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

Marine Drugs

Deepak Kumar Gupta¹  Parveen Kaur²  See Ting Leong¹  Lik Tong Tan¹  Michèle R. Prinsep³ 

[1] Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, 1 Nanyang Walk, Singapore 637616, Singapore; E-Mails:;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; E-Mail:;Department of Chemistry, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand; E-Mail:

关键词: marine cyanobacterium;    Trichodesmium erythraeum;    aplysiatoxin;    antiviral;    Chikungunya virus;   

DOI  :  10.3390/md12010115

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.