16-epiaphidicolane-3α,16β,18-triol | 94789-99-8

• 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: 16-epiaphidicolane-3α,16β,18-triol
• 英文别名: 3α,16β,18-trihydroxypraphidicolane；3α,16β,18-trihydroxyaphidicolane；aphidicolane-3α,16β,18-triol；aphidicolan-3α,16β,18-triol；aphidicolan-3α, 16, 18-triol；3,16,18-trihydroxyaphidicolane；8,11a-Methano-11aH-cyclohepta[a]naphthalene-3,9-diol, tetradecahydro-4-(hydroxymethyl)-4,9,11b-trimethyl-, (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-；(1S,2S,5R,6R,7R,10S,12R,13R)-6-(hydroxymethyl)-2,6,13-trimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
• CAS: 94789-99-8
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: HRPBVTJJLYDCOZ-XPZISPLRSA-N

物化性质

• 沸点：
  461.6±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-epiaphidicolane-3α,16β,18-triol 在 Cephalosporium aphidicola 、 Tween-80 作用下， 以 乙醇 为溶剂， 反应 144.0h， 以68 mg的产率得到艾菲地可宁
  参考文献：
  名称：

  二萜类蚜虫生物合成中C-17位羟基化

  摘要：

  aphidicolin 生物合成中 C-17 处的羟基化被 17-硫醇抑制。从 3α,18-dihydroxy-15β,16β-methanoaphidicolane 获得在 C-17 处羟基化并保留环丙烷环的代谢物，而当这些底物与真菌 Cephalosporium aphidicola 孵育时，aphidicolin 本身是从 3α,18-dihydroxyaphidicola 获得的。

  DOI：

  10.1016/s0031-9422(96)00713-3
• 作为产物：
  描述：

  艾菲地可宁 在 吡啶 、 lithium 作用下， 以 氨 为溶剂， 反应 5.75h， 生成 16-epiaphidicolane-3α,16β,18-triol
  参考文献：
  名称：

  Biosynthesis of diterpenoid aphidicolin: Isolation of intermediates from P-450 inhibitor treated mycelia of Phoma betae

  摘要：

  Treatment of Phoma betae with P-450 inhibitors caused accumulation of biosynthetic precursors 2, 3 and 4 of aphidicolin (1), Their structures were elucidated by spectroscopic analysis and they were confirmed by chemical transformations from 1, Isotopically labeled precursors were synthesized by either reductive deoxygenation of aphidicolin derivatives or microbial conversion of [1-C-14]acetate in the presence of the P-450 inhibitor, Feeding experiments of the labeled precursors confirmed late biosynthetic pathway of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00392-0

文献信息

• Oxidation of aphidicolin and its conversion into 19-noraphidicolan-16β-ol
  作者：John F. Gordon、James R. Hanson、Andrew G. Jarvis、Arnold H. Ratcliffe

  DOI：10.1039/p19920003019

  日期：——

  C-17, is described. Catalytic oxidation of aphidicolin affords 16β-hydroxy-3-oxo-19-noraphidicolan-17-oic acid. The conversion of this into 19-noraphidicolan-16β-ol and its biotransformation by the fungus, Cephalosporium aphidicola, to a 19-noraphidicolin, is reported.

  描述了蚜虫蛋白的3α，18-单丙酮化物的制备及其在C-17上的选择性氧化。蚜虫蛋白的催化氧化得到16β-羟基-3-氧代-19-诺氟哌兰-17-oic酸。据报道将其转化为19-甲萘酚-16β-ol，并通过真菌头孢蚜（Cephaloporium aphidicola）将其生物转化为19-甲萘酚。
• The biotransformation by Cephalosporium aphidicola of some aphidicolanes substituted on ring a
  作者：James R. Hanson、Andrew G. Jarvis

  DOI：10.1016/s0031-9422(00)89730-7

  日期：1994.8

  Abstract The microbiological transformation of 16β,18-dihydroxyaphidicol-2-ene by Cephalosporium aphidicola affords 2α,3α-epoxy-16β,17,18-trihydroxyaphidicolane and 6β,16β,17,18-tetrahydroxyaphidicol-2-ene, whilst 16β,18- dihydroxy-2α,3α-epoxyaphidicolane gave the above epoxy-triol and 2α,3α-epoxy-6β,16β,18-trihydroxyaphidicolane.

  摘要 Cephalosporium aphidicola 对 16β,18-dihydroxyaphidicol-2-ene 的微生物转化得到 2α,3α-epoxy-16β,17,18-trihydroxyaphidicolane 和 6β,16β,17,18-tetrahydroxyaphidicol-2-ene，而 16β,18-epoxy-16β,17,18-trihydroxyaphidicolane - dihydroxy-2α,3α-epoxyaphidicolane 得到上述环氧三醇和 2α,3α-epoxy-6β,16β,18-trihydroxyaphidicolane。
• Biotransformation of some aphidicolane derivatives by Cephalosporium aphidicola
  作者：James R. Hanson、Andrew G. Jarvis、Arnold H. Ratcliffe

  DOI：10.1016/s0031-9422(00)97540-x

  日期：1992.1

  Abstract Chlorocholine chloride (CCC) is shown to inhibit the formation of aphidicolin by Cephalosporium aphidicola . 3α,18-Dihydroxyaphidicolane is transformed into aphidicolin, whereas 3α,16α,18-trihydroxyaphidicolane is converted into 16-epi-aphidicolin.

  摘要 氯化氯胆碱 (CCC) 显示可抑制 Cephalosporium aphidicola 形成 aphidicolin。3α,18-Dihydroxyaphidicolane 转化为 aphidicolin，而 3α,16α,18-trihydroxyaphidicolane 转化为 16-epi-aphidicolin。
• Chemical modification of aphidicolin and the inhibitory effects of its derivatives on DNA polymerase .ALPHA. in vitro.
  作者：Sayoko Hiranuma、Takeshi Shimizu、Hirosuke Yoshioka、Katsuhiko Ono、Hideo Nakane、Taijo Takahashib

  DOI：10.1248/cpb.35.1641

  日期：——

  Various derivatives of aphidicolin (1) were prepared and their inhibitory effects on purified DNA polymerase α in vitro were assayed. Among these derivatives, the new 3α-, 17, 18-trihydroxyaphidicol-15-ene (24) was as inhibitory as the known 3-deoxy-and 3-oxoaphidicolins, (20) and (14). All the other derivatives with modification of any of the hydroxyl groups of 1 had no effect on the enzyme in vitro. The structure-activity relationships are discussed concerning functionalization on the aphidicolane ring.

  制备了阿菲迪霉素(1)的各种衍生物，并测定了它们对纯化的DNA聚合酶α的体外抑制作用。在这些衍生物中，新的 3α-, 17, 18-三羟基 aphidicol-15-ene (24) 与已知的 3-脱氧-和 3-oxoaphidicolins (20) 和 (14) 一样具有抑制作用。 1 的任何羟基被修饰的所有其他衍生物在体外对酶没有影响。讨论了有关 aphidicolane 环上的官能化的构效关系。
• Hanson, James R.; Hitchcock, Peter B.; Jarvis, Andrew G., Journal of the Chemical Society. Perkin transactions I, 1992, # 1, p. 41 - 46
  作者：Hanson, James R.、Hitchcock, Peter B.、Jarvis, Andrew G.、Ratcliffe, Arnold H.、Rodriguez-Perez, Elsa M.

  DOI：——

  日期：——