Formation of tetrahydro-β-carbolines and β-carbolines during the reaction of L-tryptophan with D-glucose

被引:46
作者
Rönner, B
Lerche, H
Bergmüller, W
Freilinger, C
Severin, T
Pischetsrieder, M
机构
[1] Univ Erlangen Nurnberg, Inst Pharm & Lebensmittelchem, D-91052 Erlangen, Germany
[2] Univ Munich, Inst Pharm & Lebensmittelchem, D-8000 Munich, Germany
关键词
Maillard reaction; tryptophan; tetrahydro-beta-carboline; beta-carboline;
D O I
10.1021/jf991237l
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
The reaction of L-tryptophan (Trp) with D-glucose under conditions that can occur during food processing and preparation was studied by high-performance liquid chromatography with diode array detection (HPLC/DAD). Besides the well-established glucose-tryptophan Amadori product (AP), (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (PHP-TH beta C) was identified as an important product of this reaction. For preparation, PHP-TH beta C was obtained in high yields when Trp and D-glucose were reacted under strongly acidic conditions after heating in methanol. At elevated reaction temperatures (150 degrees C) 1-acetyl-beta-carboline (acetyl-beta C), was detected in significant concentrations. The mixtures were heated under variations of reaction time and temperature, and AP, PHP-TH beta C, and acetyl-beta C were quantified. In the presence of air oxygen or mild, food relevant oxidants, such as L-dehydroascorbic acid, PHP-TH beta C was readily oxidized to a product that was identified as the previously unknown 1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-beta-carboline (PHP-beta C). Formation of PHP-TH beta C and PHP-beta C in foodstuffs would deserve particular interest because multiple physiological activity of TH beta C and beta C derivatives has been shown previously.
引用
收藏
页码:2111 / 2116
页数:6
相关论文
共 28 条
[1]   IDENTIFICATION OF TETRAHYDRO-BETA-CARBOLINE-3-CARBOXYLIC ACID IN FOODSTUFFS, HUMAN URINE AND HUMAN-MILK [J].
ADACHI, J ;
MIZOI, Y ;
NAITO, T ;
OGAWA, Y ;
UETANI, Y ;
NINOMIYA, I .
JOURNAL OF NUTRITION, 1991, 121 (05) :646-652
[2]   ENHANCING THE YIELD AND DIASTEREOSELECTIVITY OF THE PICTET-SPENGLER REACTION - A HIGHLY EFFICIENT ROUTE TO CIS-1,3-DISUBSTITUTED TETRAHYDRO-BETA-CARBOLINES [J].
BAILEY, PD ;
MOORE, MH ;
MORGAN, KM ;
SMITH, DI ;
VERNON, JM .
TETRAHEDRON LETTERS, 1994, 35 (21) :3587-3588
[3]   DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY IN THE PICTET-SPENGLER REACTION [J].
BAILEY, PD ;
HOLLINSHEAD, SP ;
MCLAY, NR ;
MORGAN, K ;
PALMER, SJ ;
PRINCE, SN ;
REYNOLDS, CD ;
WOOD, SD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :431-439
[4]  
BRACHER F, 1993, LIEBIGS ANN CHEM, P837
[5]  
BRACHER F, 1992, LIEBIGS ANN CHEM, P1315
[6]   INVESTIGATIONS ON MAILLARD-REACTION .9. REACTION OF TRYPTOPHAN WITH XYLOSE [J].
BRAUTIGAM, KH ;
SEVERIN, T .
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1974, 154 (02) :80-83
[7]   BETA-CARBOLINES - SYNTHESIS AND NEUROCHEMICAL AND PHARMACOLOGICAL ACTIONS ON BRAIN BENZODIAZEPINE RECEPTORS [J].
CAIN, M ;
WEBER, RW ;
GUZMAN, F ;
COOK, JM ;
BARKER, SA ;
RICE, KC ;
CRAWLEY, JN ;
PAUL, SM ;
SKOLNICK, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (09) :1081-1091
[8]   CHEMISTRY, ANALYSIS, NUTRITIONAL-VALUE, AND TOXICOLOGY OF TRYPTOPHAN IN FOOD - A REVIEW [J].
FRIEDMAN, M ;
CUQ, JL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (05) :1079-1093
[9]   Tryptophan glycoconjugates in food and human urine [J].
Gutsche, B ;
Grun, C ;
Scheutzow, D ;
Herderich, M .
BIOCHEMICAL JOURNAL, 1999, 343 :11-19
[10]   HPLC-MS/MS profiling of tryptophan-derived alkaloids in food: Identification of tetrahydro-beta-carbolinedicarboxylic acids [J].
Gutsche, B ;
Herderich, M .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (07) :2458-2462