Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata.
Masayuki SatakeRaku IriePatrick T HollandD Tim HarwoodFeng ShiYoshiyuki ItohFumiaki HayashiHuiping ZhangPublished in: Toxins (2021)
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.
Keyphrases
- mass spectrometry
- molecular docking
- tandem mass spectrometry
- high resolution
- liquid chromatography
- high performance liquid chromatography
- gas chromatography
- ultra high performance liquid chromatography
- ms ms
- high resolution mass spectrometry
- simultaneous determination
- structure activity relationship
- induced apoptosis
- molecular dynamics simulations
- solid phase extraction
- cell cycle arrest
- cardiovascular disease
- magnetic resonance
- type diabetes
- metabolic syndrome
- oxidative stress
- signaling pathway
- density functional theory