Estudo fitoquímico e biológico de Simira grazielae (Rubiaceae)

Abstract

The study species Simira grazielae Peixoto is popularly known as red macaw and is found in Brazil by the states of BA and ES. The aim of the present study was to contribute to the knowledge of the chemical composition of the species S. grazielae, family Rubiaceae, through the phytochemical and pharmacological study (against Rhipicephalus microplus larvae, the tyrosinase and antiinflammatory and antinociceptive enzyme) extracts and fractions. The wood material and bark was collected in the Forest Reserve of Vale do Rio Doce Company - ES, then dried at room temperature, crushed and subjected to exhaustive maceration process with methanol, without heating. The methanolic extract of the wood was subjected to liquid/liquid partition with n-hexane, dichloromethane, ethyl acetate and n-butanol, and a small amount of these partitions along with the extract were subjected to chemical prospecting. The fractions were chromatographed on standard exclusion silica gel columns (Sephadex LH-20) and analyzed by 1H and 13C NMR, GC-MS and LC-MS-IES. In addition to fractionation, extracts and partitioned fractions were subjected to dereplication analysis in the CLUE-IES-QTOF-EM/MS system in positive mode, a fast and accurate analysis for characterization of chemical profiles. The chemical prospecting tests showed positive results for the metabolites: saponins, steroids, triterpenoids, purines, coumarin derivatives, alkaloids, reducing sugars, saccharides and non-protein amino acids. Eighteen (18) substances were isolated and identified from S. grazielae wood: N-acetyl serotonin, Maxonin, Harmana, cis-N-p-coumaroyl serotonin, trans-N-p-coumaroyl serotonin, N-isoferuloil serotonin, N-feruloil serotonin (Moschamine), cis-moschamine, N-cafeloyl serotonin, Higarine, Ofiorina B, Ofiorina A, Strictosidinic Acid, Strictosidine, Mixed of Triacylglycerides, 5-Hydroxyendole-3-aldehyde, 6'-O-Vanilloylbarbutine and Desmethylisopauridiantidoyl acid unpublished in the literature. The technique of dereplication and the proposed fragmentation allowed to postulate the presence of 57 metabolites, almost all of them being indole alkaloids, of which 20 are being proposed as unpublished in the literature. The tests carried out of the species S. grazielae against the acaricidal activity on the R. microplus larvae in the fractions SGD, SGAc, SGB, SGR and on the action on the tyrosinase enzyme [Ofiorina B and the partitions (SGAc and SGB)] did not show significant results. The antiinflammatory and antinociceptive test performed on the fractions of S. grazielae wood showed to have action in these systems and this effect can be linked to the presence of serotonin-derived alkaloids. Thus, in this work we identify 18 substances isolated from S. grazielae wood and propose the additional presence of 57 metabolites through the dereplication technique involving mostly alkaloids, besides revealing the presence of fractions of the species with antiinflammatory and antinociceptive.