Asponchimides A−E: new enantiomeric N-acetyldopamine trimers from Aspongopus chinensis

作     者：NIE Jinchun MEI Fang ZHENG Yueyuan WEN Qiuyi LI Zhenwei ZHANG Daidi LI Wei GUO Dean NIE Jinchun;MEI Fang;ZHENG Yueyuan;WEN Qiuyi;LI Zhenwei;ZHANG Daidi;LI Wei;GUO Dean

作者机构：School of Pharmaceutical SciencesSouthern Medical UniversityGuangzhou 510515China Zhongshan Institute for Drug DiscoveryShanghai Institute of Materia MedicaChinese Academy of SciencesZhongshan 528400China 

出 版 物：《Chinese Journal of Natural Medicines》 (中国天然药物（英文版）)

年 卷 期：2023年第21卷第11期

页      面：859-867页

核心收录：

学科分类：1008[医学-中药学(可授医学、理学学位)] 1006[医学-中西医结合] 100602[医学-中西医结合临床] 10[医学] 

基　　金：supported by the Key Program of National Natural Science Foundation of China(NO.82130111) High-level Innovative Research Institute of Department of Science and Technology of Guangdong Province(No.2021B0909050003) High-level New R&D Institute of Department of Science and Technology of Guangdong Province(No.2019B090904008) 

主　　题：Aspongopus chinensis N-acetyldopamine trimer ECD calculations NO inhibitory activity 

摘      要：Five new racemic N-acetyldopamine (NADA) trimers, asponchimides A−E ( 1 − 5 ), were isolated from Aspongopus chinensis, a prominent traditional Chinese medicinal insect employed for alleviating pain, treating indigestion, and addressing kidney ailments. Compounds 1 − 5 were successfully resolved by chiral high-performance liquid chromatography (HPLC), yielding five pairs of enantiomers: (+)- and (−)-asponchimides A−E ( 1a / 1b − 5a / 5b ). Their structural identities were discerned by extensive spectroscopic analyses, including high-resolution mass spectrometry (HRMS), ultraviolet-visible (UV-Vis) spectroscopy, infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR), and their absolute configurations were determined by electronic circular dichroism (ECD) calculations. Compounds 1 − 5 are pioneering instances of NADA trimers featuring a Δ7 double bond. When subjected to a series of bioassays, a majority of the compounds exhibited weak inhibitory activity against nitric oxide (NO) production in LPS-induced RAW 264.7 cells.