赤式-愈创木基甘油-BETA-O-4'-二氢松柏醇 | 135820-77-8

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 赤式-愈创木基甘油-BETA-O-4'-二氢松柏醇
• 英文名称: (7S,8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan
• 英文别名: erythro-(7S,8R)-guaiacyl-glycerol-β-O-4′-dihydroconiferyl ether；erythro-(7S,8R)-guaiacyl-glycerol-β-O-4'-dihydroconiferyl ether；Erythro-1-(4-hydroxy-3-methoxyphenyl)-2-(4-(3-hydroxypropyl)-2-methoxy-phenoxy)-1,3-propanediol；(1S,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propane-1,3-diol
• CAS: 135820-77-8
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: DBIKJXXBCAHHMC-UXHICEINSA-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

• 作为产物：
  描述：

  7S,8R-erythro-7,9,9’-trihydroxy-3,3′-dimethoxy-8-O-4′-neoliganan-4-O-β-D-glucopyranoside 在 Citric acid buffer 作用下， 反应 7.0h， 生成 赤式-愈创木基甘油-BETA-O-4'-二氢松柏醇
  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

• 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 and megastigmane glucosides from the aerial parts of Isodon japonicus with cell protective effects on BaP-induced cytotoxicity
  作者：Takahiro Matsumoto、Seikou Nakamura、Souichi Nakashima、Tomoe Ohta、Keiko Ogawa、Masashi Fukaya、Junko Tsukioka、Tomohiro Hasei、Tetsushi Watanabe、Hisashi Matsuda

  DOI：10.1016/j.phytochem.2017.02.007

  日期：2017.5

  Six neolignan glucosides, named isodonosides I-VI, and a megastigmane glucoside named isodonmegastigmane I, were isolated together with 15 known compounds from the methanolic extract of aerial parts of Isodon japonicus cultivated in Tokushima, Japan. The chemical structures of the compounds were elucidated based on their MS and NMR spectroscopic analysis. The absolute configurations of the neolignan

  六种新木脂素糖苷，名为isodonosides I-VI 和一种名为isodonmegastigmane I 的巨豆苷，与15 种已知化合物一起从日本德岛栽培的Isodon japonicus 地上部分的甲醇提取物中分离出来。基于它们的MS和NMR光谱分析阐明了化合物的化学结构。新木脂素和 megastigmane 糖苷的绝对构型通过衍生化、ECD（电子圆二色性）棉花效应近似和改进的 Mosher 方法确定。此外，发现新木脂素葡萄糖苷对苯并[a]芘诱导的细胞毒性具有显着的细胞保护作用。
• SUGAR PLANT DERIVED BY-PRODUCTS AND METHODS OF PRODUCTION THEREOF
  申请人：Barbeau Julie

  公开号：US20130203688A1

  公开（公告）日：2013-08-08

  The present document describes a nutraceutical or cosmeceutical composition for the prophylaxis of an ailment comprising a therapeutically effective amount of a sugar plant syrup filtration residue in association with a pharmaceutically acceptable carrier. The present document also describes a nutraceutical or cosmeceutical composition for improving health condition of skin. The present document describes a method of producing a sugar plant syrup-derived product; wherein the improvement is characterized in the step of: collecting a sugar plant syrup residue during the production of sugar or syrup to produce a syrup-derived by-product.
• [EN] SUGAR PLANT DERIVED BY-PRODUCTS AND METHODS OF PRODUCTION THEREOF<br/>[FR] DÉRIVÉS DE PLANTE SUCRIÈRE ET LEURS PROCÉDÉS DE PRODUCTION
  申请人：FEDERATION DES PRODUCTEURS ACERICOLES DU QUEBEC

  公开号：WO2012021983A1

  公开（公告）日：2012-02-23

  The present document describes a nutraceutical or cosmeceutical composition for the prophylaxis of an ailment comprising a therapeutically effective amount of a sugar plant syrup filtration residue in association with a pharmaceutically acceptable carrier. The present document also describes a nutraceutical or cosmeceutical composition for improving health condition of skin. The present document describes a method of producing a sugar plant syrup-derived product; wherein the improvement is characterized in the step of: collecting a sugar plant syrup residue during the production of sugar or syrup to produce a syrup-derived by-product.