gorgonolide

• 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: gorgonolide
• 英文别名: (1S,3R,6S,7S,10S)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-11-ene-8,13-dione
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: RUBXBCDKYAQXTM-IAJDZVHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  gorgonolide 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以72%的产率得到1α(S),10α(R)-dihydroxy-3-oxo-11β(S)H-4-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
• 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 11.0h， 生成 gorgonolide
  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

• Sesquiterpene lactones from the endemic Cape Verdean Artemisia gorgonum
  作者：Risoleta Ortet、Soizic Prado、Elisabeth Mouray、Olivier P. Thomas

  DOI：10.1016/j.phytochem.2008.09.022

  日期：2008.12

  Leaves and flowers of Artemisia gorgonum (Asteraceae) collected in Fogo, Cape Verde islands, were phytochemically investigated and resulted in isolation and characterization of three guaianolides 1, 2, 5, and a secoguainolide 4, in addition to eight known guaianolides 6-11 and two known germacranolides 12, 13. Structures were elucidated by 1D and 2D NMR experiments. Careful examination of the (13)C

  在佛得角群岛 Fogo 收集的蒿属植物（菊科）的叶和花进行了植物化学研究，结果分离和表征了三种愈创木酚内酯 1、2、5 和 secoguainolide 4，以及八种已知的愈创木酚内酯 6-11 和两种已知的germacranolides 12, 13。通过一维和二维核磁共振实验阐明了结构。仔细检查 (13)C NMR 光谱导致将先前描述的愈创木酚内酯的结构从 2 修正为 3。大多数化合物表现出温和的抗疟原虫活性，ridentin (13) 是最有趣的，IC(50) 为 3.8+ /-0.7microgml(-1) 对抗恶性疟原虫 FcB1 和 vero 细胞系中的弱细胞毒性 (IC(50) 71.0+/-3.9microgml(-1))。
• 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.