Abstract
Hyperjaponol H (1), a new filicinic acid-based meroterpenoid, with a 6/6/10 ring system trans-fused by hetero-Diels–Alder cycloaddition between a germacrane sesquiterpenoid and a filicinic acid moiety, was isolated from aerial parts of Hypericum japonicum. The elucidation of its structure and absolute configuration were accomplished by the analyses of extensive spectroscopic data and the comparison of Cotton effects of electron circular dichroism (ECD) with previously reported ones. The bioactivity assay showed that hyperjaponol H exhibited a moderate inhibitory efficacy on lytic Epstein-Barr virus (EBV) DNA replication in B95-8 cells.
Highlights
Natural products are widely known to be a considerable resource of biologically active compounds that involve manifold and unusual scaffolds
The isolation, structural confirmation, and anti-Epstein-Barr virus (EBV) assay of compound 1, named hyperjaponol H, a metabolite of H. japonicum, are illustrated in detail
IR, UV, and electron circular dichroism (ECD) spectra were measured by Bruker Vertex 70 (Brucker Co., Karlsruhe, Germany), Varian
Summary
Natural products are widely known to be a considerable resource of biologically active compounds that involve manifold and unusual scaffolds. Most secondary metabolites from plants of Guttiferae are mainly found to be phloroglucinol derivatives with complex architectures and appealing therapeutical properties [1,2,3]. In our on-going research on the genus Hypericum for structurally fascinating and biologically appealing metabolites, we have reported some meroterpenoids of polycyclic prenylated acylphloroglucinols (PPAPs) from H. sampsonii, H. ascyron, H. attenuatum, and H. perforatum [12,13,14,15] as well as a series of filicinic acid-based meroterpenoids (Hyperjaponols A–G) from H. japonicum [16]. The isolation, structural confirmation, and anti-EBV assay of compound 1, named hyperjaponol H, a metabolite of H. japonicum, are illustrated in detail
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