4-[(2S,3S,4R,5R)-5-(4-羟基-3-甲氧基苯基)-3,4-二甲基四氢呋喃-2-基]-2-甲氧基苯酚 | 74683-16-2

• 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: 4-[(2S,3S,4R,5R)-5-(4-羟基-3-甲氧基苯基)-3,4-二甲基四氢呋喃-2-基]-2-甲氧基苯酚
• 英文名称: nectandrin-B
• 英文别名: Nectandrin B；fragransin A₂；Malabaricanol；7α,7'α,8β,8'β-4,4'-dihydroxy-3,3'-dimethoxy-7,4'-epoxylignane；Tetrahydro-furoguaiacin-A；4-[(2S,3S,4R,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
• CAS: 74683-16-2
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GMXMKSFJQLFOSO-JARDSOJUSA-N

物化性质

• 沸点：
  509.7±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(2S,3S,4R,5R)-5-(4-羟基-3-甲氧基苯基)-3,4-二甲基四氢呋喃-2-基]-2-甲氧基苯酚 、 硫酸二甲酯 在 氨 、 sodium 、 potassium carbonate 作用下， 生成 2,6-二甲氧基-4-羟基苯甲醛
  参考文献：
  名称：

  Purushothaman, K. K.; Sarada, A.; Connolly, J. D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 46 - 48

  摘要：

  DOI：
• 作为产物：
  描述：

  在 5%-palladium/activated carbon 、 氢气 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 6.5h， 生成 4-[(2S,3S,4R,5R)-5-(4-羟基-3-甲氧基苯基)-3,4-二甲基四氢呋喃-2-基]-2-甲氧基苯酚
  参考文献：
  名称：

  Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity

  摘要：

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.

  DOI：

  10.1021/jf4046396

文献信息

• O-demethylation of 7,7′-epoxylignans by Aspergillus niger
  作者：Hiroyuki Kasahara、Mitsuo Miyazawa、Hiromu Kameoka

  DOI：10.1016/0031-9422(96)00222-1

  日期：1996.9

  Biotransformation of the 7,7'-epoxylignans, (+)-veraguensin, (+)-galbelgin and galgravin by Aspergillus niger has been investigated. These lignans were converted to their corresponding 4,4'-O-demethyl derivatives, (+)-verrucosin, (+)-fragransin A2 and nectandrin B.

  已经研究了黑曲霉对 7,7'-环氧木脂素、(+)-veraguensin、(+)-galbelgin 和 galgravin 的生物转化。这些木脂素被转化为它们相应的 4,4'-O-去甲基衍生物、(+)-verrucosin、(+)-fragransin A2 和 necandrin B。
• Glycosides from the bark of<i>Machilus robusta</i>
  作者：Peng-Bin Bu、Yan-Ru Li、Ming Jiang、Fang Wang、Xiao-Liang Wang、Sheng Lin、Cheng-Gen Zhu、Jian-Gong Shi

  DOI：10.1080/10286020.2013.785530

  日期：2013.5

  Six new glycosidic constituents (1–6), together with 10 known analogs, have been isolated from the bark of Machilus robusta. Structures of the new compounds, including the absolute configurations, were determined by spectroscopic and chemical methods as ( − )-nectandrin B-β-d-glucopyranoside (1), ( − )-(7R,7′R,8S,8′R)-4,4′-dihydroxy-3,3′-dimethoxy-7,7′-epoxylignan-4-O-β-d-glucopyranoside (2), ( − )-(7R

  六个新的糖苷组分（1 - 6），用10个已知类似物一起，已经从树皮中分离润罗布斯塔。（ - ）的新化合物的结构，包括绝对构型，通过光谱和化学方法作为确定-nectandrin B-β- d吡喃葡萄糖苷（1），（ - ） - （7 - [R，7' - [R，8小号， 8' - [R）-4,4'-二羟基-3,3'-二甲氧基- 7,7'- epoxylignan -4- ö -β- d吡喃葡萄糖苷（2），（ - ） - （7 - [R，7' - [R，8 S，8′R）-4,4'-二羟基-3,3'-二甲氧基- 7,7'- epoxylignan -4'- ö -β- d吡喃葡萄糖苷（3），（ - ） - （8小号，8' - [R ） - 4,4'-二羟基-3,3'，5'- trimethoxylignan -4'- ö -β- d吡喃葡萄糖苷（4），（ - ） - （7 - [R，8 - [R）-syringylglycerol
• COMPOSITION FOR IMPROVING PHYSICAL STRENGTH OR ATHLETIC ABILITY, CONTAINING NUTMEG EXTRACT AS ACTIVE INGREDIENT
  申请人：Korea Basic Science Institute

  公开号：EP3747452A1

  公开（公告）日：2020-12-09

  The present invention relates to a composition for improving physical strength or athletic ability, containing a nutmeg extract as an active ingredient and, more specifically, to a composition for improving physical strength or athletic ability, for treating sarcopenia, for improving muscle function, and for anti-fatigue, containing a nutmeg extract as an active ingredient. The nutmeg extract of the present invention contains a high quantity of ligand-based compounds and exhibits, when taken, very excellent effects of improving athletic ability, improving endurance and improving muscular strength, and thus is effective for treating sarcopenia and can be effectively used in medical supplies, food and the like for improving physical strength or athletic ability.

  本发明涉及一种含有肉豆蔻提取物作为活性成分的用于提高体力或运动能力的组合物，更具体地说，涉及一种含有肉豆蔻提取物作为活性成分的用于提高体力或运动能力、治疗肌肉疏松症、改善肌肉功能和抗疲劳的组合物。 本发明的肉豆蔻提取物含有大量配体基化合物，服用后在提高运动能力、提高耐力和提高肌肉力量方面有非常好的效果，因此可有效治疗肌肉疏松症，并可有效地用于医疗用品、食品等，以提高体力或运动能力。
• Mangifera indica as a Sirtuin 1 activating agent
  申请人：Vital Solutions Swiss AG

  公开号：US10596212B2

  公开（公告）日：2020-03-24

  The invention relates to a Mangifera (Mango) Indica preparation as Sirtuin 1 activating agent for in vivo and in vitro applications. The preparation may be used to reduce the risk of developing obesity, type II diabetes, elevated blood lipid levels, artheriosclerosis and cardiovascular diseases, as well as a cell and DNA protector.

  本发明涉及一种作为体内和体外应用的 Sirtuin 1 激活剂的 Mangifera（芒果）Indica 制剂。该制剂可用于降低患肥胖症、II 型糖尿病、血脂升高、动脉硬化和心血管疾病的风险，也可用作细胞和 DNA 保护剂。
• PROCESS TO OBTAIN SYNTHETIC AND SEMI-SYNTHETIC LIGNAN DERIVATIVES, THEIR ANTIPARASITIC ACTIVITIES AND CORRESPONDING PHARMACEUTICAL FORMULATIONS, INCLUDING THE THERAPEUTIC METHOD USING SAID LIGNAN FOR THE TREATMENT OF PARASITOSIS
  申请人：Fundação de Amparo à Pesquisa do Estado de São Paulo - FAPESP

  公开号：EP1907380A2

  公开（公告）日：2008-04-09