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Anti-Chikungunya Viral Activities of Aplysiatoxin-Related Compounds from the Marine Cyanobacterium Trichodesmium erythraeum

Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, 1 Nanyang Walk, Singapore 637616, Singapore
Laboratory of Molecular RNA Virology and Antiviral Strategies, Department of Microbiology, Yong Lin School of Medicine, NUHS, National University of Singapore, MD4 Level 5, Science Drive 2, Singapore 117597, Singapore
Department of Chemistry, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand
Authors to whom correspondence should be addressed.
Mar. Drugs 2014, 12(1), 115-127;
Received: 14 October 2013 / Revised: 25 November 2013 / Accepted: 12 December 2013 / Published: 3 January 2014
(This article belongs to the Special Issue Compounds from Cyanobacteria)
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Tropical filamentous marine cyanobacteria have emerged as a viable source of novel bioactive natural products for drug discovery and development. In the present study, aplysiatoxin (1), debromoaplysiatoxin (2) and anhydrodebromoaplysiatoxin (3), as well as two new analogues, 3-methoxyaplysiatoxin (4) and 3-methoxydebromoaplysiatoxin (5), are reported for the first time from the marine cyanobacterium Trichodesmium erythraeum. The identification of the bloom-forming cyanobacterial strain was confirmed based on phylogenetic analysis of its 16S rRNA sequences. Structural determination of the new analogues was achieved by extensive NMR spectroscopic analysis and comparison with NMR spectral data of known compounds. In addition, the antiviral activities of these marine toxins were assessed using Chikungunya virus (CHIKV)-infected cells. Post-treatment experiments using the debrominated analogues, namely compounds 2, 3 and 5, displayed dose-dependent inhibition of CHIKV when tested at concentrations ranging from 0.1 µM to 10.0 µM. Furthermore, debromoaplysiatoxin (2) and 3-methoxydebromoaplysiatoxin (5) exhibited significant anti-CHIKV activities with EC50 values of 1.3 μM and 2.7 μM, respectively, and selectivity indices of 10.9 and 9.2, respectively. View Full-Text
Keywords: marine cyanobacterium; Trichodesmium erythraeum; aplysiatoxin; antiviral; Chikungunya virus marine cyanobacterium; Trichodesmium erythraeum; aplysiatoxin; antiviral; Chikungunya virus

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Gupta, D.K.; Kaur, P.; Leong, S.T.; Tan, L.T.; Prinsep, M.R.; Chu, J.J.H. Anti-Chikungunya Viral Activities of Aplysiatoxin-Related Compounds from the Marine Cyanobacterium Trichodesmium erythraeum. Mar. Drugs 2014, 12, 115-127.

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