(4aS,7R)-1c-β-D-glucopyranosyloxy-4'-((S)-1-hydroxy-ethyl)-5'-oxo-(4ar,7ac)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid | 132586-69-7

• 物质功能分类: 天然产物 - 环烯醚萜衍生物
• 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: (4aS,7R)-1c-β-D-glucopyranosyloxy-4'-((S)-1-hydroxy-ethyl)-5'-oxo-(4ar,7ac)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid
• 英文别名: (4aS,7R)-1c-β-D-Glucopyranosyloxy-4'-((S)-1-hydroxy-aethyl)-5'-oxo-(4ar,7ac)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carbonsaeure；15-Demethylplumieride；(1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid
• CAS: 132586-69-7
• 化学式: C₂₀H₂₄O₁₂
• 分子量: 456.403
• InChiKey: GGLAWDIODKKBQZ-SZSWQRSVSA-N

物化性质

• 沸点：
  815.5±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (4aS,7R)-1c-β-D-glucopyranosyloxy-4'-((S)-1-hydroxy-ethyl)-5'-oxo-(4ar,7ac)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid 在 吡啶 作用下， 以183 mg的产率得到(1S,4aS,7R,7aS)-4'-[(1S)-1-acetyloxyethyl]-5'-oxo-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid
  参考文献：
  名称：

  Structural Modifications of Plumieride Isolated from Plumeria bicolor and the Effect of These Modifications on in Vitro Anticancer Activity

  摘要：

  Plumieride was isolated as one of the major components from the biologically active methanolic extract of the bark of Plumeria bicolor (family Apocynaceae). For investigating the effect of substituents on cytotoxic activity it was modified into a series of compounds. Replacing the methyl ester functionality of plumieride with alkyl amides of variable carbon units improved the cytotoxic activity, and a correlation between overall lipophilicity and cytotoxic activity was observed. In plumieride, the glucose moiety was converted into a di- and trisaccharide by following the protection and deprotection approach, and the resulting compounds produced enhanced cytotoxicity. However, these compounds were found to be less effective than plumeiride containing a dodecyl (12 carbon units) amide group. Among all of the derivatives, the naturally occurring plumieride showed the least cytotoxicity (50% cell kill = 49.5 mug/mL), and the dodecyl amide analogue of plumieridepentaacetate produced the best efficacy (50% cell kill = 11.8 mug/mL). The di- and trisaccharide analogues were found to be slightly less effective than the dodecyl derivative (50% cell kill = 15-17 mug/mL). The in vitro cytotoxicity of the plumieride analogues was determined in radiation-induced fibrosarcoma (RIF) tumor cells.

  DOI：

  10.1021/jo0491408
• 作为产物：
  描述：

  鸡蛋花甙 在 barium dihydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以86%的产率得到(4aS,7R)-1c-β-D-glucopyranosyloxy-4'-((S)-1-hydroxy-ethyl)-5'-oxo-(4ar,7ac)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid
  参考文献：
  名称：

  Structural Modifications of Plumieride Isolated from Plumeria bicolor and the Effect of These Modifications on in Vitro Anticancer Activity

  摘要：

  Plumieride was isolated as one of the major components from the biologically active methanolic extract of the bark of Plumeria bicolor (family Apocynaceae). For investigating the effect of substituents on cytotoxic activity it was modified into a series of compounds. Replacing the methyl ester functionality of plumieride with alkyl amides of variable carbon units improved the cytotoxic activity, and a correlation between overall lipophilicity and cytotoxic activity was observed. In plumieride, the glucose moiety was converted into a di- and trisaccharide by following the protection and deprotection approach, and the resulting compounds produced enhanced cytotoxicity. However, these compounds were found to be less effective than plumeiride containing a dodecyl (12 carbon units) amide group. Among all of the derivatives, the naturally occurring plumieride showed the least cytotoxicity (50% cell kill = 49.5 mug/mL), and the dodecyl amide analogue of plumieridepentaacetate produced the best efficacy (50% cell kill = 11.8 mug/mL). The di- and trisaccharide analogues were found to be slightly less effective than the dodecyl derivative (50% cell kill = 15-17 mug/mL). The in vitro cytotoxicity of the plumieride analogues was determined in radiation-induced fibrosarcoma (RIF) tumor cells.

  DOI：

  10.1021/jo0491408

文献信息

• Zur Kenntnis des Plumierids. 1. Mitteilung
  作者：H. Schmid、H. Bickel、Th. M. Meijer

  DOI：10.1002/hlca.19520350154

  日期：1952.2.1

  einen α, β-ungesättigten Lactonring und eine, vermutlich α, β-ungesättigte Methylester-Gruppierung. Die Funktion des 7. O-Atoms blieb unabgeklärt. Die erste der erwähnten Doppelbindungen liess sich durch BrOCH3, die zweite durch milde katalytische Hydrierung absättigen. Bei energischer Hydrierung entstand Hexahydro-desoxy-plumierid, das als Tetraacetat gefasst wurde. Bei Versuchen, den Zucker aus Plumierid

  葡糖苷类羽黄具有分子式C 21 H 28（26） O 12。在糖苷配基部分中，它含有可酰化的羟基，一个α，β-不饱和内酯环和一个可能的α，β-不饱和甲基酯基。第7个O原子的功能尚不清楚。提到的第一个双键可能被BrOCH 3饱和，第二个被温和的催化氢化所饱和。剧烈氢化得到六氢-脱氧-溴化物，其被认为是四乙酸盐。试图将糖从plum啶或二氢-啶中分离出来，糖苷配基被严重破坏。
• Zur Kenntnis des Plumierids
  作者：F. Wessely、K. Geiger、F. Kallab

  DOI：10.1007/bf00897734

  日期：——