Analysis of furanone, pyranone, and new heterocyclic colored compounds from sugar-glycine model Maillard systems

被引:29
作者
Ames, JM [1 ]
Bailey, RG
Mann, J
机构
[1] Univ Reading, Dept Food Sci & Technol, Reading RG6 6AP, Berks, England
[2] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
关键词
Maillard reaction; colored compounds; 2-acetyl-6-(hydroxymethyl)-5,6-dihydro-4H-pyridinone; 2-acetyl-6-hydroxy-7-(hydroxymethyl)1,5,6,7-tetrahydro-4H-azepinone; 4-hydroxy-2-(hydroxymethyl)5-methyl-3(2H)-furanone; 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone; NMR;
D O I
10.1021/jf980528b
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Aqueous sugar (xylose or glucose)-glycine model systems were refluxed. for 2 h with the pH maintained at 5. Reverse-phase HPLC of the total reaction products gave two resolved peaks (one of which was colored) for the xylose system and five resolved peaks (two of which were colored) for the glucose system. The components responsible for these peaks were isolated from the ethyl acetate extracts by semipreparative HPLC. Using mainly NMR, the colored compound from the xylose system was identified as the new 2-acetyl-6-(hydroxymethyl)-5,6-dihydro-4H-pyridinone. The colored compounds from the glucose system were most likely to be two novel cis / traits ring isomers of the related new compound 2-acetyl-6-hydroxy-7-(hydroxymethyl)-1,5 These compounds are the first one-ring structures isolated from sugar-amino acid model systems that are reported to be colored. Two of the colorless components of the glucose system were identified, mainly by NMR experiments, as the related compounds 4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone. The remaining compound from the glucose system and the colorless compound from the xylose system were identified as 5-(hydroxymethyl)furfural and 4-hydroxy-5-methyl-3(2H)-furanone, respectively.
引用
收藏
页码:438 / 443
页数:6
相关论文
共 35 条
  • [1] Analysis of the methanol-extractable nonvolatile maillard reaction products of a model extrusion-cooked cereal product
    Ames, JM
    Arnoldi, A
    Bates, L
    Negroni, M
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (04) : 1256 - 1263
  • [2] LOW-MOLECULAR-WEIGHT COLORED COMPOUNDS FORMED IN XYLOSE LYSINE MODEL SYSTEMS
    AMES, JM
    APRIYANTONO, A
    ARNOLDI, A
    [J]. FOOD CHEMISTRY, 1993, 46 (02) : 121 - 127
  • [3] [Anonymous], PROGR FOOD PROTEINS
  • [4] New colored compounds from the Maillard reaction between xylose and lysine
    Arnoldi, A
    Corain, EA
    Scaglioni, L
    Ames, JM
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (03) : 650 - 655
  • [5] Bailey RG, 1996, J SCI FOOD AGR, V72, P97, DOI 10.1002/(SICI)1097-0010(199609)72:1<97::AID-JSFA626>3.0.CO
  • [6] 2-Q
  • [7] BANKS SB, 1988, CHEM IND-LONDON, P433
  • [8] Generation of proline-specific Maillard compounds by the reaction of 2-deoxyglucose with proline
    Chen, CW
    Lu, GY
    Ho, CT
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (08) : 2996 - 2999
  • [9] IN-VITRO ACTIVITY OF A-86719.1, A NOVEL 2-PYRIDONE ANTIMICROBIAL AGENT
    ELIOPOULOS, GM
    WENNERSTEN, CB
    COLE, G
    CHU, D
    PIZZUTI, D
    MOELLERING, RC
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (04) : 850 - 853
  • [10] SYNTHESIS AND ANTIMICROBIAL INVESTIGATION OF THIAZOLINOALKYL-4(1H)-PYRIDONES
    EROL, DD
    YULUG, N
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (11) : 893 - 897