title: Polycyclic Polyprenylated Xanthones from Symphonia globulifera: Isolation and Biomimetic Electrosynthesis.
abstract: Two regioisomeric polycyclic xanthones, 3,16-oxyguttiferone A (2) and 1,16-oxyguttiferone A (3), which are polyprenylated acylphloroglucinol-derived analogues, were isolated from the seeds of Symphonia globulifera, together with their presumed o-dihydroxybenzoyl precursor, guttiferone A (1). Anodic oxidation of 1 into the corresponding o-quinone species proved to be an efficient biomimetic method to generate xanthones 2 and 3 in high overall yield and to confirm their structures. Both compounds displayed cytotoxicity against the HCT 116 colon carcinoma cell line with IC₅₀ values of 8 and 3 μM, respectively.
authors.affiliation: UMR COMETE 8638 CNRS - Université Paris Descartes , Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Kevin
authors.initials: K
authors.lastname: Cottet
authors.affiliation: UMR COMETE 8638 CNRS - Université Paris Descartes , Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Neudörffer
authors.affiliation: UMR COMETE 8638 CNRS - Université Paris Descartes , Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Marina
authors.initials: M
authors.lastname: Kritsanida
authors.affiliation: UMR COMETE 8638 CNRS - Université Paris Descartes , Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Michel
authors.affiliation: UMR COMETE 8638 CNRS - Université Paris Descartes , Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Marie-Christine
authors.initials: MC
authors.lastname: Lallemand
authors.affiliation: UMR COMETE 8638 CNRS - Université Paris Descartes , Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Martine
authors.initials: M
authors.lastname: Largeron
mesh_terms: D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D028084:Clusiaceae / Q000737:chemistry*; D005616:French Guiana; D045325:HCT116 Cells; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D054876:Prenylation; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D044004:Xanthones / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D001577:Benzophenones; D044004:Xanthones; C558133:guttiferone A