Enantiomeric N-acetyldopamine trimers from Cicadae Periostracum and their absolute configurations

Fang Mei; Jinchun Nie; Yan Wen; Zhenwei Li; Daidi Zhang; Li-She Gan; Wei Li; De-An Guo

doi:10.1016/j.phytochem.2023.113780

Enantiomeric N-acetyldopamine trimers from Cicadae Periostracum and their absolute configurations

Phytochemistry. 2023 Sep:213:113780. doi: 10.1016/j.phytochem.2023.113780. Epub 2023 Jun 26.

Authors

Fang Mei¹, Jinchun Nie², Yan Wen³, Zhenwei Li⁴, Daidi Zhang⁴, Li-She Gan³, Wei Li⁵, De-An Guo⁶

Affiliations

¹ School of Pharmacy, Zunyi Medical University, Zunyi, 563006, People's Republic of China; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China.
² Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China; School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, People's Republic of China.
³ School of Biotechnology and Health Sciences, International Healthcare Innovation Institute, Wuyi University, Jiangmen, 529020, People's Republic of China.
⁴ Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China.
⁵ School of Pharmacy, Zunyi Medical University, Zunyi, 563006, People's Republic of China; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China; School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, People's Republic of China. Electronic address: liwei1@simm.ac.cn.
⁶ School of Pharmacy, Zunyi Medical University, Zunyi, 563006, People's Republic of China; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China; School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, People's Republic of China. Electronic address: daguo@simm.ac.cn.

PMID: 37379971
DOI: 10.1016/j.phytochem.2023.113780

Abstract

Six previously undescribed N-acetyldopamine (NADA) trimmer racemates, percicamides A-F (1-6), were isolated from a 70% ethanol extract of Cicadae Periostracum. Subsequent chiral-phase separation afforded six pairs of enantiomers, (+)- and (-)-percicamides A-F (1a/1b-6a/6b). Their structures including absolute configurations were elucidated by combined extensive spectroscopic data and quantum chemical calculations. Compounds 1-6 represent the first examples of NADA trimmers with a cis-relationship of H-7'/H-8' or H-7''/H-8''. Bioassays verified that all isolated compounds showed weak inhibitory effects on nitric oxide production in RAW 264.7 cells.

Keywords: Cicadae Periostracum; Cryptotympana pustulata; N-acetyldopamine trimmer; Quantum chemical calculation.

MeSH terms

1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine
Dopamine / pharmacology
Drugs, Chinese Herbal* / chemistry
Molecular Structure
Nitric Oxide

Substances

N-acetyldopamine
1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine
Drugs, Chinese Herbal
Nitric Oxide
Dopamine