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来自越南苦参根和根茎的不寻常 N-吡啶基氨基酸型生物碱。

Unusual N-pyridinium amino acid-type alkaloids from roots and rhizomes of Sophora tonkinensis Gagnep.

机构信息

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.

出版信息

Fitoterapia. 2023 Mar;165:105388. doi: 10.1016/j.fitote.2022.105388. Epub 2022 Dec 7.

Abstract

Two previously undescribed amino acid-type alkaloids with unusual N-pyridinium cation (1-2) and six known alkaloids (3-8), were isolated from the roots and rhizomes of Sophora tonkinensis Gapnea. Their structures were characterized by UV, IR, NMR, and HRESIMS spectroscopic data. The absolute configurations of compounds 1 and 2 were established through comparison of their experimental ECD spectra to the theoretical spectra of 2 calculated by TDDFT method. The plausible biosynthetic pathway of pyridinium was also proposed. Moreover, compound 4 exhibited weak XOD inhibitory activity with the inhibition rate of 65.8% at concentration of 10 μM.

摘要

从越南苦参的根和根茎中分离得到了两种以前未描述的具有不寻常 N-吡啶阳离子的氨基酸型生物碱(1-2)和六种已知生物碱(3-8)。通过 UV、IR、NMR 和 HRESIMS 光谱数据对它们的结构进行了表征。通过比较实验 ECD 光谱与通过 TDDFT 方法计算的 2 的理论光谱,确定了化合物 1 和 2 的绝对构型。还提出了吡啶阳离子的可能生物合成途径。此外,化合物 4 在 10 μM 浓度下对 XOD 的抑制活性较弱,抑制率为 65.8%。

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