vavain

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: vavain
• 英文别名: pentandrin；5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxychromen-4-one
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: KIIFCUFZMOWDHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  pentandrin 5'-β-D-glucoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 vavain
  参考文献：
  名称：

  Two New Isoflavones from Ceiba pentandra and Their Effect on Cyclooxygenase-Catalyzed Prostaglandin Biosynthesis

  摘要：

  The new isoflavone glucoside vavain 3'-O-beta-D-glucoside (1) and its aglycon, vavain (2), were isolated from the bark of Ceiba pentandra, together with the known flavan-3-ol, (+)-catechin. These novel structures were elucidated by one-and two-dimensional NMR experiments and by MS, IR, and UV spectroscopy as 5-hydroxy-7,4',5'-trimethoxyisoflavone 3'-O-beta-D-glucoside (1) and 5,3'-dihydroxy-7,4',5'-trimethoxyisoflavone (2), respectively. The compounds were isolated following bioactivity-directed fractionation, using a cyclooxygenase-1-catalyzed prostaglandin biosynthesis assay in vitro, in which compounds 1 and 2 and (+)-catechin exhibited IC50 values of 381, 97, and 80 mu M, respectively (standard: indomethacin, IC50 1.1 mu M). When further tested for their inhibitory effects on cyclooxygenase-2-catalyzed prostaglandin biosynthesis, 1 and 2 were found to be inactive (IC50 > 1200 and >900 mu M, respectively).

  DOI：

  10.1021/np970198+

文献信息

• New isoflavones from Ceiba pentandra
  作者：F.N Ngounou、A.L Meli、D Lontsi、B.L Sondengam、Atta-Ur-Rahman、M.Iqbal Choudhary、Shahid Malik、Farzana Akhtar

  DOI：10.1016/s0031-9422(00)00035-2

  日期：2000.5

  Two new isoflavones, pentandrin (1) and pentandrin glucoside (2), were isolated from the stem barks of Ceiba pentandra a along with beta-sitosterol and its 3-O-beta-D-glucopyranoside, which was isolated for the first time from this plant. The structures of these compounds were elucidated with the help of spectroscopic techniques, while the structure of 1 was unambiguously confirmed by single-crystal X-ray diffraction studies. (C) 2000 Elsevier Science Ltd. All rights reserved.
• COMPOSITIONS FOR PROLIFERATION OF CELLS AND RELATED METHODS
  申请人：The Hospital For Sick Children

  公开号：EP2598150A2

  公开（公告）日：2013-06-05
• US8748177B2
  申请人：——

  公开号：US8748177B2

  公开（公告）日：2014-06-10
• [EN] COMPOSITIONS FOR PROLIFERATION OF CELLS AND RELATED METHODS<br/>[FR] COMPOSITIONS POUR LA PROLIFÉRATION DE CELLULES ET PROCÉDÉS ASSOCIÉS
  申请人：HOSPITAL FOR SICK CHILDREN

  公开号：WO2010039679A1

  公开（公告）日：2010-04-08

  We have discovered that p63 inhibition results in increased cellular proliferation. We have also performed a screen for agents capable of increasing cellular proliferation, (e.g., of stem cells such as skin-derived precursors (SKPs)). The invention therefore invention provides compositions, methods, and kits for increasing proliferation of cells, using compounds that decrease p63 expression or activity or using the compounds described herein. The invention also features methods of using these compounds for increasing hair growth, improving skin health, or promoting skin repair in a subject.
• Two New Isoflavones from <i>Ceiba pentandra </i>and Their Effect on Cyclooxygenase-Catalyzed Prostaglandin Biosynthesis
  作者：Ylva Noreen、Hesham El-Seedi、Premila Perera、Lars Bohlin

  DOI：10.1021/np970198+

  日期：1998.1.1

  The new isoflavone glucoside vavain 3'-O-beta-D-glucoside (1) and its aglycon, vavain (2), were isolated from the bark of Ceiba pentandra, together with the known flavan-3-ol, (+)-catechin. These novel structures were elucidated by one-and two-dimensional NMR experiments and by MS, IR, and UV spectroscopy as 5-hydroxy-7,4',5'-trimethoxyisoflavone 3'-O-beta-D-glucoside (1) and 5,3'-dihydroxy-7,4',5'-trimethoxyisoflavone (2), respectively. The compounds were isolated following bioactivity-directed fractionation, using a cyclooxygenase-1-catalyzed prostaglandin biosynthesis assay in vitro, in which compounds 1 and 2 and (+)-catechin exhibited IC50 values of 381, 97, and 80 mu M, respectively (standard: indomethacin, IC50 1.1 mu M). When further tested for their inhibitory effects on cyclooxygenase-2-catalyzed prostaglandin biosynthesis, 1 and 2 were found to be inactive (IC50 > 1200 and >900 mu M, respectively).