四氢-2-(4-羟基-3-甲氧基苯基)-4-((4-羟基-3-甲氧基苯基)甲基)-3-呋喃甲醇 | 83327-19-9

• 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: 四氢-2-(4-羟基-3-甲氧基苯基)-4-((4-羟基-3-甲氧基苯基)甲基)-3-呋喃甲醇
• 中文别名: 乙酸二氢2-十七烷基-4,5--1-(2-羟基乙基)-1H-咪唑正离子；(-)-落叶松脂醇
• 英文名称: (+)-lariciresinol
• 英文别名: (7R,8S,8'S)-3,3'-dimethoxy-7,9'-epoxylignane-4,4',9-triol；(-)-Lariciresinol；4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
• CAS: 83327-19-9
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: MHXCIKYXNYCMHY-SXGZJXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氢-2-(4-羟基-3-甲氧基苯基)-4-((4-羟基-3-甲氧基苯基)甲基)-3-呋喃甲醇 在 2-碘酰基苯甲酸 、 sodium oxalate 作用下， 以 水 、 碳酸二甲酯 为溶剂， 以40%的产率得到3,3',4,4'-pentahydroxy-7,9'-epoxylignan
  参考文献：
  名称：

  A selective de-O-methylation of guaiacyl lignans to corresponding catechol derivatives by 2-iodoxybenzoic acid (IBX). The role of the catechol moiety on the toxicity of lignans

  摘要：

  我们在此报道了首次选择性去-O-甲基化一大批桂皮醇木质素，利用IBX作为主要氧化剂，在绿色条件下（碳酸二甲酯-H2O溶剂）通过原位还原程序转化为相应的儿茶酚衍生物。研究了儿茶酚基团对新木质素衍生物的细胞毒性和基因毒性的影响。获得的结果表明，儿茶酚基团的存在显著增强了致断裂潜力（例如，诱导染色体畸变）、细胞毒性以及细胞周期进程的调节，相较于母体化合物。因此，尽管通常描述儿茶酚衍生物具有体外抗氧化活性，我们的结果首次显示出其具有致断裂潜力，这在很大程度上指示了长期的遗传和癌症风险。

  DOI：

  10.1039/b822661j
• 作为产物：
  描述：

  (7R,8S,8'S)-4,4'-dibenzyloxy-3,3'-dimethoxy-7,9'-epoxylignan-9-ol 在 氢气 作用下， 生成 四氢-2-(4-羟基-3-甲氧基苯基)-4-((4-羟基-3-甲氧基苯基)甲基)-3-呋喃甲醇
  参考文献：
  名称：

  Effect of the Benzylic Structure of Lignan on Antioxidant Activity

  摘要：

  评估了木酚类化合物苄基结构对抗氧化活性的影响。没有氧的两个二级苄位的次羟基瑞士素 (1) 和3,4-双(4-羟基-3-甲氧基苄基)四氢呋喃 (2) 显示出最高的抗氧化活性。本实验中首次合成了具有光学活性的疣酮 (4)。

  DOI：

  10.1271/bbb.70275

文献信息

• Lignans and other constituents from Carissa edulis
  作者：Hans Achenbach、Reiner Waibel、Ivan Addae-Mensah

  DOI：10.1016/s0031-9422(00)86976-9

  日期：1983.1

  Abstract The methanolic extract from the root of Carissa edulis contains ca 5% lignans, the main compounds among them being (−)-nortrachelogenin, carinol and the hitherto unknown carissanol.

  摘要 Carissa edulis 根的甲醇提取物含有约 5% 的木脂素，其中主要化合物是 (-)-nortrachelogenin、carinol 和迄今为止未知的 carissanol。
• Enantioselective Lignan Synthesis by Cell-free Extracts of<i>Forsythia koreana</i>
  作者：Toshiaki Umezawa、Hiroyuki Kuroda、Toshinari Isohata、Takayoshi Higuchi、Mikio Shimada

  DOI：10.1271/bbb.58.230

  日期：1994.1

  The Forsythia koreana plant produces such lignans as ( − )-secoisolariciresinol, and ( + )-pinoresinol. Cell-free extracts from the plant catalyzed the enantioselective formation of ( − )-[2H10]secoisolariciresinol from [9, 9-2H2, OC2H3]coniferyl alcohol in the presence of NADPH and H2 O2. On the other hand, [2H10]lariciresinosl isolated from the enzymatic reaction products was found to be predominantly composed of the unnatural ( − )-enantiomer [88% enantiomer excess (e.e.)]. The stereoselectivity for the formation of these lignans can be explained, at least in part, by the finding that the enzyme system also catalyzed the stereoselective reduction of ( + )-lariciresinol, but not its ( − )-enantiomer, to ( − )-secoisolariciresinol.

  韩国连翘植物产生的木酚类物质包括（−）-半紫葳醇和（+）-松脂醇。来自这种植物的无细胞提取物在NADPH和H2O2存在下催化了（−）-[2H10]半紫葳醇从[9,9-2H2,OC2H3]香豆醇的对映选择性形成。另一方面，从酶促反应产物中分离出来的[2H10]拉里醇主要由不自然的（−）-对映体构成，具有88%的对映体超量（e.e.）。这些木酚类物质形成的立体选择性部分可以通过发现该酶系统也催化（+）-拉里醇的立体选择性还原，但不催化其（−）-对映体，形成（−）-半紫葳醇来解释。
• Recombinant Pinoresinol-Lariciresinol Reductases from Western Red Cedar (Thuja plicata) Catalyze Opposite Enantiospecific Conversions
  作者：Masayuki Fujita、David R. Gang、Laurence B. Davin、Norman G. Lewis

  DOI：10.1074/jbc.274.2.618

  日期：1999.1

  transcription-polymerase chain reaction-guided cloning strategy was employed to obtain genes encoding pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) as a means to initiate the study of its heartwood formation. (+)-Pinoresinol-(+)-lariciresinol reductase from Forsythia intermedia was used as a template for primer construction for reverse transcription-polymerase chain reaction amplifications

  尽管木本植物的心材代表了纤维和实木产品的主要来源，但对于导致其形成的生物过程是如何开始和调控的，基本上一无所知。因此，采用逆转录-聚合酶链反应指导的克隆策略从西部红柏（Thuja plicata）获得编码松脂醇-lariciresinol还原酶的基因，作为开始研究其心材形成的手段。连翘中的（+）-松脂醇-（+）-lariciresinol还原酶用作反转录-聚合酶链反应扩增引物构建的模板，随后进行同源杂交克隆，可分离出两种不同的来自西部红柏的推定的松脂醇-lariciresinol还原酶cDNA克隆。每个类别的代表表示为与β-半乳糖苷酶的融合蛋白，并进行酶活性测定。使用氘化和放射性标记的（+/-）-松脂醇作为底物，可以确定每一类cDNA编码具有不同（相反）对映体特异性的松脂醇-lariciresinol还原酶。显着地，来自一类的蛋白质将（+）-松脂醇转变为（-）-异豆油松香醇，而另一种则利用
• Identification and Stereochemical Characterization of Lignans in Flaxseed and Pumpkin Seeds
  作者：Tina Sicilia、Heike B. Niemeyer、Doris M. Honig、Manfred Metzler

  DOI：10.1021/jf0207979

  日期：2003.2.1

  Phytoestrogens of the lignan type are widely distributed in plant-derived food items and are believed to protect against hormone-dependent cancer. The richest known dietary source of lignans is flaxseed. Flaxseed has been reported to contain glycosides of secoisolariciresinol as the major lignan, together with small amounts of matairesinol, isolariciresinol, and pinoresinol. Secoisolariciresinol, but none of the other lignans, has so far been identified in pumpkin seeds. In the present study, two different methods for the hydrolysis of lignan glycosides are compared. Artifact formation and loss of lignans under acidic conditions were observed. Lariciresinol was identified by GC-MS analysis in two different types of flaxseed (Linum usitatissimum L. and Linum flavum L.) and in pumpkin seeds (Cucurbita pepo L.) for the first time. Likewise, the novel lignan demethoxy-secoisolariciresinol was tentatively identified in the flaxseed samples. Stereochemical analysis by chiral HPLC of several lignans isolated from flaxseed showed that secoisolariciresinol, matairesinol, and lariciresinol consisted predominantly of one enantiomer.
• (+)-Pinoresinol/(−)-lariciresinol reductase from<i>Linum perenne</i>Himmelszelt involved in the biosynthesis of justicidin B
  作者：Shiva Hemmati、Thomas J. Schmidt、Elisabeth Fuss

  DOI：10.1016/j.febslet.2007.01.018

  日期：2007.2.20

  A cDNA encoding a pinoresinol–lariciresinol reductase PLR (PLR‐Lp1) was isolated from a cell culture of Linum perenne Himmelszelt accumulating the arylnaphthalene lignan justicidin B. The recombinant PLR‐Lp1 prefers (+)‐pinoresinol in the first reaction step, but (−)‐lariciresinol in the second step. Therefore, it is the first PLR described with opposite enantiospecificity within the two reaction steps catalysed by PLRs. Hairy root lines transformed with an ihpRNAi construct to suppress plr gene expression show less mRNA accumulation for the plr‐Lp1 gene and PLR enzyme activity. Justicidin B accumulation was reduced down to 24% in comparison to control lines showing the involvement of PLR‐Lp1 in the biosynthesis of justicidin B.