2. Academic Validation
  3. Two new lyngbyatoxin derivatives from the Cyanobacterium, Moorea producens

Two new lyngbyatoxin derivatives from the Cyanobacterium, Moorea producens

  • Mar Drugs. 2014 Dec 1;12(12):5788-800. doi: 10.3390/md12125788.
Weina Jiang 1,  Satoshi Tan 2,  Yusuke Hanaki 3,  Kazuhiro Irie 4,  Hajime Uchida 5,  Ryuichi Watanabe 6,  Toshiyuki Suzuki 7,  Bryan Sakamoto 8,  Michiya Kamio 9,  Hiroshi Nagai 10
Affiliations

Affiliations

  • 1 Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. [email protected].
  • 2 Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. [email protected].
  • 3 Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. [email protected].
  • 4 Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. [email protected].
  • 5 Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. [email protected].
  • 6 National Research Institute of Fisheries Science, Yokohama 236-8648, Japan. [email protected].
  • 7 National Research Institute of Fisheries Science, Yokohama 236-8648, Japan. [email protected].
  • 8 Richard L. Roudebush VA Medical Center, Indianapolis, IN 46202, USA. [email protected].
  • 9 Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. [email protected].
  • 10 Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. [email protected].
PMID: 25470181 DOI: 10.3390/md12125788
Abstract

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.

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