Hyperjapones A–E, Terpenoid Polymethylated Acylphloro­glucinols from <i>Hypericum japonicum</i>

Hyperjapones A–E (<b>1</b>–<b>5</b>), novel terpenoid polymethylated acylphloroglucinols (TPAPs) with unusual architectures, were characterized from <i>Hypericum japonicum</i>. Their structures and absolute configurations were determined by comprehensive spectroscopic data and X-ray diffractions. Compound <b>1</b> 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 <b>1</b>, <b>2</b>, and <b>4</b> exhibited moderate antitumor activities <i>in vitro