(1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol | 135820-78-9

• 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: (1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol
• 英文别名: threo-guaiacylglycerol-β-O-4'-dihydroconiferyl ether；threo-(7R,8R)-guaiacylglycerol-β-O-4′-dihydroconiferyl ether；(7R,8R)-threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan；(7R,8R)-threo-guaiacylglycerol-β-O-4′-dihydroconiferyl ether；(7R,8R)-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8,4′-oxyneolignan；erythro-guaiacolglycerol-β-O-4'-dihydroconiferyl alcohol；7R,8R-4,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan；Threo-1-(4-hydroxy-3-methoxyphenyl)-2-(4-(3-hydroxypropyl)-2-methoxyphenoxy)-1,3-propanediol；(1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propane-1,3-diol
• CAS: 135820-78-9
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: DBIKJXXBCAHHMC-WOJBJXKFSA-N

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：

  (7R,8R)-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 (1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol
  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。
• Two New Lignans and Anti-HBV Constituents from Illicium henryi
  作者：Ji-Feng Liu、Zhi-Yong Jiang、Chang-An Geng、Quan Zhang、Yao Shi、Yun-Bao Ma、Xue-Mei Zhang、Ji-Jun Chen

  DOI：10.1002/cbdv.201000110

  日期：2011.4

  Two new lignans, dihydrodehydrodiconiferyl alcohol 9‐O‐β‐D‐(3″‐O‐acetyl)‐xylopyranoside (1) and threo‐4,9,9′‐trihydroxy‐3,3′‐dimethoxy‐8‐O‐4′‐neolignan 7‐O‐α‐rhamnopyranoside (2) were isolated from Illicium henryi, together with ten known compounds, 3–12. Their structures were elucidated by extensive spectroscopic analyses. The anti‐hepatitis B virus (anti‐HBV) activity of compounds 1–12 inhibiting

  两种新的木脂素，二氢脱氢二松果醇 9-O-β-D-(3″-O-乙酰基)-xylopyranoside (1) 和 threo-4,9,9'-trihydroxy-3,3'-dimethoxy-8-O- 4'-新木脂素 7-O-α-吡喃鼠李糖苷 (2) 与十种已知化合物 3-12 一起从八角茴香中分离出来。通过广泛的光谱分析阐明了它们的结构。评估了化合物 1-12 抑制 HBV 表面抗原 (HBsAg) 和 HBV e 抗原 (HBeAg) 在 Hep G2.2.15 细胞系上分泌的抗乙型肝炎病毒 (anti-HBV) 活性。(-)-二氢脱氢二松果醇 (4) 对 HBsAg 和 HBeAg 分泌均表现出中等抑制活性，IC50 值分别为 0.06 和 0.53 mM。
• MIYASE, TOSHIO;UENO, AKIRA;TAKIZAWA, NOBUO;KOBAYASHI, HIROMI;OGUCHI, HIRO+, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3713-3719
  作者：MIYASE, TOSHIO、UENO, AKIRA、TAKIZAWA, NOBUO、KOBAYASHI, HIROMI、OGUCHI, HIRO+

  DOI：——

  日期：——
• 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.