Hyperacmoses A–C, Three Seco-Norpolyprenylated Acylphloroglucinols from <i>Hypericum acmosepalum</i> with Lipid-Lowering Activity

Hyperacmoses A–C, three seco-norpolyprenylated acylphloroglucinols (PPAPs) ( 1 – 3 ), along with two processors ( 4 and 5 ), were purified from Hypericum acmosepalum . Structurally, compounds 1 and 2 represent the first seco-norPPAP with an unprecedented 5/6/5/6/5 pentacyclic framework, while compound 3 is the first seco-norPPAP with a 5/5/6/6 tetracyclic core. Three rare PPAPs had the same biosynthetic precursor, and Baeyer–Villiger oxidation of this precursor at different positions could finally give different types of PPAPs ( 1 – 3 ). Four compounds ( 1, 2, 4, and 5 ) exhibited a better triglyceride (TG) inhibitory effect than atorvastatin in oleic acid-induced HepG2 cells. The compound with the highest potential, compound 1, could prohibit the expression of lipid synthesis proteins, FASN and ACACA, by targeting ACSS2.