3-deoxyaohidicolin | 85483-00-7

• 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: 3-deoxyaohidicolin
• 英文别名: 3-deoxyaphidicolin；(1S,2S,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecan-13-ol
• CAS: 85483-00-7
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: VHWTVINEPPOCLA-DTMQFJJTSA-N

物化性质

• 沸点：
  467.3±10.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 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：

  3-deoxyaohidicolin 在 硼氘化钠 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 [17-2H]-aphidicol-16β,17,18-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
• 作为产物：
  描述：

  艾菲地可宁 在 platinum(IV) oxide 吡啶 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 11.33h， 生成 3-deoxyaohidicolin
  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

• Akanthomins A–C, aphidicolin analogs from a fungus Akanthomyces sp., that inhibit cell cycle
  作者：Koyo Honda、Yuki Hitora、Sachiko Tsukamoto

  DOI：10.1016/j.phytochem.2023.113885

  日期：2023.12

  previously undescribed aphidicolin derivatives, namely akanthomins A–C, and an undescribed chromone glycoside, specifically 9-hydroxyeugenetin 9-O-β-d-(4-O-methyl)glucopyranoside, in addition to aphidicolin. The chemical structures of these compounds were elucidated by spectroscopic analysis and chemical derivatization. Using a flow cytometer, akanthomin A and aphidicolin were found to inhibit cell cycle

  抑制细胞周期进程的天然产物可能具有作为抗癌剂的潜力。在本研究中，使用 HeLa/Fucci2 细胞通过荧光图像筛选微生物培养物提取物的细胞周期抑制作用。真菌Akanthomyces sp.的培养物提取物抑制了 S/G2/M 期的细胞周期进程，并且生物测定引导的提取物分级分离提供了三种先前未描述的阿非迪霉素衍生物，即 akanthomins A–C 和一种未描述的色酮除阿非迪霉素外，还包括 9-羟基丁子香素 9- O -β- d- (4- O-甲基)吡喃葡萄糖苷。通过光谱分析和化学衍生化阐明了这些化合物的化学结构。使用流式细胞仪发现，akanthomin A 和 aphidicolin 可以抑制 S 期细胞周期的进展。
• Ichihara, Akitami; Oikawa, Hideaki; Hayashi, Kazuko, Agricultural and Biological Chemistry, 1984, vol. 48, # 6, p. 1687 - 1690
  作者：Ichihara, Akitami、Oikawa, Hideaki、Hayashi, Kazuko、Hashimoto, Masaaki、Sakamura, Sadao、Sakai, Ryutaro

  DOI：——

  日期：——