hopeaphenol | 17912-85-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: hopeaphenol
• 英文别名: (1R,6S,7R,11bR)-1-(3,4-dihydroxyphenyl)-1,6,7,11b-tetrahydro-6-[(1R,6S,7R,11bR)-1,6,7,11b-tetrahydro-4,8,10-trihydroxy-1,7-bis(4-hydroxyphenyl)benzo[6,7]cyclohepta[1,2,3-cd]benzofuran-6-yl]-7-(4-hydroxyphenyl)benzo[6,7]cyclohepta[1,2,3-cd]benzofuran-4,8,10-triol；(-)-hopeaphenol；(1R,8R,9S,16R)-8,16-bis(4-hydroxyphenyl)-9-[(1R,8R,9S,16R)-4,6,12-trihydroxy-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaen-9-yl]-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaene-4,6,12-triol
• CAS: 17912-85-5
• 化学式: C₅₆H₄₂O₁₂
• 分子量: 906.942
• InChiKey: YQQUILZPDYJDQJ-KGDQSQJYSA-N

物化性质

• 熔点：
  >350 °C
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  68
• 可旋转键数：
  5
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  221
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  hopeaphenol 在 三甲基硅烷化重氮甲烷 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 以68%的产率得到(-)-hopeaphenol permethyl ether
  参考文献：
  名称：

  Solving the Supply of Resveratrol Tetramers from Papua New Guinean RainforestAnisopteraSpecies That Inhibit Bacterial Type III Secretion Systems

  摘要：

  The supply of (-)-hopeaphenol (1) was achieved via enzymatic biotransformation in order to provide material for preclinical investigation. High-throughput screening of a prefractionated natural product library aimed to identify compounds that inhibit the bacterial virulence type III secretion system (T3SS) identified several fractions derived from two Papua New Guinean Anisoptera species, showing activity against Yersinia pseudotuberculosis outer proteins E and H (YopE and YopH). Bioassay-directed isolation from the leaves of A. thurifera, and similarly A. polyandra, resulted in three known resveratrol tetramers, (-)-hopeaphenol (1), vatalbinoside A (2), and vaticanol B (3). Compounds 1-3 displayed IC50 values of 8.8, 12.5, and 9.9 μM in a luminescent reporter-gene assay (YopE) and IC50 values of 2.9, 4.5, and 3.3 μM in an enzyme-based YopH assay, respectively, which suggested that they could potentially act against the T3SS in Yersinia. The structures of 1-3 were confirmed through a combination of spectrometric, chemical methods, and single-crystal X-ray structure determinations of the natural product 1 and the permethyl ether analogue of 3. The enzymatic hydrolysis of the β-glycoside 2 to the aglycone 1 was achieved through biotransformation using the endogenous leaf enzymes. This significantly enhanced the yield of the target bioactive natural product from 0.08% to 1.3% and facilitates ADMET studies of (-)-hopeaphenol (1).

  DOI：

  10.1021/np500433z
• 作为产物：
  描述：

  vatalbinoside A 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到hopeaphenol
  参考文献：
  名称：

  [EN] COMPOUNDS AND USES THEREOF IN THE TREATMENT/PREVENTION OF GRAM-NEGATIVE BACTERIAL INFECTIONS
  [FR] COMPOSÉS ET LEURS UTILISATIONS DANS LE TRAITEMENT/LA PRÉVENTION D'INFECTIONS BACTÉRIENNES GRAM NÉGATIVES

  摘要：

  本公开涉及公式I的化合物在多细胞生物中治疗和/或预防革兰氏阴性细菌感染。本公开还涉及包含该化合物的制药组合物，包括通过给予该化合物治疗和/或预防该感染的方法，以及使用该化合物制造治疗和/或预防该感染的药物。本公开还涉及调节革兰氏阴性细菌的三型分泌系统的活性。

  公开号：

  WO2014138823A1

文献信息

• Resveratrol Oligomers from <i>Vatica albiramis</i>
  作者：Naohito Abe、Tetsuro Ito、Kenji Ohguchi、Minori Nasu、Yuichi Masuda、Masayoshi Oyama、Yoshinori Nozawa、Masafumi Ito、Munekazu Iinuma

  DOI：10.1021/np1002675

  日期：2010.9.24

  Five new stilbenoids, vatalbinosides A−E (1−5), and 13 known compounds (6−18) were isolated from the stem of Vatica albiramis. The effects of these new compounds on interleukin-1β-induced production of matrix metalloproteinase-1 (MMP-1) in human dermal fibroblasts were examined. Three resveratrol tetramers, (−)-hopeaphenol (6), vaticanol C (13), and stenophyllol C (14), were identified as strong inhibitors

  五个新的茋类，vatalbinosides A-E（1 - 5），以及13种公知的化合物（6 - 18）从茎中分离青梅albiramis。研究了这些新化合物对白细胞介素1β诱导的人皮肤成纤维细胞基质金属蛋白酶-1（MMP-1）产生的影响。三种白藜芦醇四聚体（-）-胡豆酚（6），梵蒂冈C（13）和十八醇C（14）被确定为MMP-1产生的强抑制剂。
• Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium
  作者：Mitchell H. Keylor、Bryan S. Matsuura、Markus Griesser、Jean-Philippe R. Chauvin、Ryan A. Harding、Mariia S. Kirillova、Xu Zhu、Oliver J. Fischer、Derek A. Pratt、Corey R. J. Stephenson

  DOI：10.1126/science.aaj1597

  日期：2016.12.9

  temperature. The authors leveraged this equilibrium to generate an efficient route to two of the tetramers, nepalensinol B and vateriaphenol C. Science, this issue p. 1260 Chemical synthesis of two plant-derived polyphenols relies on dynamic cleavage and reformation of a weak carbon-carbon bond. Persistent free radicals have become indispensable in the synthesis of organic materials through living radical

  在多酚合成中取得突破 化学合成通常与玩建模套件有很大不同。如果一个分子的两个大片段没有正确定向，通常不可能将它们分开，旋转一个，然后将它们重新粘贴在一起。然而，这正是 Keylor 等人的伎俩。用于合成两种植物来源的多酚。白藜芦醇形成多种二聚体、三聚体和四聚体。当一个中心碳-碳键连接碎片时，它的强度足以在室温下自发和可逆地断裂。作者利用这种平衡产生了一条通往两种四聚体的有效途径，nepalensinol B 和 vateriaphenol C。Science，本期第 10 页。1260 两种植物来源的多酚的化学合成依赖于弱碳-碳键的动态裂解和重组。持久性自由基在通过活性自由基聚合合成有机材料中变得不可或缺。然而，它们用于合成小分子的例子很少见。在这里，我们报告了持久性自由基和醌甲基化物中间体在白藜芦醇四聚体 nepalensinol B 和缬草酚 C 的合成中的应用。异常弱的碳 - 碳键的
• Antitumor agents 200.1 cytotoxicity of naturally occurring resveratrol oligomers and their acetate derivatives
  作者：Masayoshi Ohyama、Toshiyuki Tanaka、Tetsuro Ito、Munekazu Iinuma、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(99)00520-x

  日期：1999.10

  Eleven resveratrol oligomers and six acetylated derivatives were evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. The acetate of (-)-ampelopsin A (12) showed potent and selective cytotoxic activity with ED50 values of 0.6, 0.7 and 2.0 mu g/mL against KB, 1A9 and MCF-7 cells, respectively. Hopeaphenol (10) and pallidol hexaacetate (13) also showed significant cytotoxicity against KB cells with ED50 values of 1.2 and 1.6 mu g/mL, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• METHOD FOR THE EXTRACTION OF PHARMACEUTICALLY ACTIVE PRODUCTS FROM SPERMATOPHYTE PLANTS, PRODUCTS THUS OBTAINED AND THEIR USE IN THE MEDICAL FIELD, IN PARTICULAR AS SUBSTANCES WITH IMMUNOMODULATING ACTIVITY
  申请人：Ravagnan Giampietro

  公开号：US20080070851A1

  公开（公告）日：2008-03-20

  A method is described for the extraction of products having a pharmacological activity, in particular an immunomodulating activity, from spermatophyte plants. Said products, which are to be used in the pharmaceutical fields, consist of complex mixtures of compounds characterized by one or more stilbene groups, variously hydroxylated and/or glucosidated, and of compounds derived from said group by natural enzymatic biosynthetical processes (stilbenoids). The following compounds are preferred: T-Res, C-Res, glucosidated C-Res, ε-viniferine, H-gnetine, r-2-viniferine, r-viniferine, hopeaphenol, Ampelopepsin A and glucosidated T-Res.
• US9185909B2
  申请人：——

  公开号：US9185909B2

  公开（公告）日：2015-11-17