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Figure 1

Chemical structure of CYN: A – sulfate group, B – tricyclic guanidine moiety, C – uracil ring
Chemical structure of CYN: A – sulfate group, B – tricyclic guanidine moiety, C – uracil ring

Figure 2

Mass spectra of CYN decomposition products formed under alkaline conditions (pH 10) combined with boiling temperature: A – CP-2 or CP-3, B – CP-6
Mass spectra of CYN decomposition products formed under alkaline conditions (pH 10) combined with boiling temperature: A – CP-2 or CP-3, B – CP-6

Figure 3

Mass spectra of CYN decomposition products formed under alkaline conditions (pH 10) during UV-B irradiation: A – CPI-1, B – CPI-2, C – CPI-4, D – CPI-5
Mass spectra of CYN decomposition products formed under alkaline conditions (pH 10) during UV-B irradiation: A – CPI-1, B – CPI-2, C – CPI-4, D – CPI-5

Figure 4

Decrease in bioluminescence observed in the Deltatox® II test: A – pure CYN (aqueous solution), B – mixture of CYN decomposition products formed under alkaline conditions (pH 10) at 100°C, C – mixture of CYN decomposition products formed under alkaline conditions (pH 10) during UV-B irradiation
Decrease in bioluminescence observed in the Deltatox® II test: A – pure CYN (aqueous solution), B – mixture of CYN decomposition products formed under alkaline conditions (pH 10) at 100°C, C – mixture of CYN decomposition products formed under alkaline conditions (pH 10) during UV-B irradiation

Products of total CYN decomposition formed under alkaline conditions (pH 10) combined with boiling temperature

Decomposition products Retention [min] time [M+H]+ Fragmentation ions Proposed structure
CP-2 or CP-3 1.90 336.14 194.1, 176.1
CP-6 3.85 292.01 212.1, 194.1, 176.1

Toxicity of CYN and its decomposition products assessed with Thamnotoxkit FTM and Deltatox® II tests expressed as the concentration causing death of 50% of crustacean larvae (LC50) or 50% inhibition of the bacterial bioluminescence (IC50)

Tested substances Toxicity tests
Thamnotoxkit FTM LC50 [μg ml−1] Deltatox® II IC50 [μg ml−1]
CYN 0.39 < 0.2
CYN decomposition products formed under boiling temperature at pH 10 > 3 > 3
CYN decomposition products formed under UV-B irradiation at pH 10 > 3 > 3

Products of the total CYN decomposition formed under alkaline conditions (pH 10) during UV-B irradiation

Decomposition products Retention [min] time [M+H]+ Fragmentation ions Proposed structure
CPI-1 1.88 290.29 210.1, 192.1
CPI-2 3.87 292.15 212.1, 194.1, 176.1
CPI-4 4.46 338.34 196.1, 178.1, 137.1, 110.1
CPI-5 4.55 214.13 196.1, 178.1, 137.1, 110.1
eISSN:
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Langue:
Anglais
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Sujets de la revue:
Chemistry, other, Geosciences, Life Sciences