[(E,3S,5S)-1-(4-hydroxyphenyl)-7-phenyl-5-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyhept-6-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1335038-28-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: [(E,3S,5S)-1-(4-hydroxyphenyl)-7-phenyl-5-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyhept-6-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1335038-28-2
• 化学式: C₃₉H₃₆F₆O₇
• 分子量: 730.701
• InChiKey: QUBFBFHDCLREFS-BGCUZUOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (3S,5S)-alpinikatin 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 、 氘代吡啶 作用下， 反应 4.0h， 生成 [(E,3S,5S)-1-(4-hydroxyphenyl)-7-phenyl-5-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyhept-6-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Diarylheptanoids from the Seeds of Alpinia katsumadai as Heat Shock Factor 1 Inducers

  摘要：

  Seven new diarylheptanoids, (-)-(R)-4 ''-hydroxyyashabushiketol (1), (3S,5S)-alpinikatin (2), katsumain C (3), 7-epi-katsumain C (4), ent-alpinnanin B (5), ent-alpinnanin A (6), and ent-calyxin H (8), were isolated from the EtOAc extract of the seeds of Alpinia katsumadai together with three known compounds, alpinnanin B (7), epicalyxin H (9), and calyxin H (10). Each isomer mixture of 3 and 4,5-7, and 8-10 was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (3 and 4, 5-7, 8-10) at 1 mu M increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 M. Compounds 1 and 2 did not affect the induction of HSF1 protein.

  DOI：

  10.1021/np200355n

文献信息

• Diarylheptanoids from the Seeds of <i>Alpinia katsumadai</i> as Heat Shock Factor 1 Inducers
  作者：Joo-Won Nam、Ga-Young Kang、Ah-Reum Han、Dongho Lee、Yun-Sil Lee、Eun-Kyoung Seo

  DOI：10.1021/np200355n

  日期：2011.10.28

  Seven new diarylheptanoids, (-)-(R)-4 ''-hydroxyyashabushiketol (1), (3S,5S)-alpinikatin (2), katsumain C (3), 7-epi-katsumain C (4), ent-alpinnanin B (5), ent-alpinnanin A (6), and ent-calyxin H (8), were isolated from the EtOAc extract of the seeds of Alpinia katsumadai together with three known compounds, alpinnanin B (7), epicalyxin H (9), and calyxin H (10). Each isomer mixture of 3 and 4,5-7, and 8-10 was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (3 and 4, 5-7, 8-10) at 1 mu M increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 M. Compounds 1 and 2 did not affect the induction of HSF1 protein.