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Volume 16
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10.3390/toxins16020089
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Communication

Structural Assignment of the Product Ion Generated from a Natural Ciguatoxin-3C Congener, 51-Hydroxyciguatoxin-3C, and Discovery of Distinguishable Signals in Congeners Bearing the 51-Hydroxy Group

by
Ryogo Ukai
1,
Hideaki Uchida
2,
Kouichi Sugaya
1,
Jun-ichi Onose
1,
Naomasa Oshiro
3,
Takeshi Yasumoto
4 and
Naoki Abe
1,*
1
Department of Nutritional Science and Food Safety, Graduate School of Applied Bioscience, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya, Tokyo 156-8502, Japan
2
Japan Customer Service Organization, Agilent Technologies Japan, Ltd., 9-1 Takakura-machi, Hachioji, Tokyo 192-8510, Japan
3
National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki 210-9501, Japan
4
Tama Laboratory, Japan Food Research Laboratories, 6-11-10 Nagayama, Tama, Tokyo 206-0025, Japan
*
Author to whom correspondence should be addressed.
Toxins 2024, 16(2), 89; https://doi.org/10.3390/toxins16020089
Submission received: 25 December 2023 / Revised: 23 January 2024 / Accepted: 30 January 2024 / Published: 6 February 2024
(This article belongs to the Section Marine and Freshwater Toxins)
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Abstract

Ciguatoxins (CTXs) stand as the primary toxins causing ciguatera fish poisoning (CFP) and are essential compounds distinguished by their characteristic polycyclic ether structure. In a previous report, we identified the structures of product ions generated via homolytic fragmentation by assuming three charge sites in the mass spectrometry (MS)/MS spectrum of ciguatoxin-3C (CTX3C) using LC-MS. This study aims to elucidate the homolytic fragmentation of a ciguatoxin-3C congener. We assigned detailed structures of the product ions in the MS/MS spectrum of a naturally occurring ciguatoxin-3C congener, 51-hydroxyciguatoxin-3C (51-hydoxyCTX3C), employing liquid chromatography/quadrupole time-of-flight mass spectrometry with an atmospheric pressure chemical ionization (APCI) source. The introduction of a hydroxy substituent on C51 induced different fragmentation pathways, including a novel cleavage mechanism of the M ring involving the elimination of 51-OH and the formation of enol ether. Consequently, new cleavage patterns generated product ions at m/z 979 (C55H79O15), 439 (C24H39O7), 149 (C10H13O), 135 (C9H11O), and 115 (C6H11O2). Additionally, characteristic product ions were observed at m/z 509 (C28H45O8), 491 (C28H43O7), 481 (C26H41O8), 463 (C26H39O7), 439 (C24H39O7), 421 (C24H37O6), 171 (C9H15O3), 153 (C9H13O2), 141 (C8H13O2), and 123 (C8H11O).
Keywords: ciguatoxins (CTXs); 51-hydroxyciguatoxin-3C (51-hydroxyCTX3C); LC-APCI-QTOFMS; charge-remote fragmentation (CRF); polycyclic ethers ciguatoxins (CTXs); 51-hydroxyciguatoxin-3C (51-hydroxyCTX3C); LC-APCI-QTOFMS; charge-remote fragmentation (CRF); polycyclic ethers
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MDPI and ACS Style

Ukai, R.; Uchida, H.; Sugaya, K.; Onose, J.-i.; Oshiro, N.; Yasumoto, T.; Abe, N. Structural Assignment of the Product Ion Generated from a Natural Ciguatoxin-3C Congener, 51-Hydroxyciguatoxin-3C, and Discovery of Distinguishable Signals in Congeners Bearing the 51-Hydroxy Group. Toxins 2024, 16, 89. https://doi.org/10.3390/toxins16020089

AMA Style

Ukai R, Uchida H, Sugaya K, Onose J-i, Oshiro N, Yasumoto T, Abe N. Structural Assignment of the Product Ion Generated from a Natural Ciguatoxin-3C Congener, 51-Hydroxyciguatoxin-3C, and Discovery of Distinguishable Signals in Congeners Bearing the 51-Hydroxy Group. Toxins. 2024; 16(2):89. https://doi.org/10.3390/toxins16020089

Chicago/Turabian Style

Ukai, Ryogo, Hideaki Uchida, Kouichi Sugaya, Jun-ichi Onose, Naomasa Oshiro, Takeshi Yasumoto, and Naoki Abe. 2024. "Structural Assignment of the Product Ion Generated from a Natural Ciguatoxin-3C Congener, 51-Hydroxyciguatoxin-3C, and Discovery of Distinguishable Signals in Congeners Bearing the 51-Hydroxy Group" Toxins 16, no. 2: 89. https://doi.org/10.3390/toxins16020089

APA Style

Ukai, R., Uchida, H., Sugaya, K., Onose, J.-i., Oshiro, N., Yasumoto, T., & Abe, N. (2024). Structural Assignment of the Product Ion Generated from a Natural Ciguatoxin-3C Congener, 51-Hydroxyciguatoxin-3C, and Discovery of Distinguishable Signals in Congeners Bearing the 51-Hydroxy Group. Toxins, 16(2), 89. https://doi.org/10.3390/toxins16020089

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