2-[[[(3-β-D-glucopyranosyloxy)-1H-indol-2-yl]carbonyl]amino]benzoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-[[[(3-β-D-glucopyranosyloxy)-1H-indol-2-yl]carbonyl]amino]benzoic acid
• 英文别名: (+)-2-[3'-β-D-glucopyranosyloxy-1'H-indol-2'-ylcarboxamido]benzoic acid；isatindigotindoloside A；baphicacanthin B；2-[[3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-indole-2-carbonyl]amino]benzoic acid
• 化学式: C₂₂H₂₂N₂O₉
• 分子量: 458.425
• InChiKey: HFRBJHOTPBQYDZ-ZEENSLDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  182
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[[[(3-β-D-glucopyranosyloxy)-1H-indol-2-yl]carbonyl]amino]benzoic acid 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  Two New Alkaloids from the Roots of <i>Baphicacanthus cusia</i>

  摘要：

  对 Baphicacanthus cusia (NEES) BREMEK 根的植物化学研究提供了两种新的生物碱：baphicacanthin A (1) 和 baphicacanthin B (2)，以及 28 种已知化合物。这些化合物的化学结构是在一维和二维 (1D/2D)-NMR 以及高分辨率 (HR)-MS 光谱证据的基础上阐明的。

  DOI：

  10.1248/cpb.c16-00315

文献信息

• Indole alkaloid glucosides from the roots of <i>Isatis indigotica</i>
  作者：Yu-Feng Liu、Ming-Hua Chen、Sheng Lin、Yu-Huan Li、Dan Zhang、Jian-Dong Jiang、Jian-Gong Shi

  DOI：10.1080/10286020.2015.1117452

  日期：2016.1.2

  Five new indole alkaloid glucosides named isatindigotindolosides A-E (1-5), along with three known analogs (6-8), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including the absolute configurations were determined based on comprehensive spectroscopic data analysis, combined with chemical methods and electronic circular dichroism spectra calculations. In the preliminary assays, compounds 1, 6 and 7 showed antiviral activity against influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 14.6-33.3 mu M. Compound 1 also exhibited inhibitory effect against nitric oxide (NO) production in microglial cell BV2 with an inhibition ratio of 93.0% at 10 mu M.
• METHOD OF ISOLATING ANTI-VIRAL INGREDIENTS FROM BAPHICACANTHUS CUSIA, COMPOSITIONS COMPRISING THEM AND THEIR MEDICAL USE
  申请人：Macau University of Science and Technology

  公开号：US20170281702A1

  公开（公告）日：2017-10-05

  The present invention provides a method of isolating at least one ingredient with anti-viral efficacy from Baphicacanthus cusia. The ingredient can be an alkaloid, a triterpenoid, a lignan, a phenylethanoid, a sesquiterpene lactone, or a flavonoid. Two new alkaloids are produced, which have not been previously reported. Moreover, the method isolates 12 compounds which could not or have not been previously isolated. A pharmaceutical composition includes the at least one ingredient and at least one pharmaceutical tolerable excipient. A method of treating a subject suffering from a viral disease includes administering at least one ingredient isolated from Baphicacanthus cusia.
• Two New Alkaloids from the Roots of &lt;i&gt;Baphicacanthus cusia&lt;/i&gt;
  作者：Qi-Tong Feng、Guo-Yuan Zhu、Wei-Na Gao、Zifeng Yang、Nanshan Zhong、Jing-Rong Wang、Zhi-Hong Jiang

  DOI：10.1248/cpb.c16-00315

  日期：——

  Phytochemical investigation of the root of Baphicacanthus cusia (NEES) BREMEK afforded two new alkaloids, baphicacanthin A (1) and baphicacanthin B (2), along with 28 known compounds. The chemical structures of these compounds were elucidated on the basis of one and two dimensional (1D/2D)-NMR and high resolution (HR)-MS spectral evidence.

  对 Baphicacanthus cusia (NEES) BREMEK 根的植物化学研究提供了两种新的生物碱：baphicacanthin A (1) 和 baphicacanthin B (2)，以及 28 种已知化合物。这些化合物的化学结构是在一维和二维 (1D/2D)-NMR 以及高分辨率 (HR)-MS 光谱证据的基础上阐明的。