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 / 979 (CHO), 439 (CHO), 149 (CHO), 135 (CHO), and 115 (CHO). Additionally, characteristic product ions were observed at / 509 (CHO), 491 (CHO), 481 (CHO), 463 (CHO), 439 (CHO), 421 (CHO), 171 (CHO), 153 (CHO), 141 (CHO), and 123 (CHO).
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| http://dx.doi.org/10.3390/toxins16020089 | DOI Listing |
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