5,5'-二甲氧基落叶松脂素 | 116498-58-9

• 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 - 呋喃类木脂素
• 中文名称: 5,5'-二甲氧基落叶松脂素
• 英文名称: (+)-5,5'-dimethoxylariciresinol
• 英文别名: (7S,8R,8'R)-5,5'-dimethoxylariciresinol；(-)-syringaresinol；(8R,7'S,8'R)-5,5'-dimethoxylariciresinol；(+)-5,5′-dimethoxylariciresinol；(7S,8R,8′R)-5,5′-dimethoxylariciresinol；4-[[(3R,4R,5S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2,6-dimethoxyphenol
• CAS: 116498-58-9
• 化学式: C₂₂H₂₈O₈
• 分子量: 420.46
• InChiKey: HBBWYJVDBFYNOP-AYSMAOOMSA-N

物化性质

• 沸点：
  609.8±55.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• 储存条件：
  存放在2-8℃环境中，应保持干燥并密闭。

反应信息

• 作为反应物：
  描述：

  5,5'-二甲氧基落叶松脂素 生成 methyl 2-[(2S,3R,4R)-2-(4-acetyloxy-3,5-dimethoxyphenyl)-4-[(4-acetyloxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]acetate
  参考文献：
  名称：

  ACHENBACH, HANS;STOCKER, MARKUS;CONSTENLA, MANUEL A., PHYTOCHEMISTRY, 27,(1988) N 6, C. 1835-1841

  摘要：

  DOI：
• 作为产物：
  描述：

  (8R,7′S,8′R)-5,5′-dimethoxylariciresinol 9′-O-α-L-rhamnopyranoside 在 naringinase from Penicillum 作用下， 以 水 为溶剂， 反应 24.0h， 生成 5,5'-二甲氧基落叶松脂素
  参考文献：
  名称：

  Lignan Glycosides from the Twigs of Chaenomeles sinensis and Their Biological Activities

  摘要：

  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.

  DOI：

  10.1021/acs.jnatprod.5b00090

文献信息

• Two new lignan xylosides from the barks of Prunus ssiori and Prunus padus.
  作者：Kiyoshi YOSHINARI、Yutaka SASHIDA、Hiroko SHIMOMURA

  DOI：10.1248/cpb.37.3301

  日期：——

  Phytochemical examinations of the barks of Prunus species have led to the isolation of two new lignan xylosides, ssioriside (9) and prupaside (12). Compound 9 was obtained from Prunus (P.) ssiori and P. padus and 12 from P. padus. The spectroscopic data and chemical evidence allowed assignment of the structures of 9 and 12 as (8S, 8'S)-4, 4'-dihydroxy-3, 5, 3', 5'-tetramethoxy-8-8'-butyrolignan 9-O-β-D xylopyranoside and (8R, 7S, 8'R)-5, 5'-dimethoxylari-ciresinol 9'-O-β-D-xylopyranoside, respectively. Several previously reported compounds were also obtained and identified.

  对Prunus属树皮进行的植物化学研究发现并分离出了两种新的木脂素木糖苷——ssioriside（9）和prupaside（12）。化合物9从Prunus（P.）ssiori和P. padus中获得，12仅从P. padus中获得。根据光谱数据和化学证据，化合物9和12的结构被分别确定为(8S, 8'S)-4, 4'-二羟基-3, 5, 3', 5'-四甲氧基-8-8'-丁基木脂素9-O-β-D-木糖苷和(8R, 7S, 8'R)-5, 5'-二甲氧基芝麻素9'-O-β-D-木糖苷。此外，还获得了并鉴定了之前报道的几种化合物。
• Pinoresinol‐lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
  作者：Julianne K. Hwang、Syed G.A. Moinuddin、Laurence B. Davin、Norman G. Lewis

  DOI：10.1002/chir.23218

  日期：2020.6

  Two western red cedar pinoresinol‐lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8‐ and 8′‐linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can

  研究了两个西部红柏松脂松香醇-larresresinol还原酶（PLR）的同系物，以确定它们的对映选择性，底物通用性和动力学性质。PLR位于产生的稀疏蛋白质，针叶树醇衍生的立体选择性偶联的下游，以使其进入8和8'连接的呋喃呋喃木脂体木脂松酚。我们的研究表明，每个PLR同源物都可以通过修饰的芳环取代基对映异构地代谢不同的呋喃呋喃木脂素，但是其中C4 / C4'上的酚基对于催化是必不可少的。这些结果与PLR活性部位中醌甲基化物中间体的形成是一致的。定点诱变和动力学测量提供了对影响对映选择性和动力学性质的因素的进一步了解。根据这些数据，
• Flavonoid and other constituents of Bauhinia manca
  作者：Hans Achenbach、Markus Stöcker、Manuel A. Constenla

  DOI：10.1016/0031-9422(88)80455-2

  日期：1988.1

  Abstract Phytochemical analysis of the stem of Bauhinia manca yielded 63 compounds, among them six new natural products.

  摘要 对紫荆花茎进行植物化学分析，得到63 种化合物，其中6 种是天然产物。
• Lignan and neolignan glycosides from stems of Alangium premnifolium
  作者：Kaori Yuasa、Toshinori Ide、Hideaki Otsuka、Choei Ogimi、Eiji Hirata、Anki Takushi、Yoshio Takeda

  DOI：10.1016/s0031-9422(96)00879-5

  日期：1997.6

  From a methanol extract of stems of Alangium premnifolium, eight lignan derivatives were isolated. Structural elucidation by a spectroscopic method revealed that four of them were new lignan or neolignan glycosides.

  从 Alangium premnifolium 茎的甲醇提取物中分离出八种木脂素衍生物。光谱法结构解析表明，其中四种为新木脂素或新木脂素苷。
• Lignan bis-glucosides from Galium sinaicum
  作者：A.A. El Gamal、K. Takeya、H. Itokawa、A.F. Halim、M.M. Amer、H.-E.A. Saad

  DOI：10.1016/s0031-9422(96)00881-3

  日期：1997.6

  The new lariciresinol-based lignan bis-glucosides, 7S, 8R, 8'R-(-)-lariciresinol-4,4'-bis-O-beta-D-glucopyranoside and 7S, 8R, 8'R-(-)-5-methoxylariciresinol-4,4'-bis- together with (-)syringaresinol-4,4'-bis-O-beta-D-glucopyranside, together with (-)-syringaresinol-4,4'-bis-O-beta-D-glucopyranoside were isolated from the n-butanol extract of Galinum sinaicum roots and their structures were established by various spectroscopic techniques. The isolated compounds represent the first report of lignan glycosides from the Rubiaceae. The two lariciresinol-type glucosides exhibited weak cytotoxic activity against the P388 cell line. (C) 1997 Elsevier Science Ltd.