(-)-(7R,8R)-threo-1-C-syringylglycerol 4-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(7R,8R)-threo-1-C-syringylglycerol 4-O-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[2,6-dimethoxy-4-[(1R,2R)-1,2,3-trihydroxypropyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₇H₂₆O₁₁
• 分子量: 406.387
• InChiKey: VIKGCVPVRTWXMM-RYUTVSPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (-)-(7R,8R)-threo-1-C-syringylglycerol 4-O-β-D-glucopyranoside 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 16.0h， 以3.6 mg的产率得到(-)-(7R,8R)-syringylglycerol
  参考文献：
  名称：

  Glycosides from the Stem Bark of Fraxinus sieboldiana

  摘要：

  A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta(C8-C7) values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 mu M, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 mu M, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 mu M.

  DOI：

  10.1021/np0700467
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 甲醇 、 甲基磺酰胺 、 AD-mix β 、 四丁基溴化铵 、 sodium methylate 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 42.0h， 生成 (-)-(7R,8R)-threo-1-C-syringylglycerol 4-O-β-D-glucopyranoside
  参考文献：
  名称：

  丁香苷及其天然类似物的全合成及抗炎活性

  摘要：

  Syringin ( 1 ) 是一种从刺五加(Rupr. Maxim.) Harms的根中分离出来的天然生物活性糖苷，具有显着的抗炎活性。在这项研究中，我们已经完成了丁香苷 ( 1 ) 及其天然类似物2-12的全合成，从共同的起始材料丁香醛 ( 13 ) 开始，经过 4-8个步骤，总产率为 11.8-61.3% . 这些化合物的抗炎活性是根据 LPS 刺激的 RAW264.7 细胞中 NO 的产生来确定的。其中，化合物1 – 5、7和9表现出不同程度的抗炎活性。

  DOI：

  10.1021/acs.jnatprod.1c00585

文献信息

• Glycosides from the Stem Bark of <i>Fraxinus </i><i>sieboldiana</i>
  作者：Sheng Lin、Sujuan Wang、Mingtao Liu、Maoluo Gan、Shuai Li、Yongchun Yang、Yinghong Wang、Wenyi He、Jiangong Shi

  DOI：10.1021/np0700467

  日期：2007.5.25

  A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta(C8-C7) values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 mu M, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 mu M, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 mu M.
• Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
  作者：Hongbo Dong、Min Wu、Yingying Wang、Weihong Du、Yujiao He、Zheng Shi

  DOI：10.1021/acs.jnatprod.1c00585

  日期：2021.11.26

  glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2–12, from a common starting material, syringaldehyde (13), in 4–8 steps with an overall yields of 11.8–61.3%. The anti-inflammatory activities of these compounds were determined

  Syringin ( 1 ) 是一种从刺五加(Rupr. Maxim.) Harms的根中分离出来的天然生物活性糖苷，具有显着的抗炎活性。在这项研究中，我们已经完成了丁香苷 ( 1 ) 及其天然类似物2-12的全合成，从共同的起始材料丁香醛 ( 13 ) 开始，经过 4-8个步骤，总产率为 11.8-61.3% . 这些化合物的抗炎活性是根据 LPS 刺激的 RAW264.7 细胞中 NO 的产生来确定的。其中，化合物1 – 5、7和9表现出不同程度的抗炎活性。