天然有機化合物討論会講演要旨集
Online ISSN : 2433-1856
セッションID: 43
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43 ジョロウグモ(Nephila clavata)の神経毒Nephilatoxin類の合成研究II : 合成とその活性(口頭発表の部)
松下 正行秋月 尚紀金村 隆則畑山 範入江 寛土岐 節宮下 正昭
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会議録・要旨集 フリー

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Nephilatoxins (NPTX-1〜12) isolated from the venom of Joro spider (Nephila clavata) have been characterized as structurally new type of neurotoxins consisted of an aromatic acid, amino acids, and some polyamines. These toxins induce histamine release from rat peritoneal mast cell and exhibit potent blocking activities toward glutaminergic neurotransmission in the lobster legs. We have reported the first and efficient syntheses of NPTX-9,10,11, and 12 by the use of azide intermediates (1 and 2) which played key roles in the construction of the characteristic polyamine components such as cadaverine and putreanine. By designing a novel azide compound 3 as 9-aminopropylputreanine equivalent, we were successful in the first synthesis of NPTX-8 (Scheme 2). We also synthesized NPTX-7, the only spider toxin containing an acidic amino acid as a component, according to Scheme 3. In addition enantiomers of NPTX-8 and NPTX-12, i.e., D-NPTX-8 and D-NPTX-12 containing D-asparagine, have been synthesized to investigate the structure-toxicity relationship. From the biological tests of the seven synthetic toxins (paralyzing activity against Blattela germanica L.), it was revealed that the reported order of Nephilatoxins should be revised as NPTX-12>NPTX-10>NPTX-8> NPTX-11>NPTX-9. Interestingly, D-NPTX-8 and D-NPTX-12 have been shown to exhibit considerably potent glutaminergic blocking activities. Further synthetic studies on other spider toxins and analogues are in progress.

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© 1994 天然有機化合物討論会電子化委員会
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