title: Two new lyngbyatoxin derivatives from the Cyanobacterium, Moorea producens.
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.
authors.affiliation: Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. jwnkouina@gmail.com.
authors.forename: Weina
authors.initials: W
authors.lastname: Jiang
authors.affiliation: Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. sa19901-31@gc4.so-net.ne.jp.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Tan
authors.affiliation: Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. y_hanaki_0625@yahoo.co.jp.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Hanaki
authors.affiliation: Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. irie@kais.kyoto-u.ac.jp.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Irie
authors.affiliation: Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. huchida.msr181823@gmail.com.
authors.forename: Hajime
authors.initials: H
authors.lastname: Uchida
authors.affiliation: National Research Institute of Fisheries Science, Yokohama 236-8648, Japan. rwatanabe@affrc.go.jp.
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Watanabe
authors.affiliation: National Research Institute of Fisheries Science, Yokohama 236-8648, Japan. tsuzuki@affrc.go.jp.
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Suzuki
authors.affiliation: Richard L. Roudebush VA Medical Center, Indianapolis, IN 46202, USA. bryan.sakamoto@va.gov.
authors.forename: Bryan
authors.initials: B
authors.lastname: Sakamoto
authors.affiliation: Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. mkamio@kaiyodai.ac.jp.
authors.forename: Michiya
authors.initials: M
authors.lastname: Kamio
authors.affiliation: Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. nagai@kaiyodai.ac.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nagai
mesh_terms: D000458:Cyanobacteria / Q000737:chemistry*; D006254:Hawaii; D008235:Lyngbya Toxins / Q000737:chemistry*; D008387:Marine Toxins / Q000737:chemistry; D011493:Protein Kinase C / Q000737:chemistry
chemical_list: D008235:Lyngbya Toxins; D008387:Marine Toxins; D011493:Protein Kinase C; C019457:lyngbyatoxin A