%0 Journal Article
%T Isolation and Structural Determination of the First 8-epi-type Tetrodotoxin Analogs from the Newt, Cynops ensicauda popei, and Comparison of Tetrodotoxin Analogs Profiles of This Newt and the Puffer Fish, Fugu poecilonotus
%A Yuta Kudo
%A Takeshi Yasumoto
%A Keiichi Konoki
%A Yuko Cho
%A Mari Yotsu-Yamashita
%J Marine Drugs
%D 2012
%I MDPI AG
%R 10.3390/md10030655
%X Identification of new tetrodotoxin (TTX) analogs from TTX-possessing animals might provide insight into its biosynthesis and metabolism. In this study, four new analogs, 8- epi-5,6,11-trideoxyTTX, 4,9-anhydro-8- epi-5,6,11-trideoxyTTX, 1-hydroxy-8- epi-5,6,11-trideoxyTTX, and 1-hydroxy-4,4a-anhydro-8- epi-5,6,11-trideoxyTTX, were isolated from the newt, Cynops ensicauda popei, and their structures were determined using spectroscopic methods. These are the first 8- epi-type analogs of TTX that have been found in a natural source. Furthermore, we examined the composition of the TTX analogs in this newt and in the ovary of the puffer fish, Fugu poecilonotus, using LC/MS. The results indicate that TTX and 11-deoxyTTX were present in both sources. However, 6- epiTTX and 8- epi-type analogs were detected only in the newt, while 5,6,11-trideoxyTTX was a specific and major analog in the puffer fish. Such considerable differences among analog compositions might reflect differences in the biosynthesis or metabolism of TTX between these animals.
%K tetrodotoxin
%K 8-epi-5
%K 6
%K 11-trideoxytetrodotoxin
%K puffer fish
%K newt
%K LC/MS
%U http://www.mdpi.com/1660-3397/10/3/655