title: Autumnalamide, a prenylated cyclic peptide from the cyanobacterium Phormidium autumnale, acts on SH-SY5Y cells at the mitochondrial level.
abstract: Filamentous cyanobacteria of the genus Phormidium have been rarely studied for their chemical diversity. For the first time, the cultivable Phormidium autumnale was shown to produce a prenylated cyclic peptide named autumnalamide (1). The structure of this peptide was fully determined after a deep exploration of the spectroscopic data, including NMR and HRMS. Interestingly, a prenyl moiety was located on the guanidine end of the arginine amino acid. The absolute configurations of most amino acids were assessed using enantioselective GC/MS analysis, with (13)C NMR modeling being used for the determination of d-arginine and d-proline. The effects of 1 on sodium and calcium fluxes were studied in SH-SY5Y and hNav 1.6 HEK cells. When the Ca(2+) influx was stimulated by thapsigargin, strong inhibition was observed in the presence of 1. As a consequence, this compound may act by disrupting the normal calcium uptake of this organelle, inducing the opening of the mitochondrial permeability transition pore, which results in the indirect blockade of store-operated channels.
authors.affiliation: Institut de Chimie de Nice-PCRE, UMR 7272 CNRS, Faculty of Science, University of Nice Sophia-Antipolis , Parc Valrose, 06108 Nice, France.
authors.forename: Coralie
authors.initials: C
authors.lastname: Audoin
authors.forename: Jon Andoni
authors.initials: JA
authors.lastname: Sánchez
authors.forename: Grégory
authors.initials: G
authors.lastname: Genta-Jouve
authors.forename: Amparo
authors.initials: A
authors.lastname: Alfonso
authors.forename: Laurent
authors.initials: L
authors.lastname: Rios
authors.forename: Carmen
authors.initials: C
authors.lastname: Vale
authors.forename: Olivier P
authors.initials: OP
authors.lastname: Thomas
authors.forename: Luis M
authors.initials: LM
authors.lastname: Botana
mesh_terms: D000458:Cyanobacteria / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019284:Thapsigargin / Q000494:pharmacology
chemical_list: D010456:Peptides, Cyclic; C000593555:autumnalamide; D019284:Thapsigargin