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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16O3
Molecular Weight 256.297
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PTEROSTILBENE

SMILES

COc1cc(/C(/[H])=C(\[H])/c2ccc(cc2)O)cc(c1)OC

InChI

InChIKey=VLEUZFDZJKSGMX-ONEGZZNKSA-N
InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+

HIDE SMILES / InChI
Pterostilbene is a naturally derived compound found primarily in blueberries and Pterocarpus marsupium heartwood. The multiple benefits of pterostilbene in the treatment and prevention of human disease have been attributed to its antioxidant, anti-inflammatory, and anti-carcinogenic properties leading to improved function of normal cells and inhibition of malignant cells. The antioxidant activity of pterostilbene has been implicated in anti-carcinogenesis, modulation of neurological disease, anti-inflammation, attenuation of vascular disease, and amelioration of diabetes. Pterostilbene increases LDL and reduces blood pressure in adults. Low doses of pterostilbene seem to hold some benefit for cognition.

Originator

Sources: DOI: 10.1016/S0031-9422(00)88430-7

Approval Year

PubMed

PubMed

TitleDatePubMed
Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters.
2005 May 4
Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities.
2006 Apr
Nitric oxide mediates natural polyphenol-induced Bcl-2 down-regulation and activation of cell death in metastatic B16 melanoma.
2007 Feb 2
Pterostilbene is equally potent as resveratrol in inhibiting 12-O-tetradecanoylphorbol-13-acetate activated NFkappaB, AP-1, COX-2, and iNOS in mouse epidermis.
2008 Jun
Natural polyphenols facilitate elimination of HT-29 colorectal cancer xenografts by chemoradiotherapy: a Bcl-2- and superoxide dismutase 2-dependent mechanism.
2008 Oct
Anti-inflammatory action of pterostilbene is mediated through the p38 mitogen-activated protein kinase pathway in colon cancer cells.
2009 Jul
Pterostilbene inhibited tumor invasion via suppressing multiple signal transduction pathways in human hepatocellular carcinoma cells.
2009 Jul
Pterostilbene inhibits colorectal aberrant crypt foci (ACF) and colon carcinogenesis via suppression of multiple signal transduction pathways in azoxymethane-treated mice.
2010 Aug 11
Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands.
2010 Dec 5
Pterostilbene, a natural dimethylated analog of resveratrol, inhibits rat aortic vascular smooth muscle cell proliferation by blocking Akt-dependent pathway.
2010 Jul-Aug
In vitro evaluation of the cytotoxic, anti-proliferative and anti-oxidant properties of pterostilbene isolated from Pterocarpus marsupium.
2010 Jun
Suppression of Heregulin-β1/HER2-Modulated Invasive and Aggressive Phenotype of Breast Carcinoma by Pterostilbene via Inhibition of Matrix Metalloproteinase-9, p38 Kinase Cascade and Akt Activation.
2011
Resveratrol modulates MED28 (Magicin/EG-1) expression and inhibits epidermal growth factor (EGF)-induced migration in MDA-MB-231 human breast cancer cells.
2011 Nov 9
3,5-dibenzyloxy-4'-hydroxystilbene induces early caspase-9 activation during apoptosis in human K562 chronic myelogenous leukemia cells.
2012 Feb
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.
2012 Feb
Inhibition of nitric oxide and inflammatory cytokines in LPS-stimulated murine macrophages by resveratrol, a potent proteasome inhibitor.
2012 Jul 10
Genomic analysis of pterostilbene predicts its antiproliferative effects against pancreatic cancer in vitro and in vivo.
2012 Jun
Pterostilbene, a natural analogue of resveratrol, potently inhibits 7,12-dimethylbenz[a]anthracene (DMBA)/12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse skin carcinogenesis.
2012 Nov
Pterostilbene induces mitochondrially derived apoptosis in breast cancer cells in vitro.
2013 Apr
Pterostilbene exerts antitumor activity against human osteosarcoma cells by inhibiting the JAK2/STAT3 signaling pathway.
2013 Feb 8
Involvement of the Nrf2 pathway in the regulation of pterostilbene-induced apoptosis in HeLa cells via ER stress.
2014
In vitro and in vivo activities of pterostilbene against Candida albicans biofilms.
2014
Differences in the glucuronidation of resveratrol and pterostilbene: altered enzyme specificity and potential gender differences.
2014
Pterostilbene, a dimethyl ether derivative of resveratrol, reduces fat accumulation in rats fed an obesogenic diet.
2014 Aug 20
The stilbenes resveratrol, pterostilbene and piceid affect growth and stress resistance in mammalian cells via a mechanism requiring estrogen receptor beta and the induction of Mn-superoxide dismutase.
2014 Feb
A combination of pterostilbene with autophagy inhibitors exerts efficient apoptotic characteristics in both chemosensitive and chemoresistant lung cancer cells.
2014 Jan
Proteomic identification of pterostilbene-mediated anticancer activities in HepG2 cells.
2014 Jul 21
Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.
2014 Mar
The berry constituents quercetin, kaempferol, and pterostilbene synergistically attenuate reactive oxygen species: involvement of the Nrf2-ARE signaling pathway.
2014 Oct
Pterostilbene Ameliorates Streptozotocin-Induced Diabetes through Enhancing Antioxidant Signaling Pathways Mediated by Nrf2.
2016 Jan 19
Patents

Sample Use Guides

50 mg or 125 mg twice daily for 6-8 weeks
Route of Administration: Oral
Pterostilbene inhibited the growth of normal fibroblasts in a dose-dependent manner similar to resveratrol (IC50 60 uM for both), and pterostilbene also caused cell cycle imbalance in a manner similar to that of resveratrol.
Name Type Language
PTEROSTILBENE
WHO-DD  
Common Name English
PTEROSTILBENE [WHO-DD]
Common Name English
PHENOL, 4-((1E)-2-(3,5-DIMETHOXYPHENYL)ETHENYL)-
Systematic Name English
3,5-DIMETHOXY-4'-HYDROXY-TRANS-STILBENE
Systematic Name English
EH-301 COMPONENT PTEROSTILBENE
Common Name English
TRANS-PTEROSTILBENE
Common Name English
PTEROSTILBENE, (E)-
Common Name English
4-((1E)-2-(3,5-DIMETHOXYPHENYL)ETHENYL)PHENOL
Systematic Name English
TRANS-3,5-DIMETHOXY-4'-HYDROXYSTILBENE
Systematic Name English
Classification Tree Code System Code
DSLD 1717 (Number of products:177)
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
FDA ORPHAN DRUG 628218
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
NCI_THESAURUS C275
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
Code System Code Type Description
FDA UNII
26R60S6A5I
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
PRIMARY
WIKIPEDIA
Pterostilbene
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
PRIMARY
CAS
18259-15-9
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
EPA CompTox
537-42-8
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
PRIMARY
CAS
537-42-8
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
PRIMARY
NCI_THESAURUS
C153353
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
PRIMARY
PUBCHEM
5281727
Created by admin on Sat Jun 26 01:35:21 UTC 2021 , Edited by admin on Sat Jun 26 01:35:21 UTC 2021
PRIMARY