Rp 18 f254 0.25 mm

1 H and 13 C NMR spectra were recorded at 400 or 500 and 100 or 125 MHz in CDCl 3 or otherwise noted, on Bruker (Karlsruhe, Germany) and Varian (Palo Alto, CA, USA) instruments. The same solvent was also used as an internal standard. DEPT, COSY-45, HSQC, HMBC and experiments (Berger and Braun 2004) were performed using Bruker or Varian microprograms. ESI MS and LC/MS analyses were performed using the LC/MS TOF system AGILENT (Agilent Technologies, Milan, Italy) 6230B, HPLC 1260 Infinity. Analytical and preparative TLCs were carried out on silica gel (Kieselgel 60, F 254 , 0.25 and 0.5 mm respectively) or on reverse phase (RP-18 F 254 , 0.25 mm) plates (Merck, Darmstadt, Germany). The spots were visualized by exposure to UV radiation, or by spraying first with 10% H 2 SO 4 in MeOH, and then with 5% phosphomolybdic acid in EtOH, followed by heating at 110 C for 10 min. Column chromatography was performed using silica gel (Kieselgel 60, 0.063-0.200 mm) (Merck). The standard samples of tyrosol, p-hydroxybenzaldehyde, p-hydroxybenzoic acid and p-cresol were purchased from Sigma (Milan, Italy). A standard sample of nectriapyrone was obtained from purification of culture filtrates of a Bulgarian strain of Phomopsis foeniculi (syn Diaporthe angelicae) (Evidente et al. 2011 ).

General Experimental Procedures The NMR spectra were recorded on Bruker 250 MHz (DMX 250, Germany) and Varian 600 MHz (VNS 600, Australia) units. HR-FAB-MS spectra were recorded on a JEOL JMS-700 (Tokyo, Japan) mass spectrometer at the Daegu center of KBSI, and NCIRF at Seoul National University in Korea. Stationary phases for column chromatography (silica gel 60, 70-230 and 230-400 mesh, LiChroprep RP-18 gel, 40-63 µm, Sephadex LH-20) and TLC plates (silica-gel 60 F 254 and RP-18 F 254 , 0.25 mm) were purchased from Merck KGaA (Darmstadt, Germany). The NMR solvents, chloroform-d, pyridine-d 5 and methanol-d 4 , were purchased from Aldrich (St. Louis, MO, U.S.A.). Optical rotations were measured using a JASCO DIP-1000 (Tokyo, Japan), and ECD spectra were recorded using an Applied Photophysics Chirascan-Plus circular dichroism spectrometer (Leatherhead, Surrey, U.K.).
Plant Material Star anise (the fruit of Illicium verum HOOK. FIL., Illiciaceae) was purchased in November 2014 from Pungsan Pharm Co., in Ahndong, South Korea. Materials were confirmed taxonomically by Professor Gi-Hwan Bae, Chungnam National University, Daejeon, South Korea. A voucher specimen (YNIV-2015) was deposited at the College of Pharmacy, Yeungnam University, South Korea.