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

Molecular Formula	C14H12O3
Molecular Weight	228.2433
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 1037

Conditions

Condition	Modality	Highest Phase	Product
Seasonal allergic rhinitis 63 Sources: https://doi.org/10.1185/03007995.2014.938731	Primary	Phase III 651	Unknown Approved Use Unknown
Osteoarthritis of knee 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28965100	Palliative	Phase III 651	Unknown Approved Use Unknown
Type 2 diabetes mellitus 255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29387206	Primary	Phase III 651	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Resveratrol decreases early signaling events in washed platelets but has little effect on platelet in whole blood.	2000 Apr	11001623
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
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta.	2000 Oct	11014220
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
Downregulation of the cyclin D1/Cdk4 complex occurs during resveratrol-induced cell cycle arrest in colon cancer cell lines.	2001 Aug	11481417
The use of a high-volume screening procedure to assess the effects of dietary flavonoids on human cyp1a1 expression.	2001 Aug	11454723
Resveratrol exhibits cytostatic and antiestrogenic properties with human endometrial adenocarcinoma (Ishikawa) cells.	2001 Aug 15	11507064
Effect of resveratrol on the expression of autocrine growth modulators in human breast cancer cells.	2001 Dec	11813992
Differential response of immature rat uterine tissue to ethinylestradiol and the red wine constituent resveratrol.	2001 Jan	11218048
Resveratrol inhibits interleukin-6 production in cortical mixed glial cells under hypoxia/hypoglycemia followed by reoxygenation.	2001 Jan 1	11108930
Do wine polyphenols modulate p53 gene expression in human cancer cell lines?	2001 Jul	11522280
Resveratrol isolated from Polygonum cuspidatum root prevents tumor growth and metastasis to lung and tumor-induced neovascularization in Lewis lung carcinoma-bearing mice.	2001 Jun	11385077
Short heterodimer partner (SHP) orphan nuclear receptor inhibits the transcriptional activity of aryl hydrocarbon receptor (AHR)/AHR nuclear translocator (ARNT).	2001 Jun 1	11368516
Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide.	2001 Mar	11321505
Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts.	2001 Nov	11681415
Bcl-2 overexpression attenuates resveratrol-induced apoptosis in U937 cells by inhibition of caspase-3 activity.	2001 Oct	11577002
Involvement of a post-transcriptional mechanism in the inhibition of CYP1A1 expression by resveratrol in breast cancer cells.	2001 Oct 15	11597580
Resveratrol induced serine phosphorylation of p53 causes apoptosis in a mutant p53 prostate cancer cell line.	2002 Aug	12131363
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
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
Analysis of resveratrol-induced apoptosis in human B-cell chronic leukaemia.	2002 Jun	12060119
Pharmacological preconditioning with resveratrol: an insight with iNOS knockout mice.	2002 Jun	12003803
Resveratrol induces apoptosis in thyroid cancer cell lines via a MAPK- and p53-dependent mechanism.	2002 Mar	11889192
The antiproliferative activity of resveratrol results in apoptosis in MCF-7 but not in MDA-MB-231 human breast cancer cells: cell-specific alteration of the cell cycle.	2002 Nov 1	12392819
Resveratrol suppresses angiotensin II-induced Akt/protein kinase B and p70 S6 kinase phosphorylation and subsequent hypertrophy in rat aortic smooth muscle cells.	2002 Oct	12237323
Chronic treatment with trans resveratrol prevents intracerebroventricular streptozotocin induced cognitive impairment and oxidative stress in rats.	2002 Oct 11	12270754
Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol.	2002 Sep	12189197
Suppression of 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis in rats by resveratrol: role of nuclear factor-kappaB, cyclooxygenase 2, and matrix metalloprotease 9.	2002 Sep 1	12208745
Effects of resveratrol-related hydroxystilbenes on the nitric oxide production in macrophage cells: structural requirements and mechanism of action.	2002 Sep 13	12175900
Resveratrol, a polyphenolic phytoalexin present in red wine, enhances expression and activity of endothelial nitric oxide synthase.	2002 Sep 24	12270858
Genome-scale analysis of resveratrol-induced gene expression profile in human ovarian cancer cells using a cDNA microarray.	2003 Apr	12632063
Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals.	2003 Apr 1	12615669
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.	2003 Apr 10	12687016
Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens.	2003 Apr 30	12765243
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
p21Cip1 gene expression is modulated by Egr1: a novel regulatory mechanism involved in the resveratrol antiproliferative effect.	2003 Jun 27	12690110
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.	2003 Mar	12663506
Resveratrol induces apoptosis in human esophageal carcinoma cells.	2003 Mar	12632486
Red wine polyphenolics increase LDL receptor expression and activity and suppress the secretion of ApoB100 from human HepG2 cells.	2003 Mar	12612140
Effects of resveratrol and 4-hexylresorcinol on hydrogen peroxide-induced oxidative DNA damage in human lymphocytes.	2003 May	12797471
Different short- and long-term effects of resveratrol on nuclear factor-kappaB phosphorylation and nuclear appearance in human endothelial cells.	2003 May	12716675
The egr-1 gene is induced by DNA-damaging agents and non-genotoxic drugs in both normal and neoplastic human cells.	2003 May 16	12706485
Oral administration of trans-resveratrol to guinea pigs increases cardiac DT-diaphorase and catalase activities, and protects isolated atria from menadione toxicity.	2003 May 2	12679191

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 20:04:15 UTC 2022` Edited by `admin` on `Fri Dec 16 20:04:15 UTC 2022`
Record UNII	Q369O8926L
Record Status	`Validated (UNII)`
Record Version

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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

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