NMR-tracking for 15,16-seco-cycloartane triterpenes from Cimicifuga acerina

Liwu Lin; Haoran Zhou; Luan Wen; Abdulbaset Al-Romaima; Xingrong Peng; Minghua Qiu

doi:10.1016/j.phytochem.2023.113669

NMR-tracking for 15,16-seco-cycloartane triterpenes from Cimicifuga acerina

Phytochemistry. 2023 Jun:210:113669. doi: 10.1016/j.phytochem.2023.113669. Epub 2023 Apr 1.

Authors

Liwu Lin¹, Haoran Zhou¹, Luan Wen¹, Abdulbaset Al-Romaima¹, Xingrong Peng¹, Minghua Qiu²

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China; Yunnan Key Laboratory of Natural Medicinal Chemistry Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China; Yunnan Key Laboratory of Natural Medicinal Chemistry Chinese Academy of Sciences, Kunming 650201, People's Republic of China. Electronic address: mhchiu@mail.kib.ac.cn.

PMID: 37011706
DOI: 10.1016/j.phytochem.2023.113669

Abstract

Twelve undescribed 15,16-seco-cycloartane triterpenoids, 15,16-seco-cimiterpenes C-N, as well as five previously reported analogs were isolated by NMR-tracking methods from the rhizomes of Cimicifuga acerina (Sieb. et Zucc.) Tanaka. Among them, 15,16-seco-cimiterpenes C-N were the first 15,16-seco-cycloartane triterpenoids featuring acetal or hemiacetal structures at C-15. The chemical structures of 15,16-seco-cimiterpenes C-N were determined based on comprehensive spectroscopic analysis, chemical method, and comparison with the previous literature data. After that, all these compounds were evaluated for their lipid-lowering effects on 3T3-L1 adipocytes.15,16-seco-cimiterpene D was found to exhibit a comparable reducing lipid effect at the concentration of 50 μM, with an inhibition rate at 35.96%.

Keywords: 15,16-seco-cycloartane triterpenoids; 3T3-L1 adipocytes; Cimicifuga acerina; NMR-Tracking; Ranunculaceae.

MeSH terms

Actaea*
Cimicifuga* / chemistry
Lipids
Magnetic Resonance Spectroscopy
Molecular Structure
Triterpenes* / chemistry
Triterpenes* / pharmacology

Substances

cycloartane
Triterpenes
Lipids