Hyperjapones A—E, Terpenoid Polymethylated Acylphloroglucinols from Hypericum japonicum.

Hyperjapones A–E (1–5), novel terpenoid polymethylated acylphloroglucinols (TPAPs) with unusual architectures, were characterized from Hypericum japonicum. Their structures and absolute configurations were determined by comprehensive spectroscopic data and X-ray diffractions. Compound 1 was obtained as a racemic mixture and was separated by a column coated with cellulose tris(4-methylbenzoate) after attempts with various chiral materials. Compounds 1, 2, and 4 exhibited moderate antitumor activities in vitro.