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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

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

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency
34.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Preventing
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 1 or 2 mg/kg b.w. in 0.5 mL saline solution
Route of Administration: Intravenous
In Vitro Use Guide
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).