A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens.
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.
Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. jwnkouina@gmail.com.
Weina
W
Jiang
Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. vivitalot@gmail.com.
Wei
W
Zhou
Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. huchida.msr181823@gmail.com.
Hajime
H
Uchida
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. kikumori@kais.kyoto-u.ac.jp.
Masayuki
M
Kikumori
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. irie@kais.kyoto-u.ac.jp.
Kazuhiro
K
Irie
National Research Institute of Fisheries Science, Yokohama 236-8648, Japan. rwatanabe@affrc.go.jp.
Ryuichi
R
Watanabe
National Research Institute of Fisheries Science, Yokohama 236-8648, Japan. tsuzuki@affrc.go.jp.
Toshiyuki
T
Suzuki
Richard L. Roudebush VA Medical Center, Indianapolis, IN 46202, USA. bryan.sakamoto@va.gov.
Bryan
B
Sakamoto
Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. mkamio@kaiyodai.ac.jp.
Michiya
M
Kamio
Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan. nagai@kaiyodai.ac.jp.
Hiroshi
H
Nagai
D000818:Animals; D000970:Antineoplastic Agents / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry*; D006254:Hawaii; D006801:Humans; D007928:Lethal Dose 50; D007939:Leukemia L1210 / Q000188:drug therapy; D008235:Lyngbya Toxins / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D008968:Molecular Conformation; D033541:Palaemonidae; D011493:Protein Kinase C / Q000037:antagonists & inhibitors / Q000378:metabolism
C000593621:12-epi-lyngbyatoxin A; D000970:Antineoplastic Agents; D008235:Lyngbya Toxins; D011493:Protein Kinase C