Fissistonones A and B: Two Phenylpropanoyl Prenylated Naphthoquinones with Rearranged Carbon Skeletons from Fissistigma oldhamii

Abstract

Fissistonones A and B (1 and 2), two naphthoquinone derivatives with rearranged carbon skeletons, were obtained from the leaves of Fissistigma oldhamii. Structurally, compounds 1 and 2 featured an unprecedented phenylpropanoyl benzobicyclo[3.3.1]nonene core, which could be biosynthetically traced back to a planar naphthoquinone precursor via a cascade of intramolecular bond formation and ring cleavage. In addition, compounds 1 and 2 exhibited significant inhibitory activities on IL-8 production in the human keratinocyte HaCaT cell line.