Steroid glycosides from the roots of Marsdenia tenacissima

Xiu-Qing Song; Lin-Lin Tian; Tao Ye; Hu Liu; Hua Zhang

doi:10.1016/j.phytochem.2022.113506

Steroid glycosides from the roots of Marsdenia tenacissima

Phytochemistry. 2023 Jan:205:113506. doi: 10.1016/j.phytochem.2022.113506. Epub 2022 Nov 5.

Authors

Xiu-Qing Song¹, Lin-Lin Tian², Tao Ye², Hu Liu², Hua Zhang³

Affiliations

¹ School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250022, China; School of Biological Science and Technology, University of Jinan, Jinan, 250022, China.
² School of Biological Science and Technology, University of Jinan, Jinan, 250022, China.
³ School of Biological Science and Technology, University of Jinan, Jinan, 250022, China. Electronic address: bio_zhangh@ujn.edu.cn.

PMID: 36347308
DOI: 10.1016/j.phytochem.2022.113506

Abstract

Eleven undescribed glycosylated C₂₁ steroids and nine known homologous glycosides with diverse acyl substituents, as well as their common steroid aglycone, have been obtained from the roots of Marsdenia tenacissima. Their structures were elucidated mainly by comprehensive spectroscopic analyses and comparison with previously reported analogues, with the absolute configuration assignment being supported by chemical degradation, X-ray crystallography and ECD exciton chirality method. Among them, two pairs of regioisomers were found to exist as inseparable equilibrium mixtures due to an interesting intramolecular transesterification, and nicotinoyl substitution was first reported for metabolites from the title plant. Screening of these compounds in a panel of bioassays revealed that two glycosides displayed mild inhibition against butyrylcholinesterase.

Keywords: Apocynaceae; Butyrylcholinesterase; Intramolecular transesterification; Marsdenia tenacissima; Steroid glycosides.

MeSH terms

Butyrylcholinesterase
Marsdenia*
Steroids / pharmacology

Substances

Butyrylcholinesterase
Steroids