Piceatannol 3'-O-glucoside

Piceatannol 3'-O-glucoside, an active component of Rhubarb, activates endothelial nitric oxide (NO) synthase through inhibition of arginase activity with IC50s of 11.22 µM and 11.06 µM against arginase I and arginase II, respectively.

Product information

CAS Number: 94356-26-0

Molecular Weight: 406.38

Formula: C20H22O9

Chemical Name: (2S,3R,4S,5S,6R)-2-{5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Smiles: OC[C@H]1O[C@@H](OC2=CC(/C=C/C3C=C(O)C=C(O)C=3)=CC=C2O)[C@H](O)[C@@H](O)[C@@H]1O

InChiKey: UMGCIIXWEFTPOC-CUYWLFDKSA-N

InChi: InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-15-7-10(3-4-14(15)24)1-2-11-5-12(22)8-13(23)6-11/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Piceatannol 3'-O-glucoside (Piceatannol-3'-O-β-D-glucopyranoside; PG) is a potent component of stilbenes, inhibits the activity of arginase I and II prepared from mouse liver and kidney lysates, respectively, in a dose-dependent manner. In human umbilical vein endothelial cells, incubation of Piceatannol 3'-O-glucoside markedly blocks arginase activity and increases nitrite and nitrate (NOx) production, as measured by Griess assay. In liver lysates, incubation of different concentrations of Piceatannol 3'-O-glucoside significantly decreases arginase I activity (75±5% at 1 µM, 72±7% at 3 µM, 62±1% at 10 µM) compared to untreated control (100±9%). In kidney lysates, the residual arginase activities after incubation of 1, 3 and 10 µM Piceatannol 3'-O-glucoside are 75±6, 74±5, and 53±8%, respectively. Arginase activity is measured in the presence of different concentration of Piceatannol 3'-O-glucoside (from 0 to 120 µM) using liver lysate and kidney lysate. The 50% inhibitory concentrations (IC50) are 11.22 µM for the liver lysate and 11.06 µM for kidney lysate. The values are obtained using the software of Graphpad prizm 4.0. Piceatannol 3'-O-glucoside inhibits arginase activity and increases NO production in HUVECs. Piceatannol 3'-O-glucoside inhibits lipoxygenase activity upto 66% at the concentration of 100 µM and IC50 value is 69 µM.

In Vivo:

In order to ascertain whether Piceatannol 3'-O-glucoside (PG) ameliorates vascular function in wild-type (WT) and atherogenic model mice [apolipoprotein E-null mice (ApoE-/-)] and to investigate the possible underlying mechanism. Preincubation of aortic vessels from WT mice fed a normal diet (ND) with Piceatannol 3'-O-glucoside attenuates vasoconstriction response to U46619 and phenylephrine (PE), while the vasorelaxant response to acetylcholine (Ach) is markedly enhanced in an endothelium-dependent manner. Piceatannol 3'-O-glucoside treatment attenuates the phenylephrine (PE)-dependent contractile response, and significantly improves the acetylcholine (Ach)-dependent vasorelaxation response in aortic rings from ApoE-/- mice fed a high-cholesterol diet (HCD). Piceatannol 3'-O-glucoside administration in the drinking water significantly reduces fatty streak formation in ApoE-/- mice fed an HCD.

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