Elsevier

Phytochemistry Letters

Volume 38, August 2020, Pages 133-135
Phytochemistry Letters

Two new lignans from Anemone vitifolia Buch.-Ham. and their anti-inflammatory activity

https://doi.org/10.1016/j.phytol.2020.06.001Get rights and content

Highlights

  • Two new lignans were isolated from whole herb of Anemone vitifolia Buch.-Ham.

  • Chemical constituent of Anemone vitifolia Buch.-Ham. is rarely investigated.

  • Their anti-inflammtory activity was also evaluated.

Abstract

Two new lignans (12), together with two known lignans (34), were isolated from the whole herb of Anemone vitifolia. The structures were identified based on extensive spectroscopic data analysis and comparison with reported data. All compounds of this plant were reported for the first time. In vitro test, all compounds were evaluated for their anti-inflammatory activity via calculating the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced mouse macrophage cells-RAW 264.7.

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 (12), together with two known lignans (34), 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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