(+)-threo-syringylglycerol | 121748-11-6

• 物质功能分类: 天然产物 - 苯丙素
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (+)-threo-syringylglycerol
• 英文别名: (1S,2S)-syringe glycerol；erythro-syringylglycerol；(7S,8S)-syringylglycerol；(1S,2S)-1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,2,3-triol；(7S,8S)-syringoylglycerol；threo-1-C-Syringylglycerol
• CAS: 121748-11-6
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: GIZSHQYTTBQKOQ-XVKPBYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (+)-threo-syringylglycerol 在 sodium metabisulfite 作用下， 以 乙醇 、 水 为溶剂， 生成 threo-2,3-Dihydroxy-1-<4-hydroxy-3,5-dimethoxy-phenyl>-propan-sulfonsaeure-(1)-natriumsalz
  参考文献：
  名称：

  单体木质素磺酸。第二部分

  摘要：

  以前从废亚硫酸盐溶液中分离出来的六种丁香基系列单体木质素磺酸已经合成，其结构已经阐明。

  DOI：

  10.1039/j39670001145
• 作为产物：
  描述：

  (1'S,2'S)-1'-syringylglycerol 3'-O-β-D-glucopyranoside 在 ammonium formate 、 溶剂黄146 、 β-glucosidase 作用下， 以 水 为溶剂， 以67%的产率得到(+)-threo-syringylglycerol
  参考文献：
  名称：

  Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

  摘要：

  alpha-Glucosidase inhibitory activity was found in aqueous methanol extracts of dried hyssop (Hyssopus officinalis) leaves. Active principles against alpha-glucosidase, prepared from rat small intestine acetone powders, were isolated and characterized. The structures of these isolated compounds were determined to be (7S, 8S)-syringoylglycerol-9-O-(6'-O-cinnamoyl)-beta-D-glucopyranoside and (7S, 8S)-syringoylglycerol 9-O-beta-D-glucopyranoside by analysis of physical and spectroscopic data (FDMS, H-1 NMR, C-13 NMR, HMQC. and HMBC experiments) together with chemical syntheses. (C) 2003 Elsevier Ltd. All rights, reserved.

  DOI：

  10.1016/j.phytochem.2003.10.009

文献信息

• An ingenious method for the determination of the relative and absolute configurations of compounds containing aryl-glycerol fragments by ¹H NMR spectroscopy
  作者：Xu Zhang、Kai-Zhou Lu、Hai-Wei Yan、Zi-Ming Feng、Ya-Nan Yang、Jian-Shuang Jiang、Pei-Cheng Zhang

  DOI：10.1039/d0ra09712h

  日期：——

  established to determine the relative and absolute configurations of aryl-glycerols that depend on the chemical shift differences (Δδ) of the diastereotopic methylene protons (H-3) by 1H NMR spectroscopy. When using DMSO-d6 as the preferred solvent, the threo configuration corresponded to a larger ΔδH3a–H3b value (>0.15 ppm), whereas the erythro configuration (<0.07 ppm) corresponded to a smaller value

  建立了一种简明的方法来确定芳基甘油的相对和绝对构型，该构型取决于非对映亚甲基质子（H-3）的化学位移差异（ Δδ ），通过1 H NMR 光谱。当使用 DMSO- d 6作为首选溶剂时，苏型构型对应于较大的 Δ δ H3a–H3b值 (>0.15 ppm)，而赤型构型 (<0.07 ppm) 对应于较小的值。此外，借助莰酰氯的简单酰化反应确定了绝对构型。在苏式对映体中， 1R , 2R构型的Δδ值为<0.15ppm， 1S , 2S构型的Δδ值为>0.20ppm。赤型对映体中，1 R ,2 S的Δδ值为>0.09 ppm，1 S ,2 R的Δδ值为<0.05 ppm。值得注意的是，这个经验规则在CDCl 3中是无效的。此外，该方法还通过量子1 H NMR计算得到验证。
• Terpenoid and phenolic constituents from the roots of Ilex pubescens
  作者：Xu-Dong Zhou、Xiang-Wei Xu、Yi-Yuan Xi、Yuan Zhou

  DOI：10.1016/j.fitote.2019.104298

  日期：2019.10

  phenolic glycosides, Pubescenosides N-P (3-5), along with nineteen known ones, including liganoids, hemiterpenoids and caffeoylquinic acid derivates, were isolated from the roots of Ilex pubescens. Their structures were elucidated from extensive spectroscopic analysis, including 1D and 2D NMR experiments. This study is the first to report monoterpene glycosides with β-pinene aglycone in Aquifoliaceae

  从Ilex的根中分离出5种新的代谢物，包括2种单萜糖苷LM（1-2）和3种酚类糖苷，NP（3-5），以及19种已知的代谢物，包括褐藻素，半萜类和咖啡酰奎尼酸衍生物。 pubescens。通过广泛的光谱分析（包括1D和2D NMR实验）阐明了它们的结构。该研究是第一个报道单叶植物中单萜糖苷与β-pine烯糖苷配基的研究。在体外评估了其中的9种化合物的抗血小板聚集活性。其中，与阿司匹林相比，化合物3和4对ADP诱导的血小板聚集表现出中等抑制作用[抑制（％）：分别为32.3和33.6]。
• Glycosides from the Root of <i>Iodes</i> <i>cirrhosa</i>
  作者：Maoluo Gan、Yanling Zhang、Sheng Lin、Mingtao Liu、Weixia Song、Jiachen Zi、Yongchun Yang、Xiaona Fan、Jiangong Shi、Jinfeng Hu、Jiandong Sun、Naihong Chen

  DOI：10.1021/np7007329

  日期：2008.4.1

  Seven new neolignan glycosides (1-7), two arylglycerol glycosides (8, 9), and 18 known glycosides have been isolated from an ethanolic extract of the root of lodes cirrhosa. Their structures including absolute configurations were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo and erythro 8-4'-oxyneolignans and arylglycerols in different solvents, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and erythro derivatives was discussed. In the in vitro assays, compound 4 and liriodendrin (17) both showed activity against glutamate-induced PC12 cell damage at 10(-5) M.
• 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.
• Nimz,H., Chemische Berichte, 1965, vol. 98, p. 3153 - 3159
  作者：Nimz,H.

  DOI：——

  日期：——