Page last updated: 2024-12-10

epsilon-viniferin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

epsilon-viniferin: stilbene dimer; isolated from the Oriental medicinal plant Vitis coignetiae; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(-)-trans-epsilon-viniferin : A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
VitisgenusA plant genus in the family Vitaceae. It is a woody vine cultivated worldwide. It is best known for grapes, the edible fruit and used to make WINE and raisins.[MeSH]VitaceaeA plant family of the order Rhamnales, subclass Rosidae, class Magnoliopsida, best known for the VITIS genus, the source of grapes.[MeSH]

Cross-References

ID SourceID
PubMed CID5281728
CHEMBL ID1224875
CHEBI ID10556
SCHEMBL ID3041632
MeSH IDM0242677

Synonyms (36)

Synonym
W2075 ,
chebi:10556 ,
CHEMBL1224875 ,
(-)-.epsilon.-viniferin
epsilon-viniferin
62218-08-0
epsilon-viniferine
AC1NQYZ4 ,
1,3-benzenediol, 5-(2,3-dihydro-6-hydroxy-2(4-hydroxyphenyl)4-(2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-
0k8z2k6y7o ,
5-(2,3-dihydro-6-hydroxy-2(4-hydroxyphenyl)4-(2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-1,3-benzenediol
unii-0k8z2k6y7o
(-)-trans-epsilon-viniferin
(-)-epsilon-viniferin
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
SCHEMBL3041632
5-[(2r,3r)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(e)-2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl]benzene-1,3-diol
surecn3041632
.epsilon.-viniferin
5-((2r,3r)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-((1e)-2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-1,3-benzenediol
1,3-benzenediol, 5-((2r,3r)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-((1e)-2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-
(e)-.epsilon.-viniferin
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)))-
viniferin, epsilon-
resveratrol dimer
5-((2r,3r)-6-hydroxy-2-(4-hydroxyphenyl)-4-((e)-4-hydroxystyryl)-2,3-dihydrobenzofuran-3-yl)benzene-1,3-diol
CS-0024314
HY-N3841
mfcd12964987
epsilon-viniferin , hplc grade
Q5383943
MS-28265
-iniferin
bdbm50531887
??-?viniferin
AKOS040733117

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The effect of combined use was in support of a synergistic pharmacodynamic effect."( Towards novel anti-tumor strategies for hepatic cancer: ɛ-viniferin in combination with vincristine displays pharmacodynamic synergy at lower doses in HepG2 cells.
Akalın, G; Incesu, Z; Işcan, A; Kutlu, HM; Önder, NI; Özdemir, F; Şen, M, 2014
)
0.4

Compound-Compound Interactions

ExcerptReferenceRelevance
" IC(50) value of ɛ-viniferin in combination with vincristine was 15."( Towards novel anti-tumor strategies for hepatic cancer: ɛ-viniferin in combination with vincristine displays pharmacodynamic synergy at lower doses in HepG2 cells.
Akalın, G; Incesu, Z; Işcan, A; Kutlu, HM; Önder, NI; Özdemir, F; Şen, M, 2014
)
0.4

Bioavailability

ExcerptReferenceRelevance
" It would be important in the future to investigate the origins of the differences in wine stilbene levels in relation to the vine varieties, and the bioavailability of the newly extracted stilbene delta-viniferin in plasma after consumption of different types of wines."( Determination of stilbenes (delta-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, epsilon-viniferin) in Brazilian wines.
Bornet, A; Delaunay, JC; Mérillon, JM; Richard, T; Teissédre, PL; Valls, J; Vanderlinde, R; Vitrac, X, 2005
)
0.54
" However, the oral bioavailability of these compounds in humans is low (˂1-2%)."( The Oral Bioavailability of Trans-Resveratrol from a Grapevine-Shoot Extract in Healthy Humans is Significantly Increased by Micellar Solubilization.
Behnam, D; Bosy-Westphal, A; Calvo-Castro, LA; David, F; Ehrt, H; Frank, J; Schiborr, C; Sus, N; Voggel, J, 2018
)
0.48
"The oral bioavailability of trans-resveratrol from the grapevine-shoot extract Vineatrol30 was significantly increased using a liquid micellar formulation, without any treatment-related adverse effects, making it a suitable system for improved supplementation of trans-resveratrol."( The Oral Bioavailability of Trans-Resveratrol from a Grapevine-Shoot Extract in Healthy Humans is Significantly Increased by Micellar Solubilization.
Behnam, D; Bosy-Westphal, A; Calvo-Castro, LA; David, F; Ehrt, H; Frank, J; Schiborr, C; Sus, N; Voggel, J, 2018
)
0.48
" Its low water solubility, its photo-sensitivity and its low bioavailability make its applications in the food industry complicated."( Encapsulation of ε-viniferin in onion-type multi-lamellar liposomes increases its solubility and its photo-stability and decreases its cytotoxicity on Caco-2 intestinal cells.
Atgié, C; Courtois, A; Faure, C; Garcia, M; Krisa, S; Richard, T; Sauvant, P, 2019
)
0.51
" Although bioavailability studies have shown poor absorption and high metabolism of this stilbene, multiple studies demonstrated its biological properties."( In the shadow of resveratrol: biological activities of epsilon-viniferin.
Atgié, C; Beaumont, P; Courtois, A; Krisa, S; Richard, T, 2022
)
0.97
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
1-benzofuransA member of the class of benzofurans consisting of a 1-benzofuran skeleton and its substituted derivatives thereof.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
stilbenoidAny olefinic compound characterised by a 1,2-diphenylethylene backbone.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)19.60000.00002.37899.7700AID1624346
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1062140Antimicrobial activity against Escherichia coli O157:H7 by spectrophotometry2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1062137Antibiofilm activity against Escherichia coli O157:H7 assessed as repression of csgC expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083161Antifungal activity against Neofusicoccum parvum PER20 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1374190Estrogenic activity at ERalpha/ERbeta (unknown origin) expressed in human HepG2 cells co-expressing ERE-dependent promoter assessed as increase in ER-mediated transcriptional activation at 10 uM incubated for 24 hrs by luciferase reporter gene assay relat2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné.
AID1062134Antibiofilm activity against Escherichia coli O157:H7 assessed as repression of csgG expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1062139Antibiofilm activity against Escherichia coli O157:H7 assessed as repression of csgA expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1062130Antibiofilm activity against Escherichia coli O157:H7 assessed as induction of motB gene expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083166Antifungal activity against Diplodia seriata assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062129Antibiofilm activity against Escherichia coli O157:H7 assessed as induction of qseB gene expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083163Antifungal activity against Botryosphaeria dothidea OGE14 assessed as growth inhibition measured after 1 to 10 days relative to control2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1083169Antifungal activity against Neofusicoccum parvum assessed as growth inhibition at 500 uM measured after 1 to 10 days relative to control2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062131Antibiofilm activity against Escherichia coli O157:H7 assessed as induction of flhD gene expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1624346Inhibition of human recombinant MAO-A expressed in baculovirus infected BTI-TN-5B1-4 insect cells using p-tyramine as substrate after 15 mins by resorufin dye-based spectrometric analysis2019Bioorganic & medicinal chemistry letters, 03-15, Volume: 29, Issue:6
Osthenol, a prenylated coumarin, as a monoamine oxidase A inhibitor with high selectivity.
AID1083170Antifungal activity against Diplodia seriata assessed as growth inhibition at 500 uM measured after 1 to 10 days relative to control2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1083159Antifungal activity against Diplodia mutila BRA08 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062135Antibiofilm activity against Escherichia coli O157:H7 assessed as repression of csgF expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083154Antifungal activity against Diplodia seriata BoF98-1 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062133Antibiofilm activity against Escherichia coli O157:H7 assessed as effect on rrsG expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083162Antifungal activity against Neofusicoccum parvum Bp0014 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID504233Antiinflammatory activity in human foreskin fibroblast assessed as inhibition of IL-1-beta-induced MMP1 production at 1 uM treated for 24 hrs before IL1-beta challenge measured after 24 hrs by Western blot analysis2010Journal of natural products, Sep-24, Volume: 73, Issue:9
Resveratrol oligomers from Vatica albiramis.
AID1083158Antifungal activity against Diplodia seriata PLU03 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1083160Antifungal activity against Neofusicoccum luteum CBS110299 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062136Antibiofilm activity against Escherichia coli O157:H7 assessed as repression of csgD expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083157Antifungal activity against Lasiodiplodia theobromae CBS116460 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062128Reduction in fimbriae production in Escherichia coli O157:H7 biofilm grown on nylon filter at 20 ug/ml after 24 hrs by scanning electron microscopy2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083156Antifungal activity against Diplodia seriata LAT28 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062144Antibiofilm activity against Escherichia coli O157:H7 after 24 hrs by spectrophotometry2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083171Antifungal activity against Togninia minima SO21 assessed as susceptibility at 500 uM measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1062138Antibiofilm activity against Escherichia coli O157:H7 assessed as repression of csgB expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1062132Antibiofilm activity against Escherichia coli O157:H7 assessed as induction of fliA gene expression at 20 ug/ml after 5 hrs by qRT-PCR analysis2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
AID1083155Antifungal activity against Diplodia seriata BoF99-1 assessed as growth inhibition measured after 1 to 10 days2012Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48
Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1374189Estrogenic activity at ERalpha/ERbeta (unknown origin) expressed in human HepG2 cells co-expressing ERE-dependent promoter assessed as increase in ER-mediated transcriptional activation at 1 uM incubated for 24 hrs by luciferase reporter gene assay relati2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (83)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (1.20)18.2507
2000's14 (16.87)29.6817
2010's49 (59.04)24.3611
2020's19 (22.89)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.43

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.43 (24.57)
Research Supply Index4.44 (2.92)
Research Growth Index5.54 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.20%)5.53%
Reviews2 (2.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other80 (96.39%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]