Next Article in Journal
The Pore-Forming α-Toxin from Clostridium septicum Activates the MAPK Pathway in a Ras-c-Raf-Dependent and Independent Manner
Next Article in Special Issue
The Effect of Cyanobacterial Biomass Enrichment by Centrifugation and GF/C Filtration on Subsequent Microcystin Measurement
Previous Article in Journal
Coupling between the Basic Replicon and the Kis-Kid Maintenance System of Plasmid R1: Modulation by Kis Antitoxin Levels and Involvement in Control of Plasmid Replication
Previous Article in Special Issue
Detection of Cyanotoxins, β-N-methylamino-L-alanine and Microcystins, from a Lake Surrounded by Cases of Amyotrophic Lateral Sclerosis
Article Menu

Export Article

Open AccessArticle
Toxins 2015, 7(2), 493-515; doi:10.3390/toxins7020493

Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica

1
Cawthron Institute, Private Bag 2, Nelson 7010, New Zealand
2
Department of Chemistry, School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand
3
Environmental Research Institute, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand
4
Department of Biological Sciences, School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand
*
Author to whom correspondence should be addressed.
Academic Editor: Greg Boyer
Received: 21 December 2014 / Accepted: 3 February 2015 / Published: 10 February 2015
(This article belongs to the Collection Marine and Freshwater Toxins)
View Full-Text   |   Download PDF [811 KB, uploaded 10 February 2015]   |  

Abstract

Microcystins are hepatotoxic cyclic peptides produced by several cyanobacterial genera worldwide. In 2008, our research group identified eight new glycine-containing microcystin congeners in two hydro-terrestrial mat samples from the McMurdo Dry Valleys of Eastern Antarctica. During the present study, high-resolution mass spectrometry, amino acid analysis and micro-scale thiol derivatization were used to further elucidate their structures. The Antarctic microcystin congeners contained the rare substitution of the position-1 ᴅ-alanine for glycine, as well as the acetyl desmethyl modification of the position-5 Adda moiety (3S-amino-9S-methoxy-2S,6,8S-trimethyl-10-phenyldeca-4E,6E-dienoic acid). Amino acid analysis was used to determine the stereochemistry of several of the amino acids and conclusively demonstrated the presence of glycine in the microcystins. A recently developed thiol derivatization technique showed that each microcystin contained dehydrobutyrine in position-7 instead of the commonly observed N-methyl dehydroalanine. View Full-Text
Keywords: microcystin; Antarctica; amino acid analysis; mass spectrometry; thiol derivatization microcystin; Antarctica; amino acid analysis; mass spectrometry; thiol derivatization
Figures

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. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Puddick, J.; Prinsep, M.R.; Wood, S.A.; Cary, S.C.; Hamilton, D.P.; Holland, P.T. Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica. Toxins 2015, 7, 493-515.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Toxins EISSN 2072-6651 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top