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  • In-vitro anti-proliferative and anti-oxidant activity of galangin, fisetin and quercetin: role of localization and intermolecular interaction in model membrane.

In-vitro anti-proliferative and anti-oxidant activity of galangin, fisetin and quercetin: role of localization and intermolecular interaction in model membrane.

European journal of medicinal chemistry (2014-04-15)
Ragini Sinha, Sudha Srivastava, Akshada Joshi, Urmila J Joshi, Girjesh Govil
ABSTRACT

Flavonols are an important class of naturally occurring molecules and are known for their pharmacological activity. The activity is associated with the ability of flavonols to influence membrane-dependent processes. We have investigated the in-vitro anti-proliferative and anti-oxidant activity of galangin (GLN), fisetin (FTN) and quercetin (QTN), which possess variable number of phenolic hydroxyl groups. An attempt has been made to correlate the biological activity of these molecules with their interaction and localization in dipalmitoyl phosphatidyl choline (DPPC) bilayers, using differential dcanning calorimetry (DSC) and nuclear magnetic resonance (NMR) methods. Results indicate that GLN interacts to the alkyl chains of the lipid bilayer involving hydrophobic interactions. FTN and QTN interact with head region and sn-1-glycero region involving hydrogen bonding. Ring current induced chemical shifts of lipid protons, due to intermolecular interaction indicate that GLN acquires a parallel orientation with respect to the bilayer normal whereas FTN and QTN resume a mixed orientation. The membrane binding constants of these molecules are in the order GLN > QTN > FTN. It has been shown that the number and position of hydroxyl groups in these molecules play an important role in membrane binding and thereby in biological activity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Quercetin, ≥95% (HPLC), solid
USP
Quercetin, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Galangin, autophagy inducing flavonoid
Supelco
Quercetin, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine, semisynthetic, ≥99%
Sigma-Aldrich
2,2-Diphenyl-1-picrylhydrazyl
Sigma-Aldrich
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine, ≥99% (TLC)
Sigma-Aldrich
1,1-Diphenyl-2-picrylhydrazine, 97%