gummiferolic acid | 69842-20-2

• 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: gummiferolic acid
• 英文别名: (1R,2S,4S,5R,9S,10S,12S)-5,9-dimethyl-2-[(Z)-2-methylbut-2-enoyl]oxy-13-methylidenetetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 69842-20-2
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: ARPPVIBASXIMRQ-FKBUUSIPSA-N

物化性质

• 沸点：
  514.2±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  gummiferolic acid 在 吡啶 、 甲醇 、 lithium aluminium tetrahydride 、 Jones reagent 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 19-hydroxy-7-oxo-ent-atis-16-ene
  参考文献：
  名称：

  Biotransformation of 7α-hydroxy- and 7-oxo-ent-atis-16-ene derivatives by the fungus Gibberella fujikuroi

  摘要：

  The microbiological transformation of 7 alpha,19-dihydroxy-ent-atis-16-ene by the fungus Gibberella fujikuroi gave 19-hydroxy-7-oxo-ent-atis-16-ene, 13(R),19-dihydroxy-7-oxo-ent-atis-16-ene, 7 alpha,11 beta,19-trihydroxy-ent-atis-16-ene and 7 alpha,16 beta,19-trihydroxy-ent-atis-16-ene, while the incubation of 19-hydroxy-7-oxo-ent-atis-16-ene afforded 13(R),19-dihydroxy-7-oxo-ent-atis-16-ene and 16 beta,17-dihydroxy-7-oxo-ent-atisan-19-al. The biotransformation of 7-oxo-ent-atis-16-en-19-oic acid gave 6 beta-hydroxy-7-oxo-ent-atis-16-en-19-oic acid, 6 beta,16 beta,17-trihydroxy-7-oxo-19-nor-ent-atis-4(18)-ene and 3 beta,7 alpha-dihydroxy-6-oxo-ent-atis-16-en-19-oic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.04.024

文献信息

• Acyl Derivatives of Eudesmanolides To Boost their Bioactivity: An Explanation of Behavior in the Cell Membrane Using a Molecular Dynamics Approach
  作者：Francisco J. R. Mejías、Alexandra G. Durán、Jesús G. Zorrilla、Rosa M. Varela、José M. G. Molinillo、Manuel M. Valdivia、Francisco A. Macías

  DOI：10.1002/cmdc.202000783

  日期：2021.4.20

  lines to identify selective derivatives with a reduced negative impact upon application. The mode of action of these compounds was analyzed by anti‐caspase‐3 assays and molecular dynamics simulations with cell membrane re‐creation were also carried out. Aryl derivatives of eudesmanolide stand out from the other compounds and are better than current anticancer drugs such as etoposide in terms of selectivity

  天然产物的半合成类似物为获得更安全、更有活性的药物提供了重要途径，并且它们还具有增强的物理化学性质，如持久性、跨膜过程和生物活性。不同天然产物家族的酰基衍生物，从倍半萜内酯到苯并恶嗪类，已在我们的实验室合成和测试。这些化合物针对肿瘤和非肿瘤细胞系进行了评估，以鉴定对应用具有减少负面影响的选择性衍生物。通过抗 caspase-3 测定分析了这些化合物的作用方式，并进行了细胞膜重建的分子动力学模拟。eudesmanolide 的芳基衍生物从其他化合物中脱颖而出，在选择性和活性方面优于目前的抗癌药物，如依托泊苷。计算研究提供的证据表明，亲脂性起着关键作用，4-氟苯甲酰基衍生物可以轻松通过细胞膜。
• Gummiferolic acid, a new ent-atis-16-ene diterpenoid from Margotia gummifera
  作者：Mariano Pinar、Benjamín Rodríguez、Antonio Alemany

  DOI：10.1016/s0031-9422(00)94658-2

  日期：1978.1

  Abstract From the roots of Margotia gummifera a new diterpenoid with the ent -atis-16-ene skeleton, gummiferolic acid, has been obtained in very high yield (2% of the dry plant), together with the known ent -kaur-16-en-19-oic acid.

  摘要 从 Margotia gummifera 的根中获得了一种具有 ent-atis-16-ene 骨架的新二萜类物质，gummiferolic acid，与已知的 ent-kaur-16- 一起以非常高的产量（干植物的 2%）获得。 en-19-油酸。
• The microbiological transformation of some isoatisene diterpenoids into isoatisagibberellins and isoatisenolides by Gibberella fujikuroi
  作者：Braulio M. Fraga、Ricardo Guillermo

  DOI：10.1016/s0031-9422(00)83868-6

  日期：——

  microbiological transformations of ent -7α-hydroxy-atis-15-en-19-oic acid into isoatisagibberellins A 12 and A 15 , and of ent -19-hydroxy-atis-6,15-diene into 7β-hydroxyisoatisenolide and 7β,18-dihydroxyisoatisenolide have been demonstrated using Gibberella fujikuroi . The substrates incubated were chemically obtained from gummiferolic acid.

  摘要 ent -7α-hydroxy-atis-15-en-19-oic acid 转化为isoatisagibberellins A 12 和A 15 以及ent -19-hydroxy-atis-6,15-diene 转化为7β-hydroxyisoatisenolide 和7β , 18-dihydroxyisoatisenolide 已经使用赤霉病进行了证明。培养的底物是从树胶酸中化学获得的。
• Biotransformation of 7α-hydroxy- and 7-oxo-ent-atis-16-ene derivatives by the fungus Gibberella fujikuroi
  作者：Braulio M. Fraga、Pedro Gonzalez、Victoria Gonzalez-Vallejo、Ricardo Guillermo、Luz N. Diaz

  DOI：10.1016/j.phytochem.2010.04.024

  日期：2010.8

  The microbiological transformation of 7 alpha,19-dihydroxy-ent-atis-16-ene by the fungus Gibberella fujikuroi gave 19-hydroxy-7-oxo-ent-atis-16-ene, 13(R),19-dihydroxy-7-oxo-ent-atis-16-ene, 7 alpha,11 beta,19-trihydroxy-ent-atis-16-ene and 7 alpha,16 beta,19-trihydroxy-ent-atis-16-ene, while the incubation of 19-hydroxy-7-oxo-ent-atis-16-ene afforded 13(R),19-dihydroxy-7-oxo-ent-atis-16-ene and 16 beta,17-dihydroxy-7-oxo-ent-atisan-19-al. The biotransformation of 7-oxo-ent-atis-16-en-19-oic acid gave 6 beta-hydroxy-7-oxo-ent-atis-16-en-19-oic acid, 6 beta,16 beta,17-trihydroxy-7-oxo-19-nor-ent-atis-4(18)-ene and 3 beta,7 alpha-dihydroxy-6-oxo-ent-atis-16-en-19-oic acid. (C) 2010 Elsevier Ltd. All rights reserved.