重水素化エボジアミンの合成とLC-MS/MSによるエボジアミン定量への応用

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  • Synthesis of deuterated evodiamine and its application for determination of evodiamine by LC-MS/MS

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LC-MS/MS 測定において安定同位体試料を内部標準物質に用いることは分析精度の向上に非常に効果的である. しかし, 分析対象の安定同位体試料が存在していない, あるいは非常に高価であることが多く,これらの点を克服することで更なる高感度分析が期待できる.本研究では,近年抗肥満剤として注目されるエボジアミン(ED)の重水素化を, 白金炭素 (Pt/C)を重水中水素雰囲気下で用いる芳香環の H-D 交換反応により行った. また,得られた重水素化物を LC-MS/MS による ED の定量分析に応用し,生物試料中の ED を精度よく高感度に分析できることを明らかとした.

Stable isotopes are useful as internal standards for quantification of compounds in biological samples by LC-MS/MS. However, those are very expensive and not commercially available for many substances such as natural products. Recently H-D exchange reaction on aromatic rings was developed with Pt/C catalyst in D2O under H2 atmosphere. We expected that this reaction would afford us a lot of stable isotopes with complex molecular structures. In this study, we synthesized stable isotopes of evodiamine by the H-D exchange reaction with Pt/C. The products contained many stable isotopes with a different number of deuterium and unreacted evodiamine. We applied this product for an internal standard to determine evodiamine in mouse serum by LC-MS/MS. Consequently, deuterated evodiamine contributed to enhancing sensitivity and reliability in the quantification of evodiamine by LC-MS/MS.

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