Further characterization of glycine-containing microcystins

Details of Research

TitleFurther characterization of glycine-containing microcystins from the McMurdo Dry Valleys of AntarcticaAbstractMicrocystins 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 D-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. Copyright 2015 by the authors; licensee MDPI, Basel, Switzerland.AcknowledgementsThe authors thank Wendy Jackson, Pat Gread (University of Waikato, New Zealand), Janet Adamson and Michael Boundy (Cawthron Institute, New Zealand) for their valued technical assistance, Andy Selwood (Cawthron Institute, New Zealand) and Christopher Miles (Norwegian Veterinary Institute, Norway) for helpful discussions and technical guidance and the anonymous peer-reviewers for their comments, which have improved this manuscript. Susanna Wood and Craig Cary thank Antarctica New Zealand for logistical assistance during sample collection. This research was supported by the New Zealand Ministry of Business, Innovation and Employment (UOWX0505; Lake Biodiversity Restoration), the Marsden Fund of the Royal Society of New Zealand (12-UOW-087) and a University of Waikato Doctoral Scholarship (Jonathan Puddick).

Details

1st AuthorPuddick, J.AuthorPuddick, J.Prinsep, M.Wood, S.Cary, S.Hamilton, D.Holland, P.Year2015JournalToxinsVolume7Number2Pages493-515DOI10.3390/toxins7020493URLhttps://www.scopus.com/inward/recor.....cd5dbb67e834296b1ad2bffacKeywordsrank5

Other

TypeArticleCitationPuddick, J., Prinsep, M., Wood, S., Cary, S., Hamilton, D. and Holland, P. (2015) Further characterization of glycine-containing microcystins from the {McMurdo Dry Valleys} of Antarctica. Toxins, 7(2): 493-515 doi:10.3390/toxins7020493 IdentifierPuddick2015Relevancerank5

Linked To

Author

Cary, S.