(7S,8R)-4,7,9,3′,9′-pentahydroxy-3-methoxy-8,4′-oxyneolignan-3′-O-β-D-glucopyranoside | 1355467-98-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: (7S,8R)-4,7,9,3′,9′-pentahydroxy-3-methoxy-8,4′-oxyneolignan-3′-O-β-D-glucopyranoside
• 英文别名: (7S,8R)-4,7,9,3',9'-pentahydroxy-3-methoxyl-8,4'-oxyneolignan-3'-O-β-D-glucopyranoside；(7S,8R)-4,7,9,3',9'-pentahydroxy-3-methoxy-8,4'-oxyneolignan-3'-O-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[2-[(1S,2R)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-5-(3-hydroxypropyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1355467-98-9
• 化学式: C₂₅H₃₄O₁₂
• 分子量: 526.538
• InChiKey: XFMPEFQVKDOPPT-WEBCYTPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (7S,8R)-4,7,9,3′,9′-pentahydroxy-3-methoxy-8,4′-oxyneolignan-3′-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 葡萄糖
  参考文献：
  名称：

  Lignans from the Root of Rhodiola crenulata

  摘要：

  Rhodiola crenulata L. is an important species in genus Rhodiola widely used as a health food to reinforce immunity, improve memory and learning, scavenge active-oxygen species, and relieve altitude sickness. Eleven new lignans and a new benzonitrile compound, crenulatanoside A, were isolated from the roots of R. crenulata L. along with 25 known compounds, including 12 lignans. The structures of these compounds were elucidated by spectroscopic data and chemical evidence. Among them, compounds 1-4 and 5-7 were determined to be optical isomers of two 8-O-4' neolignan glycosides. Compounds 8-11 were aryl tetralin type lignans, and compounds 12 and 13 were dihydrobenzofuran neolignans. All of the isolated compounds were evaluated for their inhibitory activity against a-glucosidase. From the data obtained, compound 37 showed strong inhibitory activity against alpha-glucosidase with an IC50 value of 96.8 mu M.

  DOI：

  10.1021/jf204660c

文献信息

• Lignans from the Root of <i>Rhodiola crenulata</i>
  作者：Ya-nan Yang、Zhao-zhen Liu、Zi-ming Feng、Jian-shuang Jiang、Pei-cheng Zhang

  DOI：10.1021/jf204660c

  日期：2012.2.1

  Rhodiola crenulata L. is an important species in genus Rhodiola widely used as a health food to reinforce immunity, improve memory and learning, scavenge active-oxygen species, and relieve altitude sickness. Eleven new lignans and a new benzonitrile compound, crenulatanoside A, were isolated from the roots of R. crenulata L. along with 25 known compounds, including 12 lignans. The structures of these compounds were elucidated by spectroscopic data and chemical evidence. Among them, compounds 1-4 and 5-7 were determined to be optical isomers of two 8-O-4' neolignan glycosides. Compounds 8-11 were aryl tetralin type lignans, and compounds 12 and 13 were dihydrobenzofuran neolignans. All of the isolated compounds were evaluated for their inhibitory activity against a-glucosidase. From the data obtained, compound 37 showed strong inhibitory activity against alpha-glucosidase with an IC50 value of 96.8 mu M.