(S)-higenamine 4'-O-β-D-glucoside trifluoroacetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (S)-higenamine 4'-O-β-D-glucoside trifluoroacetate
• 化学式: C₂HF₃O₂*C₂₂H₂₇NO₈
• 分子量: 547.482
• InChiKey: DJHXLJDUVFIFLH-MNZRLPPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  189.17
• 氢给体数：
  8.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  盐酸多巴胺 在 四丁基氟化铵 、 氢气 、 sodium methylate 、 palladium(II) hydroxide 、 碳酸氢钠 、 三甲胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.92h， 生成 (S)-higenamine 4'-O-β-D-glucoside trifluoroacetate
  参考文献：
  名称：

  Higenamine 4′-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor

  摘要：

  Hypoglycemic effect is an efficient means to modulate elevated blood glucose levels in patients with diabetes. We found that the extract of lotus plumule (the germ of Nelumbo nucifera Gaertn. seed) showed potent glucose uptake enhancement activity against L6 myotubes, which results in a hypoglycemic effect. This activity was further investigated, and an active constituent was identified as a single bioactive compound, higenamine 4'-O-beta-D-glucoside. Mechanistic studies employing phosphatidylinositol 3-kinase (PI3K) inhibitor, AMP-activated protein kinase (AMPK) inhibitor, or adrenergic receptor antagonist showed that the compound induced its activity through beta 2-adrenergic receptor. Patients with type II diabetes mellitus frequently develop insulin resistance. Owing to the differences between the mechanism of action of insulin and of the isolated compound, the compound or lotus plumule itself may have the possibility of modulating blood glucose levels in insulin-resistant patients effectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.054

文献信息

• Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers
  作者：Eisuke Kato、Ryohei Iwata、Jun Kawabata

  DOI：10.3390/molecules22091450

  日期：——

  receptor agonist activity. Study of the biosynthesis of higenamine has shown the participation of norcoclaurine synthase, which controls the stereochemistry to construct the (S)-isomer. However, when isolated from nature, higenamine is found as the racemate, or even the (R)-isomer. We recently reported the isolation of higenamine 4′-O-β-d-glucoside. Herein, its (R)- and (S)-isomers were synthesized and compared

  Higenamine 是一种四氢异喹啉，存在于多种植物中，具有 β-肾上腺素能受体激动剂活性。对higenamine 生物合成的研究表明，去甲紫杉碱合酶参与控制立体化学以构建(S)-异构体。然而，当从自然界中分离出来时，higenamine 被发现是外消旋物，甚至是 (R)-异构体。我们最近报道了higenamine 4'-O-β-d-葡萄糖苷的分离。在此，合成并比较了其 (R)-和 (S)-异构体，以精确确定分离物的立体化学。由于它们相似的光谱特性，基于 NMR 数据确定立体化学被认为是不合适的。因此，建立了高效液相色谱法分离异构体，
• Higenamine 4′-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor
  作者：Eisuke Kato、Yosuke Inagaki、Jun Kawabata

  DOI：10.1016/j.bmc.2015.04.054

  日期：2015.7

  Hypoglycemic effect is an efficient means to modulate elevated blood glucose levels in patients with diabetes. We found that the extract of lotus plumule (the germ of Nelumbo nucifera Gaertn. seed) showed potent glucose uptake enhancement activity against L6 myotubes, which results in a hypoglycemic effect. This activity was further investigated, and an active constituent was identified as a single bioactive compound, higenamine 4'-O-beta-D-glucoside. Mechanistic studies employing phosphatidylinositol 3-kinase (PI3K) inhibitor, AMP-activated protein kinase (AMPK) inhibitor, or adrenergic receptor antagonist showed that the compound induced its activity through beta 2-adrenergic receptor. Patients with type II diabetes mellitus frequently develop insulin resistance. Owing to the differences between the mechanism of action of insulin and of the isolated compound, the compound or lotus plumule itself may have the possibility of modulating blood glucose levels in insulin-resistant patients effectively. (C) 2015 Elsevier Ltd. All rights reserved.