(7R,8S)-3,5,3′-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol | 871711-78-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (7R,8S)-3,5,3′-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol
• 英文别名: 4-[(2R,3S)-2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-2-yl]-2,6-dimethoxyphenol；7R,8S-5-methoxydihydrodehydroconiferyl alcohol；(7R,8S)-4-hydroxy-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-ol；(7R,8S)-3,3’,5-trimethoxy-4’,7-epoxy-8,5’-neolignan-4,9,9’-triol；5-methoxydihydrodehydrodiconiferyl alcohol；2,3-Dihydro-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranpropanol, (2R,3S)-；4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenol
• CAS: 871711-78-3
• 化学式: C₂₁H₂₆O₇
• 分子量: 390.433
• InChiKey: FVHJOQIXLMDURD-QRWLVFNGSA-N

物化性质

• 沸点：
  561.3±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(2R,3S)-2,3-dihydro-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-3-benzofuranyl]methyl-β-D-xylopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (7R,8S)-3,5,3′-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol
  参考文献：
  名称：

  Lindera glauca（Siebold et Zucc。）Blume的三种新的木质素衍生物

  摘要：

  两个新的芳基-四氢萘木脂素甙，linderanosides A和B（1和2，RESP），以及一个新的二氢苯并呋喃新木脂素糖苷，linderanoside C（3），加上5木脂素衍生物已知的（4 - 8）从主干分离的山胡椒。这些新化合物的结构通过光谱分析确定，包括广泛的2D NMR数据和酸水解。化合物的绝对构型通过圆二色性（CD）光谱研究得以阐明。化合物1 - 8使用磺基罗丹明评估了它们对A549（非小细胞肺腺癌），SK-OV-3（卵巢癌细胞），A498（人肾上皮细胞）和HCT-15（结肠癌细胞）人肿瘤细胞系的细胞毒性B体外测定。

  DOI：

  10.1002/hlca.201500002

文献信息

• Lignan Glycosides from the Twigs of <i>Chaenomeles sinensis</i> and Their Biological Activities
  作者：Chung Sub Kim、Lalita Subedi、Sun Yeou Kim、Sang Un Choi、Ki Hyun Kim、Kang Ro Lee

  DOI：10.1021/acs.jnatprod.5b00090

  日期：2015.5.22

  Phytochemical investigation of the twigs of Chaenomeles sinensis led to the isolation and identification of six new lignan glycosides, chaenomiside A-F (1-6), along with five known ones (7-11). Their chemical structures were determined by spectroscopic methods, including NMR, MS, ECD, and GC/MS analyses. All the isolated compounds (1-11) were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide-activated murine microglial cells and the secretion of nerve growth factor (NGF) in a C6 rat glioma cell line. Compound 6 significantly reduced NO levels in the murine microglia BV2 cells with an IC50 value of 21.3 mu M, and compounds 1, 3, and 6 were potent stimulants of NGF release with stimulation levels of 151.74 +/- 6.77%, 144.31 +/- 7.49%, and 167.61 +/- 18.5%, respectively.
• Two new neolignan glycosides from Pittosporum glabratum Lindl.
  作者：Huanxin Zhao、Tiantian Nie、Huanjie Guo、Jun Li、Hong Bai

  DOI：10.1016/j.phytol.2012.01.003

  日期：2012.6

  Two new neolignan glycosides, named pittogoside A (1) and pittogoside B (2) were isolated from the roots of Pittosporum glabratum Lindl. Their structures, including the absolute stereochemistry, were determined on the basis of spectroscopic analysis and chemical evidence, with combination of circular dichroism. (C) 2012 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.
• Three New Lignan Derivatives from<i>Lindera glauca</i>(<scp>Siebold</scp>et<scp>Zucc</scp>.)<scp>Blume</scp>
  作者：Won Se Suh、Ki Hyun Kim、Ho Kyung Kim、Sang Un Choi、Kang Ro Lee

  DOI：10.1002/hlca.201500002

  日期：2015.8

  Two new aryl‐tetralin lignan glycosides, linderanosides A and B (1 and 2, resp.), and a new dihydrobenzofuran neolignan glycoside, linderanoside C (3), together with five known lignan derivatives (4–8) were isolated from the trunk of Lindera glauca. The structures of these new compounds were determined through spectroscopic analyses, including extensive 2D‐NMR data and acid hydrolysis. The absolute

  两个新的芳基-四氢萘木脂素甙，linderanosides A和B（1和2，RESP），以及一个新的二氢苯并呋喃新木脂素糖苷，linderanoside C（3），加上5木脂素衍生物已知的（4 - 8）从主干分离的山胡椒。这些新化合物的结构通过光谱分析确定，包括广泛的2D NMR数据和酸水解。化合物的绝对构型通过圆二色性（CD）光谱研究得以阐明。化合物1 - 8使用磺基罗丹明评估了它们对A549（非小细胞肺腺癌），SK-OV-3（卵巢癌细胞），A498（人肾上皮细胞）和HCT-15（结肠癌细胞）人肿瘤细胞系的细胞毒性B体外测定。