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Two new bicyclic acylphloroglucinol derivatives, hypercalyxone A (1-[5,7-dihydroxy-2-methyl-3-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-propan-1-one, 1) and B (1-[5,7-dihydroxy-2-methyl-3-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-butan-1-one, 2), have been isolated from the petroleum ether extract of the aerial parts of Hypericum amblycalyx, together with two further compounds (1-[5,7-dihydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-propan-1-one, 3 and 1-[5,7-dihydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-butan-1-one, 4), which have been described only as semi-synthetic products. In addition, the known triterpene lup-20(29)-en-3-one was obtained. Structure elucidation was based on 1D and 2D NMR studies, as well as on data derived from mass spectrometry. The four acylphloroglucinol derivatives were evaluated for their cytotoxic and antibacterial activity. All compounds showed moderate cytotoxic activity against KB and Jurkat T cancer cells. Especially compounds 3 and 4 exhibited a strong antibacterial activity against different Gram-positive strains.

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The volatile compositions of three closely related Hypericum species growing wild on the island of Crete were studied, all belonging to the section Coridium. Hydro-distillation in a modified Clevenger-type apparatus was performed according to the Hellenic Pharmacopoeia in order to obtain the essential oils, which were analyzed by GC-MS. Identification of the compounds was carried out by comparison of MS spectra and retention indices with literature data, as well as by co-chromatography with authentic samples. In total, 123 different compounds were identified and the main compounds were by order of their abundance as follows: H. empetrifolium: α-pinene, germacrene D, β-pinene, E-caryophyllene; H. amblycalyx: β-elemene, β-selinene, α-pinene, E-caryophyllene, α-selinene; H. jovis: trans-calamenene, α-selinene, β-elemene. The chemical results revealed the differences and similarities (qualitative and quantitative) between the studied oils, supporting the hypothesis that essential oils from Hypericum spp. do not serve as chemotaxonomic markers. Moreover, the essential oils were subjected to antimicrobial screening. According to the given results, the essential oils possessed better antifungal and anticandidal activities than antibacterial activities.