4-(3",4"-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one | 69232-85-5

• 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
• 英文名称: 4-(3",4"-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one
• 英文别名: arctigenin monoacetate；arctigenin acetate；acetoxyarctigenin；(3R)-trans-3-(4-acetoxy-3-methoxy-benzyl)-4-veratryl-dihydro-furan-2-one；(3R)-trans-3-(4-Acetoxy-3-methoxy-benzyl)-4-veratryl-dihydro-furan-2-on；[4-[[(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-oxooxolan-3-yl]methyl]-2-methoxyphenyl] acetate
• CAS: 69232-85-5
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: HKCGEUVLMDJSGX-ZWKOTPCHSA-N

物化性质

• 沸点：
  558.9±50.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(3",4"-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one 在 氢氧化钾 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone
  参考文献：
  名称：

  Nishibe, Sansei; Chiba, Mariko; Sakushima, Akiyo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 3, p. 850 - 860

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸酐 、 牛蒡子苷元 在 吡啶 作用下， 反应 24.0h， 生成 4-(3",4"-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  连翘木脂素

  摘要：

  摘要 连翘的叶和茎物质含有四种主要的木脂素及其O-葡萄糖苷。这些被鉴定为二苄基丁内酯衍生物 (-)-arctigenin、arctiin [(-)-arctigenin 4'-O -glucoside]、matairesinol 和 (-)-matairesinol 4'-O-glucoside，以及呋喃木脂素 (+) -phillygenin、phillyrin [(+)-phillygenin 4-O-葡萄糖苷]、(+)-表皮树脂醇和 (+)-表皮树脂醇 4'-O-葡萄糖苷。木脂素含量因组织类型和季节而异。提供了木脂素的全光谱数据。为连油根素和表松脂醇记录的 1 H NOE 差异光谱需要逆转具有一个轴向和一个赤道芳基（epi 系列）的呋喃木脂素的 C-9 上的轴向和赤道质子的早期化学位移分配。

  DOI：

  10.1016/0031-9422(90)85050-p

文献信息

• ANTI-AGING AGENT CONTAINING ARCTIGENIN DERIVATIVE
  申请人：ROHTO Pharmaceutical Co., Ltd.

  公开号：US20150093345A1

  公开（公告）日：2015-04-02

  An arctigenin derivative used for anti-aging treatment, including protection of the skin from the sun and recovery of skin elasticity. A variety of fatty acid ester derivatives, alcohol ether derivatives and alkylated derivatives are used as the arctigenin derivatives. Agents for controlling ET-1 production, elastase inhibitors, and anti-inflammatory agents are prepared. Such arctigenin derivatives are particularly useful as an external agent for the skin, such as an anti-inflammatory external agent, a sunscreen external agent, or an external agent for recovering elasticity.

  一种用于抗衰老治疗的牛蒡素衍生物，包括保护皮肤免受阳光伤害和恢复皮肤弹性。使用各种脂肪酸酯衍生物、醇醚衍生物和烷基衍生物作为牛蒡素衍生物。制备用于控制ET-1产生的药剂、弹性蛋白酶抑制剂和抗炎药剂。这种牛蒡素衍生物特别适用于皮肤外用剂，如抗炎外用剂、防晒外用剂或恢复弹性的外用剂。
• Synthesis and biological evaluation of arctigenin ester and ether derivatives as activators of AMPK
  作者：Sida Shen、Jingjing Zhuang、Yijia Chen、Min Lei、Jing Chen、Xu Shen、Lihong Hu

  DOI：10.1016/j.bmc.2013.04.010

  日期：2013.7

  A series of new arctigenin and 9-deoxy-arctigenin derivatives bearing different ester and ether side chains at the phenolic hydroxyl positions are designed, synthesized, and evaluated for activating AMPK potency in L6 myoblasts. Initial biological evaluation indicates that some alkyl ester and phenethyl ether arctigenin derivatives display potential activities in AMPK phosphorylation improvement. Further

  设计，合成并评估了一系列在酚羟基位置带有不同酯和醚侧链的新arctigenin和9-deoxy-arctigenin衍生物对L6成肌细胞激活AMPK的作用。初步的生物学评估表明，某些烷基酯和苯乙基artigeninin衍生物在AMPK磷酸化改善中显示出潜在的活性。进一步的结构-活性关系分析表明，arctigenin酯衍生物3a，3h和9-脱氧arctigenin苯醚衍生物6a，6c，6d激活AMPK的能力比arctigenin更高。此外，6c的2-（3,4-二甲氧基苯基）乙基部分已证明作为改善AMPK磷酸化作用的潜在官能团。Arctigenin的结构优化导致6c被鉴定为有前途的先导化合物，在AMPK激活中表现出出色的活性。
• Studies on Differentiation Inducers. VI. Lignan Derivatives from Arctium Fructus. (2).
  作者：Kaoru UMEHARA、Mitsuhiro NAKAMURA、Toshio MIYAKE、Masanori KUROYANAGI、Akira UENO

  DOI：10.1248/cpb.44.2300

  日期：——

  In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modifications were carried out using the most active lignan (arctigenin, 1) and its structure-activity relationship was investigated. Its aliphatic esters were more effective in inducing the differentiation of M1 cels than its aromatic esters. Especially, n-decanoate, which was the most active derivative, induced more than half of the M1 cells into phagocytic cells at a concentration of 2 μM.

  在上一篇论文中，我们报道了从 Arctium Fructus（菊科植物 Arctium lappa L. 的果实）中提取的木犀草素对小鼠髓系白血病细胞（M1）的分化诱导活性。我们重新研究了这种提取物的活性成分，并分离出三种新的二木质素。此外，我们还对最具活性的木犀草素（arctigenin，1）进行了结构改造，并研究了其结构与活性之间的关系。在诱导 M1 细胞分化方面，其脂肪族酯类比芳香族酯类更有效。特别是正癸酸酯，它是活性最强的衍生物，在 2 μM 的浓度下可将一半以上的 M1 细胞诱导成吞噬细胞。
• Studies on Differentiation-Inducers from Arctium Fructus.
  作者：Kaoru UMEHARA、Ariko SUGAWA、Masanori KUROYANAGI、Akira UENO、Takao TAKI

  DOI：10.1248/cpb.41.1774

  日期：——

  In the course of studying differentiation-inducers from plants, their isolation was performed from the methanolic extract of Arctium Fructus (the fruits of Arctium lappa L., Compositae), and then their phagocytic activity on differentiated mouse myeloid leukemia cells (M1) was monitered. Thirteen compounds, including five new ones, were isolated as differentiation-inducers toward M1 cells. These consisted of two lignans, eight sesquilignans and three dilignans. Arctigenin (2) was the most effective compound of all those isolated, and it induced differentiation of M1 cells at a concentration 0.5 μM. Sesquilignans were less effective than lignans and dilignans showed even weaker activity. These lignoids were inactive towards a human acute promyelocytic leukemia cell line (HL-60).

  在研究植物分化诱导剂的过程中，我们从 Arctium Fructus（菊科植物 Arctium lappa L. 的果实）的甲醇提取物中分离出了这些诱导剂，然后监测了它们对分化的小鼠髓性白血病细胞（M1）的吞噬活性。结果分离出 13 种化合物（包括 5 种新化合物）可诱导 M1 细胞分化。这些化合物包括两种木脂素、八种倍半木脂素和三种稀木脂素。在所有分离出的化合物中，牛蒡甙元（2）是最有效的化合物，它能诱导浓度为 0.5 μM 的 M1 细胞分化。半木质素类化合物的效果不如木质素类化合物，而二木质素类化合物的活性更弱。这些木质素对人类急性早幼粒细胞白血病细胞株（HL-60）没有活性。
• Xu, Yubin; Chen, Guirong; Dou, Deqiang, Journal of the Chemical Society of Pakistan, 2014, vol. 36, # 5, p. 870 - 874
  作者：Xu, Yubin、Chen, Guirong、Dou, Deqiang、Jiang, Hongshuai、Kang, Tingguo

  DOI：——

  日期：——