Antimicrobial acylphloroglucinol derivatives from Hypericum linarioides (Hypericaceae)

Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

“…Using silica gel flash chromatography (solvent A: EtOAc, solvent B: hexane, flow rate: 30 mL/min, collection: 20 mL/vial, gradient: 0-60 min 0 % → 100 % A), 5.9 g of PE.2 were separated to give 6 subfractions (PE.2.1-2.6). Subfraction PE.2.2 (464 mg, 300-420 mL) was subjected to CPC (flow rate: 5 mL/min, collection: 2 mL/vial, upper phase: saturated heptane [3] (20,15,10,5, and 1 µM) as test compounds and quercetin (75, 50, 25, 10, and 1 µM) as positive control; n = 3 in sextuplicates; mean ± SD; data were subjected to 1-way ANOVA followed Dunnettʼs post-test using GraphPad Prism 5 software (significance level: *p < 0.05, **p < 0.01, ***p < 0.001); b Influence of 3 and 12 (10, 7,5, 5, 2.5, and 1 µM) as test compounds and quercetin (20,15,10,5, and 1 µM) as positive control on NO concentration in the cell supernatant of RAW 264.7 cells stimulated with LPS (10 ng/mL); control (= 100 %): NO concentration in cell supernatant of RAW 264.7 cells stimulated with LPS (10 ng/mL) without substances; n = 3 in pentatuplicates; mean ± SD; data were subjected to 1-way ANOVA followed by Dunnettʼs post test using GraphPad Prism 5 software (significance level: *p < 0.05, **p < 0.01). − 35.2 (c 0.13, MeOH), 1 H NMR data (CDCl 3 , 600 MHz) and 13 C NMR data (CDCl 3 , 150 MHz) see ▶ Table 2…”

“…& Spach [18]. Two monocyclic acylphloroglucinol derivatives, 3-geranyl-1-(2-methylpropanoyl) phloroglucinol and 3-geranyl-1-(2-methylbutanoyl)phloroglucinol have been isolated from H. linarioides Bosse [20], but until Supplementary material is available under https://doi.org/10.1055/a-1617-7573 ABSTR AC T 1 H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), while 5 further compounds showed an adamantane skeleton (15)(16)(17)(18)(19).…”