macaoside N

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: macaoside N
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(1R,2S,4S,6R,7S,8R,9S,12S,13R,16S,18S,19S)-6,19-dihydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₄₅H₇₆O₁₉
• 分子量: 921.087
• InChiKey: HWJIWDPYZVHRPJ-NMUPNISHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  64
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  macaoside N 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Anti-Inflammatory Spirostanol and Furostanol Saponins from Solanum macaonense

  摘要：

  Eight new spirostanol saponins, macaosides A-H (1-8), and 10 new furostanol saponins, macaosides I-R (9-18), together with six known spirostanol compounds (19-24) were isolated from Solanum macaonense. The structures of the new compounds were determined from their spectroscopic data, and the compounds were tested for in vitro antineutrophilic inflammatory activity. It was found that both immediate inflammation responses including superoxide anion generation and elastase release were significantly inhibited by treatment with compounds 20, 21, and 24 (superoxide anion generation: IC50 7.0, 7.6, 4.0 μM; elastase release: IC50 3.7, 4.4, 1.0 μM, respectively). However, compounds 1 and 4 exhibited effects on the inhibition of elastase release only, with IC50 values of 3.2 and 4.2 μM, respectively, while 19 was active against superoxide anion generation only, with an IC50 value of 6.1 μM. Accordingly, spirostanols may be promising lead compounds for further neutrophilic inflammatory disease studies.

  DOI：

  10.1021/np500057b

文献信息

• Anti-Inflammatory Spirostanol and Furostanol Saponins from <i>Solanum macaonense</i>
  作者：Chia-Lin Lee、Tsong-Long Hwang、Juan-Cheng Yang、Hao-Ting Cheng、Wan-Jung He、Chiao-Ting Yen、Chao-Lin Kuo、Chao-Jung Chen、Wen-Yi Chang、Yang-Chang Wu

  DOI：10.1021/np500057b

  日期：2014.8.22

  Eight new spirostanol saponins, macaosides A-H (1-8), and 10 new furostanol saponins, macaosides I-R (9-18), together with six known spirostanol compounds (19-24) were isolated from Solanum macaonense. The structures of the new compounds were determined from their spectroscopic data, and the compounds were tested for in vitro antineutrophilic inflammatory activity. It was found that both immediate inflammation responses including superoxide anion generation and elastase release were significantly inhibited by treatment with compounds 20, 21, and 24 (superoxide anion generation: IC50 7.0, 7.6, 4.0 μM; elastase release: IC50 3.7, 4.4, 1.0 μM, respectively). However, compounds 1 and 4 exhibited effects on the inhibition of elastase release only, with IC50 values of 3.2 and 4.2 μM, respectively, while 19 was active against superoxide anion generation only, with an IC50 value of 6.1 μM. Accordingly, spirostanols may be promising lead compounds for further neutrophilic inflammatory disease studies.