Cellular Antioxidant Effect of Four Bromophenols from the Red Algae, Vertebrata lanosa

Elisabeth K Olsen,Johan Isaksson,Espen Hansen,Jeanette H Andersen

doi:10.3390/md11082769

Elisabeth K Olsen, Johan Isaksson + Show 2 more

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https://doi.org/10.3390/md11082769

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Journal: Marine Drugs	Publication Date: Aug 5, 2013
Citations: 78	License type: CC BY 4.0

Affiliation: UiT The Arctic University of Norway

Abstract

Three known bromophenols, 2,3-dibromo-4,5-dihydroxybenzylaldehyde (1), 2,2′,3-tribromo-3′,4,4′,5-tetrahydroxy-6′-hydroxymethyldiphenylmethane (2) and bis(2,3-dibromo-4,5-dihydroxylbenzyl) ether (3), and one new one, 5,5″-oxybis(methylene)bis(3-bromo-4-(2′,3′-dibromo-4′,5′-dihydroxylbenzyl)benzene-1,2-diol) (4), were isolated from an extract of the red alga, Vertebrata lanosa. The antioxidant activity of these four bromophenols was examined using one biochemical and two cellular assays: Oxygen Radical Absorbance Capacity (ORAC), Cellular Antioxidant Activity (CAA) and Cellular Lipid Peroxidation Antioxidant Activity (CLPAA) assays. Compound 2 distinguished itself by showing potent activity, having a better antioxidant effect than luteolin in both the CAA and CLPAA assays and of quercetin in the CLPAA assay. Although several bromophenols are known to be potent antioxidants in biochemical assays, this is the first time their cellular antioxidant activity has been demonstrated.

Highlights

Marine macroalgae are known to contain structurally diverse natural compounds with a range of different biological activities [1]
Proton and carbon denotations are given (color codes are used for compounds 2 and 4 to distinguish them in the NMR spectra (Figures S2 to S5 in the Supplementary Material))
We found the same to be true for compound 2, as it was moderately active in the Oxygen Radical Absorbance Capacity (ORAC) assay, while displaying a high activity in the

Summary

Introduction

Marine macroalgae are known to contain structurally diverse natural compounds with a range of different biological activities [1]. The BPs are biosynthesized from polyphenols by bromoperoxidases in the presence of hydrogen peroxide and bromide [2]. They are common marine secondary metabolites [3], the algal content seems to vary with season [4] and tide [2]. The relationship between the molecular structure of some BPs and their antioxidant effect have previously been investigated [5], and the trend is that the activity is improved by both an increased number of hydroxyl groups and conjugations [6,7,8].

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