Abstract
Eupatorium japonicum Thunb. of the plant family Asteraceae is a popular traditional herb in Vietnam. However, its chemical constituents as well as bioactive principles have not been investigated yet. We investigated the phytochemistry of E. japonicum in Vietnam and isolated seventeen compounds (1–17) including phytosterols, terpenoids, phenolic acids, flavonoids, fatty alcohols, and fatty acids. They were structurally determined by MS and NMR analysis. Except for compounds 6 and 12, all the other compounds were identified for the first time from E. japonicum. Since many sesquiterpene lactones with α-methylene γ-lactone ring are reported as anti-inflammatory and anticancer agents, eupatoriopicrin (10), 1-hydroxy-8-(4,5-dihydroxytigloyloxy)eudesma-4(15),11(13)-dien-6,12-olide (11) were selected among the isolates for biological assays. Compound 10 was identified as the main bioactive sesquiterpene lactone of E. japonicum showing its potent anti-inflammatory and cytotoxic activity through inhibiting NO production and the growth of HepG2 and MCF-7 human cancer cell lines. For the first time, eupatoriopicrin (10) was demonstrated to strongly inhibit NTERA-2 human cancer stem cell (CSC) line in vitro. It is noticeable that the cytotoxicity of eupatoriopicrin against NTERA-2 cells is mediated by its apoptosis-inducing capability of 10 as demonstrated by the results of Hoechst 33342 staining, flow cytometry apoptosis analysis, and caspase-3 activity assays. The biological activities of the main bioactive constituents 1–7, 10, 12, and 15 supported the reported anti-inflammatory and anticancer properties of extracts from E. japonicum.
Highlights
In Vietnam, traditional herbal remedies are considered complementary or alternative medicines in the healthcare system
Since biological activities are the links between medicinal plants and their pharmacology and medicinal uses, we have investigated the chemical constituents and biological activities of common Eupatorium species used in Vietnamese traditional medicine such as E. fortunei [1] and E. triplinerve [2]
Electron-spray ionization-mass spectrometry (ESI-MS) spectra were measured on an Agilent 1100 LC-MSD-Trap-SL system (Agilent Technologies, USA) or ermo Fisher Scientific LTQ Orbitrap XLMS mass spectrometer in CH3OH solution. 1HNMR (SF 500.20 MHz), 13C-NMR (SF 125.13 MHz), and DEPT spectra were recorded in CDCl3 or CD3OD using a Bruker Avance 500 NMR spectrometer. e chemical shifts are expressed in ppm relative to tetramethylsilane (TMS) as an internal standard
Summary
In Vietnam, traditional herbal remedies are considered complementary or alternative medicines in the healthcare system. Many herbal remedies are clinically used without any scientific evidence of their efficacy and safety. Since biological activities are the links between medicinal plants and their pharmacology and medicinal uses, we have investigated the chemical constituents and biological activities of common Eupatorium species used in Vietnamese traditional medicine such as E. fortunei [1] and E. triplinerve [2]. Belonging to the family Asteraceae has been recorded as a medicinal plant in Vietnam, Japan, and China. In Vietnam, the species is known under the name “Son lan” or “Yen bach Nhat” (ydvn.net) and distributed in the mountainous Sapa district of the Northwestern Lao Cai province. Is perennial herb grows 1–2 m tall, blooms from August to September, and fruits from September to Evidence-Based Complementary and Alternative Medicine In Vietnam, the species is known under the name “Son lan” or “Yen bach Nhat” (ydvn.net) and distributed in the mountainous Sapa district of the Northwestern Lao Cai province. is perennial herb grows 1–2 m tall, blooms from August to September, and fruits from September to Evidence-Based Complementary and Alternative Medicine
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