柯伊利素-7-O-葡萄糖苷 | 19993-32-9

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 柯伊利素-7-O-葡萄糖苷
• 中文别名: 野决明苷
• 英文名称: chrysoeriol 7-O-glucoside
• 英文别名: 5,7,4'-trihydroxy-3'-methoxyflavone-7-O-β-D-glucopyranoside；5,4'-dihydroxy-3'-methoxy-7-O-β-D-glucopyranosylflavone；4',5,7-trihydroxy-3'-methoxyflavone 7-O-β-glucoside；isorhamnetin 7‐O‐glucopyranoside；chryosoeriol 7-O-β-D-glucopyranoside；chrysoeriol 7-O-β -D-glucopyranoside；Thermopsoside；5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 19993-32-9；28543-47-7
• 化学式: C₂₂H₂₂O₁₁
• 分子量: 462.41
• InChiKey: GAMYVSCDDLXAQW-MIUGBVLSSA-N

物化性质

• 熔点：
  176-179℃
• 沸点：
  801.6±65.0 °C(Predicted)
• 密度：
  1.609
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  11

制备方法与用途

生物活性方面，Thermopsoside 是从 Aspalathus linearis 中分离得到的一种黄酮衍生物。研究表明，Thermopsoside 对 CYP450 同工酶具有抑制作用，具体而言，其对 CYP3A4、CYP2C19、CYP2D6 和 CYP2C9 的 IC50 值分别为 6.0 μM、9.5 μM、12.0 μM 和 32.0 μM。

反应信息

• 作为反应物：
  描述：

  柯伊利素-7-O-葡萄糖苷 在 吡啶 、 盐酸 、 水 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  Phenolic constituents of the inflorescences of Sorbus torminalis (L.) Crantz

  摘要：

  Torminaloside, a new acylated flavonol glycoside (3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-[6 ''-O-(3'''-hydroxy-3'''-methylglutaroyl)]-beta-D-galactopyranoside, 6), together with five further methoxylated flavones 1-5, hyperoside (7), isoquercitrin (8), chlorogenic acid (9) and neochlorogenic acid (10), were isolated for the first time from Sorbus torminalis (L.) Crantz. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D- and 2D-NMR, LSI-MS and HR-LSI-MS experiments. In addition to torminaloside, three further flavonoids: 5,7,4'-trihydroxy-3'-methoxyflavone- 7-O-beta-D-glucopyranoside (1), 3,5,7,4'-tetrahydroxy-8,3'-dimethoxyflavone-3-O-beta-D-glucopyranoside (2), and 3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-beta-D-galactopyranoside (4) were found for the first time in the genus Sorbus. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.02.005
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 柯伊利素-7-O-葡萄糖苷
  参考文献：
  名称：

  Farooq et al., Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 400,402, 403

  摘要：

  DOI：

文献信息

• Flavonoids from phlomis lychnitys
  作者：F. Tomás、J.L. Nieto、F.A.T. Barberán、F. Ferreres

  DOI：10.1016/s0031-9422(00)81598-8

  日期：1986.4
• Flavonoids of Thermopsis alterniflora
  作者：M. P. Yuldashev、�. Kh. Batirov、A. D. Vdovin、V. M. Malikov、M. R. Yagudaev

  DOI：10.1007/bf00597707

  日期：——
• Isolation and identification of β-hematin inhibitors from Flacourtia indica as promising antiplasmodial agents
  作者：Koneni V. Sashidhara、Suriya P. Singh、Shiv Vardan Singh、Rajeev K. Srivastava、Kumkum Srivastava、J.K. Saxena、Sunil K. Puri

  DOI：10.1016/j.ejmech.2012.12.019

  日期：2013.2

  An ethanolic extract (A001) of the leaves and twigs of Flacourtia indica (Burm.f.) Merr, was purified to give a new phenolic glycoside, 2-(2-benzoyl-beta-D-glucopyranosyloxy)-7-(1 alpha,2 alpha,6 alpha-trihydroxy-3-oxocyclohex4-enoyl)-5-hydroxybenzyl alcohol (1) together with poliothrysoside (2), catechin-15,6-e]-4 beta-(3,4-dihydroxyphenyl)dihydro-2(3H)-pyranone (3), 2-(6-benzoyl-beta-D-glucopyranosyloxy)-7-(1 alpha,2 alpha,6 alpha-trihydroxy-3-oxocyclohex-4-enoyl)-5-hydroxybenzyl alcohol (4), chrysoeriol-7-O-beta-D-glucopyranoside (5), and mururin A (6). Compound 6 significantly inhibited the in vitro growth of both a chloroquine-sensitive (3D7) and a chloroquine-resistant (K1) strain of Plasmodium falciparum. It forms a complex with hematin and inhibits beta-hematin formation, suggesting that this compound act on a heme polymerization target. (C) 2012 Elsevier Masson SAS. All rights reserved.
• ——
  作者：Z. A. Khushbaktova、S. Kh. Faizieva、V. N. Syrov、M. P. Yuldashev、É. Kh. Batirov、A. U. Mamatkhanov

  DOI：10.1023/a:1010410029719

  日期：——
• Farooq et al., Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 400,402, 403
  作者：Farooq et al.

  DOI：——

  日期：——