Brevisulcenal-G, -H, and –I, Polycyclic Ether Marine Toxins from the Dinoflagellate Karenia brevisulcata

Satake, Masayuki; Irie, Raku; Hamamoto, Yuka; Tachibana, Kunihide; Holland, Patrick T.; Harwood, D. Tim; Shi, Feng; Beuzenberg, Veronica; Itoh, Yoshiyuki; Hayashi, Fumiaki; Zhang, Huiping

doi:10.3987/com-18-14014

Cited by 3 publications

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“…KBTs are lipophilic polycyclic ethers with a ladder-like structure [109]. Ten analogs are reported (Table 1); however, only six of them have been well characterized to date: KBT-A1 (ID #33), KBT-A2 (ID #34), KBT-F (ID #35), KBT-G (ID #36), KBT-H (ID #37), and KBT-I (ID #38) [75,76,78,82,110] (Figure 10). The mouse i.p.…”

Section: Brevisulcenals and Brevisulcatic Acidsmentioning

confidence: 99%

Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms

et al. 2021

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In recent decades, more than 130 potentially toxic metabolites originating from dinoflagellate species belonging to the genus Karenia or metabolized by marine organisms have been described. These metabolites include the well-known and large group of brevetoxins (BTXs), responsible for foodborne neurotoxic shellfish poisoning (NSP) and airborne respiratory symptoms in humans. Karenia spp. also produce brevenal, brevisamide and metabolites belonging to the hemi-brevetoxin, brevisin, tamulamide, gymnocin, gymnodimine, brevisulcenal and brevisulcatic acid groups. In this review, we summarize the available knowledge in the literature since 1977 on these various identified metabolites, whether they are produced directly by the producer organisms or biotransformed in marine organisms. Their structures and physicochemical properties are presented and discussed. Among future avenues of research, we highlight the need for more toxin occurrence data with analytical techniques, which can specifically determine the analogs present in samples. New metabolites have yet to be fully described, especially the groups of metabolites discovered in the last two decades (e.g tamulamides). Lastly, this work clarifies the different nomenclatures used in the literature and should help to harmonize practices in the future.

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Section: Brevisulcenals and Brevisulcatic Acidsmentioning

confidence: 99%

Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms

et al. 2021

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“…NMR and matrix-assisted laser desorption/ionization (MALDI) tandem mass spectrometry (MS) with high-energy collision-induced dissociation (HE-CID) led to the elucidation of the four KBT structures, brevisulcenal-F (KBT-F), KBT-G, KBT-H, and KBT-I, as shown in Figure 1 [ 13 , 14 ]. KBT structural features include molecular weights above 2000 and extensive ladder-frame polyether compounds comprising 24 ether rings, including a dihydrofuran, decorated with hydroxy groups, methyl groups, and conjugated unsaturated aldehyde side chains.…”

Section: Introductionmentioning

confidence: 99%

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

Satake

Irie

Holland

et al. 2021

Toxins

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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.

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Marine natural products

et al. 2020

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Brevisulcenal-G, -H, and –I, Polycyclic Ether Marine Toxins from the Dinoflagellate Karenia brevisulcata

Cited by 3 publications

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Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms

Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms

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

Marine natural products

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