2. Academic Validation
  3. Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum

Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum

  • Bioorg Med Chem. 2015 Oct 1;23(19):6327-34. doi: 10.1016/j.bmc.2015.08.028.
Serge Alain Tanemossu Fobofou 1,  Katrin Franke 2,  Giuseppina Sanna 3,  Andrea Porzel 1,  Enrica Bullita 3,  Paolo La Colla 3,  Ludger A Wessjohann 4
Affiliations

Affiliations

  • 1 Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany.
  • 2 Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany. Electronic address: kfranke@ipb-halle.de.
  • 3 Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, 09042 Monserrato (CA), Italy.
  • 4 Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany. Electronic address: wessjohann@ipb-halle.de.
PMID: 26358281 DOI: 10.1016/j.bmc.2015.08.028
Abstract

From the ethno-medicinally used leaves of Hypericum roeperianum we isolated a new tricyclic acylphloroglucinol (1), a new tetracyclic acylphloroglucinol (2), and a new prenylated bicyclic acylphloroglucinol (3) together with four known prenylated (4-7) and three known tetracyclic acylphloroglucinol derivatives (8-10). Structure elucidation was based on UV, IR, [α]D(25), 1D- and 2D-NMR experiments. Furthermore, empetrifranzinans A (8) and C (9) were synthesized regioselectively in only two steps. The isolated compounds were evaluated for their cytotoxicity against PC-3 and HT-29 Cancer cell lines as well as Antibacterial and anthelmintic activities. They were also tested in cell-based assays for cytotoxicity against MT-4 cells and for anti-HIV activity in infected MT-4 cells. Significant anthelmintic activity against Caenorhabditis elegans was exhibited by compound 7 (3-geranyl-1-(2'-methylbutanoyl)-phloroglucinol), which might provide a new lead.

Keywords

(1)H NMR profile guided isolation; Acylphloroglucinol synthesis; Empetrifranzinans; H. riparium; Hypericaceae; Madeleinol; Metabolic profiling; Natural products.

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