Two New Lyngbyatoxin Derivatives from the Cyanobacterium, Moorea producens

Marine Drugs

Weina Jiang²  Satoshi Tan²  Yusuke Hanaki⁴  Kazuhiro Irie⁴  Hajime Uchida²  Ryuichi Watanabe¹  Toshiyuki Suzuki¹  Bryan Sakamoto³  Michiya Kamio²  Hiroshi Nagai² 

[1] National Research Institute of Fisheries Science, Yokohama 236-8648, Japan; E-Mails:;Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan; E-Mails:;Richard L. Roudebush VA Medical Center, Indianapolis, IN 46202, USA; E-Mail:;Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan; E-Mails:

关键词: lyngbyatoxin A;    cyanobacteria;    Moorea producens;    toxicity;    protein kinase C;   

DOI  :  10.3390/md12125788

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.