Two new tetracyclic prenylated acylphloroglucinols, chipericumins A (1) and B (2), were isolated from the roots of Hypericum chinense, together with two new tricyclic prenylated acylphloroglucinols, chipericumins C (3) and D (4). Their structures were elucidated by spectroscopic data. Chipericumins A-D (1-4) are prenylated acylphloroglucinols having a spiro skeleton with an acyl group, a methyl group, a C(5) unit, and a monoterpene moiety in common.