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Two New Lyngbyatoxin Derivatives from the Cyanobacterium, Moorea producens

Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan
National Research Institute of Fisheries Science, Yokohama 236-8648, Japan
Richard L. Roudebush VA Medical Center, Indianapolis, IN 46202, USA
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Mar. Drugs 2014, 12(12), 5788-5800;
Received: 10 October 2014 / Revised: 11 November 2014 / Accepted: 19 November 2014 / Published: 1 December 2014
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The toxin-producing cyanobacterium, Moorea producens, is a known causative organism of food poisoning and seaweed dermatitis (also known as “swimmer’s itch”). Two new toxic compounds were isolated and structurally elucidated from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies, as well as optical rotations and CD spectra indicated two new lyngbyatoxin derivatives, 2-oxo-3(R)-hydroxy-lyngbyatoxin A (1) and 2-oxo-3(R)-hydroxy-13-N-desmethyl-lyngbyatoxin A (2). The cytotoxicity and lethal activities of 1 and 2 were approximately 10- to 150-times less potent than lyngbyatoxin A. Additionally, the binding activities of 1 and 2 possessed 10,000-times lower affinity for the protein kinase Cδ (PKCδ)-C1B peptide when compared to lyngbyatoxin A. These findings suggest that these new lyngbyatoxin derivatives may mediate their acute toxicities through a non-PKC activation pathway. View Full-Text
Keywords: lyngbyatoxin A; cyanobacteria; Moorea producens; toxicity; protein kinase C lyngbyatoxin A; cyanobacteria; Moorea producens; toxicity; protein kinase C

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Jiang, W.; Tan, S.; Hanaki, Y.; Irie, K.; Uchida, H.; Watanabe, R.; Suzuki, T.; Sakamoto, B.; Kamio, M.; Nagai, H. Two New Lyngbyatoxin Derivatives from the Cyanobacterium, Moorea producens. Mar. Drugs 2014, 12, 5788-5800.

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