(2R,3S,5S,6S,7E)-3,6-epoxy-7-megastigmen-9-one-2,5-diol 5-O-β-D-(6'-O-β-D-apiofuranosyl)glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,5S,6S,7E)-3,6-epoxy-7-megastigmen-9-one-2,5-diol 5-O-β-D-(6'-O-β-D-apiofuranosyl)glucopyranoside
• 英文别名: Milbaside B；(E)-4-[(1S,3R,4S,6S)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxy-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]but-3-en-2-one
• 化学式: C₂₄H₃₈O₁₃
• 分子量: 534.558
• InChiKey: BEZDWFCNONZRCV-LKCNFKDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2R,3S,5S,6S,7E)-3,6-epoxy-7-megastigmen-9-one-2,5-diol 5-O-β-D-(6'-O-β-D-apiofuranosyl)glucopyranoside 在 盐酸 、 水 作用下， 反应 3.0h， 生成 葡萄糖 、 D-apiose
  参考文献：
  名称：

  Chemical constituents of Miliusa balansae leaves and inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells

  摘要：

  Methanolic extract of Miliusa balansae Finet et Gagnep exerts an anti-inflammatory effect via inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophage cells. Three new megastigmane glycosides, milbasides A-C (1-3), together with fifteen known compounds (4-18), were isolated from the active fraction. Their chemical structures were elucidated using extensive spectroscopic analyses, including 1D and 2D NMR, HR ESI MS, and CD analysis, as well as comparison with previously reported data. Compounds 1-3, 11 and 14 (20.0 mu M) showed potent inhibitory activities with inhibition values of 98.5 +/- 1.6%, 90.9 +/- 7.8%, 84.8 +/- 3.5%, 91.5 +/- 8.7%, and 91.8 +/- 2.7%, respectively. Our results suggest that megastigmane glycosides from M. balansae leaves may be used to treat inflammatory diseases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.056

文献信息

• Chemical constituents of Miliusa balansae leaves and inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells
  作者：Nguyen Phuong Thao、Bui Thi Thuy Luyen、Bui Huu Tai、Nguyen Manh Cuong、Youn Chul Kim、Chau Van Minh、Young Ho Kim

  DOI：10.1016/j.bmcl.2015.07.056

  日期：2015.9

  Methanolic extract of Miliusa balansae Finet et Gagnep exerts an anti-inflammatory effect via inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophage cells. Three new megastigmane glycosides, milbasides A-C (1-3), together with fifteen known compounds (4-18), were isolated from the active fraction. Their chemical structures were elucidated using extensive spectroscopic analyses, including 1D and 2D NMR, HR ESI MS, and CD analysis, as well as comparison with previously reported data. Compounds 1-3, 11 and 14 (20.0 mu M) showed potent inhibitory activities with inhibition values of 98.5 +/- 1.6%, 90.9 +/- 7.8%, 84.8 +/- 3.5%, 91.5 +/- 8.7%, and 91.8 +/- 2.7%, respectively. Our results suggest that megastigmane glycosides from M. balansae leaves may be used to treat inflammatory diseases. (C) 2015 Elsevier Ltd. All rights reserved.