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Precise 1H- and 13C-NMR reassignment of dehydrocrebanine by 10-mg INADEQUATE and in silico analysis: With an alert for its toxicity
Tetrahedron ( IF 2.1 ) Pub Date : 2020-05-30 , DOI: 10.1016/j.tet.2020.131310
Chotika Phupong , Masahiko Suenaga , Phuangthip Bhoopong , Warangkana Chunglok , Gunlanan Jaritngam , Milandip Karak , Keiichi Yoshida , Worrapong Phupong , Kohei Torikai

During our continuous investigation on a Thai traditional medicinal plant, Stephania venosa Spreng, an alkaloid that seemed to be O-methyldehydrobulbocapnine (MDB) or dehydrocrebanine (DC), had been isolated. However, none of the previously reported 1H- and 13C-NMR data for MDB and DC matched our charts. Thus, we herein report the unambiguous determination of the alkaloid structure as DC via a successful INADEQUATE experiment using 10 mg of the unenriched natural specimen as well as an in silico estimation. Furthermore, our biological assay revealed that both the dichloromethane extract of S. venosa and the isolated DC show cytotoxicity to murine macrophage cells, which should be alerted to a folk doctor community that are using S. venosa to treat patients.



中文翻译:

用10 mg INADEQUATE和计算机分析法对脱氢克里班宁进行精确的1 H和13 C-NMR重分配:对其毒性有警惕

在我们对泰国传统药用植物进行连续调查的过程中,分离出了Stephania venosa Spreng,一种似乎是O-甲基脱氢球蛋白(MDB)或脱氢克里班宁(DC)的生物碱。但是,先前报告的MDB和DC的1 H和13 C-NMR数据均未与我们的图表匹配。因此,我们通过成功的INADEQUATE实验(使用10 mg未富集的自然标本)以及计算机估算,明确报告了将生物碱结构确定为DC 。此外,我们的生物学分析表明,两种葡萄叶提取物都存在分离出的DC对鼠巨噬细胞具有细胞毒性,应提醒正在使用S. venosa治疗患者的民间医生社区。

更新日期:2020-05-30
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