Structure and bioactivity of cholestane glycosides from the bulbs of Ornithogalum saundersiae Baker

Qing-Wei Chen; Xu Zhang; Ting Gong; Wan Gao; Shuai Yuan; Pei-Cheng Zhang; Jian-Qiang Kong

doi:10.1016/j.phytochem.2019.05.016

Structure and bioactivity of cholestane glycosides from the bulbs of Ornithogalum saundersiae Baker

Phytochemistry. 2019 Aug:164:206-214. doi: 10.1016/j.phytochem.2019.05.016. Epub 2019 Jun 6.

Authors

Qing-Wei Chen¹, Xu Zhang¹, Ting Gong¹, Wan Gao¹, Shuai Yuan¹, Pei-Cheng Zhang², Jian-Qiang Kong³

Affiliations

¹ Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, (State Key Laboratory of Bioactive Substance and Function of Natural Medicines & NHC Key Laboratory of Biosynthesis of Natural Products), Beijing, 100050, China.
² Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, (State Key Laboratory of Bioactive Substance and Function of Natural Medicines & NHC Key Laboratory of Biosynthesis of Natural Products), Beijing, 100050, China. Electronic address: pczhang@imm.ac.cn.
³ Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, (State Key Laboratory of Bioactive Substance and Function of Natural Medicines & NHC Key Laboratory of Biosynthesis of Natural Products), Beijing, 100050, China. Electronic address: jianqiangk@imm.ac.cn.

PMID: 31177053
DOI: 10.1016/j.phytochem.2019.05.016

Abstract

Eight undescribed cholestane glycosides named osaundersioside A-H, along with three previously known compounds named osaundersioside I-K were isolated from Ornithogalum saundersiae Baker bulbs (Asparagaceae). Their structures were elucidated by extensive spectroscopic analysis and chemical methods. All isolates were evaluated for their cytotoxic activity and inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production. Osaundersioside C was thus determined to exhibit specific cytotoxicity towards MCF-7 cell line with an IC₅₀ value of 0.20 μM, Osaundersioside H exhibited inhibitory effect on NO production in macrophages at the concentration of 10^-5 M, with inhibition rate of 56.81%.

Keywords: Acylated steroidal glycoside; Asparagaceae; Cholestane glycosides; Cytotoxicity; Ornithogalum saundersiae baker.

MeSH terms

Animals
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Asparagaceae / chemistry*
Cell Proliferation / drug effects
Cholestanes / chemistry
Cholestanes / isolation & purification
Cholestanes / pharmacology*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Glycosides / chemistry
Glycosides / isolation & purification
Glycosides / pharmacology*
Humans
Lipopolysaccharides / antagonists & inhibitors
Lipopolysaccharides / pharmacology
MCF-7 Cells
Macrophages / drug effects
Macrophages / metabolism
Mice
Molecular Structure
Nitric Oxide / antagonists & inhibitors
Nitric Oxide / biosynthesis
Plant Bark / chemistry
Plant Roots / chemistry
Structure-Activity Relationship

Substances

Anti-Inflammatory Agents, Non-Steroidal
Antineoplastic Agents, Phytogenic
Cholestanes
Glycosides
Lipopolysaccharides
Nitric Oxide