(22R)-3β-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16β-O-β-D-glucopyranosyl-22-hydroxycholest-5-en-12-one

• 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: (22R)-3β-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16β-O-β-D-glucopyranosyl-22-hydroxycholest-5-en-12-one
• 英文别名: (3S,8R,9S,10R,13S,14S,16S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-16-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,7,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-one
• 化学式: C₄₅H₇₄O₁₈
• 分子量: 903.072
• InChiKey: FEPJISICUMWUQU-WFPMUIGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  63
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (22R)-3β-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16β-O-β-D-glucopyranosyl-22-hydroxycholest-5-en-12-one 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Anti-inflammatory steroids from the rhizomes of Dioscorea septemloba Thunb

  摘要：

  Seven new steroid glycosides, dioscorosides A(1) (1), A(2) (2), B-1 (3), B-2 (4), C-1 (5), C-2 (6), and D (7), together with 22 known ones (8-29) were isolated from the rhizomes of Dioscorea septemloba, their structures were elucidated by chemical and spectroscopic methods. All isolates were evaluated for in vitro anti-inflammatory potential using LPS-stimulated RAW 264.7 murine macrophages. Among, them,, spirostane glycosides 18 and 21-24 exhibited significant inhibition of nitrite production. Moreover, the structure activity relationship was summarized. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.05.007

文献信息

• Anti-inflammatory steroids from the rhizomes of Dioscorea septemloba Thunb
  作者：Yi Zhang、Hai-Yang Yu、Li-Ping Chao、Lu Qu、Jing-Ya Ruan、Yan-Xia Liu、Yong-Zhe Dong、Li-Feng Han、Tao Wang

  DOI：10.1016/j.steroids.2016.05.007

  日期：2016.8

  Seven new steroid glycosides, dioscorosides A(1) (1), A(2) (2), B-1 (3), B-2 (4), C-1 (5), C-2 (6), and D (7), together with 22 known ones (8-29) were isolated from the rhizomes of Dioscorea septemloba, their structures were elucidated by chemical and spectroscopic methods. All isolates were evaluated for in vitro anti-inflammatory potential using LPS-stimulated RAW 264.7 murine macrophages. Among, them,, spirostane glycosides 18 and 21-24 exhibited significant inhibition of nitrite production. Moreover, the structure activity relationship was summarized. (C) 2016 Elsevier Inc. All rights reserved.