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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16O3
Molecular Weight 256.2964
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PTEROSTILBENE

SMILES

COC1=CC(\C=C\C2=CC=C(O)C=C2)=CC(OC)=C1

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

Molecular Formula C16H16O3
Molecular Weight 256.2964
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Nitric oxide mediates natural polyphenol-induced Bcl-2 down-regulation and activation of cell death in metastatic B16 melanoma.
2007 Feb 2
Anti-inflammatory action of pterostilbene is mediated through the p38 mitogen-activated protein kinase pathway in colon cancer 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
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
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
Stilbenes and anthocyanins reduce stress signaling in BV-2 mouse microglia.
2013 Jun 26
3,5,4'-Trimethoxystilbene, a natural methoxylated analog of resveratrol, inhibits breast cancer cell invasiveness by downregulation of PI3K/Akt and Wnt/β-catenin signaling cascades and reversal of epithelial-mesenchymal transition.
2013 Nov 1
The molecular basis for the inhibition of phosphodiesterase-4D by three natural resveratrol analogs. Isolation, molecular docking, molecular dynamics simulations, binding free energy, and bioassay.
2013 Oct
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:20:37 UTC 2023
Edited
by admin
on Sat Dec 16 08:20:37 UTC 2023
Record UNII
26R60S6A5I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PTEROSTILBENE
WHO-DD  
Common Name English
PHENOL, 4-((1E)-2-(3,5-DIMETHOXYPHENYL)ETHENYL)-
Systematic Name English
Pterostilbene [WHO-DD]
Common 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 Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
FDA ORPHAN DRUG 628218
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
NCI_THESAURUS C275
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
Code System Code Type Description
SMS_ID
100000176848
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
FDA UNII
26R60S6A5I
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
WIKIPEDIA
Pterostilbene
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
CAS
18259-15-9
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
CHEBI
8630
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID9041106
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
CAS
537-42-8
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
NCI_THESAURUS
C153353
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
PUBCHEM
5281727
Created by admin on Sat Dec 16 08:20:37 UTC 2023 , Edited by admin on Sat Dec 16 08:20:37 UTC 2023
PRIMARY
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