metarhizin C | 164740-24-3

• 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: metarhizin C
• 英文别名: BR-050；3-desacylmetarhizin A；4-hydroxy-3-(((1R,4aR,5S,6S,8aR)-6-hydroxy-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-decahydronaphthalen-1-yl)-methyl)-5,6-dimethyl-2H-pyran-2-one；3-[[(1R,4aR,5S,6S,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-4-hydroxy-5,6-dimethylpyran-2-one
• CAS: 164740-24-3
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: DZEAYBRRTVFUAI-KHVHCGRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  metarhizin C 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以49%的产率得到3-(((1R,4aR,5S,6S,8aR)-6-hydroxy-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-decahydronaphthalen-1-yl)methyl)-4-(methoxymethoxy)-5,6-dimethyl-2H-pyran-2-one
  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
• 作为产物：
  描述：

  3-[(1R,4aR,5S,6S,8aR)-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-(6-hydroxy)decahydronaphthalen-1-yl]methyl-5,6-dimethyl-2-methoxy-4H-pyran-4-one 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 metarhizin C
  参考文献：
  名称：

  真菌发酵中新型二萜吡喃酮 (+)-倍半西林和 (-)-纳兰特的对映选择性全合成

  摘要：

  我们从 (+)-5-甲基-Wieland-Miescher 酮开始以收敛和统一的方式有效地合成了 (+)-倍半西林（一种糖皮质激素拮抗剂）和 (-)-nalanthalide（一种钾通道 Kvl.3 阻滞剂）。该合成涉及以下关键步骤：（i）甲锡烷基醚的 [2,3]-Wittig 重排以在 C9 处安装立体中心，在反式萘烷部分中存在 C8 处的外亚甲基官能团，（ii）反式萘烷部分与 γ-吡喃酮部分的偶联反应以组装必需的整个碳框架，以及 (iii) γ-吡喃酮部分转化为 α-吡喃酮环以产生 (+)-倍半西林。目前的全合成已经验证了这些天然产物的绝对构型。

  DOI：

  10.3987/com-08-s(s)2

文献信息

• New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation
  作者：Haruhisa Kikuchi、Tomoko Hoshi、Minoru Kitayama、Mizuki Sekiya、Yasuhiro Katou、Kazunori Ueda、Yuzuru Kubohara、Hiroki Sato、Mitsuaki Shimazu、Shoichiro Kurata、Yoshiteru Oshima

  DOI：10.1016/j.tet.2008.11.014

  日期：2009.1

  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.
• Enantioselective Total Synthesis of Novel Diterpenoid Pyrones (+)-Sesquicillin and (-)-Nalanthalide from Fungal Fermentations
  作者：Tadashi Katoh、Takamasa Oguchi、Kazuhiro Watanabe、Hideki Abe

  DOI：10.3987/com-08-s(s)2

  日期：——

  antagonist) and (-)-nalanthalide (a potassium channel Kvl.3 blocker) in a convergent and unified manner starting from (+)-5-methyl-Wieland-Miescher ketone. The synthesis involved the following key steps: (i) a [2,3]-Wittig rearrangement of a stannylmethyl ether to install the stereogenic center at C9 and the exo-methylene functionality at C8 present in the trans-decalin portion, (ii) a coupling reaction of a

  我们从 (+)-5-甲基-Wieland-Miescher 酮开始以收敛和统一的方式有效地合成了 (+)-倍半西林（一种糖皮质激素拮抗剂）和 (-)-nalanthalide（一种钾通道 Kvl.3 阻滞剂）。该合成涉及以下关键步骤：（i）甲锡烷基醚的 [2,3]-Wittig 重排以在 C9 处安装立体中心，在反式萘烷部分中存在 C8 处的外亚甲基官能团，（ii）反式萘烷部分与 γ-吡喃酮部分的偶联反应以组装必需的整个碳框架，以及 (iii) γ-吡喃酮部分转化为 α-吡喃酮环以产生 (+)-倍半西林。目前的全合成已经验证了这些天然产物的绝对构型。