annulohypoxyloside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: annulohypoxyloside
• 英文别名: (3R)-6-hydroxy-8-methoxy-3-methylisochroman 7-O-α-D-ribofuranose；(2R,3R,4S,5R)-2-[[(3R)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-1H-isochromen-7-yl]oxy]-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₆H₂₂O₈
• 分子量: 342.346
• InChiKey: BGUPHPAXCFTSCP-PCMRRQHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  annulohypoxyloside 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以0.7 mg的产率得到D-核糖
  参考文献：
  名称：

  Isochromans and Related Constituents from the Endophytic Fungus Annulohypoxylon truncatum of Zizania caduciflora and Their Anti-Inflammatory Effects

  摘要：

  Six new isochroman derivatives (annulohypoxylomans A-C, 1-3; annulohypoxylomanols A and B, 6 and 7; and annulohypoxyloside, 8), isocoumarin (annulohypoxylomarin A, 4), and an azaphilone derivative (xylariphilone, 5) were isolated from an ethyl acetate extract derived from cultures of the endophytic fungus JS540 found in the leaves of Zizania caduciflora. The JS540 strain was identified as Annulohypoxylon truncatum. The structures of the isolated compounds were elucidated by one-and two-dimensional nuclear magnetic resonance and mass spectrometry and by comparison with related compounds from the literature. The anti-inflammatory activities of the isolated compounds were evaluated in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells. Xylariphilone (5) exhibited significant inhibitory effects on LPS-induced interleukin (IL)-6, IL-12 p40, and tumor necrosis factor (TNF)-alpha production with IC50 value, of 5.3, 19.4, and 37.6 mu M, respectively.

  DOI：

  10.1021/acs.jnatprod.6b00698

文献信息

• Isochromans and Related Constituents from the Endophytic Fungus <i>Annulohypoxylon truncatum</i> of <i>Zizania caduciflora</i> and Their Anti-Inflammatory Effects
  作者：Wei Li、Changyeol Lee、Sung Hee Bang、Jin Yeul Ma、Soonok Kim、Young-Sang Koh、Sang Hee Shim

  DOI：10.1021/acs.jnatprod.6b00698

  日期：2017.1.27

  Six new isochroman derivatives (annulohypoxylomans A-C, 1-3; annulohypoxylomanols A and B, 6 and 7; and annulohypoxyloside, 8), isocoumarin (annulohypoxylomarin A, 4), and an azaphilone derivative (xylariphilone, 5) were isolated from an ethyl acetate extract derived from cultures of the endophytic fungus JS540 found in the leaves of Zizania caduciflora. The JS540 strain was identified as Annulohypoxylon truncatum. The structures of the isolated compounds were elucidated by one-and two-dimensional nuclear magnetic resonance and mass spectrometry and by comparison with related compounds from the literature. The anti-inflammatory activities of the isolated compounds were evaluated in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells. Xylariphilone (5) exhibited significant inhibitory effects on LPS-induced interleukin (IL)-6, IL-12 p40, and tumor necrosis factor (TNF)-alpha production with IC50 value, of 5.3, 19.4, and 37.6 mu M, respectively.