7S,8S-threo-4,7,9,9’-tetrahydroxy-3,3’-dimethoxy-8-O-4’-neolignan | 182265-17-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 7S,8S-threo-4,7,9,9’-tetrahydroxy-3,3’-dimethoxy-8-O-4’-neolignan
• 英文别名: (7S,8S)-4,7,9,9'-Tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan；(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propane-1,3-diol
• CAS: 182265-17-4
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: DBIKJXXBCAHHMC-PMACEKPBSA-N

物化性质

• 沸点：
  626.4±55.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 7S,8S-threo-4,7,9,9’-tetrahydroxy-3,3’-dimethoxy-8-O-4’-neolignan 在 D(+)-10-樟脑磺酸 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以1.6 mg的产率得到
  参考文献：
  名称：

  Glycosides from the Root of Iodes cirrhosa

  摘要：

  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.

  DOI：

  10.1021/np7007329
• 作为产物：
  描述：

  (7S,8S)-threo-7,9,9'-tirhydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside 在 Citric acid buffer 作用下， 反应 7.0h， 生成 7S,8S-threo-4,7,9,9’-tetrahydroxy-3,3’-dimethoxy-8-O-4’-neolignan
  参考文献：
  名称：

  Neolignan glycosides from Symplocos caudata

  摘要：

  A phytochemical investigation of the roots of Symplocos caudata Wall (Symplocaceae) resulted in isolation and characterization of four optical isomers of a neolignan glycoside (1-4), a lignan lactone glycoside (5), a phenylpropanoid glycoside (6), as well as two known compounds (7, 8). Their structures were elucidated as (7S,8S)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside (1), (7R, 8R)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside side (2), (7R,8S)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside (3), (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-S-O-4'-neolignan-4-O-beta-D-glucopyranoside (4), 8R,8'R-matairesinol-4-O-beta-D-xylopyranosyl-(1 -> 2)-O-beta-D-glucopyranoside (5), 1-O-[beta-D-xylopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), matairesinoside (7), and (R)-1-O-(beta-D-glucopyranosyl)-2-[2-methoxy-4-(omega-hydroxypropyl)-phenoxyl]-propan-3-ol (8) on the basis of spectroscopic data (1D and 2D NMR, MS and CD) and chemical evidence. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.08.022

文献信息

• Discovery of Neolignan Glycosides with Acetylcolinesterase Inhibitory Activity from Huangjinya Green Tea Guided by Ultra Performance Liquid Chromatography–Tandem Mass Spectrometry Data and Global Natural Product Social Molecular Networking
  作者：Hao-Yue Wu、Jia-Ping Ke、Wei Wang、Ya-Shuai Kong、Peng Zhang、Tie-Jun Ling、Guan-Hu Bao

  DOI：10.1021/acs.jafc.9b05605

  日期：2019.10.30

  flavonols in Huangjinya green tea. Further, a new 8-O-4'-type neolignan glycoside, camellignanoside A (1), and 15 known compounds (2-16) were isolated through a variety of column chromatographies, and the structure was elucidated extensively by ultra performance liquid chromatography-quadrupole-time-of-flight-tandem mass spectrometry, 1H and 13C nuclear magnetic resonance, heteronuclear single-quantum

  全球自然产品基于社会功能的网络被用来跟踪植物化学成分，包括黄金雅绿茶中的九种黄酮苷，六种儿茶素和三种黄酮醇。此外，通过各种柱色谱法分离了新的8-O-4'型新木脂苷，骆驼脂苷A（1）和15种已知化合物（2-16），并通过超高效液相色谱法广泛阐明了其结构。四极杆飞行时间串联质谱，1H和13C核磁共振，异核单量子相关，异核多键相关，1H-1H相关光谱，旋转框架核Overhauser效应光谱和Nuclear Overhauser效应光谱，以及圆二色性光谱学。化合物1和2表现出对乙酰辅酶的抑制活性，
• Studies on the Constituents of Lonicera Species. X. Neolignan Glycosides from the Leaves of Lonicera gracilipes var. glandulosa MAXIM.
  作者：Noriko MATSUDA、Masao KIKUCHI

  DOI：10.1248/cpb.44.1676

  日期：——

  Four new 8-O-4'-neolignan glycosides, 4, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-7-O-β-D-glucopyranosides [7S, 8S-threo form (1) and 7S, 8R-erythro form (2)], 7R, 8R-threo-4, 7, 9, 9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-β-D-glucopyranoside (3) and 7S, 8R-erythro-7, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (4), and two known compunds, 4, 7, 9-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-9'-O-β-D-glucopyranosides [7R, 8R-threo form (5) and 7S, 8R-erythro form (6)], have been isolated from the leaves of Lonicera gracilipes var. glandulosa MAXIM. Their absolute stereostructures have been determined on the basis of spectral and chemical evidence.

  从细梗忍冬腺叶变种的叶子中分离得到4个新的8-O-4'-新木脂素苷，4，9，9'-三羟基-3，3'-二甲氧基-8-O-4'-新木脂素-7-O-β-D-吡喃葡萄糖苷[7S，8S-苏式异构体(1)和7S，8R-赤式异构体(2)]，7R，8R-苏式-4，7，9，9'-四羟基-3-甲氧基-8-O-4'-新木脂素-3'-O-β-D-吡喃葡萄糖苷(3)和7S，8R-赤式-7，9，9'-三羟基-3，3'-二甲氧基-8-O-4'-新木脂素-4-O-β-D-吡喃葡萄糖苷(4)，以及2个已知化合物，4，7，9-三羟基-3，3'-二甲氧基-8-O-4'-新木脂素-9'-O-β-D-吡喃葡萄糖苷[7R，8R-苏式异构体(5)和7S，8R-赤式异构体(6)]。根据光谱和化学证据确定了这些化合物的绝对构型。
• Isolation and structural characterization of four diastereomeric lignan glycosides from Abies holophylla and their neuroprotective activity
  作者：Joon Min Cha、Tae Hyun Lee、Lalita Subedi、Young Jun Ha、Hye Ryeong Kim、Sun Yeou Kim、Sang Un Choi、Chung Sub Kim

  DOI：10.1016/j.tet.2020.131735

  日期：2021.1

  technique, we isolated four stereoisomeric lignan glycosides, holophyllosides A–D (1–4), from the trunk of Abies holophylla Maxim. which were first isolated as a mixture 25 years ago. The planar structures of 1–4 were characterized by conventional 1D and 2D NMR data analysis and their stereochemistry was determined via empirical comparison of their 13C NMR chemical shifts and 3JH-H coupling constants

  非对映异构体是立体异构体的一种，由于其相似的物理性质，它们通常以混合物形式分离。通过HPLC技术，我们分离4个的立体异构体木脂素甙，holophyllosides A-d（1 - 4），从树干沙松马克西姆。于25年前首次分离为混合物。的平面结构1 - 4通过常规一维和二维NMR分析数据进行了表征，并经由它们的经验比较，确定其立体化学13个C NMR化学位移和3 Ĵ H-H耦合常数与报道的值，酶促水解，随后的LC-MS分析和ECD实验。中分离的四种立体异构体中，只有化合物1，3和4通过在C6细胞中诱导NGF分泌而表现出中等的神经保护活性2没有。这项研究再次强调了分子在其生物学和药学应用中的立体化学重要性。
• Neolignan glycosides from Symplocos caudata
  作者：Changhong Huo、Hong Liang、Yuying Zhao、Bin Wang、Qingying Zhang

  DOI：10.1016/j.phytochem.2007.08.022

  日期：2008.2

  A phytochemical investigation of the roots of Symplocos caudata Wall (Symplocaceae) resulted in isolation and characterization of four optical isomers of a neolignan glycoside (1-4), a lignan lactone glycoside (5), a phenylpropanoid glycoside (6), as well as two known compounds (7, 8). Their structures were elucidated as (7S,8S)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside (1), (7R, 8R)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside side (2), (7R,8S)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside (3), (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-S-O-4'-neolignan-4-O-beta-D-glucopyranoside (4), 8R,8'R-matairesinol-4-O-beta-D-xylopyranosyl-(1 -> 2)-O-beta-D-glucopyranoside (5), 1-O-[beta-D-xylopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), matairesinoside (7), and (R)-1-O-(beta-D-glucopyranosyl)-2-[2-methoxy-4-(omega-hydroxypropyl)-phenoxyl]-propan-3-ol (8) on the basis of spectroscopic data (1D and 2D NMR, MS and CD) and chemical evidence. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.