Geranyl phenyl ethers from Illicium micranthum and their anti-HBV activity

Fourteen new geranyl phenyl ethers ( 1 – 14 ) along with three known compounds ( 15 – 17 ) were isolated from Illicium micranthum, and their structures were elucidated by comprehensive spectroscopic methods. Illimicranins A–H ( 1 – 8 ) were characterized as geranyl vanillin ethers, while 9 and 10 were dimethyl acetal derivatives. Illimicranins I and J ( 11 and 12 ) were rare geranyl isoeugenol ethers. Illimicranins K and L ( 13 and 14 ) represented the first example of geranyl guaiacylacetone ether and geranyl zingerone ether, respectively. Compounds 1 , 2 and 15 exhibited anti-HBV (hepatitis B virus) activity against HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis B e antigen) secretion, and HBV DNA replication.