title: Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.
abstract: In search for new or chemo-taxonomically relevant bioactive compounds from chemically unexplored Hypericum species, four previously undescribed natural products, named peplidiforones A-D were isolated and characterized from Hypericum peplidifolium A. Rich., together with six known compounds. The structures of all compounds were elucidated by extensive 1D- and 2D-NMR experiments, high resolution mass spectrometric analyses (HR-MS), and by comparison with data reported in the literature. Seven of these compounds are phenyl polyketides while three are acylphloroglucinol type compounds. Peplidiforone C, which possesses an unusual carbon skeleton consisting of a furan ring substituted by a 2,2-dimethylbut-3-enoyl moiety, is the first example of a prenylated furan derivative isolated from the genus Hypericum. The cytotoxicity, antifungal, and anti-herpes simplex virus type 1 (HSV-1) activities of extracts and compounds are described.
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; Department of Chemistry, Middle Tennessee State University, P.O. Box 68, Murfreesboro, TN 37132, USA.
authors.forename: Chelsea Rebecca
authors.initials: CR
authors.lastname: Harmon
authors.affiliation: Laboratory of Natural Products Chemistry, Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon.
authors.forename: Antoine Honoré Nkuete
authors.initials: AH
authors.lastname: Lonfouo
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 Biology, Middle Tennessee State University, P.O. Box 60, Murfreesboro, TN 37132, USA.
authors.forename: Stephen M
authors.initials: SM
authors.lastname: Wright
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: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects; D020902:Hypericum / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010696:Phloroglucinol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D054876:Prenylation
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D061065:Polyketides; D010696:Phloroglucinol
keywords: Furans; Hypericaceae; Hypericum peplidifolium; Polyketide derivatives; Prenylated natural products; Pyranones