» Articles » PMID: 22609526

Anti-inflammatory Activity and Percutaneous Absorption of Quercetin and Its Polymethoxylated Compound and Glycosides: the Relationships to Chemical Structures

Overview
Journal Eur J Pharm Sci
Specialties Chemistry
Pharmacology
Date 2012 May 22
PMID 22609526
Citations 20
Authors
Affiliations
Soon will be listed here.
Abstract

The potential of quercetin-related compounds for topical application has not previously been systematically investigated. To better elucidate relationships of the structure and activity with skin permeation, some quercetin compounds were used as permeants, including aglycone, a polymethoxylated compound (quercetin 3,5,7,3',4'-pentamethylether, QM), and seven glycosides. Quercetin and the glycoside with glucopyranuronic acid (Q4) at a dose of 30 μM completely inhibited superoxide anion activated neutrophils. QM also potentially suppressed superoxide by 90%. Both quercetin and QM showed inhibitory activity on elastase release with respective IC(50) values of 6.25 and 15.76 μM. Glycosylation significantly diminished this activity. Both an infinite concentration and saturated solubility in pH 7 buffer were used as permeant doses for the in vitro permeation experiments. The flux or permeability coefficient, which is the indicator for total absorption of dermal delivery due to the use of nude mouse skin, was the greatest for QM, followed by the glycosides and quercetin. QM showed 26× greater flux compared to quercetin. No penetration of quercetin occurred at the dose of saturated solubility. Rutin generally exhibited the highest skin permeation among the glycosides. It was found that the glycoside enantiomers (Q2 and Q3) revealed completely different permeation profiles. The stratum corneum was the principal penetration barrier for quercetin and its glycosides but not QM. Rutin provoked some skin redness and inflammation after a 5-day administration in nude mouse. QM caused no irritation, suggesting that it is a superior candidate for topical delivery.

Citing Articles

Topical Anti-Inflammatory Effects of Quercetin Glycosides on Atopic Dermatitis-Like Lesions: Influence of the Glycone Type on Efficacy and Skin Absorption.

Yang S, Chang Z, Hsiao C, Alshetaili A, Wei S, Hsiao Y Inflammation. 2025; .

PMID: 39808370 DOI: 10.1007/s10753-025-02236-1.


The Role of Quercetin as a Plant-Derived Bioactive Agent in Preventive Medicine and Treatment in Skin Disorders.

Zaborowski M, Dlugosz A, Blaszak B, Szulc J, Leis K Molecules. 2024; 29(13).

PMID: 38999158 PMC: 11243040. DOI: 10.3390/molecules29133206.


Recent Advances in Potential Health Benefits of Quercetin.

Aghababaei F, Hadidi M Pharmaceuticals (Basel). 2023; 16(7).

PMID: 37513932 PMC: 10384403. DOI: 10.3390/ph16071020.


alleviates intestinal damage by modulating cyclooxygenase-2: and evaluation in a colitis model.

Peiter G, Moesch Queiroz T, Michalkiewicz Jr E, Chappuis R, Luz J, Casagrande Piovezani L World J Gastroenterol. 2023; 29(17):2628-2641.

PMID: 37213402 PMC: 10198052. DOI: 10.3748/wjg.v29.i17.2628.


Development of Olive Oil Containing Phytosomal Nanocomplex for Improving Skin Delivery of Quercetin: Formulation Design Optimization, In Vitro and Ex Vivo Appraisals.

Hendawy O, Al-Sanea M, Mohammed Elbargisy R, Ur Rahman H, Gomaa H, Mohamed A Pharmaceutics. 2023; 15(4).

PMID: 37111610 PMC: 10145320. DOI: 10.3390/pharmaceutics15041124.