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000151517 037__ $$aDZNE-2020-01101
000151517 041__ $$aEnglish
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000151517 1001_ $$aReinicke, Justin$$b0
000151517 245__ $$aIsolation, Structure Determination, and Synthesis of Cyclic Tetraglutamic Acids from Box Jellyfish Species Alatina alata and Chironex yamaguchii
000151517 260__ $$aBasel$$bMDPI7969$$c2020
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000151517 520__ $$aCubozoan nematocyst venoms contain known cytolytic and hemolytic proteins, but small molecule components have not been previously reported from cubozoan venom. We screened nematocyst extracts of Alatina alata and Chironex yamaguchii by LC-MS for the presence of small molecule metabolites. Three isomeric compounds, cnidarins 4A (1), 4B (2), and 4C (3), were isolated from venom extracts and characterized by NMR and MS, which revealed their planar structure as cyclic γ-linked tetraglutamic acids. The full configurational assignments were established by syntheses of all six possible stereoisomers, comparison of spectral data and optical rotations, and stereochemical analysis of derivatized degradation products. Compounds 1–3 were subsequently detected by LC-MS in tissues of eight other cnidarian species. The most abundant of these compounds, cnidarin 4A (1), showed no mammalian cell toxicity or hemolytic activity, which may suggest a role for these cyclic tetraglutamates in nematocyst discharge.
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000151517 650_2 $$2MeSH$$aAnimals
000151517 650_2 $$2MeSH$$aAquatic Organisms: chemistry
000151517 650_2 $$2MeSH$$aCell Death: drug effects
000151517 650_2 $$2MeSH$$aChromatography, High Pressure Liquid
000151517 650_2 $$2MeSH$$aChromatography, Reverse-Phase
000151517 650_2 $$2MeSH$$aCnidarian Venoms: chemistry
000151517 650_2 $$2MeSH$$aCnidarian Venoms: toxicity
000151517 650_2 $$2MeSH$$aCubozoa: chemistry
000151517 650_2 $$2MeSH$$aGlutamic Acid: biosynthesis
000151517 650_2 $$2MeSH$$aGlutamic Acid: chemistry
000151517 650_2 $$2MeSH$$aGlutamic Acid: isolation & purification
000151517 650_2 $$2MeSH$$aHEK293 Cells
000151517 650_2 $$2MeSH$$aHemolysis: drug effects
000151517 650_2 $$2MeSH$$aHumans
000151517 650_2 $$2MeSH$$aProton Magnetic Resonance Spectroscopy
000151517 650_2 $$2MeSH$$aTissue Distribution
000151517 7001_ $$aKitatani, Ryuju$$b1
000151517 7001_ $$aMasoud, Shadi Sedghi$$b2
000151517 7001_ $$0P:(DE-2719)9001336$$aGalbraith, Kelly Kawabata$$b3$$udzne
000151517 7001_ $$aYoshida, Wesley$$b4
000151517 7001_ $$aIgarashi, Ayako$$b5
000151517 7001_ $$00000-0002-0437-948X$$aNagasawa, Kazuo$$b6
000151517 7001_ $$0P:(DE-HGF)0$$aBerger, Gideon$$b7$$eCorresponding author
000151517 7001_ $$00000-0001-6908-8176$$aYanagihara, Angel$$b8$$eCorresponding author
000151517 7001_ $$0P:(DE-HGF)0$$aNagai, Hiroshi$$b9$$eCorresponding author
000151517 7001_ $$00000-0001-9409-3030$$aHorgen, F. David$$b10$$eCorresponding author
000151517 77318 $$2Crossref$$3journal-article$$a10.3390/molecules25040883$$b : MDPI AG, 2020-02-17$$n4$$p883$$tMolecules$$v25$$x1420-3049$$y2020
000151517 773__ $$0PERI:(DE-600)2008644-1$$a10.3390/molecules25040883$$gVol. 25, no. 4, p. 883 -$$n4$$p883$$tMolecules$$v25$$x1420-3049$$y2020
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