6''-O-trans-sinapoylgenipin gentiobioside | 1421493-47-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6''-O-trans-sinapoylgenipin gentiobioside
• 英文别名: methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 1421493-47-1
• 化学式: C₃₂H₄₀O₁₈
• 分子量: 712.659
• InChiKey: CSRRWPAMFHNUSX-DALANRPMSA-N

物化性质

• 沸点：
  996.7±65.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  281
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  6''-O-trans-sinapoylgenipin gentiobioside 在 盐酸 、 水 作用下， 反应 2.0h， 生成 可得然胶
  参考文献：
  名称：

  Chemical constituents from the fruit of Gardenia jasminoides and their inhibitory effects on nitric oxide production

  摘要：

  Three new iridoid glycosides, 6 ''-O-trans-caffeoylgenipin gentiobioside (1), genipin 1-O-beta-D-apiofuranosyl (1 -> 6)-beta-D-glucopyranoside (2), genipin 1-O-alpha-D-xylopyranosyl (1 -> 6)-beta-D-glucopyranoside (3), three new monocyclic monoterpenoids, jasminoside R (4), jasminoside S (5), jasminoside T (6), together with nine known iridoid glycosides (7-15) and three crocetin glycosides (16-18), were isolated from the fruit of Gardeniajasminoides. Their chemical structures were established mainly by 1D and 2D NMR techniques and mass spectrometry. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 8 and 18 showed strong inhibitory activity on NO production with IC50 values of 11.14 +/- 0.67 and 5.99 +/- 0.54 mu M, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.099

文献信息

• Chemical constituents from the fruit of Gardenia jasminoides and their inhibitory effects on nitric oxide production
  作者：Kaifeng Peng、Liguo Yang、Shizhe Zhao、Lixia Chen、Feng Zhao、Feng Qiu

  DOI：10.1016/j.bmcl.2012.11.099

  日期：2013.2

  Three new iridoid glycosides, 6 ''-O-trans-caffeoylgenipin gentiobioside (1), genipin 1-O-beta-D-apiofuranosyl (1 -> 6)-beta-D-glucopyranoside (2), genipin 1-O-alpha-D-xylopyranosyl (1 -> 6)-beta-D-glucopyranoside (3), three new monocyclic monoterpenoids, jasminoside R (4), jasminoside S (5), jasminoside T (6), together with nine known iridoid glycosides (7-15) and three crocetin glycosides (16-18), were isolated from the fruit of Gardeniajasminoides. Their chemical structures were established mainly by 1D and 2D NMR techniques and mass spectrometry. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 8 and 18 showed strong inhibitory activity on NO production with IC50 values of 11.14 +/- 0.67 and 5.99 +/- 0.54 mu M, respectively. (C) 2012 Elsevier Ltd. All rights reserved.