(1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid | 252340-31-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: cis-(1R,3S)-1-(1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid；(1R,3S)-1-[(1S,2R,3R,4R)-1,2,3,4,5-pentahydroxypentyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS: 252340-31-1
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: LCHFAYIGHOVWSA-JEZYXASSSA-N

物化性质

• 沸点：
  848.9±65.0 °C(Predicted)
• 密度：
  1.587±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.76
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  166.27
• 氢给体数：
  8.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 在 脱氢抗坏血酸 作用下， 以 acidic aq. solution 为溶剂， 反应 90.0h， 生成 (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-β-carboline
  参考文献：
  名称：

  Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of l-Tryptophan with d-Glucose

  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.

  DOI：

  10.1021/jf991237l
• 作为产物：
  描述：

  葡萄糖 、 L-tryptophan sodium salt 以 甲醇 为溶剂， 反应 2.5h， 生成 (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  Formation of Tetrahydro-β-carbolines and β-Carbolines during the Reaction of l-Tryptophan with d-Glucose

  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.

  DOI：

  10.1021/jf991237l

文献信息

• Identification and Occurrence of the Novel Alkaloid Pentahydroxypentyl-tetrahydro-β-carboline-3-carboxylic Acid as a Tryptophan Glycoconjugate in Fruit Juices and Jams
  作者：Tomas Herraiz、Juan Galisteo

  DOI：10.1021/jf020090m

  日期：2002.7.1

  The novel carbohydrate-derived beta-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 mug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-beta-carboline was also found in jams (up to 0.45 mug/g), and a relative high amount was present in tomato concentrate (6.5 mug/g) and sauce (up to 1.8 mug/g). This beta-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of D-glucose and L-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this beta-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-beta-carboline.