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Mar. Drugs 2014, 12(5), 2748-2759; doi:10.3390/md12052748
Communication

A New Lyngbyatoxin from the Hawaiian Cyanobacterium Moorea producens

1
, 1
, 1
, 2
, 2
, 3
, 3
, 4
, 1
 and 1,*
1 Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan 2 Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan 3 National Research Institute of Fisheries Science, Yokohama 236-8648, Japan 4 Richard L. Roudebush VA Medical Center, Indianapolis, IN 46202, USA
* Author to whom correspondence should be addressed.
Received: 17 February 2014 / Revised: 6 April 2014 / Accepted: 8 April 2014 / Published: 12 May 2014
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Abstract

Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of “swimmer’s itch” with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicated that the compound was a new lyngbyatoxin A derivative, 12-epi-lyngbyatoxin A (1). While 12-epi-lyngbyatoxin A showed comparable toxicities with lyngbyatoxin A in cytotoxicity and crustacean lethality tests, it showed more than 100 times lower affinity for protein kinase Cδ (PKCδ) using the PKCδ-C1B peptide when compared to lyngbyatoxin A.
Keywords: lyngbyatoxin A; cyanobacteria; Moorea producens; toxicity; protein kinase C lyngbyatoxin A; cyanobacteria; Moorea producens; toxicity; protein kinase C
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Jiang, W.; Zhou, W.; Uchida, H.; Kikumori, M.; Irie, K.; Watanabe, R.; Suzuki, T.; Sakamoto, B.; Kamio, M.; Nagai, H. A New Lyngbyatoxin from the Hawaiian Cyanobacterium Moorea producens. Mar. Drugs 2014, 12, 2748-2759.

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