Neritriterpenols A-G, euphane and tirucallane triterpenes from Euphorbia neriifolia L. and their bioactivity

Stephen S Chang; Hung-Tse Huang; Yu-Chi Lin; Chih-Hua Chao; Geng-You Liao; Zhi-Hu Lin; Hui-Chi Huang; Jenny Chun-Ling Kuo; Chia-Ching Liaw; Chen-Jei Tai; Yao-Haur Kuo

doi:10.1016/j.phytochem.2022.113199

Neritriterpenols A-G, euphane and tirucallane triterpenes from Euphorbia neriifolia L. and their bioactivity

Phytochemistry. 2022 Jul:199:113199. doi: 10.1016/j.phytochem.2022.113199. Epub 2022 Apr 12.

Authors

Affiliations

¹ Division of Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, 112026, Taiwan; Ph.D. Program in Clinical Drug Development of Herbal Medicine, College of Pharmacy, Taipei Medical University, Taipei, 110301, Taiwan.
² Division of Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, 112026, Taiwan.
³ School of Pharmacy, China Medical University, Taichung, 406040, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung, 404332, Taiwan.
⁴ Institute of Physiology, School of Medicine, National Yang Ming Chiao Tung University, Taipei, 112304, Taiwan.
⁵ Division of Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, 112026, Taiwan; Institute of Traditional Medicine, National Yang Ming Chiao Tung University, Taipei, 112304, Taiwan.
⁶ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung, 404333, Taiwan; Master Program for Food and Drug Safety, China Medical University, Taichung, 406040, Taiwan.
⁷ Division of Chinese Internal Medicine, Center for Traditional Chinese Medicine, Chang Gung Memorial Hospital, Tao-Yuan, 333, Taiwan.
⁸ Division of Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, 112026, Taiwan; Department of Biochemical Science and Technology, National Chiayi University, Chiayi, 600355, Taiwan. Electronic address: [email protected].
⁹ Ph.D. Program in Clinical Drug Development of Herbal Medicine, College of Pharmacy, Taipei Medical University, Taipei, 110301, Taiwan; Department of Chinese Medicine, Taipei Medical University Hospital, Taipei, 110301, Taiwan; Traditional Herbal Medicine Research Center, Taipei Medical University Hospital, Taipei, 110301, Taiwan. Electronic address: [email protected].
¹⁰ Division of Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, 112026, Taiwan; Ph.D. Program in Clinical Drug Development of Herbal Medicine, College of Pharmacy, Taipei Medical University, Taipei, 110301, Taiwan; Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, 404333, Taiwan. Electronic address: [email protected].

PMID: 35427651
DOI: 10.1016/j.phytochem.2022.113199

Abstract

Euphorbia neriifolia L. is widely distributed in India, Thailand, and China and has been used to treat diseases such as rotten sores and asthma as well as for its antidiabetic and anticancer effects. In this study, seven undescribed triterpenes, including six euphanes, neritriterpenols A-B and D-G, and a tirucallane, neritriterpenol C, together with four known triterpenes, were isolated from ethanolic extracts of E. neriifolia stems. Their structures with absolute configurations were determined through detailed spectroscopic data, including 1D and 2D NMR data analyses, single-crystal X-ray diffraction analysis, ECD spectra, and DP4+ NMR data calculations as well as Mo₂(OAc)₄-induced ECD analysis. Furthermore, preliminarily evaluation of the anti-inflammatory and anti-proliferative effects of the isolated triterpenes leads to the structure-activity relationship (SAR) studies implying that the unsaturated functional group at the end of the C17 side chain on euphane-type triterpenes may be correlated with the increase of anti-inflammatory and anti-proliferative activities.

Keywords: Anti-inflammation; Anti-proliferation; Euphanes; Euphorbia neriifolia; Euphorbiaceae; Neritriterpenols; Tirucallane.

MeSH terms

Euphorbia* / chemistry
Molecular Structure
Structure-Activity Relationship
Triterpenes* / chemistry
Triterpenes* / pharmacology

Substances

Triterpenes
tirucallane