Antiviral and Antioxidant Components from the Fruits of Illicium verum Hook.f. (Chinese Star Anise)

Illicium verum Hook.f. (Chinese star anise), a known Chinese traditional spice, is commonly applied in Chinese cuisine and cooking in Southeast Asia. As a kind of medicinal and edible resource, the fruit of I. verum has attracted great attention for its chemical constituents and physiological activities. In this work, the phytochemical study of the fruits of I. verum led to the isolation and identification of 20 compounds, including 6 new lignans and phenylpropanoids (1-6) and 14 known ones (7-20). Their structures were characterized by extensive analysis of spectroscopic data (IR, UV, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), one-dimensional (1D) and two-dimensional (1D) NMR), electronic circular dichroism (ECD) calculation, and by comparison with literature data. Meanwhile, all compounds (1-20) were evaluated for their antiviral and antioxidant activities. Especially, compound 7 [(-)-bornyl p-coumarate] showed strong antiviral activities against influenza virus A/Puerto Rico/8/34 H1N1 (PR8) with an IC₅₀ value of 1.74 ± 0.47 μM, which is much better than those of Tamiflu (IC₅₀ = 10.01 ± 0.92 μM) and ribavirin (IC₅₀ = 10.76 ± 1.60 μM). The antiviral activity against PR8 of compound 7 was reported for the first time, which was sufficiently confirmed by cell counting kit 8 (CCK-8), cytopathic effect (CPE) reduction, and immunofluorescence assays. In this study, the discovery of antiviral and antioxidant components from the fruits of I. verum could benefit the further development and utilization of this plant.