(+)-ε-viniferin pentaacetate | 223558-50-7

• 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: (+)-ε-viniferin pentaacetate
• 英文别名: [4-[(E)-2-[(2S,3S)-6-acetyloxy-2-(4-acetyloxyphenyl)-3-(3,5-diacetyloxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenyl] acetate
• CAS: 223558-50-7
• 化学式: C₃₈H₃₂O₁₁
• 分子量: 664.665
• InChiKey: LHVRYJIGNZCROE-UVHTWAPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+)-ε-viniferin pentaacetate 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 91.0h， 生成 viniferifuran
  参考文献：
  名称：

  来自Vitis vinifera'Kyohou '的具有苯并呋喃的新的低聚苯乙烯

  摘要：

  从酿酒葡萄“ Kyohou”中分离出三个具有苯并呋喃部分的新低聚苯磺酰胺，长春呋喃呋喃，（+）-vitisifuran A和（-）-vitisifuranB 。通过光谱学和化学方法阐明了这些寡苯乙烯的结构，包括绝对构型。此外，它们分别从（+）-ε-葡萄素，（+）-葡萄球蛋白A和（-）-葡萄球蛋白B化学转化，它们的绝对构型是已知的。

  DOI：

  10.1016/s0040-4020(99)00039-3
• 作为产物：
  描述：

  白藜芦醇 在 iron(III) chloride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 90.0h， 生成 (+)-ε-viniferin pentaacetate
  参考文献：
  名称：

  Vitisinol G 的计算指导全合成

  摘要：

  计算化学在合成有机化学中很有用，因为它不仅可以用来分析反应机制，还可以用来计算生物合成途径以及规划和评估总合成的策略。在这里，我们报告了白藜芦醇二聚体 vitisinol G 的计算指导全合成。 全尺寸图像

  DOI：

  10.1248/cpb.c22-00438

文献信息

• Investigation of monomeric and oligomeric wine stilbenoids in red wines by ultra-high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry
  作者：Ryan Moss、Qinyong Mao、Dennis Taylor、Cédric Saucier

  DOI：10.1002/rcm.6636

  日期：2013.8.30

  Stilbenoids are secondary plant metabolites responsible for the protection of multiple plant species including grape vine from bacterial and fungal infection. Red wine has been shown to be a major source of these compounds in the human diet, where they display an array of health benefits. Providing a more complete profile of the stilbenoids present in red wine, this study detects 41 stilbenoid compounds

  Stilbenoids是植物的次生代谢产物，负责保护多种植物物种，包括葡萄藤免受细菌和真菌感染。红酒已被证明是人类饮食中这些化合物的主要来源，它们在健康方面具有一系列好处。这项研究提供了红酒中存在的类胡萝卜素的完整信息，可检测出41种类胡萝卜素化合物，其中23种从未在红酒中被发现。
• Antifungal Activity of Resveratrol Derivatives against <i>Candida</i> Species
  作者：Benjamin Houillé、Nicolas Papon、Leslie Boudesocque、Eric Bourdeaud、Sébastien Besseau、Vincent Courdavault、Cécile Enguehard-Gueiffier、Guillaume Delanoue、Laurence Guérin、Jean-Philippe Bouchara、Marc Clastre、Nathalie Giglioli-Guivarc’h、Jérôme Guillard、Arnaud Lanoue

  DOI：10.1021/np5002576

  日期：2014.7.25

  trans-Resveratrol (1a) is a phytoalexin produced by plants in response to infections by pathogens. Its potential activity against clinically relevant opportunistic fungal pathogens has previously been poorly investigated. Evaluated herein are the candidacidal activities of oligomers (2a, 3-5) of la purified from Vitis vinifera grape canes and several analogues (1b-1j) of la obtained through semisynthesis using methylation and acetylation. Moreover, trans-epsilon-viniferin (2a), a dimer of la, was also subjected to methylation (2b) and acetylation (2c) under nonselective conditions. Neither the natural oligomers of la (2a, 3-5) nor the derivatives of 2a were active against Candida albicans SC5314. However, the dimethoxy resveratrol derivatives Id and le exhibited antifungal activity against C. albicans with minimum inhibitory concentration (MIC) values of 29-37 mu g/mL and against 11 other Candida species. Compound le inhibited the yeast-to-hyphae morphogenetic transition of C. albicans at 14 mu g/mL.
• KR2021/41662
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F
  作者：Yoshiaki Takaya、Ke-Xu Yan、Kenji Terashima、Junko Ito、Masatake Niwa

  DOI：10.1016/s0040-4020(02)00785-8

  日期：2002.9

  The absolute configurations of four stilbenedimers, (+)-ampelopsin- A, (+)-ampelopsins B, (-)-ampelopsins D and (+)ampelopsins F were respectively determined on the basis of chemical evidence. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.