Cytotoxic steroidal saponins from Trillium kamtschaticum

Xu-Jie Qin; Yong-Ai Si; Yu Chen; Hui Liu; Wei Ni; Huan Yan; Tong Shu; Yun-Heng Ji; Hai-Yang Liu

doi:10.1016/j.bmcl.2017.04.057

Cytotoxic steroidal saponins from Trillium kamtschaticum

Bioorg Med Chem Lett. 2017 Jun 1;27(11):2267-2273. doi: 10.1016/j.bmcl.2017.04.057. Epub 2017 Apr 19.

Authors

Xu-Jie Qin¹, Yong-Ai Si¹, Yu Chen¹, Hui Liu², Wei Ni¹, Huan Yan¹, Tong Shu², Yun-Heng Ji³, Hai-Yang Liu⁴

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; Yunnan Key Laboratory of Natural Medicinal Chemistry, 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; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
³ Key Laboratory of Plant Biodiversity and Biogeography of East Asia, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
⁴ 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; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, People's Republic of China. Electronic address: haiyangliu@mail.kib.ac.cn.

PMID: 28454671
DOI: 10.1016/j.bmcl.2017.04.057

Abstract

Eight new steroidal saponins, trillikamtosides K-R (1-8), along with three known analogues, were isolated from the whole plants of Trillium kamtschaticum. Their structures were unambiguously established by interpretation of spectroscopic data (MS and NMR) and chemical methods. Compound 1 had a rare aglycone featuring a skeleton of 16-oxaandrost-5-en-3-ol-17-one, which was reported for the first time. The isolated saponins were tested for cytotoxicities against HCT116 cells, and trillikamtoside R (8) was found to show the most cytotoxic effect with an IC₅₀ value of 4.92μM.

Keywords: Cytotoxicity; Liliaceae; Steroidal saponins; Trillium kamtschaticum.

Publication types

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

MeSH terms

Carbon-13 Magnetic Resonance Spectroscopy
HCT116 Cells
Humans
Inhibitory Concentration 50
Proton Magnetic Resonance Spectroscopy
Saponins / isolation & purification*
Saponins / pharmacology
Spectrometry, Mass, Electrospray Ionization
Steroids / isolation & purification
Steroids / pharmacology
Trillium / chemistry*

Substances

Saponins
Steroids