ac-panaxytriol | 1026268-15-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ac-panaxytriol
• 英文别名: [(3R,9R,10R)-9,10-dihydroxyheptadec-1-en-4,6-diyn-3-yl] acetate
• CAS: 1026268-15-4
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: GOKHACHKKIPPCG-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酰氯 、 ac-panaxytriol 在 吡啶 作用下， 生成 3-O-acetyl-9,10-O-di-(p-bromobenzoyl)-panaxytriol
  参考文献：
  名称：

  The Absolute Stereostructure of Panaxytriol,a Biologically Active Diacetylenic Acetogenin, from Ginseng Radix Rubra.

  摘要：

  通过改良莫舍尔法和 CD 激发子手性法，确定了人参中的一种二乙酰基成分--三七三醇（1）的绝对立体结构，并将其表示为（3R, 9R, 10R）-十七-1-烯-4, 6-二炔-3, 9, 10-三醇。

  DOI：

  10.1248/cpb.43.1595
• 作为产物：
  描述：

  (1R)-6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl acetate 在 溶剂黄146 作用下， 生成 ac-panaxytriol
  参考文献：
  名称：

  The Absolute Stereostructure of Panaxytriol,a Biologically Active Diacetylenic Acetogenin, from Ginseng Radix Rubra.

  摘要：

  通过改良莫舍尔法和 CD 激发子手性法，确定了人参中的一种二乙酰基成分--三七三醇（1）的绝对立体结构，并将其表示为（3R, 9R, 10R）-十七-1-烯-4, 6-二炔-3, 9, 10-三醇。

  DOI：

  10.1248/cpb.43.1595

文献信息

• Inhibitory Effects of Polyacetylene Compounds from <i>Panax ginseng</i> on Neurotrophin Receptor-Mediated Hair Growth
  作者：Aoi Suzuki、Daisuke Matsuura、Hirotoshi Kanatani、Shingo Yano、Mitsuo Tsunakawa、Shigeru Matsuyama、Hideyuki Shigemori

  DOI：10.1248/bpb.b17-00205

  日期：——

  Neurotrophins play an important role in the control of the hair growth cycle. Therefore, neurotrophin receptor antagonists have therapeutic potential for the treatment of hair growth disorders. In this study, we investigated the inhibitory effect of Panax ginseng, a medicinal plant commonly used to treat alopecia, on the binding of neurotrophins to their receptors. In addition, we isolated and characterized the bioactive compounds of P. ginseng extracts. P. ginseng hexane extracts strongly inhibited brain-derived neurotrophic factor (BDNF)-TrkB and β-nerve growth factor (β-NGF)-p75 neurotrophin receptor (p75NTR) binding. Furthermore, we identified the following 6 polyacetylene compounds as the bioactive components in P. ginseng hexane extract: panaxynol (1), panaxydol (2), panaxydol chlorohydrin (3), 1,8-heptadecadiene-4,6-diyne-3,10-diol (4), panaxytriol (5), and dihydropanaxacol (6). In particular, compounds 4, 5, and 6 significantly inhibited BDNF-TrkB binding in a dose-dependent manner. To identify the structural component mediating the inhibitory effect, we investigated the effects of the hydroxyl moiety in these compounds. We found that the inhibitory effect of panaxytriol (5) was strong, whereas the inhibitory effect of Ac-panaxytriol (7) was relatively weak. Our findings suggest that P. ginseng-derived polyacetylenes with a hydroxyl moiety might provide therapeutic benefits to patients with hair growth disorders such as alopecia by inhibiting the binding of neurotrophins to their receptors. Although saponins have been proposed to be the primary mediators of the effects of P. ginseng on hair growth, this study revealed that polyacetylene compounds exert similar effects.

  神经营养因子在控制头发生长周期中起着重要作用。因此，神经营养因子受体拮抗剂在治疗脱发方面具有潜在疗效。在这项研究中，我们研究了常用作治疗脱发的药用植物人参对神经营养因子与其受体结合的抑制作用。此外，我们还分离并鉴定了人参提取物的生物活性成分。人参的己烷提取物可强烈抑制脑源性神经营养因子（BDNF）-TrkB和β-神经生长因子（β-NGF）-p75神经营养因子受体（p75NTR）的结合。此外，我们还鉴定了以下6种聚乙炔化合物作为人参己烷提取物的生物活性成分：panaxynol（1）、panaxydol（2）、panaxydol chlorohydrin（3）、1,8-heptadecadiene-4,6-diyne-3,10-diol（4）、panaxytriol（5）和dihydropanaxacol（6）。特别是，化合物4、5和6以剂量依赖的方式显著抑制了BDNF-TrkB的结合。为了鉴定介导抑制作用的结构成分，我们研究了这些化合物中羟基部分的作用。我们发现panaxytriol（5）的抑制作用很强，而Ac-panaxytriol（7）的抑制作用相对较弱。我们的研究结果表明，人参