viridoxin A | 145940-93-8

• 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: viridoxin A
• 英文别名: [(1S,2S,4aR,5R,8aR)-5-[(2-methoxy-5,6-dimethyl-4-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-1-(4-methylpent-3-enyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalen-2-yl] (2R,3S)-2-hydroxy-3-methylpentanoate
• CAS: 145940-93-8
• 化学式: C₃₄H₅₂O₆
• 分子量: 556.783
• InChiKey: SGDGQLAPFROPGA-BAIGPXBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  viridoxin A 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 Nalanthalide
  参考文献：
  名称：

  Viridoxins A and B: novel toxins from the fungus Metarhizium flavoviride

  摘要：

  The structures of viridoxins A and B, two novel toxins isolated from the mycelial extract of the fungus Metarhizium flavoviride, were established by spectroscopic methods, chemical correlations, and a single-crystal X-ray analysis of viridoxin B. The absolute configuration of the viridoxins was determined by H-1 NMR analysis of chiral (R)- and (S)-O-methyl mandelate derivatives of viridoxin A.

  DOI：

  10.1021/jo00057a017
• 作为产物：
  描述：

  metarhizin A 、 三甲基硅烷化重氮甲烷 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 2.5h， 以27%的产率得到viridoxin A
  参考文献：
  名称：

  New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation

  摘要：

  To date, entomopathogenic fungi have not been extensively examined by natural product chemists. In this study, we isolated novel pyrone diterpene-type compounds, metarhizins A (1) and B (2), from methanol extracts of entomopathogenic fungus, Metarhizium flavoviride. They showed potent and selective antiproliferative activity against both insect and human cancer cell lines. These results indicate that metarhizins A (1) and B (2) can be used as novel lead compounds for anti-cancer agents and probes for cell cycle regulation. To further investigate the structural requirements for this inhibitory activity, we synthesized many metarhizin derivatives and evaluated their antiproliferative activities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.014