title: Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum.
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.
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany.
authors.forename: Serge Alain Tanemossu
authors.initials: SA
authors.lastname: Fobofou
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany. Electronic address: kfranke@ipb-halle.de.
authors.forename: Katrin
authors.initials: K
authors.lastname: Franke
authors.affiliation: Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, 09042 Monserrato (CA), Italy.
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Sanna
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany.
authors.forename: Andrea
authors.initials: A
authors.lastname: Porzel
authors.affiliation: Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, 09042 Monserrato (CA), Italy.
authors.forename: Enrica
authors.initials: E
authors.lastname: Bullita
authors.affiliation: Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, 09042 Monserrato (CA), Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: La Colla
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany. Electronic address: wessjohann@ipb-halle.de.
authors.forename: Ludger A
authors.initials: LA
authors.lastname: Wessjohann
mesh_terms: D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017173:Caenorhabditis elegans / Q000187:drug effects; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002839:Chromans / Q000737:chemistry* / Q000302:isolation & purification; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D020902:Hypericum / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000871:Anthelmintics; D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D002839:Chromans; D014966:Xanthenes; C000608910:empetrifranzinan D; C000608906:madeleinol A; C000608911:madeleinol B; D010696:Phloroglucinol
keywords: (1)H NMR profile guided isolation; Acylphloroglucinol synthesis; Empetrifranzinans; H. riparium; Hypericaceae; Madeleinol; Metabolic profiling; Natural products