title: In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
abstract: The present investigation deals with the antibiotic activity of eight natural guanidine alkaloids and two synthetic analogues against a variety of clinically relevant methicillin-resistant Staphylococcus aureus strains. Galegine (1) and pterogynidine (2) were the most potent compounds, with a minimum inhibitory concentration of 4 mg/L, to all tested strains. The preliminary chemical features correlating to anti-MRSA activity showed that the size of the side chain and the substitution pattern in the guanidine core played a key role in the antibacterial activity of the imino group. Guanidine alkaloids 1 and 2 are promising molecular models for further synthetic derivatives and, thus, for medicinal chemistry studies.
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, São Paulo State University , Rua Prof. Francisco Degni 55, Araraquara14800-900, Brazil.|Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy , 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.
authors.forename: Aline
authors.initials: A
authors.lastname: Coqueiro
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, São Paulo State University , Rua Prof. Francisco Degni 55, Araraquara14800-900, Brazil.
authors.forename: Luis Octávio
authors.initials: LO
authors.lastname: Regasini
authors.affiliation: Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy , 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.
authors.forename: Paul
authors.initials: P
authors.lastname: Stapleton
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, São Paulo State University , Rua Prof. Francisco Degni 55, Araraquara14800-900, Brazil.
authors.forename: Vanderlan
authors.initials: V
authors.lastname: da Silva Bolzani
authors.affiliation: Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy , 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.
authors.forename: Simon
authors.initials: S
authors.lastname: Gibbons
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001938:Brazil; D007887:Fabaceae / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D066298:In Vitro Techniques; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D006146:Guanidines; C542891:pterogynidine; C074315:galegine