, Volume 23, Issue 4, pp 173–185 | Cite as

Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia

  • Satvir Sekhon-Loodu
  • Ziaullah Ziaullah
  • H. P. Vasantha Rupasinghe
  • Yanwen Wang
  • Marianna Kulka
  • Fereidoon Shahidi
Research Article


Quercetin, a major flavonol, present abundantly in apples and onions, is widely studied for ameliorating metabolic syndrome abnormalities. However, quercetin is mainly present in plant food in the form of quercetin glycosides and has been reported for poor gastrointestinal absorption. The present study was designed with the purpose of imparting a lipophilic property to quercetin-3-O-glucoside (QG) by its acylation with eicosapentaenoic acid (EPA) and to study the influence of eicosapentaenoic acid ester of quercetin-3-O-glucoside (QE) on hyperlipidemia and inflammation in vivo and in vitro. QE was more effective in reducing the production of tumor necrosis factor-alpha (TNF-α), prostaglandin 2 (PGE2), cyclo-oxygenase (COX)-2 levels and nuclear expression of nuclear factor-kappa B (NF-кB) compared to the parent compounds (QG and EPA) and commercial drugs, after lipopolysaccharides (LPS) induced inflammation in THP-1 derived macrophages. Serum high-density lipoprotein (HDL)-cholesterol was significantly higher and hepatic total cholesterol concentration was lower in the rats fed high-fat diet supplemented with QE, compared to the high-fat diet with inflammation (HFL). The serum concentrations of C-reactive protein (CRP), interleukin (IL)-6, and interferon-gamma (IFN-γ) were significantly lower in QE treatment group than HFL group. EPA conjugated flavonol, QE, had significant anti-inflammatory and hypolipidemic properties and may be effective for the treatment of obesity-related disorders.

Graphical Abstract


Flavonols Eicosapentaenoic acid ester Cytokines Hyperlipidemia Inflammation Macrophage 



C-reactive protein


High fat control


High fat with lipopolysaccharide






Eicosapentaenoic acid ester of quercetin-3-O-glucoside



The authors acknowledge the funding provided by the Discovery Grant program of the Natural Sciences and Engineering Research Council (NSERC) of Canada and the Atlantic Innovation Funds Program of the Atlantic Canada Opportunities Agency (ACOA).

Complaince with ethical standards

Conflict of interest

No competing financial interests exist.

Supplementary material

10787_2015_237_MOESM1_ESM.doc (8.3 mb)
Supplementary material 1 (DOC 8546 kb)


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Copyright information

© Springer Basel 2015

Authors and Affiliations

  • Satvir Sekhon-Loodu
    • 1
  • Ziaullah Ziaullah
    • 1
  • H. P. Vasantha Rupasinghe
    • 1
    • 2
  • Yanwen Wang
    • 3
  • Marianna Kulka
    • 3
    • 4
  • Fereidoon Shahidi
    • 5
  1. 1.Department of Environmental Sciences, Faculty of AgricultureDalhousie UniversityTruroCanada
  2. 2.Departments of Pharmacology and Pathology, Faculty of MedicineDalhousie UniversityHalifaxCanada
  3. 3.Aquatic and Crop Resource DevelopmentNational Research Council of CanadaCharlottetownCanada
  4. 4.National Institute for NanotechnologyNational Research Council of CanadaEdmontonCanada
  5. 5.Department of BiochemistryMemorial University of NewfoundlandSt. John’sCanada

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