(4S)-α-terpineol 8-O-β-D-glucopyranoside | 89616-07-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-α-terpineol 8-O-β-D-glucopyranoside
• 英文别名: (4S)-α-terpinyl 8-O-β-D-glucopyranoside；(4S)-α-terpineol β-D-glucopyranoside；(R)-α-terpinyl β-D-glucopyranoside；α-terpinyl β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxane-3,4,5-triol
• CAS: 89616-07-9
• 化学式: C₁₆H₂₈O₆
• 分子量: 316.395
• InChiKey: NZNWCYFBFHHMLM-LACSLYJWSA-N

物化性质

• 沸点：
  480.2±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-α-terpineol 8-O-β-D-glucopyranoside 在 水 、 β-glucosidase 作用下， 反应 24.0h， 以1.4 mg的产率得到α-松油醇
  参考文献：
  名称：

  Galloylglucosides from Berries of Pimenta dioica

  摘要：

  Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.

  DOI：

  10.1021/np9906121
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 在 氢氧化钾 、 氰化汞 作用下， 以 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 (4S)-α-terpineol 8-O-β-D-glucopyranoside
  参考文献：
  名称：

  Inhibitory Effect of Perillosides A and C, and Related Monoterpene Glucosides on Aldose Reductase and Their Structure-Activity Relationships.

  摘要：

  从紫苏（Perilla frutescens）叶中获得的单萜葡萄糖苷，紫苏苷A和C，被发现是醛糖还原酶（EC 1.1.1.21）的抑制剂，该酶被认为是糖尿病并发症如白内障的关键酶。紫苏苷A和C对大鼠晶状体醛糖还原酶的抑制作用相对于甘油醛是竞争性的，其Ki值分别为1.4×10-4和2.3×10-4M。它们的四乙酸酯对同一底物的抑制类型是非竞争性的，尽管其抑制效果比紫苏苷提高了大约一个数量级，Ki值分别为2.5×10-5和7.1×10-5M。我们还制备了相关的单萜葡萄糖苷及其四乙酸酯，并测定了它们对醛糖还原酶的抑制活性，以便阐明结构与抑制活性之间的关系。

  DOI：

  10.1248/cpb.43.920

文献信息

• Cacalol Derivatives from <i>Roldana angulifolia</i>
  作者：Amira Arciniegas、Ana-L. Pérez-Castorena、José Luis Villaseñor、Alfonso Romo de Vivar

  DOI：10.1021/np0604073

  日期：2006.12.1

  Four new modified eremophilanes, angulifolide (1) and angulifolins A-C (2-4), and two new triacetylglucosides (7 and 8) were isolated from Roldana angulifolia, together with several known compounds. The structures of the new compounds were elucidated by spectroscopic analysis and chemical reactions. The absolute configuration of compounds 2 and 3 was established by Mosher ester methodology. Cytotoxicity against selected human cancer cell lines was determined for the more abundant isolated metabolites.
• Inhibitory Effect of Perillosides A and C, and Related Monoterpene Glucosides on Aldose Reductase and Their Structure-Activity Relationships.
  作者：Tomoyuki FUJITA、Kumiko OHIRA、Kazutaka MIYATAKE、Yoshihisa NAKANO、Mitsuru NAKAYAMA

  DOI：10.1248/cpb.43.920

  日期：——

  Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent type of inhibition of rat lens aldose reductase by perillosides A and C was competitive with respect to glyceraldehyde and their Ki values were 1.4×10-4 and 2.3×10-4M, respectively. The type of inhibition by their tetraacetates was non-competitive with respect to the same substrate, although their inhibitory effects were increased by about one order of magnitude compared with those of the perillosides and the Ki values were 2.5×10-5 and 7.1×10-5M, respectively. We also prepared related monoterpene glucosides and their tetraacetates and determined their inhibitory activities towards aldose reductase in order to elucidate the relationship between structure and inhibitory activity.

  从紫苏（Perilla frutescens）叶中获得的单萜葡萄糖苷，紫苏苷A和C，被发现是醛糖还原酶（EC 1.1.1.21）的抑制剂，该酶被认为是糖尿病并发症如白内障的关键酶。紫苏苷A和C对大鼠晶状体醛糖还原酶的抑制作用相对于甘油醛是竞争性的，其Ki值分别为1.4×10-4和2.3×10-4M。它们的四乙酸酯对同一底物的抑制类型是非竞争性的，尽管其抑制效果比紫苏苷提高了大约一个数量级，Ki值分别为2.5×10-5和7.1×10-5M。我们还制备了相关的单萜葡萄糖苷及其四乙酸酯，并测定了它们对醛糖还原酶的抑制活性，以便阐明结构与抑制活性之间的关系。
• Galloylglucosides from Berries of <i>Pimenta dioica</i>
  作者：Hiroe Kikuzaki、Akemi Sato、Yoko Mayahara、Nobuji Nakatani

  DOI：10.1021/np9906121

  日期：2000.6.1

  Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.