ampelopsin A | 130608-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: ampelopsin A
• 英文别名: (1S,8S,9R,16S)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaene-4,6,9,12-tetrol
• CAS: 130608-11-6
• 化学式: C₂₈H₂₂O₇
• 分子量: 470.478
• InChiKey: LHUHHURKGTUZHU-QWMXJGQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ampelopsin A 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以53%的产率得到(1S,6R,7S,11bS)-4,8,10-Trimethoxy-1,7-bis-(4-methoxy-phenyl)-1,6,7,11b-tetrahydro-2-oxa-dibenzo[cd,h]azulen-6-ol
  参考文献：
  名称：

  Absolute configurations of some oligostilbenes from Vitis coignetiae and Vitis vinifera ‘Kyohou’

  摘要：

  Hepatotoxic oligostilbenes, (+)-vitisin A and (+)-cis-vitisin A were isolated as a pure form, respectively by the method of recycled HPLC. The structure of cis-vitisin A was confirmed by the photochemical transformation of vitisin A. The absolute configurations of (+)-ampelopsin A, (+)-ampelopsin B, (+)-vitisin A, (+)-cis-vitisin A and (+)-vitisin D were also determined by chemical and spectroscopic methods. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00332-9
• 作为产物：
  描述：

  (+)-ε-viniferin pentaacetate 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 ampelopsin A
  参考文献：
  名称：

  Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F

  摘要：

  The absolute configurations of four stilbenedimers, (+)-ampelopsin- A, (+)-ampelopsins B, (-)-ampelopsins D and (+)ampelopsins F were respectively determined on the basis of chemical evidence. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00785-8

文献信息

• Antitumor agents 200.1 cytotoxicity of naturally occurring resveratrol oligomers and their acetate derivatives
  作者：Masayoshi Ohyama、Toshiyuki Tanaka、Tetsuro Ito、Munekazu Iinuma、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(99)00520-x

  日期：1999.10

  Eleven resveratrol oligomers and six acetylated derivatives were evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. The acetate of (-)-ampelopsin A (12) showed potent and selective cytotoxic activity with ED50 values of 0.6, 0.7 and 2.0 mu g/mL against KB, 1A9 and MCF-7 cells, respectively. Hopeaphenol (10) and pallidol hexaacetate (13) also showed significant cytotoxicity against KB cells with ED50 values of 1.2 and 1.6 mu g/mL, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F
  作者：Yoshiaki Takaya、Ke-Xu Yan、Kenji Terashima、Junko Ito、Masatake Niwa

  DOI：10.1016/s0040-4020(02)00785-8

  日期：2002.9

  The absolute configurations of four stilbenedimers, (+)-ampelopsin- A, (+)-ampelopsins B, (-)-ampelopsins D and (+)ampelopsins F were respectively determined on the basis of chemical evidence. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Absolute configurations of some oligostilbenes from Vitis coignetiae and Vitis vinifera ‘Kyohou’
  作者：Junko Ito、Kanako Gobaru、Tomoyuki Shimamura、Masatake Niwa、Yoshiaki Takaya、Yoshiteru Oshima

  DOI：10.1016/s0040-4020(98)00332-9

  日期：1998.6

  Hepatotoxic oligostilbenes, (+)-vitisin A and (+)-cis-vitisin A were isolated as a pure form, respectively by the method of recycled HPLC. The structure of cis-vitisin A was confirmed by the photochemical transformation of vitisin A. The absolute configurations of (+)-ampelopsin A, (+)-ampelopsin B, (+)-vitisin A, (+)-cis-vitisin A and (+)-vitisin D were also determined by chemical and spectroscopic methods. (C) 1998 Elsevier Science Ltd. All rights reserved.