(S)-malic acid 1-O-β-D-glucopyranoside | 6784-91-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-malic acid 1-O-β-D-glucopyranoside
• 英文别名: 2-O-β-D-glucopyranosyl-L-malic acid；(S)-morelid；(2S)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanedioic acid
• CAS: 6784-91-4；7178-64-5
• 化学式: C₁₀H₁₆O₁₀
• 分子量: 296.231
• InChiKey: OCIAPZWBJQRATB-UALZLMCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-malic acid 1-O-β-D-glucopyranoside 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 Sodium; (S)-3-carboxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propionate
  参考文献：
  名称：

  Isolation and characterization of 2-O-β-d-Glucopyranosyl-l-malic acid from Synadenium pereskiifolium

  摘要：

  DOI：

  10.1016/0031-9422(90)85107-q
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 barium dihydroxide 、 2,6-二叔丁基-4-甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 18.0h， 生成 (S)-malic acid 1-O-β-D-glucopyranoside
  参考文献：
  名称：

  Activity-Guided Identification of (S)-Malic Acid 1-O-d-Glucopyranoside (Morelid) and γ-Aminobutyric Acid as Contributors to Umami Taste and Mouth-Drying Oral Sensation of Morel Mushrooms (Morchella deliciosa Fr.)

  摘要：

  Although morel mushrooms are widely used as tasty ingredients in savory dishes, knowledge of the key compounds evoking their attractive taste is still very fragmentary. In the present study, taste activity-guided fractionation of an aqueous morel extract by means of the recently developed taste dilution analysis (TIDA) enabled the localization of several umami-like-tasting fractions as well as a fraction imparting an intense mouth-drying sensation to the oral cavity. Hydrophilic interaction liquid chromatography (HILIC), LC-MS, and amino acid analysis led to the successful identification of gamma-aminobutyric acid as the chemical inducer of the mouth-drying and mouth-coating oral sensations imparted by the morel extract. Besides the well-known umami-like taste contributors L-glutamic acid, L-aspartic acid, and succinic acid, an additional HILIC fraction was isolated and evaluated as tasting umami-like. LC-MS and NMR studies revealed that this fraction consisted of a mixture of (S)-malic acid 1-O-alpha-D-glucopyranoside and (S)-malic acid 1-O-beta-D-glucopyranoside, the structure of which could be successfully confirmed by independent synthesis. To the best of our knowledge, this morel-derived glycoside, which we named (S)-morelid, has previously not been reported in any food products. Sensory analysis of aqueous solutions of the compounds identified revealed threshold concentrations of 0.02 mmol/L for the mouth-drying effect of gamma-aminobutyric acid and 6.0 mmol/L for the umami-like, slightly sour taste of (S)-morelid.

  DOI：

  10.1021/jf050056i

文献信息

• Activity-Guided Discovery of (<i>S</i>)-Malic Acid 1′-<i>O</i>-β-Gentiobioside as an Angiotensin I-Converting Enzyme Inhibitor in Lettuce (Lactuca sativa)
  作者：Annika Lagemann、Andreas Dunkel、Thomas Hofmann

  DOI：10.1021/jf3022157

  日期：2012.7.25

  Angiotensin-converting enzyme (ACE), playing a crucial role in the renin angiotensin aldosterone system, is well-known to catalyze the conversion of the decapeptide angiotensin I into the physiologically active octapeptide angiotensin II,. triggering blood pressure increasing mechanisms. To meet the demand for natural phytochemicals as antihypertensive agents in functional food development, extracts prepared from a series of vegetables were screened for their ACE inhibitory activity by means of a LC-MS/MS-based in vitro assay. By far the highest ACE inhibition was found for a lettuce extract, in which the most active compound was located by means of activity-guided fractionation. LC-MS, NMR spectroscopy, and hydrolysis experiments followed by ion chromatography led to the unequivocal identification of the ACE inhibitor as the previously not reported (S)malic acid 1'-O-beta-gentiobioside. This glycoside represents a novel class of ACE inhibiting phytochemicals with a low IC50 value of 27.8 mu M. First incubation experiments in saliva and aqueous hydrochloric acid demonstrated the stability of (S)-malic acid 1'-O-beta-gentiobioside against salivary glycosidases and stomach acid.
• Activity-Guided Identification of (<i>S</i>)-Malic Acid 1-<i>O</i>-<scp>d</scp>-Glucopyranoside (Morelid) and γ-Aminobutyric Acid as Contributors to Umami Taste and Mouth-Drying Oral Sensation of Morel Mushrooms (<i>Morchella deliciosa</i> Fr.)
  作者：Nina Rotzoll、Andreas Dunkel、Thomas Hofmann

  DOI：10.1021/jf050056i

  日期：2005.5.1

  Although morel mushrooms are widely used as tasty ingredients in savory dishes, knowledge of the key compounds evoking their attractive taste is still very fragmentary. In the present study, taste activity-guided fractionation of an aqueous morel extract by means of the recently developed taste dilution analysis (TIDA) enabled the localization of several umami-like-tasting fractions as well as a fraction imparting an intense mouth-drying sensation to the oral cavity. Hydrophilic interaction liquid chromatography (HILIC), LC-MS, and amino acid analysis led to the successful identification of gamma-aminobutyric acid as the chemical inducer of the mouth-drying and mouth-coating oral sensations imparted by the morel extract. Besides the well-known umami-like taste contributors L-glutamic acid, L-aspartic acid, and succinic acid, an additional HILIC fraction was isolated and evaluated as tasting umami-like. LC-MS and NMR studies revealed that this fraction consisted of a mixture of (S)-malic acid 1-O-alpha-D-glucopyranoside and (S)-malic acid 1-O-beta-D-glucopyranoside, the structure of which could be successfully confirmed by independent synthesis. To the best of our knowledge, this morel-derived glycoside, which we named (S)-morelid, has previously not been reported in any food products. Sensory analysis of aqueous solutions of the compounds identified revealed threshold concentrations of 0.02 mmol/L for the mouth-drying effect of gamma-aminobutyric acid and 6.0 mmol/L for the umami-like, slightly sour taste of (S)-morelid.
• Isolation and characterization of 2-O-β-d-Glucopyranosyl-l-malic acid from Synadenium pereskiifolium
  作者：Kerstin Hermansson、Lennart Kenne、Geoffrey M. Rukunga、Gunnar Samuelsson

  DOI：10.1016/0031-9422(90)85107-q

  日期：1990.1