Antioxidant activity and electrochemical elucidation of the enigmatic redox behavior of curcumin and its structurally modified analogues

Jha, Niki S and Mishra, Satyendra and Jha, Shailendra K and Surolia, Avadhesha (2015) Antioxidant activity and electrochemical elucidation of the enigmatic redox behavior of curcumin and its structurally modified analogues. In: ELECTROCHIMICA ACTA, 151 . pp. 574-583.

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Abstract

Here, we report studies on the antioxidant activity and redox behavior of curcumin and its structurally modified synthetic analogues. We have synthesized a number of analogues of curcumin which abrogate its keto-enol tautomerism or substitute the methylene group at the centre of its heptadione moiety implicated in the hydride transfer and studied their redox property. From cyclic voltammetric studies, it is demonstrated that H-atom transfer from CH2 group at the center of the heptadione link also plays an important role in the antioxidant properties of curcumin along with that of its phenolic -OH group. In addition, we also show that the conversion of 1, 3-dicarbonyl moiety of curcumin to an isosteric heterocycle as in pyrazole curcumin, which decreases its rotational freedom, leads to an improvement of its redox properties as well as its antioxidant activity. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	ELECTROCHIMICA ACTA
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Additional Information:	Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords:	Curcumin; Antioxidant; Free radical; Cyclic voltammetry; Alkoxyl radical; Hepatadione
Department/Centre:	Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited:	06 Feb 2015 14:30
Last Modified:	06 Feb 2015 14:30
URI:	http://eprints.iisc.ac.in/id/eprint/50765

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