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.