Toxic aromatic compounds from fruits of Narthecium ossifragum L.

The intake of Narthecium ossifragum, commonly known as bog asphodel, has been associated with toxic effects observed in sheep for centuries. Although the plant has been studied for five centuries little is known about its chemical constituents. Six previously undescribed natural products, naringenin(3 â†’ 6″)luteolin, naringenin(3 â†’ 6″)chrysoeriol, liovil 4-O-ß-glucopyranoside, 2,6-dimethoxy cinnamic acid, (E)-4-(3-hydroxy-2,2-dimethylchroman-6-yl)but-3-en-2-one and (E)-4-(4-(((E)-4-hydroxy-3-methylbut-2-en-1-yl)oxy)phenyl)but-3-en-2-one, have been identified from fruits of N. ossifragum for the first time. In addition, the rare natural product 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde and the five known compounds 4-hydroxycinnamic acid, quercetin 3,3'-dimethyl ether, quercetin 3,7-dimethyl ether, chrysoeriol 7-O-ß-glucopyranoside and the di-C-glycosylflavone isoschaftoside were all characterized for the first time from the fruits of N. ossifragum. The discovery of sufficient amounts of 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde in fresh plant material of N. ossifragum to allow complete structure elucidation by NMR and HRMS supports the possibility that fungi associated with N. ossifragum may be able to produce enough toxins to play a significant role in the pathogenicity of N. ossifragum. 4-Hydroxy-3-(3-methylbut-2-enyl)benzaldehyde showed mild toxicity towards normal rat kidney (NRK) and more profound activity towards MOLM13 acute myeloid leukemia cells (IC50 = 430 µM and 68 µM, respectively). Naringenin(3 â†’ 6″)luteolin had IC50 of 230 µM towards NRK cells, and 115 µM towards MOLM13 cells. Microscopic evaluation suggests that these two compounds induce cell death by different mechanisms.

Z-Isomers of (4α→6″, 2α→O→1″)-phenylflavan substituted with R'=R=OH. Conformational properties, electronic structure and aqueous solvent effects.

Procyanidins are highly hydroxylated polymers known as antioxidant compounds, thereby exhibiting beneficial effects. These compounds are protective agents against oxidative stress and the damage induced by free radicals in membranes and nucleic acids. This paper describes a study of the conformational space of (4α→6″, 2α→O→1″)-phenylflavan substituted with R'=R=OH as part of a larger study of similar structures with different substitutions. The relationships between aqueous solution-vacuum variations of some properties were studied, as well as the stabilization and reactivity of (4α→6″, 2α→O→1″)-phenylflavan substituted with R'=R=H, R'=H, R=OH, R'=R=OH, and (+)-catechin. The variations in geometric parameters and electronic properties due to conformational changes, as well as the effects of substituents and polar solvents, were evaluated and analyzed. Bader's theory of atoms in molecules was applied to characterize intramolecular interactions, along with a natural bond orbital analysis for each conformer described. The molecular electrostatic potential was rationalized by charge delocalization mechanisms and interatomic intramolecular interactions, relating them to the structural changes and topological properties of the electron charge density. Molecular polarizability and permanent electric dipole moment values were estimated. The results show the importance of a knowledge of the conformational space, and values for each conformer. Based on our previous results, we showed the existence of electron charge delocalization mechanisms acting cooperatively as "delocalization routes", showing interactions between different rings not even sharing the same plane. These "delocalization routes" were more effective for (4α→6″, 2α→O→1″)-phenylflavan substituted with R'=R=OH than for (+)-catechin, and are proposed as adding insight into the structure-antioxidant activity relationship of flavans.

Qualidade da carne de bovinos terminados em pastejo / Quality of bovine meat finished in grazing / Calidad de la carne de bovinos terminados en pastaje

A carne bovina é uma importante fonte de proteína para alimentação humana, e as exportações de carne contribuem significativamente com a balança comercial brasileira. Entretanto, a conquista e consolidação de novos mercados depende da compreensão que o consumidor tem da qualidade da carne. Com o consumidor mais consciente, o foco da qualidade da carne vem passando do produtor e da indústria (peso da carcaça, rendimento de carcaça, etc.) para o consumidor, com avaliação das características organolépticas e valor nutricional. Apesar do confinamento de bovinos ter crescido nos últimos anos, a terminação a pasto é predominante no país e o rebanho é composto basicamente por animais zebuínos. Esta modalidade de terminação garante a carne características qualitativas particulares, e embora animais terminados em pastejo apresentem carne menos macia e com menos marmoreio, tais características podem ser melhoradas por meio do manejo nutricional e cruzamentos. Já o valor nutritivo da carne tende a ser melhor em animais terminados em pastejo, apresentando menor teor de gordura, e com melhor perfil lipídico, com maior concentração de ácidos graxos insaturados, ácido linoleico conjugado (CLA) e menor relação Ω6:Ω3. Tais características tornam a carne de animais produzidos em pastejo um alimento funcional, podendo ser trabalhado para agregar valor à carne brasileira, que poderá atender a nichos específicos de mercado.

Beef is an important source of protein for human consumption, and meat exports significantly contribute to the Brazilian trade balance. However, the conquest and consolidation of new markets depend on the understanding the consumer has of the quality of meat. With consumers being more aware, the focus of quality meat is shifting from the producer and the industry (carcass weight, carcass yield, etc.) to the consumer, with the evaluation of organoleptic characteristics and nutritional value. Despite the growth in cattle confinement in recent years, the termination in grazing is prevalent in the country and the flock is basically composed of zebu animals. This form of termination ensures the meat presents particular quality characteristics, and although animals finished on grazing have less soft flesh and less marbling, such characteristics can be improved through nutrition management and cross-breeding. The nutritional value of the meat, on the other hand, tends to be better in animals finished on grazing, with less fat, and better lipid profile with higher concentration of unsaturated fatty acids, conjugated linoleic acid (CLA) and lower Ω6:Ω3 relationship. These characteristics make the meat produced from animals in grazing in a functional food, and can bring added value to the Brazilian beef, which can cater to specific niche markets.

La carne bovina es una importante fuente de proteína para la alimentación humana, y las exportaciones de carne contribuyen significativamente con la balanza comercial brasileña. Sin embargo, la conquista y consolidación de nuevos mercados depende de la comprensión que el consumidor tiene de la calidad de la carne. Con el consumidor más consciente, el foco de la calidad de la carne viene pasando del productor y de la industria (peso de caparazón, rendimiento de caparazón, etc.) para el consumidor, con evaluación de las características organolépticas y valor nutricional. A pesar del confinamiento de bovinos haber crecido en los últimos años, la terminación a pasto es predominante en el país y el rebaño es compuesto básicamente por animales cebús. Esta modalidad de terminación garantiza a la carne características cualitativas particulares, y aunque los animales terminados en pastaje presenten carne menos blanda y con menos marmoleo, tales características pueden ser mejoradas a través del manejo nutricional y cruzamientos. Ya el valor nutritivo de la carne tiende a ser mejor en animales terminados en pastaje, presentando menor tenor de grasa, y con mejor perfil lipidio, con mayor concentración de ácidos grasos insaturados, ácido linoleico conjugado (CLA) y menor relación Ω6:Ω3. Tales características hacen la carne de animales producidos en pastaje un alimento funcional, pudiendo ser trabajado para agregar valor a la carne brasileña, que podrá atender a nichos específicos de mercado.