Epsilon-Viniferin (BioDeep_00000396627)

Main id: BioDeep_00000002776

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


1,3-BENZENEDIOL, 5-(2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-(2-(4-HYDROXYPHENYL)ETHENYL)-3-BENZOFURANYL)-, (2R-(2.ALPHA.,3.BETA.,4(E)))-

化学式: C28H22O6 (454.1416312)
中文名称: 葡萄素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
InChI: InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1

描述信息

(-)-trans-epsilon-viniferin is a stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol. It has a role as a metabolite. It is a member of 1-benzofurans, a polyphenol and a stilbenoid. It is functionally related to a trans-resveratrol. It is an enantiomer of a (+)-trans-epsilon-viniferin.
Epsilon-viniferin is a natural product found in Dipterocarpus grandiflorus, Dipterocarpus hasseltii, and other organisms with data available.
A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.

同义名列表

26 个代谢物同义名

1,3-BENZENEDIOL, 5-(2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-(2-(4-HYDROXYPHENYL)ETHENYL)-3-BENZOFURANYL)-, (2R-(2.ALPHA.,3.BETA.,4(E)))-; 1,3-BENZENEDIOL, 5-((2R,3R)-2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-3-BENZOFURANYL)-; 5-{(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol; 5-((2R,3R)-2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-3-BENZOFURANYL)-1,3-BENZENEDIOL; 5-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl]benzene-1,3-diol; 5-((2R,3R)-6-Hydroxy-2-(4-hydroxyphenyl)-4-((E)-4-hydroxystyryl)-2,3-dihydrobenzofuran-3-yl)benzene-1,3-diol; 1,3-Benzenediol, 5-(2,3-dihydro-6-hydroxy-2(4-hydroxyphenyl)4-(2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-; 5-(2,3-Dihydro-6-hydroxy-2(4-hydroxyphenyl)4-(2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-1,3-benzenediol; epsilon-Viniferin , HPLC Grade; (-)-Trans-epsilon-viniferin; (E)-.EPSILON.-VINIFERIN; (-)-.epsilon.-Viniferin; (-)-epsilon-Viniferin; .EPSILON.-VINIFERIN; VINIFERIN, EPSILON-; epsilon-viniferine; Epsilon-viniferin; Resveratrol dimer; UNII-0K8Z2K6Y7O; ??-?Viniferin; ε-Viniferin; 0K8Z2K6Y7O; -iniferin; Viniferin; AC1NQYZ4; epsilon-Viniferin



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

79 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。



文献列表

  • David Taillis, Oussama Becissa, Anthony Pébarthé-Courrouilh, Elodie Renouf, Antonio Palos-Pinto, Tristan Richard, Stéphanie Cluzet. Antifungal Activities of a Grapevine Byproduct Extract Enriched in Complex Stilbenes and Stilbenes Metabolization by Botrytis cinerea. Journal of agricultural and food chemistry. 2023 Mar; 71(11):4488-4497. doi: 10.1021/acs.jafc.2c07843. [PMID: 36912343]
  • Saioa Gómez-Zorita, Iñaki Milton-Laskibar, Itziar Eseberri, Pauline Beaumont, Arnaud Courtois, Stéphanie Krisa, María P Portillo. Beneficial Effects of ε-Viniferin on Obesity and Related Health Alterations. Nutrients. 2023 Feb; 15(4):. doi: 10.3390/nu15040928. [PMID: 36839286]
  • Pauline Beaumont, Arnaud Courtois, Claude Atgié, Tristan Richard, Stéphanie Krisa. In the shadow of resveratrol: biological activities of epsilon-viniferin. Journal of physiology and biochemistry. 2022 May; 78(2):465-484. doi: 10.1007/s13105-022-00880-x. [PMID: 35312966]
  • Pauline Beaumont, Chrystel Faure, Arnaud Courtois, Michael Jourdes, Axel Marchal, Pierre-Louis Teissedre, Tristan Richard, Claude Atgié, Stéphanie Krisa. Trans-ε-Viniferin Encapsulation in Multi-Lamellar Liposomes: Consequences on Pharmacokinetic Parameters, Biodistribution and Glucuronide Formation in Rats. Nutrients. 2021 Nov; 13(12):. doi: 10.3390/nu13124212. [PMID: 34959765]
  • Kyung-Eon Oh, Hyeji Shin, Mi Kyeong Lee, Byoungduck Park, Ki Yong Lee. Characterization and Optimization of the Tyrosinase Inhibitory Activity of Vitis amurensis Root Using LC-Q-TOF-MS Coupled with a Bioassay and Response Surface Methodology. Molecules (Basel, Switzerland). 2021 Jan; 26(2):. doi: 10.3390/molecules26020446. [PMID: 33467011]
  • Ruijuan Liu, Yang Zhang, Xin Yao, Qi Wu, Minggang Wei, Zhaowei Yan. ε-Viniferin, a promising natural oligostilbene, ameliorates hyperglycemia and hyperlipidemia by activating AMPK in vivo. Food & function. 2020 Nov; 11(11):10084-10093. doi: 10.1039/d0fo01932a. [PMID: 33140813]
  • Luce M Mattio, Giorgia Catinella, Andrea Pinto, Sabrina Dallavalle. Natural and nature-inspired stilbenoids as antiviral agents. European journal of medicinal chemistry. 2020 Sep; 202(?):112541. doi: 10.1016/j.ejmech.2020.112541. [PMID: 32652408]
  • Ching-Yi Cheng, Yin-Ku Lin, Shih-Chun Yang, Ahmed Alalaiwe, Chia-Jung Lin, Jia-You Fang, Chwan-Fwu Lin. Percutaneous absorption of resveratrol and its oligomers to relieve psoriasiform lesions: In silico, in vitro and in vivo evaluations. International journal of pharmaceutics. 2020 Jul; 585(?):119507. doi: 10.1016/j.ijpharm.2020.119507. [PMID: 32512223]
  • Ema Kosović, Martin Topiař, Petra Cuřínová, Marie Sajfrtová. Stability testing of resveratrol and viniferin obtained from Vitis vinifera L. by various extraction methods considering the industrial viewpoint. Scientific reports. 2020 03; 10(1):5564. doi: 10.1038/s41598-020-62603-w. [PMID: 32221407]
  • Sungjin Lee, Karabasappa Mailar, Mi Il Kim, Minkyung Park, Jiseon Kim, Dal-Hee Min, Tae-Hwe Heo, Soo Kyung Bae, Wonjun Choi, Choongho Lee. Plant-Derived Purification, Chemical Synthesis, and In Vitro/In Vivo Evaluation of a Resveratrol Dimer, Viniferin, as an HCV Replication Inhibitor. Viruses. 2019 09; 11(10):. doi: 10.3390/v11100890. [PMID: 31547617]
  • Itay Maoz, Mirko De Rosso, Tatiana Kaplunov, Antonio Dalla Vedova, Noa Sela, Riccardo Flamini, Efraim Lewinsohn, Amnon Lichter. Metabolomic and transcriptomic changes underlying cold and anaerobic stresses after storage of table grapes. Scientific reports. 2019 02; 9(1):2917. doi: 10.1038/s41598-019-39253-8. [PMID: 30814549]
  • Arnaud Courtois, Claude Atgié, Axel Marchal, Ruth Hornedo-Ortega, Caroline Lapèze, Chrystel Faure, Tristan Richard, Stéphanie Krisa. Tissular Distribution and Metabolism of trans-ε-Viniferin after Intraperitoneal Injection in Rat. Nutrients. 2018 Nov; 10(11):. doi: 10.3390/nu10111660. [PMID: 30400351]
  • Laura A Calvo-Castro, Christina Schiborr, Franziska David, Heidi Ehrt, Jenny Voggel, Nadine Sus, Dariush Behnam, Anja Bosy-Westphal, Jan Frank. The Oral Bioavailability of Trans-Resveratrol from a Grapevine-Shoot Extract in Healthy Humans is Significantly Increased by Micellar Solubilization. Molecular nutrition & food research. 2018 05; 62(9):e1701057. doi: 10.1002/mnfr.201701057. [PMID: 29534330]
  • Bo Yu, Yu Jiang, Bo Zhang, Hong Yang, Tonghui Ma. Resveratrol dimer trans-ε-viniferin prevents rotaviral diarrhea in mice by inhibition of the intestinal calcium-activated chloride channel. Pharmacological research. 2018 03; 129(?):453-461. doi: 10.1016/j.phrs.2017.11.016. [PMID: 29155014]
  • SeonJu Park, Yun Na Kim, Hee Jae Kwak, Eun Ju Jeong, Seung Hyun Kim. Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné. Bioorganic & medicinal chemistry letters. 2018 02; 28(4):552-557. doi: 10.1016/j.bmcl.2018.01.063. [PMID: 29402747]
  • Jan Tříska, Naděžda Vrchotová, Josef Balík, Ivo Soural, Radek Sotolář. Variability in the Content of Trans-Resveratrol, Trans-ε-Viniferin and R2-Viniferin in Grape Cane of Seven Vitis vinifera L. Varieties during a Three-Year Study. Molecules (Basel, Switzerland). 2017 Jun; 22(6):. doi: 10.3390/molecules22060928. [PMID: 28587209]
  • Yeh-Lin Lu, Shyr-Yi Lin, Sheng-Uei Fang, Ying-Ying Hsieh, Chiy-Rong Chen, Chi-Luan Wen, Chi-I Chang, Wen-Chi Hou. Hot-Water Extracts from Roots of Vitis thunbergii var. taiwaniana and Identified ε-Viniferin Improve Obesity in High-Fat Diet-Induced Mice. Journal of agricultural and food chemistry. 2017 Mar; 65(12):2521-2529. doi: 10.1021/acs.jafc.7b00327. [PMID: 28285527]
  • Jiseon Kim, Jee Sun Min, Doyun Kim, Yu Fen Zheng, Karabasappa Mailar, Won Jun Choi, Choongho Lee, Soo Kyung Bae. A simple and sensitive liquid chromatography-tandem mass spectrometry method for trans-ε-viniferin quantification in mouse plasma and its application to a pharmacokinetic study in mice. Journal of pharmaceutical and biomedical analysis. 2017 Feb; 134(?):116-121. doi: 10.1016/j.jpba.2016.11.044. [PMID: 27902942]
  • 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]
  • Leo-Paul Tisserant, Jane Hubert, Michelle Lequart, Nicolas Borie, Nicolas Maurin, Serge Pilard, Philippe Jeandet, Aziz Aziz, Jean-Hugues Renault, Jean-Marc Nuzillard, Christophe Clément, Michèle Boitel-Conti, Eric Courot. 13C NMR and LC-MS Profiling of Stilbenes from Elicited Grapevine Hairy Root Cultures. Journal of natural products. 2016 11; 79(11):2846-2855. doi: 10.1021/acs.jnatprod.6b00608. [PMID: 27933900]
  • Hiroki Hamada, Hatsuyuki Hamada, Kei Shimoda. Synthesis of ε-Viniferin Glycosides by Glucosyltransferase from Phytolacca americana and their Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells. Natural product communications. 2015 Jun; 10(6):1017-8. doi: ". [PMID: 26197540]
  • Kaituo Wang, Yunxia Liao, Jianquan Kan, Lin Han, Yonghua Zheng. Response of direct or priming defense against Botrytis cinerea to methyl jasmonate treatment at different concentrations in grape berries. International journal of food microbiology. 2015 Feb; 194(?):32-9. doi: 10.1016/j.ijfoodmicro.2014.11.006. [PMID: 25461606]
  • Said Qsaib, Nuno Mateus, Fatima Ez-zohra Ikbal, Lala Aicha Rifai, Victor De Freitas, Tayeb Koussa. Direct identification and characterization of phenolic compounds from crude extracts of buds and internodes of grapevine (Vitis vinifera cv Merlot). Natural product communications. 2014 Nov; 9(11):1569-72. doi: ". [PMID: 25532283]
  • Jian-Bo Yang, Ai-Guo Wang, Teng-Fei Ji, Ya-Lun Su. Two new oligostilbenes from the stem of Parthenocissus quinquefolia. Journal of Asian natural products research. 2014; 16(3):275-80. doi: 10.1080/10286020.2013.877451. [PMID: 24456249]
  • Norizan Ahmat, Agustono Wibowo, Sharifah Aminah Syed Mohamad, Anis Lou Muhammad Low, Adila Sahida Sufian, Muhd Izwan Muhd Yusof, Jalifah Latip. A new symmetrical tetramer oligostilbenoid containing tetrahydrofuran ring from the stem bark of Dryobalanops lanceolata. Journal of Asian natural products research. 2014; 16(11):1099-107. doi: 10.1080/10286020.2014.938059. [PMID: 25034352]
  • Carole Lambert, Tristan Richard, Elodie Renouf, Jonathan Bisson, Pierre Waffo-Téguo, Louis Bordenave, Nathalie Ollat, Jean-Michel Mérillon, Stéphanie Cluzet. Comparative analyses of stilbenoids in canes of major Vitis vinifera L. cultivars. Journal of agricultural and food chemistry. 2013 Nov; 61(47):11392-9. doi: 10.1021/jf403716y. [PMID: 24171397]
  • Hyun Seob Cho, Jin-Hyung Lee, Shi Yong Ryu, Sang Woo Joo, Moo Hwan Cho, Jintae Lee. Inhibition of Pseudomonas aeruginosa and Escherichia coli O157:H7 biofilm formation by plant metabolite ε-viniferin. Journal of agricultural and food chemistry. 2013 Jul; 61(29):7120-6. doi: 10.1021/jf4009313. [PMID: 23819562]
  • Sebastian Macke, Gerold Jerz, Michael T Empl, Pablo Steinberg, Peter Winterhalter. Activity-guided isolation of resveratrol oligomers from a grapevine-shoot extract using countercurrent chromatography. Journal of agricultural and food chemistry. 2012 Dec; 60(48):11919-27. doi: 10.1021/jf3030584. [PMID: 23157192]
  • Carole Lambert, Jonathan Bisson, Pierre Waffo-Téguo, Yorgos Papastamoulis, Tristan Richard, Marie-France Corio-Costet, Jean-Michel Mérillon, Stéphanie Cluzet. Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family. Journal of agricultural and food chemistry. 2012 Dec; 60(48):11859-68. doi: 10.1021/jf303290g. [PMID: 23145924]
  • Yin-Shiou Lin, Yeh-Lin Lu, Guei-Jane Wang, Lih-Geeng Chen, Chi-Luan Wen, Wen-Chi Hou. Ethanolic extracts and isolated compounds from small-leaf grape (Vitis thunbergii var. taiwaniana) with antihypertensive activities. Journal of agricultural and food chemistry. 2012 Aug; 60(30):7435-41. doi: 10.1021/jf302445x. [PMID: 22762395]
  • Takuya Yashiro, Manami Nanmoku, Makoto Shimizu, Jun Inoue, Ryuichiro Sato. Resveratrol increases the expression and activity of the low density lipoprotein receptor in hepatocytes by the proteolytic activation of the sterol regulatory element-binding proteins. Atherosclerosis. 2012 Feb; 220(2):369-74. doi: 10.1016/j.atherosclerosis.2011.11.006. [PMID: 22153697]
  • 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]
  • Ha Yeon Jeong, Joo Youn Kim, Hong Kyu Lee, Do Thi Ha, Kyung-Sik Song, KiHwan Bae, Yeon Hee Seong. Leaf and stem of Vitis amurensis and its active components protect against amyloid β protein (25-35)-induced neurotoxicity. Archives of pharmacal research. 2010 Oct; 33(10):1655-64. doi: 10.1007/s12272-010-1015-6. [PMID: 21052941]
  • Naohito Abe, Tetsuro Ito, Kenji Ohguchi, Minori Nasu, Yuichi Masuda, Masayoshi Oyama, Yoshinori Nozawa, Masafumi Ito, Munekazu Iinuma. Resveratrol oligomers from Vatica albiramis. Journal of natural products. 2010 Sep; 73(9):1499-506. doi: 10.1021/np1002675. [PMID: 20735051]
  • Erkan Karacabey, Giuseppe Mazza. Optimization of solid-liquid extraction of resveratrol and other phenolic compounds from milled grape canes (Vitis vinifera). Journal of agricultural and food chemistry. 2008 Aug; 56(15):6318-25. doi: 10.1021/jf800687b. [PMID: 18636680]
  • Luigi Bavaresco, Silvia Vezzulli, Silvia Civardi, Matteo Gatti, Paola Battilani, Amedeo Pietri, Federico Ferrari. Effect of lime-induced leaf chlorosis on ochratoxin A, trans-resveratrol, and epsilon-viniferin production in grapevine (Vitis vinifera L.) berries infected by Aspergillus carbonarius. Journal of agricultural and food chemistry. 2008 Mar; 56(6):2085-9. doi: 10.1021/jf073456+. [PMID: 18290620]
  • 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]
  • Bertrand Piver, François Berthou, Yvonne Dreano, Danièle Lucas. Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: comparison with resveratrol and polyphenols from alcoholized beverages. Life sciences. 2003 Jul; 73(9):1199-213. doi: 10.1016/s0024-3205(03)00420-x. [PMID: 12818727]
  • Christian Billard, Jean-Claude Izard, Viviana Roman, Catherine Kern, Claire Mathiot, Franck Mentz, Jean-Pierre Kolb. Comparative antiproliferative and apoptotic effects of resveratrol, epsilon-viniferin and vine-shots derived polyphenols (vineatrols) on chronic B lymphocytic leukemia cells and normal human lymphocytes. Leukemia & lymphoma. 2002 Oct; 43(10):1991-2002. doi: 10.1080/1042819021000015952. [PMID: 12481898]
  • Nanik S Aminah, Sjamsul A Achmad, Norio Aimi, Emilio L Ghisalberti, Euis H Hakim, Mariko Kitajima, Yana M Syah, Hiromitsu Takayama. Diptoindonesin A, a new C-glucoside of epsilon-viniferin from Shorea seminis (Dipterocarpaceae). Fitoterapia. 2002 Oct; 73(6):501-7. doi: 10.1016/s0367-326x(02)00179-x. [PMID: 12385874]
  • Christelle Privat, João Paulo Telo, Vania Bernardes-Genisson, Abel Vieira, Jean-Pierre Souchard, Françoise Nepveu. Antioxidant properties of trans-epsilon-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media. Journal of agricultural and food chemistry. 2002 Feb; 50(5):1213-7. doi: 10.1021/jf010676t. [PMID: 11853506]
  • J Z Yang, L X Zhou, Y Ding. [Studies on chemical constituents of oligostilbenes from Vitis davidii Foex]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2001 Aug; 26(8):553-5. doi: ". [PMID: 12776371]
  • T Tanaka, T Ito, K Nakaya, M Iinuma, S Riswan. Oligostilbenoids in stem bark of Vatica rassak. Phytochemistry. 2000 May; 54(1):63-9. doi: 10.1016/s0031-9422(00)00026-1. [PMID: 10846749]
  • Y Oshima, K Namao, A Kamijou, S Matsuoka, M Nakano, K Terao, Y Ohizumi. Powerful hepatoprotective and hepatotoxic plant oligostilbenes, isolated from the Oriental medicinal plant Vitis coignetiae (Vitaceae). Experientia. 1995 Jan; 51(1):63-6. doi: 10.1007/bf01964921. [PMID: 7843333]