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Seven filicinic acid–based meroterpenoids (1–7), possessing 6/6/11, 6/6/7/5, or 6/6/10 ring systems, were isolated from Hypericum japonicum. All of them have novel skeletons with the incorporation of sesquiterpenoid moieties to an acylated filicinic acid. Compounds 2a and 4 exhibited significant efficacy on anti-Epstein–Barr virus, with EC50 values of 0.57 and 0.49 μM, respectively. Furthermore, compounds 2a and 4 were well accommodated to the binding pocket of 2GV9 predicted by the molecular docking.

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.

From the aerial part of Hypericum japonicum, two new compounds, japonica acid and 3,4-epoxy-5-hydroxy-1-cyclohexenecarboxylic acid; one found naturally for the first time, 5-O-coumaroylquinic acid methyl ester; were isolated together with four known compounds. Their structures were elucidated by spectroscopic and chemical methods. © 1998 John Wiley & Sons, Ltd.