Mar. Drugs 2012, 10(3), 655-667; doi:10.3390/md10030655
Article

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

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Received: 28 February 2012; in revised form: 16 March 2012 / Accepted: 17 March 2012 / Published: 22 March 2012
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.
Abstract: 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.
Keywords: tetrodotoxin; 8-epi-5,6,11-trideoxytetrodotoxin; puffer fish; newt; LC/MS
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MDPI and ACS Style

Kudo, Y.; Yasumoto, T.; Konoki, K.; Cho, Y.; Yotsu-Yamashita, M. 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 . Mar. Drugs 2012, 10, 655-667.

AMA Style

Kudo Y, Yasumoto T, Konoki K, Cho Y, Yotsu-Yamashita M. 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 . Marine Drugs. 2012; 10(3):655-667.

Chicago/Turabian Style

Kudo, Yuta; Yasumoto, Takeshi; Konoki, Keiichi; Cho, Yuko; Yotsu-Yamashita, Mari. 2012. "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 ." Mar. Drugs 10, no. 3: 655-667.

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