6-(β-D-xylopyranosyloxy)-2,6-dimethyl-[S,(E)]-2,7-octadienoic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(β-D-xylopyranosyloxy)-2,6-dimethyl-[S,(E)]-2,7-octadienoic acid
• 英文别名: (6S)-menthiafolic acid 6-O-β-D-xyloside；(6S)-2-trans-6-O-β-D-xylopyranosyl-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid；(2E,6S)-2,6-dimethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyocta-2,7-dienoic acid
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: SUXYTSNUWGRMRJ-DHPDYHBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-[(O-α-L-arabinopyranosyl-(1→2)-O-α-L-arabinopyranosyl-(1→6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl)oxy]-(3β)-olean-12-en-28-oic acid O-β-D-xylopyranosyl-(1→3)-O-β-D-xylopyranosyl-(1→4)-O-[β-D-glucopyranosyl-(1→3)]-O-6-deoxy-α-L-mannopyranosyl-(1→2)-6-O-[(2E,6S)-6-[[2-O-[(2E,6S)-6-[[6-deoxy-2-O-[(2E,6S)-2,6-dimethyl-1-oxo-6-(β-D-xylopyranosyloxy)-2,7-octadienyl]-β-D-glucopyranosyl]oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-β-D-xylopyranosyl]oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-β-D-glucopyranosyl ester 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以1.8 mg的产率得到6-(6-deoxy-β-D-glucopyranosyloxy)-2,6-dimethyl[S-(E)]-2,7-octadienoic acid
  参考文献：
  名称：

  一种来自Calliandra pulcherrima的新型复合三萜皂苷，具有溶血活性和辅助作用

  摘要：

  通过色谱法从Calliandra pulcherrima的叶片中分离出一种新的复杂的三萜皂苷。根据化学证据，对已知化合物进行光谱分析和比较，确定其结构为3-[（O- α - l-阿拉伯吡喃糖基- （1→2）-O- α - l-阿拉伯吡喃糖基-（1→6） -2-（乙酰基氨基）-2-脱氧β - d吡喃葡萄糖基）氧基] - （3- β）-olean -12-烯-28-酸O- β - d -xylopyranosyl-（1→3）-O - β - d -xylopyranosyl-（1→4）-O - [（β - d-吡喃葡萄糖基- （1→3）]-O-6-脱氧-α - 1-甘露吡喃糖基- （1→2）-6-O-[（2E，6S）-6-[[2-O-[（2E ，6S）-6-[[[6-脱氧-2-O-[（2E，6S）-2,6-二甲基-1-氧代-6-（β - d-吡喃吡喃糖基氧基）-2,7-辛二烯基]- β - d-吡喃葡萄糖基]氧基]

  DOI：

  10.1016/j.phytol.2013.08.009

文献信息

• Studies on the Constituents of Calliandra anomala (KUNTH) MACBR. I. Structure Elucidation of Two Acylated Triterpenoidal Saponins.
  作者：Tadahiro TAKEDA、Takatoshi NAKAMURA、Shigeki TAKASHIMA、Osamu YANO、Yukio OGIHARA

  DOI：10.1248/cpb.41.2132

  日期：——

  Two novel triterpenoidal saponins, called calliandra saponins A and E, were isolated from the branches of Calliandra anomala (KUNTH) MACBR. On the basis of the chemical and physicochemical evidence, their structures were defined as 3-O-α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranosyl echinocystic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-[(6S)-2-trans-2, 6-dimethyl-6-O-β-D-xylopyranosyl-2, 7-octadienoyl-(1→6)]-β-D-glucopyranosyl} ester (4) and 3-O-α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranosyl echinocystic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyransoyl-(1→2)-[(6'S)-2'-trans-2', 6'-dimethyl-6'-O-(2-O-(6S)-2-trans-2, 6-dimethyl-6-hydroxy-2, 7-octadienoyl)-β-D-xylopyranosyl-2', 7'-octadienoyl-(1→6)-β-D-glucopyranosyl} ester (5), respectively.

  从Calliandra anomala (KUNTH) MACBR的枝条中分离出了两种新的三萜类皂苷，即Calliandra皂苷A和E。根据化学和物理化学证据、根据化学和理化证据，它们的结构被定义为 3-O-α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranosyl echinocystic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-[(6S)-2-trans-2,6-二甲基-6-O-β-D-吡喃木糖基-2、7-辛二烯酰-(1→6)]-β-D-吡喃葡萄糖}酯 (4) 和 3-O-α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-葡吡喃糖基棘皮囊酸 28-O-β-D-吡喃葡萄糖基-(1→3)-[β-D-吡喃木糖基-(1→3)-β-D-吡喃木糖基-(1→4)]-α-L-鼠李糖基-(1→2)-[(6'S)-2'-反式-2'、6'-二甲基-6'-O-(2-O-(6S)-2-反式-2, 6-二甲基-6-羟基-2, 7-辛二烯酰)-β-D-鼠李糖基-2', 7'-辛二烯酰-(1→6)-β-D-吡喃葡萄糖}酯 (5)。
• A new complex triterpenoid saponin from Calliandra pulcherrima with haemolytic activity and adjuvant effect
  作者：Bernadete Pereira da Silva、José Paz Parente

  DOI：10.1016/j.phytol.2013.08.009

  日期：2013.11

  compounds its structure was established as 3-[(O-α-l-arabinopyranosyl-(1 → 2)-O-α-l-arabinopyranosyl-(1 → 6)-2-(acetylamino)-2-deoxy-β-d-glucopyranosyl)oxy]-(3β)-olean-12-en-28-oic acid O-β-d-xylopyranosyl-(1 → 3)-O-β-d-xylopyranosyl-(1 → 4)-O-[(β-d-glucopyranosyl-(1 → 3)]-O-6-deoxy-α-l-mannopyranosyl-(1 → 2)-6-O-[(2E,6S)-6-[[2-O-[(2E,6S)-6-[[6-deoxy-2-O-[(2E,6S)-2,6-dimethyl-1-oxo-6-(β-d-xylopyranosyloxy)-2

  通过色谱法从Calliandra pulcherrima的叶片中分离出一种新的复杂的三萜皂苷。根据化学证据，对已知化合物进行光谱分析和比较，确定其结构为3-[（O- α - l-阿拉伯吡喃糖基- （1→2）-O- α - l-阿拉伯吡喃糖基-（1→6） -2-（乙酰基氨基）-2-脱氧β - d吡喃葡萄糖基）氧基] - （3- β）-olean -12-烯-28-酸O- β - d -xylopyranosyl-（1→3）-O - β - d -xylopyranosyl-（1→4）-O - [（β - d-吡喃葡萄糖基- （1→3）]-O-6-脱氧-α - 1-甘露吡喃糖基- （1→2）-6-O-[（2E，6S）-6-[[2-O-[（2E ，6S）-6-[[[6-脱氧-2-O-[（2E，6S）-2,6-二甲基-1-氧代-6-（β - d-吡喃吡喃糖基氧基）-2,7-辛二烯基]- β - d-吡喃葡萄糖基]氧基]