CHEBI:45713 - trans-resveratrol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name trans-resveratrol
ChEBI ID CHEBI:45713
ChEBI ASCII Name trans-resveratrol
Definition A resveratrol in which the double bond has E configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:36000, CHEBI:45712
Supplier Information ChemicalBook:CB32735437, ChemicalBook:CB7325012, Selleckchem:Resveratrol, ZINC000000006787
Download Molfile XML SDF
more structures >>
Wikipedia License
Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts. Although commonly used as a dietary supplement and studied in laboratory models of human diseases, there is no high-quality evidence that resveratrol improves lifespan or has a substantial effect on any human disease.
Read full article at Wikipedia
Formula C14H12O3
Net Charge 0
Average Mass 228.24328
Monoisotopic Mass 228.07864
InChI InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+
InChIKey LUKBXSAWLPMMSZ-OWOJBTEDSA-N
SMILES Oc1ccc(cc1)\C=C\c1cc(O)cc(O)c1
Metabolite of Species Details
Vitis vinifera (NCBI:txid29760) See: PubMed
Arachis hypogaea (NCBI:txid3818) Found in seed (BTO:0001226). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via resveratrol )
radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
phytoalexin
A toxin made by a plant that acts against an organism attacking it.
(via resveratrol )
quorum sensing inhibitor
Any compound that interferes with bacterial communication (quorum sensing, QS).
glioma-associated oncogene inhibitor
An inhibitor of any of the glioma-associated oncogene (GLI) proteins.
(via resveratrol )
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
(via resveratrol )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trans-resveratrol (CHEBI:45713) has role antioxidant (CHEBI:22586)
trans-resveratrol (CHEBI:45713) has role phytoalexin (CHEBI:26115)
trans-resveratrol (CHEBI:45713) has role plant metabolite (CHEBI:76924)
trans-resveratrol (CHEBI:45713) has role quorum sensing inhibitor (CHEBI:138977)
trans-resveratrol (CHEBI:45713) has role radical scavenger (CHEBI:48578)
trans-resveratrol (CHEBI:45713) is a resveratrol (CHEBI:27881)
Incoming (−)-trans-ε-viniferin (CHEBI:10556) has functional parent trans-resveratrol (CHEBI:45713)
(+)-trans-ε-viniferin (CHEBI:76137) has functional parent trans-resveratrol (CHEBI:45713)
(2R,3R)-trans-δ-viniferin (CHEBI:76147) has functional parent trans-resveratrol (CHEBI:45713)
(2R,3S)-trans-ε-viniferin (CHEBI:76143) has functional parent trans-resveratrol (CHEBI:45713)
(2S,3R)-trans-ε-viniferin (CHEBI:76140) has functional parent trans-resveratrol (CHEBI:45713)
(2S,3S)-trans-δ-viniferin (CHEBI:76141) has functional parent trans-resveratrol (CHEBI:45713)
(E)-trans-miyabenol C (CHEBI:76193) has functional parent trans-resveratrol (CHEBI:45713)
3-methoxy-4',5-dihydroxy-trans-stilbene (CHEBI:63672) has functional parent trans-resveratrol (CHEBI:45713)
4'-O-methyl-trans-resveratrol (CHEBI:232084) has functional parent trans-resveratrol (CHEBI:45713)
trans-diptoindonesin B (CHEBI:76196) has functional parent trans-resveratrol (CHEBI:45713)
trans-piceid (CHEBI:8198) has functional parent trans-resveratrol (CHEBI:45713)
resveratrol-3-O-sulfate (CHEBI:84040) has functional parent trans-resveratrol (CHEBI:45713)
IUPAC Name
5-[(1E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Synonyms Sources
(E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol ChemIDplus
(E)-resveratrol ChEBI
3,4',5-stilbenetriol ChemIDplus
3,4',5-trihydroxy-trans-stilbene MetaCyc
3,4',5-trihydroxystilbene ChemIDplus
3,5,4'-trihydroxystilbene ChemIDplus
5-[(E)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol PDBeChem
RESVERATROL PDBeChem
Resveratrol KEGG COMPOUND
trans-resveratrol UniProt
Manual Xrefs Databases
C00002903 KNApSAcK
C03582 KEGG COMPOUND
CPD-83 MetaCyc
DB02709 DrugBank
HMDB0003747 HMDB
LMPK13090005 LIPID MAPS
Resveratrol Wikipedia
STL PDBeChem
View more database links
Registry Numbers Types Sources
1912434 Beilstein Registry Number Beilstein
1912434 Reaxys Registry Number Reaxys
501-36-0 CAS Registry Number ChemIDplus
501-36-0 CAS Registry Number NIST Chemistry WebBook
Citations
Chen T, Sheng J, Fu Y, Li M, Wang J, Jia AQ (2017)
1H NMR-Based Global Metabolic Studies of Pseudomonas aeruginosa upon Exposure of the Quorum Sensing Inhibitor Resveratrol.
Journal of proteome research 16, 824-830 [PubMed:28094526]
[show Abstract]
Chirumbolo S (2015)
Resveratrol in spermatogenesis.
Cell biology international 39, 775-776 [PubMed:25684680]
Wang JF, Ma L, Xi HF, Wang LJ, Li SH (2015)
Resveratrol synthesis under natural conditions and after UV-C irradiation in berry skin is associated with berry development stages in 'Beihong' (V. vinifera×V. amurensis).
Food chemistry 168, 430-438 [PubMed:25172731]
[show Abstract]
Zhao X, Ma F, Li P, Li G, Zhang L, Zhang Q, Zhang W, Wang X (2015)
Simultaneous determination of isoflavones and resveratrols for adulteration detection of soybean and peanut oils by mixed-mode SPE LC-MS/MS.
Food chemistry 176, 465-471 [PubMed:25624257]
[show Abstract]
Zhao Y, Shi M, Ye JH, Zheng XQ, Lu JL, Liang YR (2015)
Photo-induced chemical reaction of trans-resveratrol.
Food chemistry 171, 137-143 [PubMed:25308653]
[show Abstract]
Ma F, Li P, Zhang Q, Yu L, Zhang L (2015)
Rapid determination of trans-resveratrol in vegetable oils using magnetic hydrophilic multi-walled carbon nanotubes as adsorbents followed by liquid chromatography-tandem mass spectrometry.
Food chemistry 178, 259-266 [PubMed:25704710]
[show Abstract]
Freitas JV, Praça FS, Bentley MV, Gaspar LR (2015)
Trans-resveratrol and beta-carotene from sunscreens penetrate viable skin layers and reduce cutaneous penetration of UV-filters.
International journal of pharmaceutics 484, 131-137 [PubMed:25724133]
[show Abstract]
Biagi M, Bertelli AA (2015)
Wine, alcohol and pills: What future for the French paradox?
Life sciences 131, 19-22 [PubMed:25841977]
[show Abstract]
Chen L, Yang S, Zumbrun EE, Guan H, Nagarkatti PS, Nagarkatti M (2015)
Resveratrol attenuates lipopolysaccharide-induced acute kidney injury by suppressing inflammation driven by macrophages.
Molecular nutrition & food research 59, 853-864 [PubMed:25643926]
[show Abstract]
Pang C, Cao L, Wu F, Wang L, Wang G, Yu Y, Zhang M, Chen L, Wang W, Lv W, Chen L, Zhu J, Pan J, Zhang H, Xu Y, Ding L (2015)
The effect of trans-resveratrol on post-stroke depression via regulation of hypothalamus-pituitary-adrenal axis.
Neuropharmacology 97, 447-456 [PubMed:25937213]
[show Abstract]
Heebøll S, Thomsen KL, Clouston A, Sundelin EI, Radko Y, Christensen LP, Ramezani-Moghadam M, Kreutzfeldt M, Pedersen SB, Jessen N, Hebbard L, George J, Grønbæk H (2015)
Effect of resveratrol on experimental non-alcoholic steatohepatitis.
Pharmacological research 95-96, 34-41 [PubMed:25814186]
[show Abstract]
Etxeberria U, Arias N, Boqué N, Macarulla MT, Portillo MP, Martínez JA, Milagro FI (2015)
Reshaping faecal gut microbiota composition by the intake of trans-resveratrol and quercetin in high-fat sucrose diet-fed rats.
The Journal of nutritional biochemistry 26, 651-660 [PubMed:25762527]
[show Abstract]
Sales JM, Resurreccion AV (2014)
Resveratrol in peanuts.
Critical reviews in food science and nutrition 54, 734-770 [PubMed:24345046]
[show Abstract]
Francioso A, Mastromarino P, Restignoli R, Boffi A, d'Erme M, Mosca L (2014)
Improved stability of trans-resveratrol in aqueous solutions by carboxymethylated (1,3/1,6)-β-D-glucan.
Journal of agricultural and food chemistry 62, 1520-1525 [PubMed:24467639]
[show Abstract]
Dudley J, Das S, Mukherjee S, Das DK (2009)
Resveratrol, a unique phytoalexin present in red wine, delivers either survival signal or death signal to the ischemic myocardium depending on dose.
The Journal of nutritional biochemistry 20, 443-452 [PubMed:18789672]
[show Abstract]
Anekonda TS, Adamus G (2008)
Resveratrol prevents antibody-induced apoptotic death of retinal cells through upregulation of Sirt1 and Ku70.
BMC research notes 1, 122 [PubMed:19046449]
[show Abstract]
Rubiolo JA, Mithieux G, Vega FV (2008)
Resveratrol protects primary rat hepatocytes against oxidative stress damage: activation of the Nrf2 transcription factor and augmented activities of antioxidant enzymes.
European journal of pharmacology 591, 66-72 [PubMed:18616940]
[show Abstract]
Kirimlioglu V, Sozen H, Turkoglu S, Haberal M (2008)
Protective effect of resveratrol, a red wine constituent polyphenol, on rats subjected to portal vein thrombosis.
Transplantation proceedings 40, 290-292 [PubMed:18261608]
[show Abstract]
Gedik E, Girgin S, Ozturk H, Obay BD, Ozturk H, Buyukbayram H (2008)
Resveratrol attenuates oxidative stress and histological alterations induced by liver ischemia/reperfusion in rats.
World journal of gastroenterology 14, 7101-7106 [PubMed:19084917]
[show Abstract]
Bradamante S, Barenghi L, Villa A (2004)
Cardiovascular protective effects of resveratrol.
Cardiovascular drug reviews 22, 169-188 [PubMed:15492766]
[show Abstract]
Stojanović S, Sprinz H, Brede O (2001)
Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation.
Archives of biochemistry and biophysics 391, 79-89 [PubMed:11414688]
[show Abstract]
Wu JM, Wang ZR, Hsieh TC, Bruder JL, Zou JG, Huang YZ (2001)
Mechanism of cardioprotection by resveratrol, a phenolic antioxidant present in red wine (Review).
International journal of molecular medicine 8, 3-17 [PubMed:11408943]
[show Abstract]
Last Modified
10 November 2017