U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PINORESINOL

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

HIDE SMILES / InChI
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

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Rat: 1 or 2 mg/kg b.w. in 0.5 mL saline solution
Route of Administration: Intravenous
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).
Name Type Language
PINORESINOL
Common Name English
PHENOL, 4,4'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYLBIS(2-METHOXY-, (1S-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-
Common Name English
PHENOL, 4,4'-((1S,3AR,4S,6AR)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXY-
Common Name English
PINORESINOL, (+)-
Common Name English
NSC-35444
Code English
D-PINORESINOL
Common Name English
(+)-PINORESINOL
Common Name English
Code System Code Type Description
WIKIPEDIA
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
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CHEBI
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
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FDA UNII
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
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CAS
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
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NSC
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
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PUBCHEM
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
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EPA CompTox
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
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