atractyligenin | 10391-47-6

• 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: atractyligenin
• 英文别名: 18-nor-ent-kaurane；(4aR)-2c.7t-Dihydroxy-11bt-methyl-8-methylen-(4arH.11acH)-tetradecahydro-6at.9t-methano-cyclohepta[a]naphthalin-carbonsaeure-(4t)；(10R)-2β.15α-Dihydroxy-18-nor-kauren-(16)-saeure-(19)；(-)-Atractyligenin；(1R,4R,5R,7R,9R,10S,13R,15S)-7,15-dihydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 10391-47-6
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: YRHWUYVCCPXYMB-JIMOHSCASA-N

物化性质

• 熔点：
  159-164°C
• 沸点：
  515.2±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  乙醇（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  atractyligenin 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 5.22h， 生成 methyl (1'R,4'R,5'R,9'R,10'S,13'R,15'R)-15'-hydroxy-9'-methyl-14'-methylidenespiro[1,3-dioxolane-2,7'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-5'-carboxylate
  参考文献：
  名称：

  Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

  摘要：

  Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 mu M, respectively. These two 1-analogues are promising lead compounds for further investigation.

  DOI：

  10.1021/np060504w
• 作为产物：
  描述：

  ATRACTYLOSIDE POTASSIUM SALT 在 水 、 potassium hydroxide 作用下， 反应 6.0h， 以84%的产率得到atractyligenin
  参考文献：
  名称：

  Structural Characterization and Antimicrobial Evaluation of Atractyloside, Atractyligenin, and 15-Didehydroatractyligenin Methyl Ester

  摘要：

  We report the first complete structure elucidation of the ent-kaurane diterpenoid glycoside atractyloside (1) by means of NMR and X-ray diffractometry techniques. Extensive one- and two-dimensional NMR experiments were employed to assign the proton and carbon signals of 1, and crystallography experiments established the configurations of all stereogenic centers. Furthermore, we present a novel semisynthetic route for the preparation of the highly cytotoxic aglycone derivative of 1, 15-didehydroatractyligenin methyl ester (3). All compounds were tested for their antibiotic activity against Enterococcus faecalis, Escherichia coli, and several strains of Staphylococcus aureus, including fluoroquinolone-resistant (SA1199B) and two epidemic MRSA (EMRSA-15 and -16) strains. Compound 3 exhibited moderate activity against all of the Staph. aureus strains with an MIC value of 128 mg/L.

  DOI：

  10.1021/np300080w

文献信息

• Inunicosides A−K, rare polyacylated ent-kaurane diterpenoid glycosides from the flowers of Inula japonica
  作者：Zhi-Pu Yu、Jin-Hai Yu、Jun-Sheng Zhang、Shu-Juan Yu、Hua Zhang

  DOI：10.1016/j.tet.2019.130732

  日期：2019.12

  Inunicosides A−K (1–11), eleven unusual polyacylated ent-kaurane diterpenoid glycosides, were isolated from the flowers of a traditional Chinese herbal plant Inula japonica. Their structures with absolute configurations were determined on the basis of comprehensive spectroscopic analyses, chemical degradation, enzymatic hydrolysis and ECD experiments. Among these isolates, inunicoside K (11) showed

  Inunicosides A-K（1-11）是从传统中草药植物旋覆花（Inula japonica）的花朵中分离出的十一种不寻常的多酰化对映体-月桂烷双萜类糖苷。在全面的光谱分析，化学降解，酶水解和ECD实验的基础上确定了它们具有绝对构型的结构。在这些分离株中，inunicoside K（11）对金黄色葡萄球菌ATCC 25923表现出温和的抗菌活性。在Inula物种中几乎没有二萜成分的报道，因此发现这组化合物极大地丰富了Inula属代谢产物的化学多样性。。
• Enzyme-Catalysed Transformations ofent-Kaurane Diterpenoids
  作者：Leandro N. Monsalve、Sergio Rosselli、Maurizio Bruno、Alicia Baldessari

  DOI：10.1002/ejoc.200400862

  日期：2005.5

  Nicolas. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Oficina de Coordinacion Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos en Quimica Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos en Quimica Organica; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales

  菲尔：蒙萨尔维，莱安德罗·尼古拉斯。Consejo Nacional de Investigaciones Cientificas y Tecnicas。Oficina de Coordinacion Administrativa Ciudad Universitaria。Unidad de Microanalisis y Metodos Fisicos en Quimica Organica。布宜诺斯艾利斯大学。Facultad de Ciencias Exactas y Naturales。Unidad de Microanalisis y Metodos Fisicos en Quimica Organica；阿根廷。布宜诺斯艾利斯大学。Facultad de Ciencias Exactas y Naturales。Departamento de Quimica Organica;
• Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement
  作者：Natale Badalamenti、Alessandro Vaglica、Antonella Maggio、Maurizio Bruno、Luana Quassinti、Massimo Bramucci、Filippo Maggi

  DOI：10.1016/j.phytochem.2022.113435

  日期：2022.12

  active with IC50 values of 0.427 and 0.723 μM against A375 melanoma cell line. Excellent results were also obtained against the colon cancer cell line CaCo2, with slightly lower antiproliferative activity. An interesting extension of the study should be to analyze the atractyligenin derivatives also as target for human melanoma and human colon cancer cells.

  对白术苷、羧义白菜苷、它们的苷分配白术绿素和几种合成衍生物进行了测试，发现对一组人类肿瘤细胞系具有活性。白术木红素经氧化、溴化和消除反应，得到几种化合物。通过从 3β-溴-2,15-二酮苍术木质素甲酯开始的化学重排合成单一骨架。合成的化合物对所有测试的细胞系均具有活性。特别是，15-酮苍术木根素甲酯和 3β-溴-2,15-二酮苍术木根素甲酯对 A375 黑色素瘤细胞系的 IC50 值为 0.427 和 0.723 μM。对结肠癌细胞系 CaCo2 也获得了极好的结果，抗增殖活性略低。该研究的一个有趣的扩展应该是分析白术木素衍生物也作为人类黑色素瘤和人类结肠癌细胞的靶标。
• Ajello,T. et al., Gazzetta Chimica Italiana, 1963, vol. 93, p. 867 - 915
  作者：Ajello,T. et al.

  DOI：——

  日期：——
• Ajello, Gazzetta Chimica Italiana, 1934, vol. 64, p. 938,940, 944
  作者：Ajello

  DOI：——

  日期：——