A New Saxitoxin Analogue from a Xanthid Crab Atergatis Floridus

Overview

Journal Toxicon

Specialty Toxicology

Date 1995 Dec 1

PMID 8866615

Citations 13

Authors

O Arakawa

S Nishio

T Noguchi

Y Shida

Y Onque

Affiliations

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Abstract

A novel paralytic toxin was isolated from toxic specimens of a xanthid crab Atergatis floridus inhabiting the Pacific coast of Shikoku Island. Its structure was deduced to be 11-saxitoxinethanoic acid (SEA) based on high-performance liquid chromatography, electrospray ionization mass spectrometry, and 1H and 13C-NMR spectrometries. This acid was assumed to exist as an equilibrium mixture of three tautomers, the main tautomer being the hydrate form 11 beta-epimer. SEA showed a specific toxicity of 830 mouse units per mumole on i.p. injection into mice.

Citing Articles

Tetrodotoxin Profiles in Xanthid Crab and Blue-Lined Octopus cf. from the Same Site in Nagasaki, Japan.

Zhang Y, Yamate Y, Takegaki T, Arakawa O, Takatani T Toxins (Basel). 2023; 15(3).

PMID: 36977084 PMC: 10052739. DOI: 10.3390/toxins15030193.

Silylpyrrole Oxidation En Route to Saxitoxin Congeners Including 11-Saxitoxinethanoic Acid.

Tang D, Merit J, Bedell T, Du Bois J J Org Chem. 2021; 86(24):17790-17803.

PMID: 34874731 PMC: 8857915. DOI: 10.1021/acs.joc.1c02116.

Complete mitochondrial genome of xanthid crab (Linnaeus, 1767).

Karagozlu M, Barbon M, Dinh T, Demayo C, Kim C Mitochondrial DNA B Resour. 2021; 3(1):202-204.

PMID: 33474118 PMC: 7799886. DOI: 10.1080/23802359.2018.1437832.

Synthetic Approaches to Zetekitoxin AB, a Potent Voltage-Gated Sodium Channel Inhibitor.

Adachi K, Ishizuka H, Odagi M, Nagasawa K Mar Drugs. 2020; 18(1).

PMID: 31888062 PMC: 7024329. DOI: 10.3390/md18010024.

A Direct C11 Alkylation Strategy on the Saxitoxin Core: A Synthesis of (+)-11-Saxitoxinethanoic Acid.

Paladugu S, James C, Looper R Org Lett. 2019; 21(19):7999-8002.

PMID: 31553620 PMC: 8567775. DOI: 10.1021/acs.orglett.9b02986.