Seladelicatulasine A-G, C27 steroidal glycosides with cholinesterase inhibitory activities from Selaginella delicatula

Cai-Ping Yao; Jing Li; Jian-Feng Liu; Zhen-Xing Zou; Feng-Hua Kang; Xiao-Min Li; Dai Li; Kang-Ping Xu; Ping-Sheng Xu; Gui-Shan Tan

doi:10.1016/j.phytochem.2020.112514

Seladelicatulasine A-G, C₂₇ steroidal glycosides with cholinesterase inhibitory activities from Selaginella delicatula

Phytochemistry. 2020 Dec:180:112514. doi: 10.1016/j.phytochem.2020.112514. Epub 2020 Sep 17.

Authors

Cai-Ping Yao¹, Jing Li², Jian-Feng Liu³, Zhen-Xing Zou⁴, Feng-Hua Kang⁴, Xiao-Min Li², Dai Li², Kang-Ping Xu⁴, Ping-Sheng Xu⁵, Gui-Shan Tan⁶

Affiliations

¹ Phase 1 Clinical Trial Center, Xiangya Hospital, Central South University, Changsha, 410008, PR China; The First Affiliated Hospital of Hunan University of Medicine, Huaihua, 418000, PR China.
² Phase 1 Clinical Trial Center, Xiangya Hospital, Central South University, Changsha, 410008, PR China.
³ The First Affiliated Hospital of Hunan University of Medicine, Huaihua, 418000, PR China.
⁴ Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, 410013, PR China.
⁵ Phase 1 Clinical Trial Center, Xiangya Hospital, Central South University, Changsha, 410008, PR China. Electronic address: xps201901@csu.edu.cn.
⁶ Phase 1 Clinical Trial Center, Xiangya Hospital, Central South University, Changsha, 410008, PR China; Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, 410013, PR China. Electronic address: tgs395@csu.edu.cn.

PMID: 32950771
DOI: 10.1016/j.phytochem.2020.112514

Abstract

Seven undescribed C₂₇ steroidal glycosides, Seladelicatulasine A-G, including six cholestanol glycosides and one spirostanol glycoside, were isolated from Selaginella delicatula. Their structures were elucidated by 1D/2D NMR spectra and HRESIMS analyses. The absolute configurations of the sugars were determined by enzymatic hydrolysis and GC/MS analyses. These cholestanol glycosides were isolated from the family Selaginellaceae for the first time. Seladelicatulasine F is characterized as a rare B-5,6-secosteroid. In addition, all the compounds were evaluated for their inhibitory activities against cholinesterase (AChE/BChE) and monoamine oxidase (MAO-A/MAO-B). These steroidal glycosides displayed selective inhibition activities on cholinesterase. Seladelicatulasine A, B and E inhibited the AChE activity with IC₅₀ values of 0.31, 0.09, and 0.04 μM, respectively. Seladelicatulasine A and F showed the strongest inhibition activity on BChE with IC₅₀ values of 0.37 and 0.65 μM, respectively.

Keywords: Cholinesterase; Monoamine oxidase; Selaginella delicatula; Selaginellaceae; Steroidal glycosides.

MeSH terms

Cholinesterase Inhibitors / pharmacology
Cholinesterases
Glycosides / pharmacology
Molecular Structure
Monoamine Oxidase
Selaginellaceae*

Substances

Cholinesterase Inhibitors
Glycosides
Monoamine Oxidase
Cholinesterases