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
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+
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2649 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12033810 |
19.8 µM [IC50] | ||
Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12033810 |
83.9 µM [IC50] | ||
Target ID: WP408 |
|||
Target ID: WP400 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19549798 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Preventing | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25057276
50 mg or 125 mg twice daily for 6-8 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11316812
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
Edited
Sat Dec 16 08:20:37 UTC 2023
by
admin
on
Sat Dec 16 08:20:37 UTC 2023
|
Record UNII |
26R60S6A5I
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |