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
  • 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: [email protected].
  • 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: [email protected].
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.