RESVERATROL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12O3
Molecular Weight	228.2433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1

InChI

InChIKey=LUKBXSAWLPMMSZ-OWOJBTEDSA-N

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+

HIDE SMILES / InChI

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02130440 | https://clinicaltrials.gov/ct2/show/NCT02905799 | https://www.ncbi.nlm.nih.gov/pubmed/26221416 | https://www.ncbi.nlm.nih.gov/pubmed/29387206

Resveratrol, a natural non-flavonoid polyphenol, exhibits a wide range of beneficial properties as an anticancer agent, a platelet anti-aggregation agent, and an antioxidant, as well as its anti-aging, anti-inflammatory, antiallergenic. This compound is in phase III clinical trials in combination with carboxymethyl-β-glucan for improving nasal symptoms in children with pollen-induced allergic rhinitis. Also in phase III clinical trial in the treatment of painful knee osteoarthritis and in type 2 diabetic patients. It has been demonstrated that resveratrol may prevent type 2 diabetic by targeting Sirtuin type 1 (SIRT1), indicating that SIRT1 may be a novel therapeutic target for diabetes prevention.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NAD-dependent protein deacetylase sirtuin-1 3 Target ID: Q96EB6 Gene ID: 23411.0 Gene Symbol: SIRT1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29387206	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: https://doi.org/10.1185/03007995.2014.938731	Primary	Phase III 656	Unknown Approved Use Unknown
Osteoarthritis of knee 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28965100	Palliative	Phase III 656	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29387206	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of resveratrol on 12-O-tetradecanoylphorbol-13-acetate-induced oxidative events and gene expression in mouse skin.	1998 Dec 11	10381133
Inhibitory effect of resveratrol on free radical generation in blood platelets.	1999	10824865
Resveratrol inhibits cyclooxygenase-2 transcription in human mammary epithelial cells.	1999	10668496
Cancer chemopreventive activity of resveratrol.	1999	10370867
Effects of the wine polyphenolics quercetin and resveratrol on pro-inflammatory cytokine expression in RAW 264.7 macrophages.	1999 Apr 15	10086329
Cell cycle effects and control of gene expression by resveratrol in human breast carcinoma cell lines with different metastatic potentials.	1999 Aug	10402233
Resveratrol is a selective human cytochrome P450 1A1 inhibitor.	1999 Aug 19	10448061
Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells.	1999 Dec 1	10606230
Suppression of nitric oxide synthase and the down-regulation of the activation of NFkappaB in macrophages by resveratrol.	1999 Feb	10188978
Resveratrol inhibits MAPK activity and nuclear translocation in coronary artery smooth muscle: reversal of endothelin-1 stimulatory effects.	1999 May 14	10356984
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.	1999 Nov 26	10594344
Resveratrol inhibition of herpes simplex virus replication.	1999 Oct	10551373
Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity.	1999 Oct	10496962
Inhibition of aryl hydrocarbon-induced cytochrome P-450 1A1 enzyme activity and CYP1A1 expression by resveratrol.	1999 Oct	10496959
Resveratrol prevents apoptosis in K562 cells by inhibiting lipoxygenase and cyclooxygenase activity.	1999 Oct 1	10491155
Deactivation of cultured human liver myofibroblasts by trans-resveratrol, a grapevine-derived polyphenol.	2000 Apr	10733549
Effect of resveratrol, a natural polyphenolic compound, on reactive oxygen species and prostaglandin production.	2000 Apr 1	10718345
Ligand structure-dependent differences in activation of estrogen receptor alpha in human HepG2 liver and U2 osteogenic cancer cell lines.	2000 Apr 25	10854714
Grape-derived chemopreventive agent resveratrol decreases prostate-specific antigen (PSA) expression in LNCaP cells by an androgen receptor (AR)-independent mechanism.	2000 Jan-Feb	10769659
Chemopreventive properties of trans-resveratrol are associated with inhibition of activation of the IkappaB kinase.	2000 Jul 1	10910059
Resveratrol suppresses TNF-induced activation of nuclear transcription factors NF-kappa B, activator protein-1, and apoptosis: potential role of reactive oxygen intermediates and lipid peroxidation.	2000 Jun 15	10843709
24R,25-(OH)(2)D(3) mediates its membrane receptor-dependent effects on protein kinase C and alkaline phosphatase via phospholipase A(2) and cyclooxygenase-1 but not cyclooxygenase-2 in growth plate chondrocytes.	2000 Mar	10653606
Expression of cyclooxygenase (COX)-1 and COX-2 in adaptive cytoprotection induced by mild stress.	2000 Mar-Apr	10791687
Resveratrol induces Fas signalling-independent apoptosis in THP-1 human monocytic leukaemia cells.	2000 May	10848832
Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure.	2000 May	10783318
Trans-resveratrol modulates the catalytic activity and mRNA expression of the procarcinogen-activating human cytochrome P450 1B1.	2000 Nov	11100935
Synergistic inhibition of HIV-1 in activated and resting peripheral blood mononuclear cells, monocyte-derived macrophages, and selected drug-resistant isolates with nucleoside analogues combined with a natural product, resveratrol.	2000 Nov 1	11115955
Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway.	2000 Nov 15	11020457
Resveratrol reverses tumor-promoter-induced inhibition of gap-junctional intercellular communication.	2000 Sep 7	10973802
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.	2001	11962253
Resveratrol inhibits intestinal tumorigenesis and modulates host-defense-related gene expression in an animal model of human familial adenomatous polyposis.	2001	11588890
Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2).	2001	11455568
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.	2001 Feb	11236827
Resveratrol-induced activation of p53 and apoptosis is mediated by extracellular-signal-regulated protein kinases and p38 kinase.	2001 Feb 15	11245472
Classic NSAID and selective cyclooxygenase (COX)-1 and COX-2 inhibitors in healing of chronic gastric ulcers.	2001 Jun 1	11376495
Induction of endothelin-1 expression by oxidative stress in vascular smooth muscle cells.	2001 Nov-Dec	11755377
Redox-sensitive interaction between KIAA0132 and Nrf2 mediates indomethacin-induced expression of gamma-glutamylcysteine synthetase.	2002 Apr 1	11909699
Gene expression profiles with activation of the estrogen receptor alpha-selective estrogen receptor modulator complex in breast cancer cells expressing wild-type estrogen receptor.	2002 Aug 1	12154049
Antioxidants induce different phenotypes by a distinct modulation of signal transduction.	2002 Dec 18	12482581
Mechanism of resveratrol-mediated suppression of tissue factor gene expression.	2002 Jan	11858183
Transcriptional induction of CYP1A1 by oltipraz in human Caco-2 cells is aryl hydrocarbon receptor- and calcium-dependent.	2002 Jul 5	11959854
Resveratrol enhances the expression of non-steroidal anti-inflammatory drug-activated gene (NAG-1) by increasing the expression of p53.	2002 Mar	11895857
Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol.	2002 Sep	12189197
Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate.	2003	12569440
Effect of trans-resveratrol on signal transduction pathways involved in paclitaxel-induced apoptosis in human neuroblastoma SH-SY5Y cells.	2003 Apr	12510025
Resveratrol blocks interleukin-1beta-induced activation of the nuclear transcription factor NF-kappaB, inhibits proliferation, causes S-phase arrest, and induces apoptosis of acute myeloid leukemia cells.	2003 Aug 1	12689943
Phytoestrogen regulation of a Vitamin D3 receptor promoter and 1,25-dihydroxyvitamin D3 actions in human breast cancer cells.	2003 Feb	12710998
Suppression of IL-8 gene transcription by resveratrol in phorbol ester treated human monocytic cells.	2003 Jun	12765200
Effects of resveratrol and 4-hexylresorcinol on hydrogen peroxide-induced oxidative DNA damage in human lymphocytes.	2003 May	12797471

Patents

Sample Use Guides

In Vivo Use Guide

Seasonal Allergic Rhinitis: 2 sprays per nostril 3 times a day for a period of two months knee osteoarthritis: resveratrol will be administered orally, at the dose of 40 mg (2 caplets) twice a day for one week, then at the dose of 20 mg (1 caplet) twice a day, for a total duration of 6 months.

Route of Administration: Other

In Vitro Use Guide

The insulinoma cell line clone 1E (INS-1E) was treated with palmitic acid (PA). PA suppressed the expression of SIRT1 in a dose- and time-dependent manner. In PA-induced INS-1E cells, it was demonstrated that 10 µM resveratrol modulated the expression of PGC-1α and FOXO3a via SIRT1 and regulated the expression of mitochondrial biogenesis-associated, lipid metabolism-associated and β-cells-associated proteins.

Name

Type

Language

RESVERATROL

Official Name

English

Resveratrol [WHO-DD]

Common Name

English

CA 1201

Common Name

English

RESVERATROL(E)-FORM

Common Name

English

RESVIDA

Common Name

English

RESVERATROL [INCI]

Common Name

English

5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-1,3-BENZENEDIOL

Systematic Name

English

TRANS-RESVERATROL [USP-RS]

Common Name

English

BIOFORT

Common Name

English

BIA-6-512

Code

English

NSC-327430

Code

English

RESVERATROL [MART.]

Common Name

English

(E)-RESVERATROL

Common Name

English

(E)-5-(P-HYDROXYSTYRYL)RESORCINOL

Common Name

English

SRT 501M

Common Name

English

TRANS-RESVERATROL

Common Name

English

CUSPIDATIN

Common Name

English

RESVERATROL P 5

Common Name

English

Jotrol

Brand Name

English

MELINJO RESVERATROL 20

Common Name

English

BIA 6-512

Code

English

POLYGONIN

Common Name

English

RESVERATROL [HSDB]

Common Name

English

RESVERATROL [VANDF]

Common Name

English

5-((E)-2-(4-HYDROXYPHENYL)-ETHENYL) BENZENE-1,3 DIOL

Systematic Name

English

RESVERATROL [MI]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/16/1827