an important Maillard reaction intermediate through the formation of melanoidins. Melanoidins have many positive physiologic effects.
  • Takashi OKAZAKI, Shinya YAMAUCHI, Tatsuo YONEDA, Kanichi SUZUKI
    Food Science and Technology Research
    2001年 7 巻 4 号 285-289
    発行日: 2001年
    公開日: 2007/01/30
    ジャーナル フリー
    The effect of the combination of heating and pressurization on Maillard reaction was investigated using a model solution of glucose and glycine, and a white sauce. The apparent browning rates were calculated from the relationship between the treatment time and the absorbance of the model solution at 430 nm. The apparent activation volume was estimated from the relationship between the apparent browning rate and the pressure, and the apparent activation energy estimated from the rate and the temperature. High hydrostatic pressure (HHP) up to 400 MPa retarded the Maillard reaction in a temperature range of 100–115°C. The apparent activation volumes fell into 3.8–4.5 cm3·mol−1 in a temperature range of 100–115°C, and the apparent activation energies into 94.3–105.3 kJ·mol−1 in a pressure range of 0.1–400 MPa. The HHP treatment also suppressed the browning of the white sauce, which was heated at 115°C for 30 min under 300 MPa.
  • 川村 信一郎
    日本農芸化学会誌
    1982年 56 巻 12 号 1199-1202
    発行日: 1982年
    公開日: 2008/11/21
    ジャーナル フリー
  • MUNETADA OIMOMI, FUMIHIKO HATA, NAOYA IGAKI, SHOGO MASUTA, TSUNEO NAKAMICHI, YUICHIRO MAEDA, SHIGEKI NISHIMOTO, SHINICHIRO MATSUMOTO, SHIGEAKI BABA
    臨床化学
    1988年 17 巻 2 号 91-93
    発行日: 1988/10/31
    公開日: 2012/11/27
    ジャーナル フリー
    We extracted α-ketoaldehyde dehydrogenase (α-KAD) from rabbit's liver (New Zealand White, body weight 3kg). The α-KAD reacted with methylglyoxal as a substrate in the presence of coenzyme NAD with a Km value of 0.24 mM. Preincubation of glycated bovine serum albumin as a substrate with NAD and α-KAD at 0°C or 30°C for 2 hours caused significantly smaller increases in fluorescence intensity after subsequent incubation for 7 days at 37°C, compared with samples preincubated without α-KAD at 37°C. Preincubation of glycated bovine serum albumin for 2 hours with α-KAD and NAD at 30°C caused the smallest increase in fluorescence intensity after 7 days of subsequent incubation.
    These findings suggest that α-KAD may inhibit the formation of the advanced Maillard products.
  • Nobuyasu Matsuura, Tadashi Aradate, Chihiro Sasaki, Hiroyuki Kojima, Mitsuharu Ohara, Junichi Hasegawa, Makoto Ubukata
    Journal of Health Science
    2002年 48 巻 6 号 520-526
    発行日: 2002年
    公開日: 2002/12/05
    ジャーナル フリー
    An assay for the Maillard reaction has been developed to screen efficiently inhibitors from natural resources such as extracts of plants. The fluorometric analysis of fluorescent material based on advanced glycation endproducts (AGEs) was applied to measurement of an inhibitory index of the Maillard reaction to detect all of the inhibitors at each step of the complicated reaction. To solve the two major problems, slowness of the reaction rate and the existence of interfering substances such as quencher and fluorescent material in the screening sources, we devised the following procedures. Slowness of the reaction rate was solved by raising the reaction temperature to 60°C at which the conformation of bovine serum albumin (BSA) did not change greatly. To remove the interfering substances, AGEs-BSA was precipitated from the reaction mixture. Thus, an efficient assay system by measuring the fluorescent intensity based on AGEs was established to isolate the glycation inhibitors from natural product extracts.
  • Jean MAURON
    Journal of Nutritional Science and Vitaminology
    1990年 36 巻 4-SupplementI 号 S57-S69
    発行日: 1990年
    公開日: 2009/06/16
    ジャーナル フリー
    In the first part the reactions and interactions of protein with macroconstituents of our food during processing are exposed from the chemical point of view. The reactions involving only protein (formation of isopeptides, of lysinoalanine, racemization) and the interactions with carbohydrates (Maillard reaction), oxidized lipids and polyphenols are briefly presented. Emphasis is put on the Maillard reaction since it is the most frequent reaction occurring during food processing and storage. The key compound rendering lysine unavailable in processed and stored foodstuffs is Nε-fructoselysine (FL). Its oxidative degradation product, Nε-carboxymethyllysine (CML) is found in variable but significant amounts in heat processed proteins. An interesting newer finding is that tryptophan can participate in a Maillard reaction with its indole-NH-group.
    In the second part an overview is given on the impact these reactions have on the two components of protein nutritive value, namely digestibility and biological value. Again, most examples will be related to the Maillard reaction. Protein digestibility may be reduced by the modification of the protein molecule (blocking of active amino acid side-chains, establishment of crosslinks) or by the formation of compounds that inhibit digestive enzymes. (Inhibition of aminopeptidase by an advanced Maillard derivative of lysine). Biological value may be diminished by the loss of essential amino acids and/or their reduced specific availability. Ion-exchange chromatography of the protein hydrolyzate is the method of choice to determine amino acid losses. It also provides some clues for the type of processing damage by the presence of unusual amino acids in the chromatogramme (e.g. furosine, lysinoalanine). Global amino acid bioavailability is defined. It is of a complex nature and can only be truely determined in a bioassay in the animal. Specific availability of an amino acid is linked to particular structural features. Thus, specific lysine availability is determined by the presence of a free or “reactive” ε-amino group. This is the basis for the analytical methods for available lysine.
    In the third part, the practical application of this knowledge to processed foods is shown using milk and vegetable protein as examples. Figures for the reduction in available lysine (blocked lysine) in different milk products processed according to conventional procedures are given and discussed. More subtile effects of milk processing on milk digestibility and stomach emptying are mentioned. The effects on protein nutritional value of extrusion-cooking of legume seeds and cereal flours are, then, presented. Whereas sulphur amino acid bioavailability and protein digestibility in legumes are improved by appropriate extrusion-cooking, extensive lysine loss and nutritional damage can take place when cereal flours are extruded under severe conditions.
    It is concluded that, nowadays, extensive knowledge of the reaction mechanisms, appropriate analytical methods and flexible processing operations are available to prevent to a large extent protein nutritional losses.
  • Yoshikazu Yonei, Masayuki Yagi, Sawako Hibino, Nobuyasu Matsuura
    ANTI-AGING MEDICINE
    2008年 5 巻 10 号 93-98
    発行日: 2008年
    公開日: 2009/09/30
    ジャーナル フリー
    Objectives: Accumulation of end-stage products of the Maillard reaction, also called advanced glycation end products (AGEs), is a hallmark of aging and the pathogenesis of chronic diabetic complications. The aim of this study was to determine whether safe and effective substances contained in four extracts of foodstuffs might slow the development of diabetic complications as well as slow the progression of aging.
    Design: We evaluated the in-vitro activity of four extracts of dried herbs available in Japan (Anthemis nobilis, Crataegus oxyacantha, Houttuynia coradata, Vitis vinifera) and a mixture of these to inhibit the Maillard reaction. We also assessed whether a 12-week feeding of mixed herbal extract (MHE) admixed in MF chow to streptozotocin (STZ)-induced diabetic rats prevented the development of diabetic complications.
    Results: Each of the four herbal extracts as well as the mixed extract dose-dependently inhibited the generation of Maillard reaction products in vitro with a potency similar to that of aminoguanidine (AG), a drug used for treating diabetic complications. Furthermore, after a 12-week, MHE supplemental feeding to STZ-induced diabetic rats, serum pentosidine and Nε-(carboxymethyl)lysine levels and wet weight of the kidney tended to decrease. MHE elicited AG-like actions and produced an inhibitory effect on pentosidine generation at lower concentrations than those observed for AG.
    Conclusion: Through the inhibition of the Maillard reaction, MHE may slow the development of chronic diabetic complications as well as slow the progression of aging.
  • Teruyuki USUI, Fumitaka HAYASE
    Bioscience, Biotechnology, and Biochemistry
    2003年 67 巻 4 号 930-932
    発行日: 2003年
    公開日: 2003/06/28
    ジャーナル フリー
      Glyceraldehyde (200 mM) and Nα-acetyllysine (100 mM) were incubated in 0.2 M sodium phosphate buffer (pH 7.4) at 37°C for a week. A major compound, glyceraldehyde-related Maillard reaction product, was purified from the reaction mixture using reverse phase (ODS)-HPLC. It was identified as 1-(5-acetylamino-5-carboxypentyl)-3-hydroxy-5-hydroxymethyl-pyridinium, named as GLAP (Glyceraldehyde derived Pyridinium compound), using NMR and MS analyses. It was suggested that GLAP as a novel advanced glycation end product (AGE) is one of the key compounds in the glyceraldehyde-related Maillard reaction.
  • 矢島 絢介, 小野寺 秀一, 竹田 保之, 加藤 勲, 塩見 徳夫
    Journal of Applied Glycoscience
    2007年 54 巻 3 号 165-168
    発行日: 2007年
    公開日: 2007/08/21
    ジャーナル フリー
    メイラード反応を利用してβ-lactoglobulin (β-LG)に,xylobioseを導入した.得られたβ-LG-xylobioseのin vitroにおける抗酸化活性をβ-LG-lactoseと比較検討した.7日間の反応を行ったところ,β-LG-xylobioseの分子量はSDS-PAGE分析により19-22 kDaと推定され,MALDI TOF-MS分析から約21 kDaを中心に多く分布していることがわかった.ガスクロマトグラフィー分析を行ったところ,xylobioseがβ-LGに結合していることが確認された.また,β-LG-xylobiose 1 mg当たり108 μgのxylobioseが結合したと算出され,遊離ε-アミノ基は約40%に減少したと算出された.DPPHを用いたラジカル捕捉能試験の結果より,β-LG-xylobioseはβ-LGよりも高いラジカル捕捉能を有していることが明らかになり,β-LG-lactoseのラジカル捕捉能よりも高かった.この結果より,xylobioseはタンパク質の糖化修飾における修飾糖として適したオリゴ糖と考えられる.以上の結果より,メイラード反応を利用したxylobiose糖化修飾によってβ-LGのラジカル捕捉能が向上することが確認された.
  • Satomi SHIZUUCHI, Fumitaka HAYASE
    Bioscience, Biotechnology, and Biochemistry
    2003年 67 巻 1 号 54-59
    発行日: 2003年
    公開日: 2003/06/25
    ジャーナル フリー
      A blue compound was prepared from 1 M D-xylose and 0.1 M glycine, and designated Blue-M1, an intermediate color product of melanoidins. As melanoidins are well known to have antioxidative activity as well as high scavenging activity against active oxygen species, the antioxidative activity of Blue-M1 against the peroxidation of linoleic acid was investigated, in addition to the scavenging activity of Blue-M1 toward hydroxyl and DPPH radicals.
      Blue-M1 suppressed the peroxidation of linoleic acid as effectively as melanoidins did. The scavenging activity of Blue-M1 toward hydroxyl and DPPH radicals was also as strong as that of melanoidins. Blue-M1 showed higher activity with increasing concentration. The pyrrolopyrrole ring and a methine bridge between two pyrrolopyrrole rings in Blue-M1 could be related to the ability for radical scavenging activity, but not four carboxyl groups.
  • MUNETADA OIMOMI, SHOGO MASUDA, TSUNEO NAKAMICHI, YUICHIRO MAEDA, FUMIHIKO HATA, YOSHIAKI KITAMURA, SHINICHIRO MATSUMOTO, HIROSHI HATANAKA, SHIGEAKI BABA
    臨床化学
    1987年 16 巻 2 号 120-123
    発行日: 1987/11/30
    公開日: 2012/11/27
    ジャーナル フリー
    Furosine (ε-N-(2-furoylmethyl)-L-lysine), which is an acid-hydrolysis product derived from the Amadori compoud fructose-lysine (ε-N-(1-deoxy-D-fructose-1-yl)-L-lysine) was used in determining the nonenzymatic glycation of tissue proteins. The furosine level in the aorta obtained at autopsy was significantly higher in the aged (over 65 years) than in the neonate. A significant positive correlation was found between the visually estimated severity of sclerosis of the aorta and the furosine level in the aorta in the aged.
    These results suggest that an increase in nonenzymatic glycation in the human aorta may be an etiological factor of arteriosclerosis.
  • Munetada OIMOMI, Naoya IGAKI, Makoto SAKAI, Tsuneyoshi OHARA, Shigeaki BABA, Hiromichi KATO
    Agricultural and Biological Chemistry
    1989年 53 巻 6 号 1727-1728
    発行日: 1989年
    公開日: 2006/04/05
    ジャーナル フリー
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