51(P-13) 独居性カリバチ毒嚢に含まれる低分子量含窒素成分の構造解析(ポスター発表の部)

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Solitary wasps paralyze other insects for several weeks to feed their larvae using their stings and venom. The mechanism of the long-term paralysis in molecular level has received much attention for a long period. We emerge that low-molecular weight amine compounds in the venom would modulate neurotransmission of insects leading the paralysis. The amount of the venom available from solitary wasp is extremely limited, because of the following reasons: i) solitary wasps hunt insects independently that is obstructive to collect the wasps and ii) the venom is much smaller than those of social wasps. These facts led us to develop sensitive method for the identification of the low-molecular components in wasp venom. We describe herein the construction of rapid and accurate method using LC/high resolution MS (LC/HRMS) which can be analyzed with 3 parameters: retention time, molecular weight and exact mass. We also discuss structural determination of the novel amine found in the LC/HRMS by ^1H-NMR, MS/MS and chemical synthesis. The LC/MS system consists of ODS column and heptafluoro-n-butyric acid as an ion-pair reagent in the mobile phase. MS spectrum was obtained with Q-tof equipped with ESI ionization interface. The standard amine compounds were histamine, octopamine, GABA, spermidine, spermine, serotonin, lysine, arginine, acetylcholine, dopamine, nicotine, tyramine, adenosine, alanine, glutamic acid, putrescine, cadaverine, adrenaline and noradrenaline. High-resolution mass spectra were obtained by means of Leu-Enkephalin in post-column as an internal standard. The standard amines can be detected in approximately ten picomols. Thus the venom extracts (9 species of wasps) using 1/100-1/10 amount of the extract were analyzed. The major contents were found to be GABA, histamine, and acetylcholine. We found a new signal (m/z 174), whose retention time is not identical with any amines employed as the standard samples from Eumeninae wasp. The structure of this compound was elucidated to be butyrylcholine from spectral analysis. Butyrylcholine is a new choline ester found in wasp.
天然有機化合物討論会の論文
2002-09-01

51(P-13) 独居性カリバチ毒嚢に含まれる低分子量含窒素成分の構造解析(ポスター発表の部)

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