去乙酰氧母菊素 | 17946-87-1

• 物质功能分类: 天然产物 - 倍半萜
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 去乙酰氧母菊素
• 中文别名: (3S,3AS,9AS,9BS)-3,3A,4,5,9A,9B-六氢-3,6,9-三甲基并[4,5-B]呋喃-2,7-二酮；(3S,3aS,9aS,9bS)-3,3a,4,5,9a,9b-六氢-3,6,9-三甲基薁并[4,5-b]呋喃-2,7-二酮
• 英文名称: leucodin
• 英文别名: leucodine；leukodin；leucomisine；Desacetoxymatricarin；(3S,3aS,9aS,9bS)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• CAS: 17946-87-1
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: BJPSSVHNEGMBDQ-NUZBWSBOSA-N

物化性质

• 熔点：
  208℃
• 比旋光度：
  D24 +52.5° (c = 1 in chloroform)
• 沸点：
  436.2±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• LogP：
  1.920 (est)
• 碰撞截面：
  154.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  去乙酰氧母菊素 在 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以32 mg的产率得到1α,10α-epoxydesacetoxymatricarin
  参考文献：
  名称：

  Sesquiterpene lactones from Achillea abrotanoides

  摘要：

  DOI：

  10.1016/s0031-9422(00)97843-9
• 作为产物：
  描述：

  (3aS,9aS,9bS)-6,9-二甲基-3-亚甲基-4,5,9a,9b-四氢-3aH-薁并[5,4-d]呋喃-2,7-二酮 在 sodium tetrahydroborate 作用下， 生成 achillin 、 去乙酰氧母菊素
  参考文献：
  名称：

  The effect of dehydroleucodine in adipocyte differentiation

  摘要：

  Dehydroleucodine (DhL) is a sesquiterpene lactone of the guaianolide group with gastric cytoprotective activity. Recent studies have also demonstrated that DhL inhibits the proliferation of vascular smooth muscle cells. In this study we examined the effect of DhL in the differentiation of 3T3-L1 preadipocytes. The addition of DhL significantly inhibited the differentiation of 3T3-L1 preadipocytes along with a significant decrease in the accumulation of lipid content by a dramatic downregulation of the expression of adipogenic-specific transcriptional factors PPAR gamma and C-EBP alpha. However, phosphorylation of AMPK alpha, Erk1/2 and Akt1 was not inhibited by DhL treatment. Interestingly, we also found that 11,13-dihydrodehydroleucodine, a derivative of DhL with inactivated alpha-methylene-gamma-lactone function, also inhibited the differentiation of 3T3-L1 preadipocytes. Taken together, these data suggest that DhL has an important inhibitory effect in cellular pathways regulating adipocyte differentiation by modulating the PPAR gamma expression, which is known to play a pivotal role during adipogenesis. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2011.09.033

文献信息

• Plant enzymes for bioconversion
  申请人：Bouwmeester Jan Hendrik

  公开号：US20050019882A1

  公开（公告）日：2005-01-27

  The invention provides the use of enzymes derived from plants in biocatalysis. The regio- and stercoselective introduction of an oxygen group into an unactivated organic compound is still a largely unresolved challenge to organic chemistry (Faber, 2000). We have shown that enzymes of Asteraceae species are capable of converting with high regio- and stereospecificity for example sesquiterpene olefins to commercially interesting products.

  本发明提供了植物来源酶在生物催化中的应用。将氧基引入未活化有机化合物中的区域和立体选择性仍然是有机化学中一个基本未解决的挑战（Faber，2000）。我们已经证明，菊科物种的酶能够高度区域和立体特异性地将倍半萜烯烃等转化为商业上有趣的产物。
• Reduction of the natural sesquiterpene lactone leucomisin
  作者：A. B. Plutno、I. D. Sham'yanov、G. G. Galust'yan

  DOI：10.1007/bf01167572

  日期：1995.1
• STEFANOVIC, M.;DJERMANOVIC, V.;GORUNVIC, M., PHYTOCHEMISTRY, 28,(1989) N, C. 1765-1767
  作者：STEFANOVIC, M.、DJERMANOVIC, V.、GORUNVIC, M.

  DOI：——

  日期：——
• The effect of dehydroleucodine in adipocyte differentiation
  作者：Adriana Galvis、Adriana Marcano、Chad Stefancin、Nicole Villaverde、Horacio A. Priestap、Carlos E. Tonn、Luis A. Lopez、Manuel A. Barbieri

  DOI：10.1016/j.ejphar.2011.09.033

  日期：2011.12

  Dehydroleucodine (DhL) is a sesquiterpene lactone of the guaianolide group with gastric cytoprotective activity. Recent studies have also demonstrated that DhL inhibits the proliferation of vascular smooth muscle cells. In this study we examined the effect of DhL in the differentiation of 3T3-L1 preadipocytes. The addition of DhL significantly inhibited the differentiation of 3T3-L1 preadipocytes along with a significant decrease in the accumulation of lipid content by a dramatic downregulation of the expression of adipogenic-specific transcriptional factors PPAR gamma and C-EBP alpha. However, phosphorylation of AMPK alpha, Erk1/2 and Akt1 was not inhibited by DhL treatment. Interestingly, we also found that 11,13-dihydrodehydroleucodine, a derivative of DhL with inactivated alpha-methylene-gamma-lactone function, also inhibited the differentiation of 3T3-L1 preadipocytes. Taken together, these data suggest that DhL has an important inhibitory effect in cellular pathways regulating adipocyte differentiation by modulating the PPAR gamma expression, which is known to play a pivotal role during adipogenesis. (C) 2011 Elsevier B.V. All rights reserved.
• Sesquiterpene lactones from Achillea abrotanoides
  作者：Milutin Stefanović、Verica Djermanović、Momčilo Gorunvić、Miodrag Djermanović、Slobodan Macura、Slobodan Milosavljević

  DOI：10.1016/s0031-9422(00)97843-9

  日期：1989.1