ChemInform Abstract: Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog.

Adachi, Masaatsu; Imazu, Takuya; Sakakibara, Ryo; Satake, Yuki; Isobe, Mitsuaki; Nishikawa, Toshio

doi:10.1002/chin.201430216

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…No. 206-11071, FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan) was dissolved in ultra-pure water at 1.5 × 10 -3 M. Two types of TTX analogs, 4,9-anhydroTTX and 5,6,11-trideoxyTTX, were synthesized and purified according to the methods described by Adachi et al (2014a) and Adachi et al (2014b), respectively. Synthesized TTX analogs were dissolved in 2.5 × 10 -2 N acetic acid at 10 -3 M and stored at −30°C until use.…”

Section: Animalsmentioning

confidence: 99%

An almost nontoxic tetrodotoxin analog, 5,6,11-trideoxytetrodotoxin, as an odorant for the grass puffer

Noguchi

Suzuki

Matsutani

et al. 2021

Preprint

Self Cite

View full text Add to dashboard Cite

Toxic puffers contain the potent neurotoxin, tetrodotoxin (TTX). Although TTX is considered to serve as a defense substance, previous behavioral studies have demonstrated that TTX (extracted from the ovary) acts as an attractive pheromone for some toxic puffers. To determine the putative pheromonal action of TTX, we examined whether grass puffers (Takifugu alboplumbeus) can detect TTX using electrophysiological, morphological, and behavioral experiments. Electroolfactogram results suggest that the olfactory epithelium of grass puffers responded in a dose-dependent manner to a type of TTX analog (5,6,11-trideoxyTTX), although it did not respond to TTX. We also examined the attractive action of 5,6,11-trideoxyTTX on grass puffers by recording their swimming behavior under dark conditions. Grass puffers preferred to stay on the side of the aquarium where 5,6,11-trideoxyTTX was administered, and their swimming speed decreased. Additionally, odorant-induced labeling of olfactory sensory neurons using a fluorescent dextran conjugate or immunohistochemistry against phosphorylated extracellular signal regulated kinase (pERK) revealed that labeled olfactory sensory neurons were localized in the region surrounding "islets" where there was abundant cilia on the olfactory lamella. 5,6,11-trideoxyTTX has been known to accumulate in grass puffers, but its toxicity is much lower (almost nontoxic) than TTX. Our results suggest that grass puffers can detect 5,6,11-trideoxyTTX using their nose and may positively use this functionally unknown TTX analog as an olfactory chemoattractant.

show abstract

Section: Animalsmentioning

confidence: 99%