2-O-alpha-L-鼠李吡喃糖甙鸢尾酚酮 | 943989-68-2

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-O-alpha-L-鼠李吡喃糖甙鸢尾酚酮
• 中文别名: 2-O-ALPHA-L-鼠李吡喃糖甙鸢尾酚酮
• 英文名称: 4,4',6-trihydroxybenzophenone 2-O-α-L-rhamnopyranoside
• 英文别名: iriflophenone 2-O-α-L-rhamnopyranoside；iriflophenone-2-O-α-L-rhamnopyranoside；riflophenone 2-O-α-L-rhamnopyranoside；iriflophenone 2-O-α-L-rhamnoside；iriflophenone 2-O-α-rhamnoside；Iriflophenone 2-O-rhamnoside；[2,4-dihydroxy-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenyl]-(4-hydroxyphenyl)methanone
• CAS: 943989-68-2
• 化学式: C₁₉H₂₀O₉
• 分子量: 392.362
• InChiKey: BDUFDLBIUJUAJE-KONKAKAUSA-N

物化性质

• 沸点：
  725.8±60.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-O-alpha-L-鼠李吡喃糖甙鸢尾酚酮 在 硫酸 作用下， 反应 2.0h， 生成 鸢尾酚酮
  参考文献：
  名称：

  Laxative Effect of Agarwood Leaves and Its Mechanism

  摘要：

  我们研究了沉香叶提取物的泻药活性。通过统计小鼠的排便次数和排便重量来测量泻药活性，并通过口服给药。沉香叶的丙酮提取物和番泻叶（一种代表性泻药）都增加了排便次数和重量，但甲醇提取物没有。丙酮提取物的泻药效果比蒽醌类泻药番泻叶更温和，前者不会引起严重的腹泻副作用。我们将丙酮提取物中的主要泻药活性成分鉴定为芹菜素5-O-β-刺槐糖苷（化合物4）。化合物4增强了自发运动并诱导回肠收缩。化合物4诱导的回肠收缩被阿托品抑制，但不被阿扎司琼抑制，这表明化合物4的作用是通过乙酰胆碱受体介导的，而不是通过血清素。化合物4的泻药机制可能部分涉及通过乙酰胆碱受体刺激肠道运动。

  DOI：

  10.1271/bbb.70361
• 作为产物：
  描述：

  4'-O-benzyl-6-hydroxy-4-O-benzyl-benzophenone 2-O-(2,3,4-tri-O-acetyl)-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 2-O-alpha-L-鼠李吡喃糖甙鸢尾酚酮
  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

• Laxative Effect of Agarwood Leaves and Its Mechanism
  作者：Hideaki HARA、Yasuaki ISE、Nobutaka MORIMOTO、Masamitsu SHIMAZAWA、Koji ICHIHASHI、Masayoshi OHYAMA、Munekazu IINUMA

  DOI：10.1271/bbb.70361

  日期：2008.2.23

  We investigated the laxative activity of an extract of agarwood leaves from Aquilaria sinensis. The laxative activity was measured in mice by counting the stool frequency and stool weight, and the drugs were orally administered. An acetone extract of agarwood leaves and senna (a representative laxative drug) both increased the stool frequency and weight, but a methanol extract did not. The laxative effect of the acetone extract was milder than that of the anthraquinoid laxative, senna, and the former did not induce diarrhea as a severe side effect. We identified the main constituent contributing to the laxative effect of the acetone extract as genkwanin 5-O-β-primeveroside (compound 4). Compound 4 strengthened the spontaneous motility and induced contraction in the ileum. This ileal contraction induced by compound 4 was inhibited by atropine, but not by azasetron, suggesting that the effect of compound 4 was mediated by acetylcholine receptors, and not by serotonin. The laxative mechanism for compound 4 may in part involve stimulation of intestinal motility via acetylcholine receptors.

  我们研究了沉香叶提取物的泻药活性。通过统计小鼠的排便次数和排便重量来测量泻药活性，并通过口服给药。沉香叶的丙酮提取物和番泻叶（一种代表性泻药）都增加了排便次数和重量，但甲醇提取物没有。丙酮提取物的泻药效果比蒽醌类泻药番泻叶更温和，前者不会引起严重的腹泻副作用。我们将丙酮提取物中的主要泻药活性成分鉴定为芹菜素5-O-β-刺槐糖苷（化合物4）。化合物4增强了自发运动并诱导回肠收缩。化合物4诱导的回肠收缩被阿托品抑制，但不被阿扎司琼抑制，这表明化合物4的作用是通过乙酰胆碱受体介导的，而不是通过血清素。化合物4的泻药机制可能部分涉及通过乙酰胆碱受体刺激肠道运动。
• 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。