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Volume 13
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10.3390/toxins13020082
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Article

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

by
Masayuki Satake
1,*,
Raku Irie
1,2,
Patrick T. Holland
3,
D Tim Harwood
3,
Feng Shi
3,
Yoshiyuki Itoh
4,
Fumiaki Hayashi
5 and
Huiping Zhang
5
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.
Toxins 2021, 13(2), 82; https://doi.org/10.3390/toxins13020082
Submission 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)
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Abstract

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.
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://doi.org/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://doi.org/10.3390/toxins13020082

Chicago/Turabian Style

Satake, Masayuki, Raku Irie, Patrick T. Holland, D Tim 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://doi.org/10.3390/toxins13020082

APA Style

Satake, M., Irie, R., Holland, P. T., Harwood, D. T., Shi, F., Itoh, Y., Hayashi, F., & Zhang, H. (2021). Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata. Toxins, 13(2), 82. https://doi.org/10.3390/toxins13020082

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