Mar. Drugs 2016, 14(11), 197; doi:10.3390/md14110197
Evaluation of the Antioxidant Activity of the Marine Pyrroloiminoquinone Makaluvamines
Eva Alonso 1,†, Rebeca Alvariño 1,†, Marta Leirós 1, Jioji N. Tabudravu 2, Klaus Feussner 3, Miriam A. Dam 2, Mostafa E. Rateb 2, Marcel Jaspars 2 and Luis M. Botana 1,*
1
Departamento de Farmacología, Facultad de Veterinaria, Universidad de Santiago de Compostela, Lugo 27002, Spain
2
Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, MestonWalk, Aberdeen AB24 3UE, UK
3
Institute of Applied Sciences, University of the South Pacific, P.O. Box 1168, Suva, Fiji
†
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Kirsten Benkendorff
Received: 26 September 2016 / Revised: 19 October 2016 / Accepted: 20 October 2016 / Published: 27 October 2016
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
Abstract
Makaluvamines are pyrroloiminoquinones isolated from Zyzzya sponges. Until now, they have been described as topoisomerase II inhibitors with cytotoxic effects in diverse tumor cell lines. In the present work, seven makaluvamines were tested in several antioxidant assays in primary cortical neurons and neuroblastoma cells. Among the alkaloids studied, makaluvamine J was the most active in all the assays. This compound was able to reduce the mitochondrial damage elicited by the well-known stressor H2O2. The antioxidant properties of makaluvamine J are related to an improvement of the endogenous antioxidant defenses of glutathione and catalase. SHSY5Y assays proved that this compound acts as a Nrf2 activator leading to an improvement of antioxidant defenses. A low concentration of 10 nM is able to reduce the reactive oxygen species release and maintain a correct mitochondrial function. Based on these results, non-substituted nitrogen in the pyrrole plus the presence of a p-hydroxystyryl without a double bond seems to be the most active structure with a complete antioxidant effect in neuronal cells. View Full-TextKeywords:
makaluvamine; Zyzzya; oxidative stress; neurons; marine sponge; nrf2
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Alonso, E.; Alvariño, R.; Leirós, M.; Tabudravu, J.N.; Feussner, K.; Dam, M.A.; Rateb, M.E.; Jaspars, M.; Botana, L.M. Evaluation of the Antioxidant Activity of the Marine Pyrroloiminoquinone Makaluvamines. Mar. Drugs 2016, 14, 197.
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