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Structure Elucidation and in Vitro Toxicity of New Azaspiracids Isolated from the Marine Dinoflagellate Azadinium poporum.

Krock B, Tillmann U, Potvin É, Jeong HJ, Drebing W, Kilcoyne J, Al-Jorani A, Twiner MJ, Göthel Q, Köck M - Mar Drugs (2015)

Bottom Line: Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids.Approximately 0.9 mg of pure AZA-36 (1) and 1.3 mg of pure AZA-37 (2) were isolated from the Korean (870 L) and North Sea (120 L) strains, respectively.The structures were determined to be 3-hydroxy-8-methyl-39-demethyl-azaspiracid-1 (1) and 3-hydroxy-7,8-dihydro-39-demethyl-azaspiracid-1 (2) by ¹H- and (13)C-NMR.

View Article: PubMed Central - PubMed

Affiliation: Alfred-Wegener-Institut, Helmholtz-Zentrum für Polar- und Meeresforschung, Am Handelshafen 12, Bremerhaven 27570, Germany. Bernd.Krock@awi.de.

ABSTRACT
Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids. Approximately 0.9 mg of pure AZA-36 (1) and 1.3 mg of pure AZA-37 (2) were isolated from the Korean (870 L) and North Sea (120 L) strains, respectively. The structures were determined to be 3-hydroxy-8-methyl-39-demethyl-azaspiracid-1 (1) and 3-hydroxy-7,8-dihydro-39-demethyl-azaspiracid-1 (2) by ¹H- and (13)C-NMR. Using the Jurkat T lymphocyte cell toxicity assay, (1) and (2) were found to be 6- and 3-fold less toxic than AZA-1, respectively.

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Effect on T lymphocyte cell viability. Jurkat T cells exposed to various concentrations of (A) AZA-1; (B) AZA-36 (1); and (C) AZA-37 (2) for 24, 48, or 72 h and viability assessed using the MTS assay. All data (mean ± SE; n = 4) were normalized to the control (10% methanol vehicle). Non-linear, three parameter dose-response (variable slope) analysis was performed and EC50 values were calculated (Table 4).
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marinedrugs-13-06687-f002: Effect on T lymphocyte cell viability. Jurkat T cells exposed to various concentrations of (A) AZA-1; (B) AZA-36 (1); and (C) AZA-37 (2) for 24, 48, or 72 h and viability assessed using the MTS assay. All data (mean ± SE; n = 4) were normalized to the control (10% methanol vehicle). Non-linear, three parameter dose-response (variable slope) analysis was performed and EC50 values were calculated (Table 4).

Mentions: The toxicity of (1) and (2) was assessed using the Jurkat T lymphocyte cell assay. In order to compare this data to the known toxicities of other AZAs, AZA-1 was included in this assay and individual toxicities were expressed as relative potencies. Similar to AZA-1, (1) and (2) elicited concentration- and time-dependent cytotoxic effects towards T lymphocytes but with variable potencies, clearly seen from the dose-response curves of the three compounds (Figure 2). The cytotoxic effects induced by AZA-1 are consistent with previously published studies [31,32,33].


Structure Elucidation and in Vitro Toxicity of New Azaspiracids Isolated from the Marine Dinoflagellate Azadinium poporum.

Krock B, Tillmann U, Potvin É, Jeong HJ, Drebing W, Kilcoyne J, Al-Jorani A, Twiner MJ, Göthel Q, Köck M - Mar Drugs (2015)

Effect on T lymphocyte cell viability. Jurkat T cells exposed to various concentrations of (A) AZA-1; (B) AZA-36 (1); and (C) AZA-37 (2) for 24, 48, or 72 h and viability assessed using the MTS assay. All data (mean ± SE; n = 4) were normalized to the control (10% methanol vehicle). Non-linear, three parameter dose-response (variable slope) analysis was performed and EC50 values were calculated (Table 4).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4663548&req=5

marinedrugs-13-06687-f002: Effect on T lymphocyte cell viability. Jurkat T cells exposed to various concentrations of (A) AZA-1; (B) AZA-36 (1); and (C) AZA-37 (2) for 24, 48, or 72 h and viability assessed using the MTS assay. All data (mean ± SE; n = 4) were normalized to the control (10% methanol vehicle). Non-linear, three parameter dose-response (variable slope) analysis was performed and EC50 values were calculated (Table 4).
Mentions: The toxicity of (1) and (2) was assessed using the Jurkat T lymphocyte cell assay. In order to compare this data to the known toxicities of other AZAs, AZA-1 was included in this assay and individual toxicities were expressed as relative potencies. Similar to AZA-1, (1) and (2) elicited concentration- and time-dependent cytotoxic effects towards T lymphocytes but with variable potencies, clearly seen from the dose-response curves of the three compounds (Figure 2). The cytotoxic effects induced by AZA-1 are consistent with previously published studies [31,32,33].

Bottom Line: Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids.Approximately 0.9 mg of pure AZA-36 (1) and 1.3 mg of pure AZA-37 (2) were isolated from the Korean (870 L) and North Sea (120 L) strains, respectively.The structures were determined to be 3-hydroxy-8-methyl-39-demethyl-azaspiracid-1 (1) and 3-hydroxy-7,8-dihydro-39-demethyl-azaspiracid-1 (2) by ¹H- and (13)C-NMR.

View Article: PubMed Central - PubMed

Affiliation: Alfred-Wegener-Institut, Helmholtz-Zentrum für Polar- und Meeresforschung, Am Handelshafen 12, Bremerhaven 27570, Germany. Bernd.Krock@awi.de.

ABSTRACT
Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids. Approximately 0.9 mg of pure AZA-36 (1) and 1.3 mg of pure AZA-37 (2) were isolated from the Korean (870 L) and North Sea (120 L) strains, respectively. The structures were determined to be 3-hydroxy-8-methyl-39-demethyl-azaspiracid-1 (1) and 3-hydroxy-7,8-dihydro-39-demethyl-azaspiracid-1 (2) by ¹H- and (13)C-NMR. Using the Jurkat T lymphocyte cell toxicity assay, (1) and (2) were found to be 6- and 3-fold less toxic than AZA-1, respectively.

Show MeSH
Related in: MedlinePlus