Targeted Metabolite Fingerprints of Thirteen Gambierdiscus , Five Coolia and Two Fukuyoa Species

The genus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this study, the metabolite fingerprint was mapped for thirteen , five and two species (34 isolates) by assessing the production of 56 characterised secondary metabo...

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Published in:	Marine drugs Vol. 22; no. 3; p. 119
Main Authors:	Murray, J Sam, Passfield, Emillie M F, Rhodes, Lesley L, Puddick, Jonathan, Finch, Sarah C, Smith, Kirsty F, van Ginkel, Roel, Mudge, Elizabeth M, Nishimura, Tomohiro, Funaki, Hiroshi, Adachi, Masao, Prinsep, Michèle R, Harwood, D Tim
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 02-03-2024 MDPI
Subjects:	Acids Algae benthic dinoflagellate bioactive Biocompatibility ciguatera poisoning Ciguatoxin Ciguatoxins Coolia Dinoflagellida Ethers Fingerprints Gambierdiscus Hydrocarbons Lipophilic Maitotoxin mass spectrometry Metabolites Microorganisms Mode of action Polyethers Secondary metabolites Serogroup Species Toxicity Pacific region maitotoxin toxicity ciguatoxin benthic dinoflagellate ciguatera poisoning mass spectrometry bioactive
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Abstract	The genus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this study, the metabolite fingerprint was mapped for thirteen , five and two species (34 isolates) by assessing the production of 56 characterised secondary metabolites. was the only species to produce Pacific-ciguatoxin-3B (P-CTX3B), P-CTX3C, iso-P-CTX3B/C, P-CTX4A, P-CTX4B and iso-P-CTX4A/B. produced maitotoxin-1 (MTX-1) and MTX-5, produced MTX-6 and produced MTX-7. Ubiquitous production of 44-methylgambierone was observed amongst all the isolates, with nine species also producing gambierone. Additional gambierone analogues, including anhydrogambierone (tentatively described herein), were also detected in all species, two and two species. Gambieroxide was detected in and and gambieric acid A was detected in ten species, with (CAWD381) being the only isolate to produce gambieric acids A-D. This study has demonstrated that the isolates tested to date produce the known CTXs or MTXs, but not both, and highlighted several species that produced 'unknown' compounds displaying characteristics of cyclic polyethers, which will be the focus of future compound discovery efforts.
AbstractList	The genus Gambierdiscus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this study, the metabolite fingerprint was mapped for thirteen Gambierdiscus, five Coolia and two Fukuyoa species (34 isolates) by assessing the production of 56 characterised secondary metabolites. Gambierdiscus polynesiensis was the only species to produce Pacific-ciguatoxin-3B (P-CTX3B), P-CTX3C, iso-P-CTX3B/C, P-CTX4A, P-CTX4B and iso-P-CTX4A/B. G. australes produced maitotoxin-1 (MTX-1) and MTX-5, G. cheloniae produced MTX-6 and G. honu produced MTX-7. Ubiquitous production of 44-methylgambierone was observed amongst all the Gambierdiscus isolates, with nine species also producing gambierone. Additional gambierone analogues, including anhydrogambierone (tentatively described herein), were also detected in all Gambierdiscus species, two Coolia and two Fukuyoa species. Gambieroxide was detected in G. lewisii and G. pacificus and gambieric acid A was detected in ten Gambierdiscus species, with G. australes (CAWD381) being the only isolate to produce gambieric acids A–D. This study has demonstrated that the isolates tested to date produce the known CTXs or MTXs, but not both, and highlighted several species that produced ‘unknown’ compounds displaying characteristics of cyclic polyethers, which will be the focus of future compound discovery efforts. The genus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this study, the metabolite fingerprint was mapped for thirteen , five and two species (34 isolates) by assessing the production of 56 characterised secondary metabolites. was the only species to produce Pacific-ciguatoxin-3B (P-CTX3B), P-CTX3C, iso-P-CTX3B/C, P-CTX4A, P-CTX4B and iso-P-CTX4A/B. produced maitotoxin-1 (MTX-1) and MTX-5, produced MTX-6 and produced MTX-7. Ubiquitous production of 44-methylgambierone was observed amongst all the isolates, with nine species also producing gambierone. Additional gambierone analogues, including anhydrogambierone (tentatively described herein), were also detected in all species, two and two species. Gambieroxide was detected in and and gambieric acid A was detected in ten species, with (CAWD381) being the only isolate to produce gambieric acids A-D. This study has demonstrated that the isolates tested to date produce the known CTXs or MTXs, but not both, and highlighted several species that produced 'unknown' compounds displaying characteristics of cyclic polyethers, which will be the focus of future compound discovery efforts. The genus Gambierdiscus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this study, the metabolite fingerprint was mapped for thirteen Gambierdiscus , five Coolia and two Fukuyoa species (34 isolates) by assessing the production of 56 characterised secondary metabolites. Gambierdiscus polynesiensis was the only species to produce Pacific-ciguatoxin-3B (P-CTX3B), P-CTX3C, iso-P-CTX3B/C, P-CTX4A, P-CTX4B and iso-P-CTX4A/B. G. australes produced maitotoxin-1 (MTX-1) and MTX-5, G. cheloniae produced MTX-6 and G. honu produced MTX-7. Ubiquitous production of 44-methylgambierone was observed amongst all the Gambierdiscus isolates, with nine species also producing gambierone. Additional gambierone analogues, including anhydrogambierone (tentatively described herein), were also detected in all Gambierdiscus species, two Coolia and two Fukuyoa species. Gambieroxide was detected in G. lewisii and G. pacificus and gambieric acid A was detected in ten Gambierdiscus species, with G. australes (CAWD381) being the only isolate to produce gambieric acids A–D. This study has demonstrated that the isolates tested to date produce the known CTXs or MTXs, but not both, and highlighted several species that produced ‘unknown’ compounds displaying characteristics of cyclic polyethers, which will be the focus of future compound discovery efforts.
Author	Puddick, Jonathan Mudge, Elizabeth M Murray, J Sam van Ginkel, Roel Harwood, D Tim Nishimura, Tomohiro Adachi, Masao Finch, Sarah C Prinsep, Michèle R Passfield, Emillie M F Rhodes, Lesley L Funaki, Hiroshi Smith, Kirsty F
AuthorAffiliation	1 Cawthron Institute, Private Bag 2, Nelson 7040, New Zealand; emillie.passfield@cawthron.org.nz (E.M.F.P.); lesley.rhodes@cawthron.org.nz (L.L.R.); jonathan.puddick@cawthron.org.nz (J.P.); kirsty.smith@cawthron.org.nz (K.F.S.); roel.vanginkel@cawthron.org.nz (R.v.G.); nishimura_tomohiro49@fra.go.jp (T.N.); tim.harwood@cawthron.org.nz (D.T.H.) 2 New Zealand Food Safety Science and Research Centre, Massey University, Private Bag 11 222, Palmerston North 4442, New Zealand 6 Japan Fisheries Research and Education Agency, 2-17-5 Maruishi, Hatsukaichi 739-0452, Hiroshima, Japan 3 School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand; michele.prinsep@waikato.ac.nz 7 Faculty of Agriculture and Marine Science, Kochi University, 200 Otsu, Monobe, Nankoku 783-8502, Kochi, Japan; h-funaki@kochi-u.ac.jp (H.F.); madachi@kochi-u.ac.jp (M.A.) 4 AgResearch, Ruakura Research Centre, Private Bag 3123, Hamilton 3240, New Zealand; sarah.finch@agresearch.co.nz 5 Biotoxin Metrolog
AuthorAffiliation_xml	– name: 4 AgResearch, Ruakura Research Centre, Private Bag 3123, Hamilton 3240, New Zealand; sarah.finch@agresearch.co.nz – name: 6 Japan Fisheries Research and Education Agency, 2-17-5 Maruishi, Hatsukaichi 739-0452, Hiroshima, Japan – name: 5 Biotoxin Metrology, National Research Council Canada, 1411 Oxford Street, Halifax, NS B3H 3Z1, Canada; elizabeth.mudge@nrc-cnrc.gc.ca – name: 3 School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand; michele.prinsep@waikato.ac.nz – name: 2 New Zealand Food Safety Science and Research Centre, Massey University, Private Bag 11 222, Palmerston North 4442, New Zealand – name: 7 Faculty of Agriculture and Marine Science, Kochi University, 200 Otsu, Monobe, Nankoku 783-8502, Kochi, Japan; h-funaki@kochi-u.ac.jp (H.F.); madachi@kochi-u.ac.jp (M.A.) – name: 1 Cawthron Institute, Private Bag 2, Nelson 7040, New Zealand; emillie.passfield@cawthron.org.nz (E.M.F.P.); lesley.rhodes@cawthron.org.nz (L.L.R.); jonathan.puddick@cawthron.org.nz (J.P.); kirsty.smith@cawthron.org.nz (K.F.S.); roel.vanginkel@cawthron.org.nz (R.v.G.); nishimura_tomohiro49@fra.go.jp (T.N.); tim.harwood@cawthron.org.nz (D.T.H.)
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Snippet	The genus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this study, the... The genus Gambierdiscus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this... The genus Gambierdiscus produces an array of bioactive hydrophilic and lipophilic secondary metabolites that range in mode of action and toxicity. In this...
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Title	Targeted Metabolite Fingerprints of Thirteen Gambierdiscus , Five Coolia and Two Fukuyoa Species
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