13-hydroxylobolide | 77965-81-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 13-hydroxylobolide
• 英文别名: 20-O-acetyl-sinularolide B；(7E,11E)-18-acetoxy-3,4-epoxy-13β-hydroxy-7,11,15(17)-cembratrien-16,14-olide；[(1R,3R,5S,8E,12E,14R,15R)-14-hydroxy-9,13-dimethyl-18-methylidene-17-oxo-4,16-dioxatricyclo[13.3.0.03,5]octadeca-8,12-dien-5-yl]methyl acetate
• CAS: 77965-81-2
• 化学式: C₂₂H₃₀O₆
• 分子量: 390.477
• InChiKey: KORREFUCEHZSEK-VKZBYXBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  13-hydroxylobolide 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 以0.6 mg的产率得到
  参考文献：
  名称：

  Durumolides A–E, anti-inflammatory and antibacterial cembranolides from the soft coral Lobophytum durum

  摘要：

  Chemical investigations on the acetone extract of the soft coral Lobophytum durum have afforded five new cembranoids with a trans-fused alpha-methylene-gamma-lactone, durumolides A-E (1, 6, and 8-10), and five previously characterized cembrane-based diterpenoids (2-5 and 7). The Structures of the isolated metabolites were elucidated through extensive spectroscopic analyses, while the relative stereochemistry of 4 was confirmed by X-ray diffraction analyses. Moreover, the absolute configurations of 3-5 and 8 were established by application of modified Mosher's method. The anti-inflammatory effects, antibacterial activities, and inhibition assay of HCMV (Human cytomegalovirus) endonuclease activity of these isolated metabolites 1-10 were evaluated in Vitro. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.104

文献信息

• Structural and Stereochemical Studies of α-Methylene-γ-lactone-Bearing Cembrane Diterpenoids from a South China Sea Soft Coral <i>Lobophytum crassum</i>
  作者：Wen Zhang、Karsten Krohn、Jian Ding、Ze-Hong Miao、Xiu-Hong Zhou、Si-Han Chen、Gennaro Pescitelli、Piero Salvadori、Tibor Kurtan、Yue-Wei Guo

  DOI：10.1021/np800081p

  日期：2008.6.1

  Lobophytum crassum. Their structures and relative stereochemistry were established by a combination of detailed spectroscopic data analysis and chemical correlations. The structures of 1- 9 were further confirmed by an X-ray diffraction study on a single crystal of sinularolide B (1). The absolute configurations of sinularolide B (1) and presinularolide B (7) were determined by a novel solid-state CD/TDDFT

  四个新的带有α-亚甲基-γ-内酯的天花粉，20-乙酰基芥酸内酯B（6），芥兰醇内酯B（7），3-脱羟基麦角芥内酯B（8）和3-脱羟基20-乙酰基芥兰醇内酯B（9）从南中国海一个软珊瑚牙垢中分离出五个已知的类似物，芥子油苷BE（1-4）和20-乙酰基芥子油C（5）。通过详细的光谱数据分析和化学相关性的结合，确定了它们的结构和相对立体化学。1-9的结构进一步通过对单核苷B（1）的单晶进行X射线衍射研究得到了证实。分别通过新型的固态CD / TDDFT方法和改进的Mosher方法确定了芥子油苷B（1）和芥子油苷B（7）的绝对构型。这项研究还表明，内甲硫氨酸质子（（3）J 1,2）之间的偶联常数随环膜上不同官能团的不同而有很大差异，并且基于该偶联常数确定内酯环融合的立体化学是危险的。在生物测定中，芥子油苷B和C（1和2）以及新的侧柏7和8对肿瘤细胞系A-549和P-388表现出体外细胞毒性。