6-O-acetyl-aucubin | 135743-80-5

• 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-acetyl-aucubin
• 英文别名: 6-O-acetylaucubin；[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl] acetate
• CAS: 135743-80-5
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: DSSROTZNBIUOAZ-QHDSNVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-aucubin 在 吡啶 、 potassium cyanide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 145.92h， 生成 (1S,4aR,5R,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside
  参考文献：
  名称：

  蜂胶立体选择性转化为多官能团的四氢-1 H-环戊[ c ]呋喃糖苷

  摘要：

  2'，3'，4'，6'，10-penta- O-吡咯丙酸酯（6）与邻苯二甲酰亚胺，三苯基膦和偶氮二羧酸二乙酯的Mitsunobu反应得到（6 R）-6-邻苯二甲酰亚胺-过吡咯并戊二酮糖苷（10）（方案1））。用perpivaloylaucubin（12）进行的选择性氧化反应分别产生（1 R）-和（1 S）-3（β -D-吡喃葡萄糖基氧基）-1 H-环戊[ c ]呋喃-1-羧醛13和14（方案2） 。同样，perpivaloyl-6-epiaucubin（9）和10得到相应的（1S）-甲醛18和（1R）-甲醛16。以这种方式获得的受保护的环戊呋喃糖苷是通用的合成子，可能被证明可用于进一步的化学多样化。

  DOI：

  10.1002/hlca.200390005
• 作为产物：
  描述：

  Hexaacetylaucubin 在 potassium cyanide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 以519 mg的产率得到桃叶珊瑚苷（杜仲甙）
  参考文献：
  名称：

  Efficient Conversion of Aucubin into 6-epi-Aucubin

  摘要：

  Selective deprotection of peracetylaucubin (3) by use of KCN led to 6-O-acetylaucubin (4), which was readily converted into 2',3',4',6',10-penta-O-benzoylaucubin (7). Configuration inversion performed on 7, using a modified Mitsunobu reaction, followed by deprotection, afforded 6-epi-aucubin (2).

  DOI：

  10.1021/np9804583

文献信息

• Iridoid Based Formulations
  申请人：West Brett Justin

  公开号：US20110217394A1

  公开（公告）日：2011-09-08

  Embodiments of the invention relate to fortified food and dietary supplement products which may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relates to the administration of products enhanced with plant products and iridoids.
• Acai and Iridoid Based Formulations
  申请人：West Brett Justin

  公开号：US20110206786A1

  公开（公告）日：2011-08-25

  Embodiments of the invention relate to fortified food and dietary supplement products, which may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relate to the administration of products enhanced with Acai and iridoids.
• Morinda Citrifolia and Iridoid Based Formulations
  申请人：West Brett Justin

  公开号：US20110206787A1

  公开（公告）日：2011-08-25

  Embodiments of the invention relate to fortified food and dietary supplement products which may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relates to the administration of products enhanced with Morinda citrifolia and iridoids.
• Garcinia Mangostana L. and Iridoid Based Formulations
  申请人：West Brett Justin

  公开号：US20120021079A1

  公开（公告）日：2012-01-26

  Embodiments of the invention relate to fortified food and dietary supplement products, which may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relate to the administration of products enhanced with Garcinia mangostana L. and iridoids.
• Morinda Citrifolia Juice Formulations Comprising Iridoids
  申请人：West Brett Justin

  公开号：US20150086655A1

  公开（公告）日：2015-03-26

  Embodiments of the invention relate to fortified food and dietary supplement products which may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relates to the administration of products enhanced with plant products and iridoids. A study was performed to evaluate the iridoid content, as well as the in vitro and in vivo bioactivities, of a beverage containing noni fruit, Cornelian cherries, and olive leaf extract. The major iridoids present were identified as asperulosidic acid, deacetylasperulosidic acid, oleuropein, morroniside, loganic acid, and loganin In the 2,2-Diphenylpicrylhydrazyl (DPPH) radical scavenging assay, remarkably high in vitro antioxidant activity was observed, with an IC 50 of 3.8 μL/mL. In vivo bioactivities were evaluated in type 2 diabetic Sprague Dawley rats. In a dose-dependent manner, the composition reduced abnormal weight gain, blood glucose levels, and serum advanced glycation end products (AGEs), as well as improved immunity via increased T cell counts and CD4+/CD8 + ratios.