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从华钩吻茎枝中分离得到的单萜吲哚生物碱。

Monoterpenoid indole alkaloids isolated from the stems and twigs of Strychnos cathayensis.

作者信息

Pan Qi-Ming, Li Yu-Huan, Zhang Jian-Jun, Li Yong, Ma Shuang-Gang, Yu Shi-Shan

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, People's Republic of China.

Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, People's Republic of China.

出版信息

Phytochemistry. 2022 Nov;203:113353. doi: 10.1016/j.phytochem.2022.113353. Epub 2022 Aug 23.

Abstract

Seven undescribed monoterpenoid indole alkaloids, two N(4)-chloromethylation artifacts, and 10 known alkaloids were isolated from the stems and twigs of Strychnos cathayensis. The corresponding structures were elucidated via spectroscopic data interpretation and electronic circular dichroism. The absolute configuration of (17S)-12-hydroxy-11-methoxydiaboline, the major anomer of 12-hydroxy-11-methoxydiaboline, was characterized by X-ray diffraction analysis for the first time. At an intraperitoneal dose of 30 mg/kg, 12-hydroxy-11-methoxy-N(4)-chloromethyldiaboline and (-)-macusine A exhibited potential analgesic effects with prolongation rates of 99% and 47% for the latency time of hind-paw licking, respectively, compared to the blank control. 12-Hydroxy-11-methoxydiaboline, 12-hydroxy-11-methoxydiaboline N(4)-oxide, retuline N-oxide, and (-)-vincosamide exhibited antiviral activity against Coxsackie virus B3 (CVB3) with IC values of 33.33 μM.

摘要

从华钩吻的茎和嫩枝中分离出7种未描述的单萜吲哚生物碱、2种N(4)-氯甲基化产物和10种已知生物碱。通过光谱数据解释和电子圆二色性阐明了相应的结构。首次通过X射线衍射分析确定了12-羟基-11-甲氧基二氢番木鳖碱的主要端基异构体(17S)-12-羟基-11-甲氧基二氢番木鳖碱的绝对构型。腹腔注射剂量为30 mg/kg时,与空白对照组相比,12-羟基-11-甲氧基-N(4)-氯甲基二氢番木鳖碱和(-)-马库新A分别对后爪舔舐潜伏期的延长率为99%和47%,表现出潜在的镇痛作用。12-羟基-11-甲氧基二氢番木鳖碱、12-羟基-11-甲氧基二氢番木鳖碱N(4)-氧化物、瑞吐灵N-氧化物和(-)-长春酰胺对柯萨奇病毒B3(CVB3)具有抗病毒活性,IC值为33.33 μM。

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