10,12-dihydroxypicrotoxane 10,12-di-O-β-D-glucopyranoside

• 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: 10,12-dihydroxypicrotoxane 10,12-di-O-β-D-glucopyranoside
• 英文别名: dendronobiloside A；dendronobiloside B；(2R,3R,4S,5S,6R)-2-[[(1S,3aR,4R,5R,7aS)-7a-methyl-5-propan-2-yl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₇H₄₈O₁₂
• 分子量: 564.671
• InChiKey: BZZQPBIRQSCVAL-QSTLOTDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  10,12-dihydroxypicrotoxane 10,12-di-O-β-D-glucopyranoside 在 β-cellulase 、 水 作用下， 反应 168.0h， 以3 mg的产率得到[(1S,3aR,4R,5R,7aS)-4-(hydroxymethyl)-7a-methyl-5-propan-2-yl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]methanol
  参考文献：
  名称：

  Three New Sesquiterpene Glycosides from Dendrobium nobile with Immunomodulatory Activity

  摘要：

  Dendroside A (1) and dendronobilosides A and B (2 and 3), three new sesquiterpene glycosides, have been isolated from the stems of Dendrobium nobile, a plant used in Chinese traditional medicine. Their structures and stereochemistry were determined as 10 beta ,12,14-trihdroxyalloaromadendrane 14-O-beta -D-glucopyranoside (1), 10,12-dihydroxypicrotoxane 10,12-di-O-beta -D-glucopyranoside (2), and 6a,10,12-trihydroxypicrotoxane 10-O-beta -D-glucopyranoside (3), respectively, on the basis of spectroscopic and chemical methods. Quantum chemistry calculations were used in support of the structural determination of 1. Compounds 1 and 2 were found to stimulate the proliferation of murine T and B lymphocytes in vitro, while compound 3 showed inhibitory activity in this same assay.

  DOI：

  10.1021/np0102612

文献信息

• Three New Sesquiterpene Glycosides from <i>Dendrobium </i><i>n</i><i>obile </i>with Immunomodulatory Activity
  作者：Weimin Zhao、Qinghua Ye、Xiaojian Tan、Hualiang Jiang、Xiaoyu Li、Kaixian Chen、A. Douglas Kinghorn

  DOI：10.1021/np0102612

  日期：2001.9.1

  Dendroside A (1) and dendronobilosides A and B (2 and 3), three new sesquiterpene glycosides, have been isolated from the stems of Dendrobium nobile, a plant used in Chinese traditional medicine. Their structures and stereochemistry were determined as 10 beta ,12,14-trihdroxyalloaromadendrane 14-O-beta -D-glucopyranoside (1), 10,12-dihydroxypicrotoxane 10,12-di-O-beta -D-glucopyranoside (2), and 6a,10,12-trihydroxypicrotoxane 10-O-beta -D-glucopyranoside (3), respectively, on the basis of spectroscopic and chemical methods. Quantum chemistry calculations were used in support of the structural determination of 1. Compounds 1 and 2 were found to stimulate the proliferation of murine T and B lymphocytes in vitro, while compound 3 showed inhibitory activity in this same assay.