Ribifolin, an orbitide from Jatropha ribifolia, and its potential antimalarial activity

Meri Emili F Pinto; João M Batista Jr; Johannes Koehbach; Pratibha Gaur; Abhinay Sharma; Myna Nakabashi; Eduardo Maffud Cilli; Guilherme M Giesel; Hugo Verli; Christian W Gruber; Ewan W Blanch; Joseam F Tavares; Marcelo S da Silva; Celia R S Garcia; Vanderlan S Bolzani

doi:10.1021/np5007668

Ribifolin, an orbitide from Jatropha ribifolia, and its potential antimalarial activity

J Nat Prod. 2015 Mar 27;78(3):374-80. doi: 10.1021/np5007668. Epub 2015 Feb 20.

Authors

Meri Emili F Pinto¹, João M Batista Jr^{1

2}, Johannes Koehbach^{3

4}, Pratibha Gaur⁵, Abhinay Sharma⁵, Myna Nakabashi⁵, Eduardo Maffud Cilli¹, Guilherme M Giesel⁶, Hugo Verli⁶, Christian W Gruber⁴, Ewan W Blanch², Joseam F Tavares⁷, Marcelo S da Silva⁷, Celia R S Garcia⁵, Vanderlan S Bolzani¹

Affiliations

¹ †Institute of Chemistry, São Paulo State University-UNESP, 14800-060, Araraquara, São Paulo, Brazil.
² ‡Manchester Institute of Biotechnology and Faculty of Life Sciences, The University of Manchester, M1 7DN, Manchester, United Kingdom.
³ §School of Biomedical Sciences, The University of Queensland, 4072, St. Lucia, Queensland, Australia.
⁴ ⊥Center for Physiology and Pharmacology, Medical University of Vienna, 1090, Vienna, Austria.
⁵ ∥Departament of Physiology, Institute of Biosciences, The University of São Paulo-USP, 05508-900, São Paulo, Brazil.
⁶ #Center of Biotechnology, Federal University of Rio Grande do Sul-UFRGS, 91500-970, Porto Alegre, Rio Grande do Sul, Brazil.
⁷ □Laboratory of Pharmaceutical Technology, Federal University of Paraíba-UFPB, 58051-970, João Pessoa, Paraíba, Brazil.

PMID: 25699574
DOI: 10.1021/np5007668

Abstract

A new orbitide named ribifolin was isolated and characterized from Jatropha ribifolia using mass spectrometry, NMR spectroscopy, quantitative amino acid analysis, molecular dynamics/simulated annealing, and Raman optical activity measurements and calculations. Ribifolin (1) and its linear form (1a) were synthesized by solid-phase peptide synthesis, followed by evaluation of its antiplasmodial and cytotoxicity activities. Compound 1 was moderately effective (IC50 = 42 μM) against the Plasmodium falciparum strain 3D7.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antimalarials* / chemistry
Antimalarials* / isolation & purification
Antimalarials* / pharmacology
Drug Screening Assays, Antitumor
Jatropha / chemistry*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Parasitic Sensitivity Tests
Peptides, Cyclic* / chemistry
Peptides, Cyclic* / isolation & purification
Peptides, Cyclic* / pharmacology
Plant Extracts / chemistry
Plasmodium falciparum / drug effects*
Solid-Phase Synthesis Techniques

Substances

Antimalarials
Peptides, Cyclic
Plant Extracts
ribifolin