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
[H][C@]12CO[C@H](C3=CC(OC)=C(O)C=C3)[C@@]1([H])CO[C@@H]2C4=CC=C(O)C(OC)=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 |
|||
Target ID: GO:0042348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20093790 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Preventing | Unknown Approved UseUnknown |
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
by
admin
on
Edited
Fri Dec 15 20:10:33 GMT 2023
by
admin
on
Fri Dec 15 20:10:33 GMT 2023
|
Record UNII |
V4N1UDY811
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
PINORESINOL
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY | |||
|
40
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY | |||
|
V4N1UDY811
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY | |||
|
487-36-5
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY | |||
|
35444
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY | |||
|
73399
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY | |||
|
DTXSID20964099
Created by
admin on Fri Dec 15 20:10:33 GMT 2023 , Edited by admin on Fri Dec 15 20:10:33 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
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.
|