78(P65) ミクロネシア産海綿Dysidea herbaceaより単離された神経毒アミノ酸Dysiherbaineの構造(ポスター発表の部)

概要

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A new amino acid dysiherbaine (1), was isolated from a Micronesian sponge Dysidea herbacea. The structure was determined spectroscopically by using FABMS, ESIMS, FABMS/CID/MS, and one- and two-dimensional NMR experiments of 1 and its dimethyl derivative 2 to be a novel di-amino di-carboxylic acid, which consisted of a cis fused-hexahydrofuro[3,2-b] pyran ring substituted with a 3-[2-amino propanoic acid] side chain. The relative configuration of the bicyclic portion of 1 was determined by 3^J_<H.H>analysis and deference NOE experiments, and that of acyclic side chain was assigned by additional ^<2.3>J_<C.H>analysis, measured by conventional proton NMR and newer hetero half-filtered TOCSY (HETLOC) and phase sensitive HMBC experiments. A systemic administration of 1 induced typical neurotoxic symptoms in mice which were reminiscent of neuroexcitatory amino acids, such as domoic acid. Dysiherbaine inhibited bindings of [^3H]kainic acid (KA) and [^3H]1-amino-3-hydroxy-5-methyl-4-isoxazol-propionic acid (AMPA), but not not [^3H]CGS-19755, an NMDA receptor agonist, to the rat brain synaptic membranes, suggesting that 1 is a specific agonist of KA/AMPA class glutamate receptors in the central nervous system.
天然有機化合物討論会の論文
1996-09-02