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 |
19.8 µM [IC50] | ||
Target ID: CHEMBL4321 |
83.9 µM [IC50] | ||
Target ID: WP400 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. | 2005 May 4 |
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| Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities. | 2006 Apr |
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| 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 |
|
| Pterostilbene is more potent than resveratrol in preventing azoxymethane (AOM)-induced colon tumorigenesis via activation of the NF-E2-related factor 2 (Nrf2)-mediated antioxidant signaling pathway. | 2011 Mar 23 |
|
| 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 |
|
| 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 |
|
| 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 |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:20:37 GMT 2023
by
admin
on
Sat Dec 16 08:20:37 GMT 2023
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| Record UNII |
26R60S6A5I
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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DSLD |
1717 (Number of products:177)
Created by
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FDA ORPHAN DRUG |
628218
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NCI_THESAURUS |
C275
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100000176848
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26R60S6A5I
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Pterostilbene
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18259-15-9
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NON-SPECIFIC STEREOCHEMISTRY | |||
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8630
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DTXSID9041106
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537-42-8
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C153353
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5281727
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| Related Record | Type | Details | ||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
