title: Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
abstract: The novel iridoid glycoside 2 was prepared in six steps (15% overall yield) from natural aucubin (1) and fully characterized. Compound 2, which comprises the same conjugated cyclopentenone pharmacophore as known antitumor oxylipins and prostaglandins, displayed significant antiproliferative in vitro activity towards leukemia L1210 cells. The Michael addition of nucleophilic thiols to compound 2 occurred on a different position compared to classical delta7-prostaglandin A1 methyl ester. The resulting adducts 7a and 7b were fully characterized, and their MS fragmentation patterns were elucidated.
authors.affiliation: Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. no8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, F-75006 Paris.
authors.forename: Christine
authors.initials: C
authors.lastname: Mouriès
authors.forename: Vokatsoa C
authors.initials: VC
authors.lastname: Rakotondramasy
authors.forename: Francine
authors.initials: F
authors.lastname: Libot
authors.forename: Michel
authors.initials: M
authors.lastname: Koch
authors.forename: François
authors.initials: F
authors.lastname: Tillequin
authors.forename: Brigitte
authors.initials: B
authors.lastname: Deguin
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D005960:Glucosides / Q000737:chemistry*; D057888:Iridoid Glucosides; D039823:Iridoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D015394:Molecular Structure
chemical_list: D000970:Antineoplastic Agents; D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; C006650:aucubin