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Open AccessArticle

MS/MS-Based Molecular Networking Approach for the Detection of Aplysiatoxin-Related Compounds in Environmental Marine Cyanobacteria

1
Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, Singapore 637616, Singapore
2
School of Biological Sciences, Nanyang Technological University, Singapore 637551, Singapore
3
Singapore Phenome Centre, Lee Kong Chian School of Medicine, Nanyang Technological University, Singapore 636921, Singapore
4
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, La Jolla, CA 92093, USA
*
Author to whom correspondence should be addressed.
These two authors contributed equally to this article.
Mar. Drugs 2018, 16(12), 505; https://doi.org/10.3390/md16120505
Received: 12 November 2018 / Revised: 5 December 2018 / Accepted: 10 December 2018 / Published: 13 December 2018
Certain strains of cyanobacteria produce a wide array of cyanotoxins, such as microcystins, lyngbyatoxins and aplysiatoxins, that are associated with public health issues. In this pilot study, an approach combining LC-MS/MS and molecular networking was employed as a rapid analytical method to detect aplysiatoxins present in four environmental marine cyanobacterial samples collected from intertidal areas in Singapore. Based on 16S-ITS rRNA gene sequences, these filamentous cyanobacterial samples collected from Pulau Hantu were determined as Trichodesmium erythraeum, Oscillatoria sp. PAB-2 and Okeania sp. PNG05-4. Organic extracts were prepared and analyzed on LC-HRMS/MS and Global Natural Product Social Molecular Networking (GNPS) for the presence of aplysiatoxin-related molecules. From the molecular networking, six known compounds, debromoaplysiatoxin (1), anhydrodebromoaplysiatoxin (2), 3-methoxydebromoaplysiatoxin (3), aplysiatoxin (4), oscillatoxin A (5) and 31-noroscillatoxin B (6), as well as potential new analogues, were detected in these samples. In addition, differences and similarities in molecular networking clusters related to the aplysiatoxin molecular family were observed in extracts of Trichodesmium erythraeum collected from two different locations and from different cyanobacterial species found at Pulau Hantu, respectively. View Full-Text
Keywords: filamentous marine cyanobacteria; aplysiatoxin; molecular networking; Trichodesmium erythraeum; Okeania sp.; Oscillatoria sp. filamentous marine cyanobacteria; aplysiatoxin; molecular networking; Trichodesmium erythraeum; Okeania sp.; Oscillatoria sp.
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Ding, C.Y.G.; Pang, L.M.; Liang, Z.-X.; Goh, K.K.K.; Glukhov, E.; Gerwick, W.H.; Tan, L.T. MS/MS-Based Molecular Networking Approach for the Detection of Aplysiatoxin-Related Compounds in Environmental Marine Cyanobacteria. Mar. Drugs 2018, 16, 505.

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