Spirostanol and sesquiterpenoid glycosides from the rhizomes of Trillium tschonoskii

Dan Li; Huan Yan; Jie Wang; Qian Yu; Wei Ni; Lin-Kun An; Xu-Jie Qin; Hai-Yang Liu

doi:10.1016/j.steroids.2019.108569

Spirostanol and sesquiterpenoid glycosides from the rhizomes of Trillium tschonoskii

Steroids. 2020 Mar:155:108569. doi: 10.1016/j.steroids.2019.108569. Epub 2019 Dec 30.

Authors

Dan Li¹, Huan Yan², Jie Wang¹, Qian Yu³, Wei Ni², Lin-Kun An³, Xu-Jie Qin⁴, Hai-Yang Liu⁵

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100049, China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
³ Institute of Medicinal Chemistry and Chemical Biology, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. Electronic address: qinxujie@mail.kib.ac.cn.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. Electronic address: haiyangliu@mail.kib.ac.cn.

PMID: 31899263
DOI: 10.1016/j.steroids.2019.108569

Abstract

Three new spirostanol glycosides, trilliumosides K-M (1-3), one new sesquiterpenoid glycoside, tritschsesuquiside A (4), along with three known analogues (5-7) were obtained from the rhizomes of Trillium tschonoskii. The structures of new glycosides were elucidated by spectroscopic analyses (HRMS and NMR) and chemical methods. Glycosides 5-7 displayed cytotoxicities against five human cancer cell lines with IC₅₀ values ranging from 10.5 ± 1.0 to 1.0 ± 0.2 μM, with 7 being the most cytotoxic compound with IC₅₀ values of 1.0 ± 0.2, 2.2 ± 1.2, and 3.4 ± 0.4 μM against Huh7, CCRF-CEM, and HeLa cell lines, respectively. The flow cytometric results revealed that both 5 and 6 could induce apoptosis of HCT116 and Huh7 cells.

Keywords: Apoptosis; Cytotoxicity; Sesquiterpenoid glycoside; Spirostanol glycosides; Trillium tschonoskii.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Glycosides / chemistry
Glycosides / isolation & purification
Glycosides / pharmacology*
HCT116 Cells
HeLa Cells
Humans
Models, Molecular
Molecular Conformation
Rhizome / chemistry*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Spirostans / chemistry
Spirostans / isolation & purification
Spirostans / pharmacology*
Structure-Activity Relationship
Trillium / chemistry*
Tumor Cells, Cultured

Substances

Antineoplastic Agents, Phytogenic
Glycosides
Sesquiterpenes
Spirostans