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@ARTICLE{Reinicke:151517,
      author       = {Reinicke, Justin and Kitatani, Ryuju and Masoud, Shadi
                      Sedghi and Galbraith, Kelly Kawabata and Yoshida, Wesley and
                      Igarashi, Ayako and Nagasawa, Kazuo and Berger, Gideon and
                      Yanagihara, Angel and Nagai, Hiroshi and Horgen, F. David},
      title        = {{I}solation, {S}tructure {D}etermination, and {S}ynthesis
                      of {C}yclic {T}etraglutamic {A}cids from {B}ox {J}ellyfish
                      {S}pecies {A}latina alata and {C}hironex yamaguchii},
      journal      = {Molecules},
      volume       = {25},
      number       = {4},
      issn         = {1420-3049},
      address      = {Basel},
      publisher    = {MDPI7969},
      reportid     = {DZNE-2020-01101},
      pages        = {883},
      year         = {2020},
      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.},
      keywords     = {Animals / Aquatic Organisms: chemistry / Cell Death: drug
                      effects / Chromatography, High Pressure Liquid /
                      Chromatography, Reverse-Phase / Cnidarian Venoms: chemistry
                      / Cnidarian Venoms: toxicity / Cubozoa: chemistry / Glutamic
                      Acid: biosynthesis / Glutamic Acid: chemistry / Glutamic
                      Acid: isolation $\&$ purification / HEK293 Cells /
                      Hemolysis: drug effects / Humans / Proton Magnetic Resonance
                      Spectroscopy / Tissue Distribution},
      cin          = {Bonn Pre 2020},
      ddc          = {540},
      cid          = {I:(DE-2719)6000011},
      pnm          = {341 - Molecular Signaling (POF3-341)},
      pid          = {G:(DE-HGF)POF3-341},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:32079282},
      pmc          = {pmc:PMC7070617},
      doi          = {10.3390/molecules25040883},
      url          = {https://pub.dzne.de/record/151517},
}