(2R,3S)-5,7,3',4'-tetrahydroxyflavanonol 4"-acetylrhamnoside | 1298135-51-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3S)-5,7,3',4'-tetrahydroxyflavanonol 4"-acetylrhamnoside
• 英文别名: (2R,3S)-4"-acetylisoastilbin；[(2S,3R,4S,5R,6S)-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-3-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl] acetate
• CAS: 1298135-51-9
• 化学式: C₂₃H₂₄O₁₂
• 分子量: 492.436
• InChiKey: ZAFYNBZYABCDCS-RYTLQRITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3S)-5,7,3',4'-tetrahydroxyflavanonol 4"-acetylrhamnoside 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

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.