Hyperlanins A and B, Two Highly Rearranged Meroterpenoids from Hypericum lancasteri

Abstract

Comprehensive SummaryHyperlanins A (1) and B (2), two highly rearranged polycyclic polyprenylated acylphloroglucinol (PPAP)‐related meroterpenoids based on different new carbon skeletons, were isolated from Hypericum lancasteri. Compound 1 incorporates an unprecedented 5/6/7/5 ring system featuring a 3,13‐dioxatetracyclo[9.2.1.12,5.01,8]pentadecane core. Compound 2 possesses a unique compact 6/6/5/6/6/5/6 ring system with a caged tetracyclo[6.2.1.13,8.05,11]dodecane motif. Their structures were established by spectroscopic data, X‐ray diffraction, and computational approaches. Both compounds showed anti‐inflammatory activity in vitro. Compounds 1 and 2 could decrease the lipopolysaccharide (LPS)‐/nigericin‐induced IL‐1β release in THP‐1 cells. Both compounds also showed inhibition in hypoxia‐inducible factor‐1α (HIF‐1α) pathway luciferase reporter assay.