delta-Viniferin (BioDeep_00000226720)

   

human metabolite natural product


代谢物信息卡片


5-[(2S,3S)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

  化学式: C28H22O6 (454.1416)
中文名称:
  谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=CC4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
InChI: InChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m0/s1


描述信息

Delta-viniferin, also known as resveratrol (E)-dehydrodimer or delta-viniferin, is a member of the class of compounds known as 2-arylbenzofuran flavonoids. 2-arylbenzofuran flavonoids are phenylpropanoids containing the 2-phenylbenzofuran moiety. Delta-viniferin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delta-viniferin can be found in grape wine, which makes delta-viniferin a potential biomarker for the consumption of this food product. Delta-viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine (Vitis vinifera) leaves. It is also found in plant cell cultures. or in wine. It can also be found in Rheum maximowiczii .
Delta-viniferin, also known as resveratrol (E)-dehydrodimer or δ-viniferin, is a member of the class of compounds known as 2-arylbenzofuran flavonoids. 2-arylbenzofuran flavonoids are phenylpropanoids containing the 2-phenylbenzofuran moiety. Delta-viniferin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delta-viniferin can be found in grape wine, which makes delta-viniferin a potential biomarker for the consumption of this food product. Delta-viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine (Vitis vinifera) leaves. It is also found in plant cell cultures. or in wine. It can also be found in Rheum maximowiczii .

同义名列表

7 个代谢物同义名

5-[(2S,3S)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol; Resveratrol trans-dehydrodimer; (2S,3S)-trans-delta-viniferin; Resveratrol (E)-dehydrodimer; (2S,3S)-trans-Δ-viniferin; delta-Viniferin; Δ-viniferin



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

20 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Robin Huber, Laurence Marcourt, Margaux Héritier, Alexandre Luscher, Laurie Guebey, Sylvain Schnee, Emilie Michellod, Stéphane Guerrier, Jean-Luc Wolfender, Leonardo Scapozza, Thilo Köhler, Katia Gindro, Emerson Ferreira Queiroz. Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold. Scientific reports. 2023 09; 13(1):15986. doi: 10.1038/s41598-023-43000-5. [PMID: 37749179]
  • Arnaud Charles-Antoine Zwygart, Chiara Medaglia, Robin Huber, Romain Poli, Laurence Marcourt, Sylvain Schnee, Emilie Michellod, Beryl Mazel-Sanchez, Samuel Constant, Song Huang, Meriem Bekliz, Sophie Clément, Katia Gindro, Emerson Ferreira Queiroz, Caroline Tapparel. Antiviral properties of trans-δ-viniferin derivatives against enveloped viruses. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Jul; 163(?):114825. doi: 10.1016/j.biopha.2023.114825. [PMID: 37148860]
  • Su Hyun Park, Yu Jeong Jeong, Sung-Chul Park, Soyoung Kim, Yong-Goo Kim, Gilok Shin, Hyung Jae Jeong, Young Bae Ryu, Jiyoung Lee, Ok Ran Lee, Jae Cheol Jeong, Cha Young Kim. Highly Efficient Bioconversion of trans-Resveratrol to δ-Viniferin Using Conditioned Medium of Grapevine Callus Suspension Cultures. International journal of molecular sciences. 2022 Apr; 23(8):. doi: 10.3390/ijms23084403. [PMID: 35457219]
  • Sung-Chul Park, Jang Won Pyun, Yu Jeong Jeong, Su Hyun Park, Soyoung Kim, Yun-Hee Kim, Jong Rok Lee, Cha Young Kim, Jae Cheol Jeong. Overexpression of VlPRX21 and VlPRX35 genes in Arabidopsis plants leads to bioconversion of trans-resveratrol to δ-viniferin. Plant physiology and biochemistry : PPB. 2021 May; 162(?):556-563. doi: 10.1016/j.plaphy.2021.03.015. [PMID: 33773231]
  • Davide Righi, Robin Huber, Alexey Koval, Laurence Marcourt, Sylvain Schnee, Anaïs Le Floch, Verena Ducret, Remo Perozzo, Concetta C de Ruvo, Nicole Lecoultre, Emilie Michellod, Samad N Ebrahimi, Elisabeth Rivara-Minten, Vladimir L Katanaev, Karl Perron, Jean-Luc Wolfender, Katia Gindro, Emerson F Queiroz. Generation of Stilbene Antimicrobials against Multiresistant Strains of Staphylococcus aureus through Biotransformation by the Enzymatic Secretome of Botrytis cinerea. Journal of natural products. 2020 08; 83(8):2347-2356. doi: 10.1021/acs.jnatprod.0c00071. [PMID: 32705864]
  • Mina Nagumo, Masayuki Ninomiya, Natsuko Oshima, Tomohiro Itoh, Kaori Tanaka, Atsuyoshi Nishina, Mamoru Koketsu. Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities. Bioorganic & medicinal chemistry letters. 2019 09; 29(17):2475-2479. doi: 10.1016/j.bmcl.2019.07.026. [PMID: 31350127]
  • Leo-Paul Tisserant, Aziz Aziz, Nathalie Jullian, Philippe Jeandet, Christophe Clément, Eric Courot, Michèle Boitel-Conti. Enhanced Stilbene Production and Excretion in Vitis vinifera cv Pinot Noir Hairy Root Cultures. Molecules (Basel, Switzerland). 2016 Dec; 21(12):. doi: 10.3390/molecules21121703. [PMID: 27973421]
  • Sébastien Bruisson, Pascale Maillot, Paul Schellenbaum, Bernard Walter, Katia Gindro, Laurence Deglène-Benbrahim. Arbuscular mycorrhizal symbiosis stimulates key genes of the phenylpropanoid biosynthesis and stilbenoid production in grapevine leaves in response to downy mildew and grey mould infection. Phytochemistry. 2016 Nov; 131(?):92-99. doi: 10.1016/j.phytochem.2016.09.002. [PMID: 27623505]
  • Silvana Ficarra, Ester Tellone, Davide Pirolli, Annamaria Russo, Davide Barreca, Antonio Galtieri, Bruno Giardina, Paolo Gavezzotti, Sergio Riva, Maria Cristina De Rosa. Insights into the properties of the two enantiomers of trans-δ-viniferin, a resveratrol derivative: antioxidant activity, biochemical and molecular modeling studies of its interactions with hemoglobin. Molecular bioSystems. 2016 Apr; 12(4):1276-86. doi: 10.1039/c5mb00897b. [PMID: 26883599]
  • Qingwang Liu, Xiaolin Liao, Jie Xu, Jie Zhao, Jianguang Luo, Lingyi Kong. Development and validation of a sensitive and selective LC-MS/MS method for the determination of trans δ-veniferin, a resveratrol dehydrodimer, in rat plasma and its application to pharmacokinetics and bioavailability studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 May; 958(?):124-9. doi: 10.1016/j.jchromb.2014.03.026. [PMID: 24735927]
  • Anna Maria Timperio, Angelo D'Alessandro, Marco Fagioni, Paolo Magro, Lello Zolla. Production of the phytoalexins trans-resveratrol and delta-viniferin in two economy-relevant grape cultivars upon infection with Botrytis cinerea in field conditions. Plant physiology and biochemistry : PPB. 2012 Jan; 50(1):65-71. doi: 10.1016/j.plaphy.2011.07.008. [PMID: 21821423]
  • Anna Rita Santamaria, Nadia Mulinacci, Alessio Valletta, Marzia Innocenti, Gabriella Pasqua. Effects of elicitors on the production of resveratrol and viniferins in cell cultures of Vitis vinifera L. cv Italia. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9094-101. doi: 10.1021/jf201181n. [PMID: 21751812]
  • Xavier Vitrac, Aurélie Bornet, Regina Vanderlinde, Josep Valls, Tristan Richard, Jean-Claude Delaunay, Jean-Michel Mérillon, Pierre-Louis Teissédre. Determination of stilbenes (delta-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, epsilon-viniferin) in Brazilian wines. Journal of agricultural and food chemistry. 2005 Jul; 53(14):5664-9. doi: 10.1021/jf050122g. [PMID: 15998130]
  • Roger Pezet, Camille Perret, Julien Bernard Jean-Denis, Raffaele Tabacchi, Katia Gindro, Olivier Viret. Delta-viniferin, a resveratrol dehydrodimer: one of the major stilbenes synthesized by stressed grapevine leaves. Journal of agricultural and food chemistry. 2003 Aug; 51(18):5488-92. doi: 10.1021/jf030227o. [PMID: 12926902]
  • R H Cichewicz, S A Kouzi, M T Hamann. Dimerization of resveratrol by the grapevine pathogen Botrytis cinerea. Journal of natural products. 2000 Jan; 63(1):29-33. doi: 10.1021/np990266n. [PMID: 10650073]