title: Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis.
abstract: Crotalaria genus belongs to the subfamily Papilionoideae comprising about 600 species spread throughout tropical, neotropical and subtropical regions. In this study, seeds of Crolatalaria pallida were used to the isolation of usaramine, a pyrrolizidine alkaloid. Thus, Pseudomonas aeruginosa and Staphylococcus epidermidis were utilized as strains to test some activities of this alkaloid, such as antibiofilm and antibacterial. Meanwhile, monocrotaline obtained from Crotalaria retusa seeds, was used as the starting material for synthesis of necine base derivatives with anti-Trichomonas vaginalis potential. Alkaloids were characterized by 1D and 2D NMR techniques and GC-MS analysis. Usaramine demonstrated a highlighted antibiofilm activity against S. epidermidis by reducing more than 50% of biofilm formation without killing the bacteria, thus it could be assumed as a prototype for the development of new antibiofilm molecules for pharmaceutical and industrial purposes. Monocrotaline activity against T. vaginalis was evaluated and results indicated inhibition of 80% on parasite growth at 1mg/mL, in addition, neither cytotoxicity against vaginal epithelial cells nor hemolytic activity were observed. On the other hand, retronecine showed no anti-T. vaginalis activity while azido-retronecine was more active than monocrotaline killing 85% of the parasites at 1mg/mL. In conclusion, pyrrolizidine alkaloids are suggested as promising prototypes for new drugs especially for topical use.
authors.affiliation: Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: theminegreiros@yahoo.com.br.
authors.forename: Themístocles
authors.initials: T
authors.lastname: da Silva Negreiros Neto
authors.affiliation: USDA, ARS, Poisonous Plant Research Laboratory, 1150 East 1400 North, Logan, UT 84341, USA. Electronic address: dale.gardner@ars.usda.gov.
authors.forename: Dale
authors.initials: D
authors.lastname: Gardner
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco, Avenida Professor Moraes Rego, 1235, CEP 50670-901, Recife, PE, Brazil. Electronic address: hallwass@ufpe.br.
authors.forename: Fernando
authors.initials: F
authors.lastname: Hallwass
authors.affiliation: Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: ana@analeite.org.
authors.forename: Ana Jéssica Matias
authors.initials: AJM
authors.lastname: Leite
authors.affiliation: Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Juiz de Fora, Campus Martelos, CEP 36036-330, Juiz de Fora, MG, Brazil. Electronic address: camilagdealmeida@gmail.com.
authors.forename: Camila Guimarães
authors.initials: CG
authors.lastname: de Almeida
authors.affiliation: Centro de Biotecnologia and Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil. Electronic address: lauransilva@gmail.com.
authors.forename: Laura Nunes
authors.initials: LN
authors.lastname: Silva
authors.affiliation: Herbário da UFRN, Universidade Federal do Rio Grande do Norte, Campus Universitário Lagoa Nova, CEP 59078-970, Natal, RN, Brazil. Electronic address: alan.ufrn@gmail.com.
authors.forename: Alan
authors.initials: A
authors.lastname: de Araújo Roque
authors.affiliation: Laboratório de Pesquisa em Parasitologia, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil. Electronic address: fe_gobbi@hotmail.com.
authors.forename: Fernanda Gobbi
authors.initials: FG
authors.lastname: de Bitencourt
authors.affiliation: Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: euzebiobg@gmail.com.
authors.forename: Euzébio Guimarães
authors.initials: EG
authors.lastname: Barbosa
authors.affiliation: Laboratório de Pesquisa em Parasitologia, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil. Electronic address: tiana.tasca@ufrgs.br.
authors.forename: Tiana
authors.initials: T
authors.lastname: Tasca
authors.affiliation: Centro de Biotecnologia and Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil. Electronic address: alexandre.macedo@ufrgs.br.
authors.forename: Alexandre José
authors.initials: AJ
authors.lastname: Macedo
authors.affiliation: Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Juiz de Fora, Campus Martelos, CEP 36036-330, Juiz de Fora, MG, Brazil. Electronic address: mauro.almeida@ufjf.edu.br.
authors.forename: Mauro Vieira
authors.initials: MV
authors.lastname: de Almeida
authors.affiliation: Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: raquebg@hotmail.com.
authors.forename: Raquel Brandt
authors.initials: RB
authors.lastname: Giordani
mesh_terms: D018441:Biofilms / Q000187:drug effects*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002460:Cell Line; D005260:Female; D006801:Humans; D050296:Microbial Viability / Q000187:drug effects; D016686:Monocrotaline / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D066244:Proton Magnetic Resonance Spectroscopy; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013212:Staphylococcus epidermidis / Q000187:drug effects / Q000648:ultrastructure; D014246:Trichomonas vaginalis / Q000187:drug effects / Q000502:physiology*
chemical_list: D011763:Pyrrolizidine Alkaloids; C014795:retronecine; D016686:Monocrotaline; C003300:retrorsine
keywords: Biological activity; Monocrotaline; Pyrrolizidine alkaloids; Usaramine