Orbitides from Jatropha gossipifolia (L.): Isolation, identification, stereospecific synthesis and biological activities
Jatropha gossipifolia, a species with occurrence in the caatinga biome of northeastern Brazil, is popularly known as “pinhão roxo” and belongs to the Euphorbiaceae family. This species is widely used in traditional medicine as antiparasitic, antibiotic, insecticidal and has been an important source for phytochemical studies due to be rich in interesting compounds as orbitides [1]. Orbitides are cyclic peptides characterized by present a “tail-head” cyclization with about 5 to 12 amino acids residues in its structure, free of disulfide bonds [2]. Previously, phytochemical studies with J. gossipifolia described two orbitides isolated from its latex: cyclogossine A (1) and cyclogossine B [4,3]. This work aimed the re-investigation of latex, searching to identify novel orbitides and, subsequently, the synthesis and biological activities of them and some stereospecific analogues. For isolation of the metabolites, solid-phase extraction and HPLC were employed. Were possible the isolation of 3 orbitides: cyclogossine A (1), cyclogossine B and a novel orbitide that were characterized by MS and NMR techniques. The synthesis of cyclogossine A (1) and their analogues: linear (1a), retro (2), inverse (3) and retro-inverse (4), were obtained through solid phase peptide synthesis (SPPS) [5]. Recent studies described that ribifolin, an octapeptide from J. ribifolia present antimalarial activity [6], in this perspective, the compounds were evaluated for antiparasitic activity.