Antioxidant and Anti-Inflammatory Activities of Barettin

Abstract

In this paper, we present novel bioactivity for barettin isolated from the marine sponge Geodia barretti. We found that barettin showed strong antioxidant activity in biochemical assays as well as in a lipid peroxidation cell assay. A de-brominated synthetic analogue of barettin did not show the same activity in the antioxidant cell assay, indicating that bromine is important for cellular activity. Barettin was also able to inhibit the secretion of the inflammatory cytokines IL-1β and TNFα from LPS-stimulated THP-1 cells. This combination of anti-inflammatory and antioxidant activities could indicate that barettin has an atheroprotective effect and may therefore be an interesting product to prevent development of atherosclerosis.

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…As shown in Table 2, and in contrast to the 20 marine compounds ( 115 – 134 ) with described anti-inflammatory mechanisms of action, for marine compounds ( 135 – 157 ), only anti-inflammatory activity, namely IC 50 , was reported, but the molecular mechanism of action remained undetermined: A. polyacanthus steroids ( 135 , 136 ) [137]; barettin ( 137 ) [138]; briarenolide F ( 138 ) [139]; diketopiperazine ( 139 ) [140]; 6- epi -cladieunicellin F ( 140 ) [141]; crassarosteroside A ( 141 ) [142]; cystodione A ( 142 ) [143]; densanins A and B ( 143 , 144 ) [144]; dissesterol ( 145 ) [145]; echinohalimane A ( 146 ) [146]; eunicidiol ( 147 ) [147]; flexibilisolide C ( 148 ) [148]; flexibilisquinone ( 149 ) [149]; lobocrassin F ( 150 ) [150]; perthamide J ( 151 ) [151]; pseudoalteromone A ( 152 ) [152]; sarcocrassocolide M ( 153 ) [153]; sclerosteroids K and M ( 154 , 155 ) [154]; seco-briarellinone ( 156 ) [155]; and sinularioside ( 157 ) [156]. …”

Ultrasound‐Assisted Synthesis and Antioxidant Activity of 3‐Selanyl‐1 H‐indole and 3‐Selanylimidazo[1,2‐a]pyridine Derivatives

“…This may indicate that the antioxidant activity of both compounds relies strongly on their ability to act as a reducing agent and transfer electrons to a free radical. Interestingly, the presence of bromine was important for the antioxidant and anti‐inflammatory properties of a naturally occurring compound, when compared with a de‐brominated synthetic analog . Moreover, compound 1 a was able to scavenge ABTS + .…”

Analysis of alkaloids (indole alkaloids, isoquinoline alkaloids, tropane alkaloids)

“…Barettin was also able to inhibit the secretion of the inflammatory cytokines IL-1β and TNFα from LPS-stimulated human acute monocytic leukemia cell line THP-1 cells (Lind et al, 2013).…”

“…According to their experiment, barettin showed a potential antioxidant profile in a dose-dependent manner. At a concentration of 30 μg/mL barettin had FRAP and ORAC values of 77 and 5.5 μM Trolox equivalents (TE), respectively (Lind et al, 2013).…”