Two new lignans from Anemone vitifolia Buch.-Ham. and their anti-inflammatory activity
Graphical abstract
Introduction
The genus Anemone (Ranunculaceae) consists of more than 150 species, which is mainly distributed in northwestern and southwestern China, Sikkim, Nepal, northern Burma, Bhutan and northern India (Bai et al., 2017a). Anemone vitifolia Buch.-Ham. is a common species with highly medicinal values. It is used to treat various human diseases such as enteritis, rheumatoid joint pain, and diarrhea in Chinese traditional medicine (Chen et al., 2017). Phytochemical studies revealed that Anemone species mainly contain triterpene saponins, lignans and lactones (Liu et al., 2020). Lignan has extensive physiological activities, which are associated with antibacterial and anti-inflammatory applications (Bai et al., 2017b; Ren et al., 2017; Woo et al., 2019; Yang et al., 2019). Simultaneously, it showed cytotoxic and antifungal activity (Liu et al., 2018; Sriphana et al., 2013). Studies also found that lignans show superoxide radical scavenging, antioxidant and antiestrogenic activities (Lee et al., 2009; Thongphasuk et al., 2004; Muhit et al., 2016). Accordingly, variety of bioactivities inspired researchers to explore other novel natural products in A. vitifolia.
Previous studies mainly investigated the n-butanol fraction of the plant extract and no new compounds were reported (Bai et al., 2017a, 2017b; Deng et al., 2019). However, the chemical principles of the ethyl acetate (EA) fraction remains to be investigated. In this study we report the isolation of two new tetrahydrofuranoid lignans named (+)-8′β,8α,9α-4′-hydroxy-3,3′,4,9-tetramethoxy-9,9′-epoxylignan (1) and (-)-8′β,8α,9β-4′-hydroxy-3,3′,4,9-tetramethoxy-9,9′-epoxylignan (2), and two known compounds including (7S,8S,8′R)-4,7-Dihydroxy-3,3′,4′-trimethoxyl-9-oxo dibenzylbutyrolactone lignan (3) (Yang et al., 2015), buplerol (4) (Estévez-Braun et al., 1996). Their structures are shown in Fig. 1. Under the guidance of looking for anti-inflammatory active lead drugs, all compounds isolated from the EA fraction were evaluated for their inhibitory activity on LPS-induced NO production in RAW264.7 cells.
Section snippets
Structural elucidation
Compound 1 was obtained as colourless gum with molecular formula of C22H28O6, according to its 13C NMR data and HR-ESI-MS at m/z 411.1786 [M + Na]+ (calcd 411.1778) with 9 indices of hydrogen deficiency. The IR spectral data indicated the presence of hydroxyl (3434 cm−1) and aromatic ring group (1640 and 1444 cm−1). Its 13C NMR and DEPT data exhibited 22 carbon resonances, including two aromatic rings, three methines, three methylenes, and four methoxys. In 1H NMR spectrum, three aromatic
General experimental procedures
The 1D and 2D NMR spectra were recorded on a Bruker AVANCE III-400 and III-600 NMR spectrometer with TMS as the internal standard (Bruker, Germany), respectively. HR-ESI-MS were performed on a Agilent 1290 UPLC/6540 Q-TOF spectrometer (Agilent Technologies, USA). Optical rotations were measured on an autopol v plus automatic polarimeter (Rudolph Research Analytical, USA). IR spectra were recorded on a Nicoiet Is10 (Thermo Fisher Scientific) with KBr pallets. Semi-preparative HPLC experiments
Conclusion
Two new lignans (1–2), together with two known lignans (3–4), were isolated from A. vitifolia with the great assistance of the HPLC instrument. The structures were identified based on extensive spectroscopic data analysis and comparison with reported data. All compounds were isolated from this plant for the first time. In vitro tests showed that all compounds exhibited promising anti-inflammatory activity.
Declaration of Competing Interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgements
This research was supported by the National Natural Science Foundation of China (Grant No. 21262048).
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