Journal Article

DZNE-2020-01101

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Isolation, Structure Determination, and Synthesis of Cyclic Tetraglutamic Acids from Box Jellyfish Species Alatina alata and Chironex yamaguchii

Reinicke, J. ; Kitatani, R. ; Masoud, S. S. ; Galbraith, K. K.DZNE* ; Yoshida, W. ; Igarashi, A. ; Nagasawa, K. ; Berger, G. (Corresponding author) ; Yanagihara, A. (Corresponding author) ; Nagai, H. (Corresponding author) ; Horgen, F. D. (Corresponding author)

2020
MDPI7969 Basel

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Please use a persistent id in citations: doi:10.3390/molecules25040883

Abstract: Cubozoan nematocyst venoms contain known cytolytic and hemolytic proteins, but small molecule components have not been previously reported from cubozoan venom. We screened nematocyst extracts of Alatina alata and Chironex yamaguchii by LC-MS for the presence of small molecule metabolites. Three isomeric compounds, cnidarins 4A (1), 4B (2), and 4C (3), were isolated from venom extracts and characterized by NMR and MS, which revealed their planar structure as cyclic γ-linked tetraglutamic acids. The full configurational assignments were established by syntheses of all six possible stereoisomers, comparison of spectral data and optical rotations, and stereochemical analysis of derivatized degradation products. Compounds 1–3 were subsequently detected by LC-MS in tissues of eight other cnidarian species. The most abundant of these compounds, cnidarin 4A (1), showed no mammalian cell toxicity or hemolytic activity, which may suggest a role for these cyclic tetraglutamates in nematocyst discharge.

Keyword(s): Animals (MeSH) ; Aquatic Organisms: chemistry (MeSH) ; Cell Death: drug effects (MeSH) ; Chromatography, High Pressure Liquid (MeSH) ; Chromatography, Reverse-Phase (MeSH) ; Cnidarian Venoms: chemistry (MeSH) ; Cnidarian Venoms: toxicity (MeSH) ; Cubozoa: chemistry (MeSH) ; Glutamic Acid: biosynthesis (MeSH) ; Glutamic Acid: chemistry (MeSH) ; Glutamic Acid: isolation & purification (MeSH) ; HEK293 Cells (MeSH) ; Hemolysis: drug effects (MeSH) ; Humans (MeSH) ; Proton Magnetic Resonance Spectroscopy (MeSH) ; Tissue Distribution (MeSH)

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Contributing Institute(s):

1. Bonn Pre 2020 (Bonn Pre 2020)

Research Program(s):

1. 341 - Molecular Signaling (POF3-341) (POF3-341)

Appears in the scientific report 2020

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