Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H22O6 |
| Molecular Weight | 358.3851 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=CC=C1O)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C4=CC(OC)=C(O)C=C4
InChI
InChIKey=HGXBRUKMWQGOIE-AFHBHXEDSA-N
InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1
| Molecular Formula | C20H22O6 |
| Molecular Weight | 358.3851 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Pinoresinol is a common component of the lignan fraction found in olive oil, in Styrax sp. and in Forsythia suspense and in other plants. Many experimental studies have been focused on the strong antioxidant activity of pinoresinol. Enzymatic hydrolysis of maltose is inhibited by (+)-pinoresinol through competitive and noncompetitive manners. Pinoresinol caused an upregulation of the CDK inhibitor p21(WAF1/Cip1) both at mRNA and protein levels so suggesting that this could be a mechanism by which pinoresinol reduced proliferation and induced differentiation on HL60 leukemia cells. Pinoresinol may have a therapeutic potential to prevent breast cancer development via the reduction of intracellular oxidative stress and DNA damage in human mammary epithelial cells. In vivo, pinoresinol ameliorates CCl4-induced acute liver injury, and this protection is likely due to anti-oxidative activity and down-regulation of inflammatory mediators through inhibition of NF-kappaB and AP-1.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3513 |
34.4 µM [IC50] | ||
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27604292 |
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Target ID: GO:0042348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20093790 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Balanochalcone, a new chalcone from Balanophora laxiflora Hemsl. | 2018-04 |
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| Association between dietary phytoestrogens intakes and prostate cancer risk in Sicily. | 2018-03 |
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| Characterization and evaluation of phenolic profiles and color as potential discriminating features among Spanish extra virgin olive oils with protected designation of origin. | 2018-02-15 |
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| Inositol Derivatives and Phenolic Compounds from the Roots of Taraxacum coreanum. | 2017-08-14 |
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| Differences in Chemical Component and Anticancer Activity of Green and Ripe Forsythiae Fructus. | 2017 |
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| A Novel Soybean Dirigent Gene GmDIR22 Contributes to Promotion of Lignan Biosynthesis and Enhances Resistance to Phytophthora sojae. | 2017 |
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| Influence of Boiling Duration of GCSB-5 on Index Compound Content and Antioxidative and Anti-inflammatory Activity. | 2016-09-25 |
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| Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity. | 2013-10 |
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| Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives. | 2001-07 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25243351
Rat: 1 or 2 mg/kg b.w. in 0.5 mL saline solution
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27604292
The percentage of non-tumorigenic human mammary epithelial cells death following treatment with 0.001 uM pinoresinol was much lower (10 %) than in breast cancer cells (29 % for MDA-MB-231 and 20 % for MCF7 cells).
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 20:04:17 GMT 2025
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admin
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Mon Mar 31 20:04:17 GMT 2025
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| Record UNII |
V4N1UDY811
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| Record Status |
Validated (UNII)
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| Record Version |
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PINORESINOL
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V4N1UDY811
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487-36-5
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35444
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73399
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DTXSID20964099
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay(DPPH) IC50 expressed as ug/mL = 34.7+/- 5.0. In vitro hydroxyl radical scavenging assay(Hydroxy Radical) IC50 expressed as ug/mL = 1.8+/- 0.20.
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