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Article

Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata

1
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
2
Graduate School of Nanobioscience, Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan
3
Cawthron Institute, Private Bag 2, Nelson 7010, New Zealand
4
MS Business Unit, JEOL Ltd., Musashino, Akishima, Tokyo 196-8558, Japan
5
NMR Science and Development Division, RIKEN SPring-8 Center, Suehiro-cho, Tsurumi-ku, Yokohama 230-0045, Japan
*
Author to whom correspondence should be addressed.
Received: 29 December 2020 / Revised: 17 January 2021 / Accepted: 20 January 2021 / Published: 22 January 2021
(This article belongs to the Special Issue Marine Toxins from Harmful Algae and Seafood Safety)
Two different types of polycyclic ether toxins, namely brevisulcenals (KBTs) and brevisulcatic acids (BSXs), produced by the red tide dinoflagellate Karenia brevisulcata, were the cause of a toxic incident that occurred in New Zealand in 1998. Four major components, KBT-F, -G, -H, and -I, shown to be cytotoxic and lethal in mice, were isolated from cultured K. brevisulcata cells, and their structures were elucidated by spectroscopic analyses. New analogues, brevisulcenal-A1 (KBT-A1) and brevisulcenal-A2 (KBT-A2), toxins of higher polarity than that of known KBTs, were isolated from neutral lipophilic extracts of bulk dinoflagellate culture extracts. The structures of KBT-A1 and KBT-A2 were elucidated as sulfated analogues of KBT-F and KBT-G, respectively, by NMR and matrix-assisted laser desorption/ionization tandem mass spectrometry (MALDI TOF/TOF), and by comparison with the spectra of KBT-F and KBT-G. The cytotoxicities of the sulfate analogues were lower than those of KBT-F and KBT-G. View Full-Text
Keywords: marine polyether; dinoflagellate; red tide incident; harmful algal bloom marine polyether; dinoflagellate; red tide incident; harmful algal bloom
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MDPI and ACS Style

Satake, M.; Irie, R.; Holland, P.T.; Harwood, D.T.; Shi, F.; Itoh, Y.; Hayashi, F.; Zhang, H. Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata. Toxins 2021, 13, 82. https://0-doi-org.brum.beds.ac.uk/10.3390/toxins13020082

AMA Style

Satake M, Irie R, Holland PT, Harwood DT, Shi F, Itoh Y, Hayashi F, Zhang H. Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata. Toxins. 2021; 13(2):82. https://0-doi-org.brum.beds.ac.uk/10.3390/toxins13020082

Chicago/Turabian Style

Satake, Masayuki, Raku Irie, Patrick T. Holland, D T. Harwood, Feng Shi, Yoshiyuki Itoh, Fumiaki Hayashi, and Huiping Zhang. 2021. "Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata" Toxins 13, no. 2: 82. https://0-doi-org.brum.beds.ac.uk/10.3390/toxins13020082

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