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Mar. Drugs 2014, 12(1), 115-127; doi:10.3390/md12010115
Article

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

1
, 2
, 1
, 1,* , 3
 and 2,*
1 Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, 1 Nanyang Walk, Singapore 637616, Singapore 2 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 3 Department of Chemistry, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand
* Authors to whom correspondence should be addressed.
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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Abstract

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.
Keywords: marine cyanobacterium; Trichodesmium erythraeum; aplysiatoxin; antiviral; Chikungunya virus marine cyanobacterium; Trichodesmium erythraeum; aplysiatoxin; antiviral; Chikungunya virus
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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