Cycloartane-type triterpenoids and steroids from Trichilia connaroides and their multidrug resistance reversal activities

Sibei Wang; Zhaoyu Shi; Han Zhang; Jiantong Hou; Dongho Lee; Jing Xu; Yuanqiang Guo

doi:10.1016/j.phytochem.2023.113867

Cycloartane-type triterpenoids and steroids from Trichilia connaroides and their multidrug resistance reversal activities

Phytochemistry. 2023 Dec:216:113867. doi: 10.1016/j.phytochem.2023.113867. Epub 2023 Sep 26.

Authors

Sibei Wang¹, Zhaoyu Shi¹, Han Zhang¹, Jiantong Hou¹, Dongho Lee², Jing Xu³, Yuanqiang Guo⁴

Affiliations

¹ State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin, 300350, China.
² Department of Plant Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul, 02841, South Korea.
³ State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin, 300350, China; State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, People's Republic of China. Electronic address: xujing611@nankai.edu.cn.
⁴ State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin, 300350, China. Electronic address: victgyq@nankai.edu.cn.

PMID: 37757926
DOI: 10.1016/j.phytochem.2023.113867

Abstract

Four undescribed cycloartane-type triterpenoids (1-4) and seven undescribed steroids (6-12), along with five known analogues (5 and 13-16), were isolated from the leaves of Trichilia connaroides. Their structures were identified based on the NMR data and HRESIMS, and the absolute configurations were determined through single-crystal X-ray diffraction analysis, Mosher's method, and ECD calculations. The multidrug resistance (MDR) reversal activities of all the isolates were assessed, and compounds 10 and 11 showed significant activities to reverse the MDR of MCF-7/DOX cells with IC₅₀ values of 2.90 and 3.76 μM, respectively. These bioactive compounds may bring fresh insights into the research and development of MDR reversal agents.

Keywords: Cycloartane-type triterpenoids; Meliaceae; Multidrug resistance reversal activities; Steroids; Trichilia connaroides.

MeSH terms

Limonins* / chemistry
Meliaceae* / chemistry
Molecular Structure
Steroids / pharmacology
Triterpenes* / chemistry
Triterpenes* / pharmacology

Substances

cycloartane
Limonins
Triterpenes
Steroids