The seed oil of Annona salzmannii A. DC. was analyzed by GC-MS and 1H qNMR, revealing a mixture of unsaturated (80.5%) and saturated (18.7%) fatty acids. Linoleic (45.3%) and oleic (33.5%) acid were the major unsaturated fatty acids identified, while palmitic acid (14.3%) was the major saturated fatty acid. The larvicidal effects of A. salzmannii seed oil were evaluated against third-instar larvae of Aedes aegypti (Linn.). The oil exhibited moderate larvicidal activity, with a LC50 of 569.77 ppm (95% CI = 408.11 to 825.88 ppm). However, when the cytotoxic effects of the oil were evaluated, no expressive antiproliferative effects were observed in tumor cell lines B16-F10 (mouse melanoma), HepG2 (human hepatocellular carcinoma), K562 (human chronic myelocytic leukemia), HL-60 (human promyelocytic leukemia), and non-tumor cell line PBMC (peripheral blood mononuclear cells), with IC50 values > 50 μg·mL-1. This is the first study to evaluate the chemical composition, larvicidal and cytotoxic activity of A. salzmannii seed oil.

O sucesso no tratamento do câncer está intrinsicamente relacionado à sua prévia detecção, até mesmo antes dos sintomas surgirem. Neste contexto, estratégias metabonômicas baseadas na espectroscopia de ressonância magnética nuclear de ¹H (¹H NMR) foram empregadas para identificar as alterações metabólicas ocorridas na composição química de biofluidos de camundongos como consequência do surgimento de tumores. Através da análise discriminante por mínimos quadrados parciais (PLS-DA) dos espectros de ¹H NMR foi possível diagnosticar a presença dos tumores de Ehrlich e Sarcoma 180 após cinco e dez dias da indução dos tumores, respectivamente. Lipídeos, lipoproteínas e lactato foram os biomarcadores mais importantes indicativos do processo carcinogênico. Portanto, estratégias metabonômicas baseadas na espectroscopia de NMR podem ser valiosas ferramentas para investigar os efeitos do surgimento de anomalias celulares na composição química dos biofluidos.

The success of cancer treatment is directly related to early detection before symptoms emerge, although nowadays few cancers can be detected early. In this sense, ¹H nuclear magnetic resonance (¹H NMR)-based metabonomics was used to identify metabolic changes in biofluid as a consequence of tumours growing in mice. Through partial least squares discriminant analysis (PLS-DA) analysis of ¹H NMR spectra from serum samples it was possible to diagnose Ehrlich ascites and Sarcoma 180 tumours five and ten days after cell inoculation, respectively. Lipids, lipoproteins and lactate were the main biomarkers at onset as well as in the progress of carcinogenic process. Thus, NMR-based metabonomics can be a valuable tool to study the effects of tumour establishment on the chemical composition of biofluids.

Brown, red and green algae from the Southeastern coast of Brazil were successively extracted with chloroform/methanol 2:1 and 1:2 (v/v). The crude lipid extract was partitioned according to Folch and the lower phase enriched in glycolipids was fractionated on a silica gel column chromatography eluted with chloroform, acetone and methanol. Three major orcinol-reactive bands present in the acetone and methanol fractions were detected by thin-layer chromatography with chromatographic mobilities corresponding to sulfoglycolipids and glycosyldiacylglycerols. These fractions exhibited potent antiviral activity against HSV-1-ACVs and HSV-1-ACVr and present low toxicity for cell cultures. Purification and identification of these bioactive glycolipids will be necessary in order to elucidate their primary structures and mechanism of action.

Arabinose e galactose foram tratadas com metanol anidro contendo quantidades catalíticas de H2SO4 e HCl a 25ºC visando a formação de suas respectivas misturas de alpha- e beta-metil- glicofuranose, as quais foram confirmadas por ressonância magnética nuclear (RMN) unidimensional e bidimensional. A mistura de alpha, beta-Me-Araf foi oxidada com NaIO4, dando origem somente à Me-alpha-Araf, mostrando que o isômero beta é oxidado preferencialmente. Cada derivado furanosídico foi metilado pelo reagente de Purdie (Ag2O/MeI) a 25ºC, dando origem a misturas de metil glicofuranosídeos parcialmente metilados (Me-GFP), os quais tiveram seus respectivos graus de metilação monitorados por cromatografia em camada delgada (CCD), que variaram inicialmente em altos rendimentos de derivados mono metilados de Me-GFP a derivados com alto grau de metilação. Os produtos da reação foram convertidos a derivados alditol acetato parcialmente metilados (AAPM), após hidrólise, seguida de redução com NaBD4 e posterior acetilação. Os derivados obtidos podem ser utilizados como padrões de AAPM em CG-EM para auxiliar na análise de metilação de carboidratos complexos que possam conter unidades de arabinofuranose e galactofuranose. Os derivados AAPM de 6-MeGal, 5,6-Me2Gal, 2,5-Me2Gal, 2,5,6-Me3Gal, 3,5,6-Me3Gal, 5-MeAra, 2,5-Me2Ara e 3,5-Me2Ara mostraram espectros de eletroimpacto e tempos de retenção de maior interesse pois são de difícil síntese. A avaliação da reatividades dos grupos hidroxílicos nesta metilação mostrou que a mistura de alpha, beta-Me-Galf reage preferencialmente em HO-2 > HO-3 > HO-6 > HO-5, a mistura de alpha, beta-Me-Araf em HO-2 > HO-3 > HO-5, alpha-Me-Araf em HO-2 > HO-3 > HO-5.

Arabinose and galactose were treated with MeOH containing traces of H2SO4 or HCl at 25ºC to give mixtures of their methyl alpha- and beta-furanosides, as shown by 1D and 2D nuclear magnetic resonance (NMR). Oxidation of the Me alpha,beta-Araf mixture with NaIO4 preferentially oxidised the beta-isomer, to give pure Me alpha-Araf . Each product was progressively O-methylated using the Purdie reagent (MeI/Ag2O) at 25ºC and resulting mixtures of partially methylated glycosides (PMGs) were rapidly assayed by thin layer chromatography (TLC) first to favour higher yields of mono-O-methyl derivatives and later for products with higher degrees of methylation. The products were converted to complex mixtures of partially O-methylated alditol acetate derivatives (PMAAs) by successive hydrolysis, reduction with NaBD4, and acetylation. These can be used as gas chromatography-mass spectrometry (GC-MS) standards in methylation analysis of complex carbohydrates containing arabinofuranosyl and galactofuranosyl units. Of particular interest were the retention times and electron impact MS of the difficult to prepare alditol acetates of 5,6-Me2Gal, 2,5-Me2Gal, 2,5,6-Me3Gal, 3,5,6-Me3Gal, 5-MeAra, 2,5-Me2Ara, and 3,5-Me2Ara. The relative reactivities of hydroxyl groups for mixtures of Me alpha- and Me beta-Galf were HO-2 > HO-3 > HO-6 > HO-5, that of Me alpha and Me beta-Araf HO-2 > HO-3 > HO-5, and that of Me alpha-Araf HO-2 > HO-3 > HO-5.