tetramethylellagic acid | 2080-25-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: tetramethylellagic acid
• 英文别名: 3,3',4,4'-tetra-O-methylellagic acid；3,3′,4,4′-tetra-O-methylellagic acid；6,7,13,14-Tetramethoxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
• CAS: 2080-25-3
• 化学式: C₁₈H₁₄O₈
• 分子量: 358.304
• InChiKey: UPDMQTYYPHMZOD-UHFFFAOYSA-N

物化性质

• 熔点：
  341-342 °C(Solv: ethylene glycol (107-21-1))
• 沸点：
  594.8±50.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetramethylellagic acid 生成 dimethyl (S)-4,4',5,5',6,6'-hexamethoxydiphenoate
  参考文献：
  名称：

  Chemical investigation of Schizandra chinensis

  摘要：

  DOI：

  10.1007/bf00905306
• 作为产物：
  描述：

  鞣花酸 在 重氮甲烷 、 甲醇 、 乙醚 作用下， 生成 tetramethylellagic acid
  参考文献：
  名称：

  Plant Polyphenols. I. The Polyphenolic Constituents of the Pellicle of the Walnut (Juglans regia)¹

  摘要：

  DOI：

  10.1021/ja01595a050

文献信息

• Urolithin as a Converging Scaffold Linking Ellagic acid and Coumarin Analogues: Design of Potent Protein Kinase CK2 Inhibitors
  作者：Giorgio Cozza、Alessandra Gianoncelli、Paolo Bonvini、Elisa Zorzi、Riccardo Pasquale、Angelo Rosolen、Lorenzo A. Pinna、Flavio Meggio、Giuseppe Zagotto、Stefano Moro

  DOI：10.1002/cmdc.201100338

  日期：2011.12.9

  Ki=60 nM). Comparing the crystallographic binding modes of both ellagic acid and DBC, an X‐ray structure‐driven merging approach was taken to design novel CK2 inhibitors with improved target affinity. A urolithin moiety is proposed as a possible bridging scaffold between the two known CK2 inhibitors, ellagic acid and DBC. Optimization of urolithin A as the bridging moiety led to the identification of 4‐bromo‐3

  酪蛋白激酶2（CK2）是一种普遍存在的，必不可少的，高度多效的蛋白激酶。其异常高的本构活性被怀疑是其在瘤形成和其他相关疾病中的致病潜能的基础。以前，使用不同的计算机筛选方法，我们小组确定了两种有效的选择性CK2抑制剂：鞣花酸，天然存在的鞣酸衍生物（K i = 20 n M）和3,8-dibromo‐7‐hydroxy‐4 -甲基铬n-2-one（DBC，K i = 60 n M）。比较鞣花酸和DBC的晶体学结合模式，采用X射线结构驱动的合并方法设计了具有改善的靶标亲和力的新型CK2抑制剂。尿石素部分被提议作为两种已知的CK2抑制剂鞣花酸和DBC之间的可能搭桥支架。优化尿石素A作为桥联部分导致鉴定出4-溴-3,8-二羟基苯并[c] chromen-6-one作为新型，有效和选择性的CK2抑制剂，其K i值为7 n M对抗蛋白激酶，与两个亲本片段相比，对靶标的亲和力显着提高。
• Studies on aldose reductase inhibitors from natural products. Part III. Studies on aldose reductase inhibitors from medicinal plant of "Sinfito," Potentilla candicans, and further synthesis of their related compounds.
  作者：Satoshi TERASHIMA、Mineo SHIMIZU、Hajime NAKAYAMA、Masatoshi ISHIKURA、Yutaka UEDA、Kunihiro IMAI、Akio SUZUI、Naokata MORITA

  DOI：10.1248/cpb.38.2733

  日期：——

  For several years we have screened natural products having aldose reductase (AR) inhibitory activity. 3, 3', 4-Tri-O-methylellagic acid 4'-sulfate potassium salt (2) was isolated from a Mexican herb "Sinfito" (Potentilla candicans) as a potent AR inhibitory active constituent. 2 was more potent (IC<50>=8.0×10<-8>M) than ellagic acid, which is one of the natural inhibitors of AR. So we examined the synthesis of ellagic acid derivatives and found that the sulfate group is one of the important function.

  在过去几年里，我们对具有醛糖还原酶（AR）抑制活性的天然产物进行了筛选。从一种墨西哥香草“Sinfito”（Potentilla candicans）中分离出了3, 3', 4-三-O-甲基鞣酸4'-硫酸钾盐（2），作为一种有效的AR抑制活性成分。其活性比鞣酸更强（IC<50>=8.0×10<-8>M），而鞣酸是AR的自然抑制剂之一。因此，我们研究了鞣酸衍生物的合成，并发现硫酸酯基团是一个重要的功能团。
• Tannins and Related Polyphenols of Melastomataceous Plants. III. Nobotanins G, H and I, Dimeric Hydrolyzable Tannins from Heterocentron roseum.
  作者：Takashi YOSHIDA、Kumiko HABA、Fumihisa NAKATA、Yoshiaki OKANO、Tetsuro SHINGU、Takuo OKUDA

  DOI：10.1248/cpb.40.66

  日期：——

  Three new hydrolyzable tannin dimers, nobotanins G (6), H (12) and I (13), have been isolated from the leaves of Heterocentron roseum (Melastomataceae), and their structures were elucidated on the basis of chemical degradations and nuclear magnetic resonance spectral analyses. Nobotanin I (13) is a novel dimer possessing a depsidone-forming valoneoyl group in the molecule. Five known tannins, casuarictin (1), strictinin (2), geraniin (3), and nobotanins B (4) and F (5), were also isolated.

  三种新的水解单宁二聚体，诺博塔宁G (6)、H (12) 和I (13)，已从玫瑰异菊（Melastomataceae）叶中分离出来，其结构通过化学降解和核磁共振光谱分析得以阐明。诺博塔宁I (13) 是一种新型二聚体，分子中具有形成环状酮的香豆酸基团。此外，还分离出了五种已知的单宁，包括卡苏里克丁 (1)、严格单宁 (2)、香草松 (3)、以及诺博塔宁B (4) 和F (5)。
• Dimeric phenolic constituents from the roots of Tamarix nilotica
  作者：M.A.M. Nawwar、J. Buddrus、H. Bauer

  DOI：10.1016/s0031-9422(82)85054-1

  日期：1982.1

  Abstract The debarked roots of Tamarix nilotica contain the furanofuran lignan (±)-syringaresinol so far not reported from the Tamaricaceae, and the new natural product ellagic acid 3,3′-dimethyl ether 4- O -β- d -glucopyranoside. Further constituents were isoferulic acid, gallic acid, dehydrodigallic acid and ellagic acid. The structure of the isolated compounds was determined mostly by 1 H and 13

  摘要 柽柳的去皮根中含有柽柳科尚未报道的呋喃呋喃木脂素(±)-丁香脂素和新的天然产物鞣花酸3,3'-二甲醚4-O-β-d-吡喃葡萄糖苷。其他成分是异阿魏酸、没食子酸、脱氢没食子酸和鞣花酸。分离出的化合物的结构主要由 1 H 和 13 C NMR 光谱确定。
• Oenotheins D, F and G, hydrolysable tannin dimers from Oenothera laciniata
  作者：Takashi Yoshida、Tong Chou、Tetsuro Shingu、Takuo Okuda

  DOI：10.1016/0031-9422(95)00267-b

  日期：1995.9

  Three new dimeric hydrolysable tannins, oenotheins D, F and G, together with known tannins including the macrocyclic oligomers, oenotheins A and B, have been isolated from roots and stems of Oenothera laciniata. Their structures were elucidated on the basis of chemical and spectral evidence. Oenotheins D and F were macrocyclic dimers isomeric with oenothein B in relation to the orientation of the valoneoyl

  从月见草的根和茎中分离出三种新的二聚体可水解单宁，月见草苷 D、F 和 G，以及已知的单宁，包括大环低聚物，月见草苷 A 和 B。根据化学和光谱证据阐明了它们的结构。Oenotheins D 和 F 是大环二聚体，与 Oenothein B 的异构体与连接单体的丙戊酰基团的方向有关。