4,4',6-O-trihydroxybenzophenone 2-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside | 1286747-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4',6-O-trihydroxybenzophenone 2-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside
• 英文别名: iriflophenone 2-O-β-D-glucopyranosyl-(1->4)-O-α-L-rhamnopyranoside；aquilarisinin；[2-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,6-dihydroxyphenyl]-(4-hydroxyphenyl)methanone
• CAS: 1286747-51-0
• 化学式: C₂₅H₃₀O₁₄
• 分子量: 554.505
• InChiKey: BNMVADRPOBTNIG-GJZCLZIISA-N

物化性质

• 沸点：
  912.0±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  236
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4,4',6-O-trihydroxybenzophenone 2-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside 在 硫酸 作用下， 反应 1.0h， 生成 可得然胶 、 L-(+)-鼠李糖
  参考文献：
  名称：

  Bio-assay guided isolation and identification of α-glucosidase inhibitors from the leaves of Aquilaria sinensis

  摘要：

  Eight alpha-glucosidase inhibitors including four new compounds were isolated from the 70% aqueous ethanolic extract of leaves of Aquilaria sinensis (Lour.) Gilg by activity-directed fractionation and purification processes. The ethanolic extract was first separated into petroleum ether, ethyl acetate, n-butanol and water soluble fractions and screened for inhibitory activity against alpha-glucosidase. Further activity-directed investigation lead to the isolation of four new compounds with moderate inhibitory activity, viz, aquilarisinin (1), aquilarisin (2), hypolaetin 5-O-beta-D-glucuronopyranoside (3) and aquilarixanthone (4) from the n-butanol fraction, and four known compounds showing potent activity including mangiferin (5), iriflophenone 2-O-alpha-L-rhamnopyranoside (6), iriflophenone 3-C-beta-D-glucoside (7) and iriflophenone 3,5-C-beta-D-diglucopyranoside (8) from the most potent ethyl acetate fraction. The structures of these compounds were determined by extensive spectroscopic analyses, including IR. UV, ESIMS, HRESIMS, 1D and 2D NMR. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2010.11.025
• 作为产物：
  描述：

  4'-O-benzyl-6-hydroxy-4-O-benzyl-benzophenone 2-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside] 在 10% Pd/C 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 4,4',6-O-trihydroxybenzophenone 2-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside
  参考文献：
  名称：

  α-葡萄糖苷酶抑制剂二苯甲酮O-糖苷的合成与评价

  摘要：

  从沉香的叶子中分离出的二苯甲酮 O-糖苷（iriflophenone 2-O-α-L-rhamnopyranoside：1 和 aquilarisinin：2）的首次全合成是通过适当的保护基操作完成的从市售的 L-鼠李糖、D-葡萄糖、D-半乳糖、D-甘露糖、D-木糖和 1,3,5-三羟基苯开始糖基化。评估了所有合成的二苯甲酮 O-糖苷对 α-葡萄糖苷酶的抑制活性。其中，与阳性对照阿卡波糖的 IC50 值相比，二苯甲酮 O-糖苷 4 和 10 对 α-葡萄糖苷酶的体外抑制活性最强，IC50 值分别为 168.7 ± 13.9 和 210.1 ± 23.9 µM 569.3 ± 49.7 µM。

  DOI：

  10.1002/ardp.201200125

文献信息

• Bio-assay guided isolation and identification of α-glucosidase inhibitors from the leaves of Aquilaria sinensis
  作者：Jie Feng、Xiu-Wei Yang、Ru-Feng Wang

  DOI：10.1016/j.phytochem.2010.11.025

  日期：2011.2

  Eight alpha-glucosidase inhibitors including four new compounds were isolated from the 70% aqueous ethanolic extract of leaves of Aquilaria sinensis (Lour.) Gilg by activity-directed fractionation and purification processes. The ethanolic extract was first separated into petroleum ether, ethyl acetate, n-butanol and water soluble fractions and screened for inhibitory activity against alpha-glucosidase. Further activity-directed investigation lead to the isolation of four new compounds with moderate inhibitory activity, viz, aquilarisinin (1), aquilarisin (2), hypolaetin 5-O-beta-D-glucuronopyranoside (3) and aquilarixanthone (4) from the n-butanol fraction, and four known compounds showing potent activity including mangiferin (5), iriflophenone 2-O-alpha-L-rhamnopyranoside (6), iriflophenone 3-C-beta-D-glucoside (7) and iriflophenone 3,5-C-beta-D-diglucopyranoside (8) from the most potent ethyl acetate fraction. The structures of these compounds were determined by extensive spectroscopic analyses, including IR. UV, ESIMS, HRESIMS, 1D and 2D NMR. (C) 2011 Published by Elsevier Ltd.
• Synthesis and Evaluation of Benzophenone<i>O</i>-Glycosides as α-Glucosidase Inhibitors
  作者：Qingchao Liu、Tiantian Guo、Wenhong Li、Dong Li、Zili Feng

  DOI：10.1002/ardp.201200125

  日期：2012.10

  5‐trihydroxybenzene. All synthesized benzophenone O‐glycosides were evaluated for their inhibitory activities against α‐glucosidase. Of these, benzophenone O‐glycosides 4 and 10 exhibited the most potent inhibitory activity in vitro against α‐glucosidase with IC50 values of 168.7 ± 13.9 and 210.1 ± 23.9 µM, respectively, when compared with that of the positive control acarbose with an IC50 value of 569.3 ± 49.7 µM

  从沉香的叶子中分离出的二苯甲酮 O-糖苷（iriflophenone 2-O-α-L-rhamnopyranoside：1 和 aquilarisinin：2）的首次全合成是通过适当的保护基操作完成的从市售的 L-鼠李糖、D-葡萄糖、D-半乳糖、D-甘露糖、D-木糖和 1,3,5-三羟基苯开始糖基化。评估了所有合成的二苯甲酮 O-糖苷对 α-葡萄糖苷酶的抑制活性。其中，与阳性对照阿卡波糖的 IC50 值相比，二苯甲酮 O-糖苷 4 和 10 对 α-葡萄糖苷酶的体外抑制活性最强，IC50 值分别为 168.7 ± 13.9 和 210.1 ± 23.9 µM 569.3 ± 49.7 µM。