(+)-plagiochiline A | 67779-73-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-plagiochiline A
• 英文别名: plagiochiline A；plagiochilin A；[(1R,2S,4S,7S,8R,9R)-9-acetyloxy-3,3-dimethylspiro[10-oxatricyclo[6.4.0.02,4]dodec-11-ene-7,2'-oxirane]-12-yl]methyl acetate
• CAS: 67779-73-1
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: PJNBMVOSONBSAO-AOCJLEPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-plagiochiline A 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  来自地衣 Plagiochila fruticosa 的神经营养性 secoaromadendrane 型倍半萜

  摘要：

  摘要 从地草 Plagiochila fruticosa 中分离出的一种新倍半萜二醛 plagiochilal B 不仅能加速神经突的萌发，还能增强 10 -5 M 时胎鼠大脑半球神经元细胞培养物中胆碱乙酰转移酶的活性。此外，两种新的 secoaromadendranes , plagiochilines J 和 K 被分离出来。通过广泛的 2D NMR 数据和与 plagiochiline A 的化学相关性建立了新的 secoaromadendrane 型倍半萜烯的结构。

  DOI：

  10.1016/0031-9422(91)83467-y

文献信息

• Insect antifeedant secoaromadendrane-type sesquiterpenes from Plagiochila species
  作者：Yoshinori Asakawa、Masao Yoyota、Tsunematsu Takemoto、Isao Kubo、Koji Nakanishi

  DOI：10.1016/s0031-9422(00)82212-8

  日期：1980.1

  known plagiochiline C were isolated from P. yokogurensis. Plagiochilal A, which may be a precursor of plagiochilide and its related hemiacetals, and a bitter principle, plagiochiline B were also isolated from P. hattoriana. P. ovalifolia contained plagiochilines A, B and C. From P. fruticosa, plagiochilide and plagiochilines A, B and C were isolated. The structures of the new secoaromadendrane-type sesquiterpenes

  摘要 Plagiochila 种 P. fruticosa、P. hattoriana、P.ovalifolia 和 P. yokogurensis 的特征性辛辣是由于一种新的 ent-secoaromadendrane 型倍半萜烯半缩醛，plagiochiline A，它对非洲军队表现出很强的拒食活性。蠕虫，Spodoptera permita，浓度为 1–10 ng/cm2。从 P. yokogurensis 中分离出两种新的 secoaromadendranes、plagiochilide 和 furanoplagiochilal A，以及先前已知的 plagiochiline C。Plagiochilal A 可能是 plagiochilide 及其相关半缩醛的前体，以及一种苦味成分 plagiochiline B 也从 P. hattoriana 中分离出来。P.ovalifolia
• Stereostructure of Plagiochiline A and Conversion of Plagiochiline A and Stearoylvelutinal into Hot-Tasting Compounds by Human Saliva.
  作者：Toshihiro HASHIMOTO、Hironao TANAKA、Yoshinori ASAKAWA

  DOI：10.1248/cpb.42.1542

  日期：——

  The stereostructure of plagiochiline A (1) isolated from the liverwort Plagiochila fruticosa has been established by X-ray crystallographic analysis. Plagiochiline A was converted into plagiochilal B (2) and furanoplagiochilal (3) by human saliva, and stearoylvelutinal (4) isolated from the fungus Lactarius vellerus was converted into velleral (5), also by human saliva.

  通过 X 射线晶体学分析，确定了从肝草 Plagiochila fruticosa 中分离出来的 plagiochiline A（1）的立体结构。Plagiochiline A 在人体唾液的作用下转化为 plagiochilal B (2) 和 furanoplagiochilal (3)，而从 Lactarius vellerus 真菌中分离出来的硬脂酰绒毛醛 (4) 也在人体唾液的作用下转化为 velleral (5)。
• Three ent-secoaromadendrane-type sesquiterpene hemiacetals and a bicyclogermacrene from Plagiochila ovalifolia and Plagiochila yokogurensis
  作者：Yoshinori Asakawa、Masao Toyota、Tsunematsu Takemoto

  DOI：10.1016/s0031-9422(00)82211-6

  日期：1980.1
• Neurotrophic secoaromadendrane-type sesquiterpenes from the liverwort Plagiochila fruticosa
  作者：Yoshiyasu Fukuyama、Yoshinori Asakawa

  DOI：10.1016/0031-9422(91)83467-y

  日期：1991.1

  Abstract A new sesquiterpene dialdehyde, plagiochilal B, isolated from the liverwort Plagiochila fruticosa exhibits not only acceleration of neurite sprouting but also enhancement of choline acetyltransferase activity on a neuronal cell culture of fetal rat cerebral hemisphere at 10 −5 M. Additionally, two new secoaromadendranes, plagiochilines J and K were isolated. The structures of the new secoaromadendrane-type

  摘要 从地草 Plagiochila fruticosa 中分离出的一种新倍半萜二醛 plagiochilal B 不仅能加速神经突的萌发，还能增强 10 -5 M 时胎鼠大脑半球神经元细胞培养物中胆碱乙酰转移酶的活性。此外，两种新的 secoaromadendranes , plagiochilines J 和 K 被分离出来。通过广泛的 2D NMR 数据和与 plagiochiline A 的化学相关性建立了新的 secoaromadendrane 型倍半萜烯的结构。