异落新妇苷 | 54081-48-0

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 异落新妇苷
• 英文名称: (2R,3S)-dihydroquercetin 3-O-α-L-rhamnoside
• 英文别名: neoisoastilbin；isoastilbin；(2R,3S)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
• CAS: 54081-48-0
• 化学式: C₂₁H₂₂O₁₁
• 分子量: 450.399
• InChiKey: ZROGCCBNZBKLEL-OOHAXVOVSA-N

物化性质

• 熔点：
  278-280 °C (decomp)
• 沸点：
  801.1±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

概述

异落新妇苷（isoastilbin，IA）是一种二氢黄酮醇苷类化合物。研究表明，它在抗氧化方面表现出良好的效果。

用途

异落新妇苷广泛存在于土茯苓、黄芪等中药中。已有研究显示，土茯苓具有抗痛风性关节炎和抗高尿酸血症的作用。

生物活性

isoastilbin 是一种源自土茯苓（Rhizoma Smilacis glabrae）和黄芪（Astragalus membranaceus）的二氢黄酮醇糖苷化合物。其抑制葡萄糖基转移酶 (GTase) 的 IC50 值为 54.3 μg/mL，同时还能抑制酪氨酸酶 (tyrosinase) 活性。此外，isoastilbin 还具有神经保护、抗氧化、抗微生物和抗凋亡的特性，并可用于阿尔茨海默氏病的研究。

靶点

• IC50: 54.3 μg/mL (葡萄糖基转移酶 (GTase)

反应信息

• 作为反应物：
  描述：

  异落新妇苷 在 硫酸 、 吡啶 、 D-cysteine 、 三甲基氯硅烷 、 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.5h， 生成 L-rhamnopyranose
  参考文献：
  名称：

  Estrogenic and anti-estrogenic compounds from the Thai medicinal plant, Smilax corbularia (Smilacaceae)

  摘要：

  From the rhizomes of Smilax corbularia Kunth. (Smilacaceae), 11 compounds, (2R,3R)-2 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl astilbin, (2R,3R)-4 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl engeletin, (2R,35)-4 ''-acetyl isoastilbin, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-10-(3,4-dihydroxyphenyl)-(2R,3R, 10R)-2H,8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy -10-(3,4-dihydroxyphenyl)-(2R,3R,10S)-2H, 8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 3,4-dihydro- 7-hydroxy-4-(3,4-dihydroxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(3,4-dihydroxy-phenyl)-5-[(1E)-2-(3,4-dihydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, and 5,7,3',4'-tetrahydroxy-3-phenylcoumarin along with 34 known compounds were isolated and characterized as 19 flavonoids, 14 catechin derivatives, 6 stilbene derivatives, and 6 miscellaneous substances. All isolates had their estrogenic and anti-estrogenic activities determined using the estrogen-responsive human breast cancer cell lines MCF-7 and T47D. The major constituents were recognized as flavanonol rhamnosides by the suppressive effect on estradiol induced cell proliferation at a concentration of 1 mu M. Meanwhile, flavanonol rhamnoside acetates demonstrated estrogenic activity in both MCF-7 and T47D cells at a concentration of 100 mu M, and they enhanced the effects of co-treated E2 on T47D cell proliferation at concentrations of more than 0.1 mu M. 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.12.018
• 作为产物：
  描述：

  落新妇苷 在 吡啶 作用下， 生成 异落新妇苷 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Tominaga, Yakugaku Zasshi, 1958, vol. 78, p. 1077

  摘要：

  DOI：

文献信息

• Estrogenic and anti-estrogenic compounds from the Thai medicinal plant, Smilax corbularia (Smilacaceae)
  作者：Boonsong Wungsintaweekul、Kaoru Umehara、Toshio Miyase、Hiroshi Noguchi

  DOI：10.1016/j.phytochem.2010.12.018

  日期：2011.4

  From the rhizomes of Smilax corbularia Kunth. (Smilacaceae), 11 compounds, (2R,3R)-2 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl astilbin, (2R,3R)-4 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl engeletin, (2R,35)-4 ''-acetyl isoastilbin, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-10-(3,4-dihydroxyphenyl)-(2R,3R, 10R)-2H,8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy -10-(3,4-dihydroxyphenyl)-(2R,3R,10S)-2H, 8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 3,4-dihydro- 7-hydroxy-4-(3,4-dihydroxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(3,4-dihydroxy-phenyl)-5-[(1E)-2-(3,4-dihydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, and 5,7,3',4'-tetrahydroxy-3-phenylcoumarin along with 34 known compounds were isolated and characterized as 19 flavonoids, 14 catechin derivatives, 6 stilbene derivatives, and 6 miscellaneous substances. All isolates had their estrogenic and anti-estrogenic activities determined using the estrogen-responsive human breast cancer cell lines MCF-7 and T47D. The major constituents were recognized as flavanonol rhamnosides by the suppressive effect on estradiol induced cell proliferation at a concentration of 1 mu M. Meanwhile, flavanonol rhamnoside acetates demonstrated estrogenic activity in both MCF-7 and T47D cells at a concentration of 100 mu M, and they enhanced the effects of co-treated E2 on T47D cell proliferation at concentrations of more than 0.1 mu M. 2011 Elsevier Ltd. All rights reserved.
• Tominaga, Yakugaku Zasshi, 1958, vol. 78, p. 1077
  作者：Tominaga

  DOI：——

  日期：——