Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis

  • Biomed Pharmacother. 2016 Oct;83:323-329. doi: 10.1016/j.biopha.2016.06.033.
Themístocles da Silva Negreiros Neto  1 ,  Dale Gardner  2 ,  Fernando Hallwass  3 ,  Ana Jéssica Matias Leite  4 ,  Camila Guimarães de Almeida  5 ,  Laura Nunes Silva  6 ,  Alan de Araújo Roque  7 ,  Fernanda Gobbi de Bitencourt  8 ,  Euzébio Guimarães Barbosa  9 ,  Tiana Tasca  10 ,  Alexandre José Macedo  11 ,  Mauro Vieira de Almeida  12 ,  Raquel Brandt Giordani  13
Affiliations
  • 1. Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: [email protected].
  • 2. USDA, ARS, Poisonous Plant Research Laboratory, 1150 East 1400 North, Logan, UT 84341, USA. Electronic address: [email protected].
  • 3. Departamento de Química Fundamental, Universidade Federal de Pernambuco, Avenida Professor Moraes Rego, 1235, CEP 50670-901, Recife, PE, Brazil. Electronic address: [email protected].
  • 4. Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: [email protected].
  • 5. 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: [email protected].
  • 6. Centro de Biotecnologia and Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil. Electronic address: [email protected].
  • 7. Herbário da UFRN, Universidade Federal do Rio Grande do Norte, Campus Universitário Lagoa Nova, CEP 59078-970, Natal, RN, Brazil. Electronic address: [email protected].
  • 8. 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: [email protected].
  • 9. Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: [email protected].
  • 10. 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: [email protected].
  • 11. Centro de Biotecnologia and Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752, 90610-000, Porto Alegre, RS, Brazil. Electronic address: [email protected].
  • 12. 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: [email protected].
  • 13. Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Gustavo Cordeiro de Faria, SN, CEP 59010-180, Natal, RN, Brazil. Electronic address: [email protected].
PMID: 27399809 DOI: 10.1016/j.biopha.2016.06.033
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.

Keywords
Biological activity; Monocrotaline; Pyrrolizidine alkaloids; Usaramine.
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