((1S,2S,4aR,5R,8aR)-5-((4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) (R)-2-hydroxy-3-methylbutanoate | 1114452-63-9

• 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: ((1S,2S,4aR,5R,8aR)-5-((4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) (R)-2-hydroxy-3-methylbutanoate
• 英文别名: metarhizin B；[(1S,2S,4aR,5R,8aR)-5-[(4-hydroxy-5,6-dimethyl-2-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)-2-hydroxy-3-methylbutanoate
• CAS: 1114452-63-9
• 化学式: C₃₂H₄₈O₆
• 分子量: 528.73
• InChiKey: XDYDDEKCBXMMDK-ZZAVWAEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((1S,2S,4aR,5R,8aR)-5-((4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) (R)-2-hydroxy-3-methylbutanoate 在 Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以46%的产率得到((1S,2S,4aR,5R,6R,8aR)-5-((4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a,6-trimethyl-1-(4-methylpentyl)decahydronaphthalen-2-yl) (R)-2-hydroxy-3-methylbutanoate
  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：

  ((1S,2S,4aR,5R,8aR)-5-((4-(methoxymethoxy)-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) (R)-2-acetoxy-3-methylbutanoate 在 sodium methylate 、 Dowex 50W (H+ form) 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以63%的产率得到((1S,2S,4aR,5R,8aR)-5-((4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) (R)-2-hydroxy-3-methylbutanoate
  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

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.