1β(R),10β(S)-dihydroxy-3-oxo-11β (S)H-4,11(13)-guaien-6α(S),12-olide | 1202791-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1β(R),10β(S)-dihydroxy-3-oxo-11β (S)H-4,11(13)-guaien-6α(S),12-olide
• 英文别名: 1β(R),10β(S)-dihydroxy-3-oxo-11β(S)H-4-guaien-6α(S),12-olide；(3S,3aS,6S,6aR,9bS)-6,6a-dihydroxy-3,6,9-trimethyl-3,3a,4,5,7,9b-hexahydroazuleno[4,5-b]furan-2,8-dione
• CAS: 1202791-95-4
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: OMTYHDHOXQNGSH-ZAHDETNWSA-N

物化性质

• 沸点：
  489.9±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  山道年 在 硫酸 、 水 、 potassium hydrogencarbonate 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 107.0h， 生成 1β(R),10β(S)-dihydroxy-3-oxo-11β (S)H-4,11(13)-guaien-6α(S),12-olide
  参考文献：
  名称：

  Facile Preparation of Bioactiveseco-Guaianolides and Guaianolides fromArtemisia gorgonumand Evaluation of Their Phytotoxicity

  摘要：

  Commercially available santonin was used to synthesize seven sesquiterpene lactones using a fade strategy that involved a high-yielding photochemical reaction. Three natural products from Artemisia gorgonum were synthesized in good yields, and in the case of two compounds, absolute configurations were determined from X-ray quality crystals. The structures previously reported for these compounds were revised. Sesquiterpene lactones were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species, seco-Guaianolide (4) showed higher phytotoxic activities than the known herbicide Logran. This high activity could be due to the presence of a cyclopentenedione ring. These results suggest that compound 4 should be involved in defense of A. gorgorum, displaying a wide range of activities that allow proposing them as new leads for development of a natural herbicide model with a seco-guaianolide skeleton.

  DOI：

  10.1021/np300639b

文献信息

• Iso-<i>seco</i>-tanapartholides: Isolation, Synthesis and Biological Evaluation
  作者：Edward F. Makiyi、Raquel F. M. Frade、Tomas Lebl、Ellis G. Jaffray、Susan E. Cobb、Alan L. Harvey、Alexandra M. Z. Slawin、Ronald T. Hay、Nicholas J. Westwood

  DOI：10.1002/ejoc.200901016

  日期：2009.11

  The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappaB signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of

  描述了天然产物iso-seco-tanapartholide家族中两种植物来源的NF-kappaB信号通路抑制剂的分离，鉴定和总合成。有效反应顺序中的关键步骤是后期的氧化裂解反应，该反应在不存在保护基的情况下进行，直接得到天然产物。合成材料与天然产物样品的详细比较证明是有益的。对合成材料的生物学研究证实，这些化合物在NF-κB信号传导途径中起着晚期作用。（（c）Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，德国，2009年）。
• Facile Preparation of Bioactive<i>seco</i>-Guaianolides and Guaianolides from<i>Artemisia gorgonum</i>and Evaluation of Their Phytotoxicity
  作者：Francisco A. Macías、Alejandro Santana、Azusa Yamahata、Rosa M. Varela、Frank R. Fronczek、José M. G. Molinillo

  DOI：10.1021/np300639b

  日期：2012.11.26

  Commercially available santonin was used to synthesize seven sesquiterpene lactones using a fade strategy that involved a high-yielding photochemical reaction. Three natural products from Artemisia gorgonum were synthesized in good yields, and in the case of two compounds, absolute configurations were determined from X-ray quality crystals. The structures previously reported for these compounds were revised. Sesquiterpene lactones were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species, seco-Guaianolide (4) showed higher phytotoxic activities than the known herbicide Logran. This high activity could be due to the presence of a cyclopentenedione ring. These results suggest that compound 4 should be involved in defense of A. gorgorum, displaying a wide range of activities that allow proposing them as new leads for development of a natural herbicide model with a seco-guaianolide skeleton.