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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
Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives.
2001 Jul
Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity.
2013 Oct
Differences in Chemical Component and Anticancer Activity of Green and Ripe Forsythiae Fructus.
2017
A Novel Soybean Dirigent Gene GmDIR22 Contributes to Promotion of Lignan Biosynthesis and Enhances Resistance to Phytophthora sojae.
2017
Inositol Derivatives and Phenolic Compounds from the Roots of Taraxacum coreanum.
2017 Aug 14
Influence of Boiling Duration of GCSB-5 on Index Compound Content and Antioxidative and Anti-inflammatory Activity.
2017 Jul-Sep
Balanochalcone, a new chalcone from Balanophora laxiflora Hemsl.
2018 Apr
Characterization and evaluation of phenolic profiles and color as potential discriminating features among Spanish extra virgin olive oils with protected designation of origin.
2018 Feb 15
Association between dietary phytoestrogens intakes and prostate cancer risk in Sicily.
2018 Mar
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
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CHEBI
40
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FDA UNII
V4N1UDY811
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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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