受賞区分：国内学会・会議・シンポジウム等の賞 

受賞区分：国内学会・会議・シンポジウム等の賞 

記述言語：日本語   出版者・発行元：公益社団法人 有機合成化学協会  

DOI： 10.5059/yukigoseikyokaishi.82.63

CiNii Research

記述言語：英語   出版者・発行元：Toxicon  

Tetrodotoxin (TTX) is a potent neurotoxin that binds to voltage-gated sodium channels and blocks the passage of sodium ions. TTX is widely distributed in both terrestrial and marine organisms, and the toxic puffers are believed to accumulate TTX through the food chain. Although pufferfish was previously thought to be attracted by TTX, recent finding from electroolfactogram (EOG) studies have indicated that the olfactory epithelium of T. alboplumbeus responded to 5, 6, 11-trideoxyTTX (TDT), but not to TTX itself. In this study, we examined behavioral experiments for Takifugu rubripes to distinguish between TTX and TDT under static and flow-through conditions. Our data clearly suggested that T. rubripes juveniles were attracted to TDT, not TTX. Moreover, we determined that the minimum effective dose of TDT to attract the puffer was 1–2 nmol of TDT under static conditions and 50–60 nmol of TDT under flow-through conditions. Following the experiments under static conditions, numerous bite marks by the pufferfish were found solely on the agarose gel infused with TDT. Based on these finding, we hypothesize that the pufferfish are attracted to TDT derived from prey, leading them effectively become toxic.

DOI： 10.1016/j.toxicon.2023.107539

Web of Science

Scopus

PubMed

記述言語：日本語   出版者・発行元：Journal of Organic Chemistry  

The collective synthesis of the four spiro-cyclic guanidines Tb-210B, Tb-226, Tb-242C, and Tb-258, all of which have been isolated from puffer fish and are considered possible biosynthetic intermediates of tetrodotoxin, has been achieved. Our synthesis is based on the stepwise deoxygenation or hydroxylation of a common intermediate, prepared from a known oxazoline.

DOI： 10.1021/acs.joc.2c00704

Web of Science

Scopus

PubMed

記述言語：日本語   出版者・発行元：Organic Letters  

Despite decades of research, the biosynthesis of tetrodotoxin, also known as a puffer fish toxin, remains an unsolved mystery. We disclose a synthesis of the 8-deoxy analogue of 4,9-anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a possible biosynthetic precursor of tetrodotoxin isolated from the Japanese toxic newt, by an intramolecular radical cyclization of a known starting material.

DOI： 10.1021/acs.orglett.1c03565

Web of Science

Scopus

PubMed

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： doi.org/10.1002/anie.202007280

記述言語：日本語   会議種別：口頭発表（一般）  

開催地：広島  

開催年月日： 2020年11月

記述言語：日本語   会議種別：ポスター発表  

開催地：愛知   国名：日本国  

記述言語：日本語   会議種別：口頭発表（一般）  

開催地：仙台・オンライン  

記述言語：日本語   会議種別：ポスター発表  

開催地：静岡・オンライン  

記述言語：日本語   会議種別：口頭発表（一般）  

開催地：京都   国名：日本国