(1S,2R,3R)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxyethylsulfanyl)-2,3-dihydro-1H-indene-2,4,5,6-tetrol | 1262536-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2R,3R)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxyethylsulfanyl)-2,3-dihydro-1H-indene-2,4,5,6-tetrol
• CAS: 1262536-98-0
• 化学式: C₁₇H₁₈O₇S
• 分子量: 366.392
• InChiKey: XHWRSHBLYOXJCE-CSMYWGQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  167
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',5',7-pentahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 、 2-巯基乙醇 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 生成 (1S,2S,3R)-3-(2,4-dihydroxyphenyl)-1-(2-hydroxyethylsulfanyl)-2,3-dihydro-1H-indene-2,4,5,6-tetrol 、 (1R,2R,3R)-3-(2,4-dihydroxyphenyl)-1-(2-hydroxyethylsulfanyl)-2,3-dihydro-1H-indene-2,4,5,6-tetrol 、 (1S,2R,3R)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxyethylsulfanyl)-2,3-dihydro-1H-indene-2,4,5,6-tetrol
  参考文献：
  名称：

  α-Amylase and Lipase Inhibitory Activity and Structural Characterization of Acacia Bark Proanthocyanidins

  摘要：

  The bark extract of Acacia mearnsii showed strong lipase and alpha-amylase inhibition activities. Fractionation of the extract by column chromatography and subsequent C-13 NMR and MALDI-TOF-MS analysis revealed that the active substances are proanthocyanidin oligomers mainly composed of 5-deoxyflavan-3-ol units. In addition, 4'-O-methylrobinetinidol 3'-O-beta-D-glucopyranoside, fisetinidol-(4 alpha,6)-gallocatechin, and epirobinetinidol-(4 beta,8)-catechin were isolated as new compounds, and their structures were determined from spectroscopic data. Furthermore, a modified thiol degradation method using strongly acidic conditions was applied to the extract to yield three thiol degradation products dezived from robinetinidol units. This method is useful for characterizing acacia proanthocyanidins (wattle tannins).

  DOI：

  10.1021/np100372t

文献信息

• α-Amylase and Lipase Inhibitory Activity and Structural Characterization of Acacia Bark Proanthocyanidins
  作者：Rie Kusano、Sosuke Ogawa、Yosuke Matsuo、Takashi Tanaka、Yoshikazu Yazaki、Isao Kouno

  DOI：10.1021/np100372t

  日期：2011.2.25

  The bark extract of Acacia mearnsii showed strong lipase and alpha-amylase inhibition activities. Fractionation of the extract by column chromatography and subsequent C-13 NMR and MALDI-TOF-MS analysis revealed that the active substances are proanthocyanidin oligomers mainly composed of 5-deoxyflavan-3-ol units. In addition, 4'-O-methylrobinetinidol 3'-O-beta-D-glucopyranoside, fisetinidol-(4 alpha,6)-gallocatechin, and epirobinetinidol-(4 beta,8)-catechin were isolated as new compounds, and their structures were determined from spectroscopic data. Furthermore, a modified thiol degradation method using strongly acidic conditions was applied to the extract to yield three thiol degradation products dezived from robinetinidol units. This method is useful for characterizing acacia proanthocyanidins (wattle tannins).