Bioactive prenylated c₆–c₃ derivatives from the roots of Illicium brevistylum

Abstract

Three new prenylated C₆–C₃ compounds (1–3), together with two known prenylated C₆–C₃ compounds (4–5) and one known C₆–C₃ derivative (6), were isolated from the roots of Illicium brevistylum A. C. Smith. The structures of 1–3 were elucidated by spectroscopic methods including 1D and 2D NMR, HRESIMS, CD experiments and ECD calculations. The structure of illibrefunone A (1) was confirmed by single-crystal X-ray diffraction analysis. All compounds were evaluated in terms of their anti-inflammatory potential on nitric oxide (NO) generation in lipopolysaccharide-stimulated murine RAW264.7 macrophages and murine BV2 microglial cells, antiviral activity against Coxsackievirus B3 (CVB3) and influenza virus A/Hanfang/359/95 (H3N2). Compounds 3 and 4 exhibited potent inhibitory effects on the production of NO in RAW 264.7 cells with IC₅₀ values of 20.57 and 12.87 μM respectively, which were greater than those of dexamethasone (positive control). Compounds 1 and 4–6 exhibited weak activity against Coxsackievirus B3, with IC₅₀ values ranging from 25.87 to 33.33 μM.

Keywords:

• Illicium brevistylum
• roots
• prenylated C₆–C₃ derivatives
• anti-inflammatory activity
• anti-Coxsackievirus B3
• anti-influenza virus A

Acknowledgements

We would like to thank Prof. Li Li of Department of Synthetic Medicinal Chemistry of our institute for ECD calculation. We are grateful to the Department of Instrumental Analysis of our institute for the acquisition of the IR, NMR, and MS spectra, and to the State Key Laboratory of Natural and Biomimetic Drugs of Peking University for the X-ray crystallographic measurements and analyses.

Disclosure statement

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.

Additional information

Funding

This work was financially supported by grants from the National Natural Science Foundation of China (Nos: 22177135 and 82073863) and CAMS Innovation Fund for Medical Sciences (CIFMS) (2021-I2M-1-016).