Hydroxylated derivatives of dimethoxy-1,4-benzoquinone as redox switchable earth-alkaline metal ligands and radical scavengers

Gulaboski, Rubin and Bogeski, Ivan and Mirceski, Valentin and Saul, Stephanie and Pasieka, Bastian and Haeri, Haleh H. and Stefova, Marina and Petreska Stanoeva, Jasmina and Mitrev, Sasa and Hoth, Markus and Kappl, Reinhard (2013) Hydroxylated derivatives of dimethoxy-1,4-benzoquinone as redox switchable earth-alkaline metal ligands and radical scavengers. Scientific Reports (Nature), 3. pp. 1-8. ISSN 2045-2322

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Official URL: http://dx.doi.org/10.1038/srep01865

Abstract

Benzoquinones (BQ) have important functions in many biological processes. In alkaline environments, BQs can be hydroxylated at quinoid ring proton positions. Very little is known about the chemical reaction leading to these structural transformations as well as about the properties of the obtained hydroxyl benzoquinones. We analyzed the behavior of the naturally occurring 2,6-dimethoxy-1,4-benzoquinone under alkaline conditions and show that upon substitution of methoxy-groups, poly-hydroxyl-derivatives (OHBQ) are formed. The emerging compounds with one or several hydroxyl-substituents on single or fused quinone-rings exist in oxidized or reduced states and are very stable under physiological conditions. In comparison with the parent BQs, OHBQs are stronger radical scavengers and redox switchable earth-alkaline metal ligands. Considering that hydroxylated quinones appear as biosynthetic intermediates or as products of enzymatic reactions, and that BQs present in food or administered as drugs can be hydroxylated by enzymatic pathways, highlights their potential importance in biological systems.

Item Type: Article
Uncontrolled Keywords: antioxidants, reactive oxygen species, voltammetry, hydroxylated benzoquinones, voltammetry, EPR, NMR, HPLC MS, redox potential, metal ligands
Subjects: Agricultural Sciences > Agricultural biotechnology
Medical and Health Sciences > Basic medicine
Natural sciences > Biological sciences
Natural sciences > Chemical sciences
Natural sciences > Physical sciences
Divisions: Faculty of Agriculture
Depositing User: Rubin Gulaboski
Date Deposited: 21 May 2013 14:28
Last Modified: 06 Apr 2015 08:22
URI: http://eprints.ugd.edu.mk/id/eprint/6376

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