Asponchimides A-E: new enantiomeric N-acetyldopamine trimers from Aspongopus chinensis.
10.1016/S1875-5364(23)60483-2
- Author:
Jinchun NIE
1
,
2
;
Fang MEI
3
;
Yueyuan ZHENG
3
;
Qiuyi WEN
3
;
Zhenwei LI
3
;
Daidi ZHANG
3
;
Wei LI
1
,
4
;
Dean GUO
1
,
5
Author Information
1. School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China
2. Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China.
3. Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China.
4. Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China. Electronic address: liwei1@simm.ac.cn.
5. Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China. Electronic address: daguo@simm.ac.cn.
- Publication Type:Journal Article
- Keywords:
Aspongopus chinensis;
ECD calculations;
N-acetyldopamine trimer;
NO inhibitory activity
- MeSH:
Molecular Structure;
Magnetic Resonance Spectroscopy;
Dopamine;
Nitric Oxide
- From:
Chinese Journal of Natural Medicines (English Ed.)
2023;21(11):859-867
- CountryChina
- Language:English
-
Abstract:
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.
