title: A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf.
abstract: The isolation and structural elucidation of a macrocyclic alkaloid, characterized by the presence of a 13-membered macrolactam ring containing a spermidine unit N-linked to a benzoyl group is hereby reported. The structure of this previously unknown spermidine alkaloid isolated from Gymnosporia arenicola (Celastraceae) leaves has been elucidated by (1)H and (13)C NMR spectroscopy (including bidimensional analysis) and further characterized by high-resolution mass spectrometry and polarimetry. A route for the biosynthesis of this new bioactive macrocycle is proposed and the cytotoxicity of the compound was evaluated against two ATCC cell lines - one normal-derived (MCF10A) and one cancer-derived cell line (MCF7) - using the MTT assay. The alkaloid revealed to be non-cytotoxic against both cell lines. The IC50 values from the cells were also determined.
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal.
authors.forename: Gustavo
authors.initials: G
authors.lastname: da Silva
authors.affiliation: Health Sciences Research Centre, University of Beira Interior (CICS-UBI), Rua Marquês d'Avila e Bolama, 6201-001 Covilhã, Portugal.
authors.forename: Ana
authors.initials: A
authors.lastname: Martinho
authors.affiliation: Department of Chemistry & QOPNA, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.
authors.forename: Raquel González
authors.initials: RG
authors.lastname: Soengas
authors.affiliation: Health Sciences Research Centre, University of Beira Interior (CICS-UBI), Rua Marquês d'Avila e Bolama, 6201-001 Covilhã, Portugal.
authors.forename: Ana Paula
authors.initials: AP
authors.lastname: Duarte
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal.
authors.forename: Rita
authors.initials: R
authors.lastname: Serrano
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal.
authors.forename: Elsa Teixeira
authors.initials: ET
authors.lastname: Gomes
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal. Electronic address: odsilva@ff.ulisboa.pt.
authors.forename: Olga
authors.initials: O
authors.lastname: Silva
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D029753:Celastraceae / Q000737:chemistry*; D002460:Cell Line; D006801:Humans; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry*; D013095:Spermidine / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D000470:Alkaloids; D013095:Spermidine
keywords: Celastraceae; Gymnosporia arenicola; Macrolactam ring; Spermidine alkaloid; Structural characterization