Farmacología de Terpenoides de Helianthus annuus L / Pharmacology of Terpenoids from Helianthus annuus L

Desde los albores de la humanidad, las plantas han sido fuente de interés porsus características nutricionales y medicinales. Por ello, se realizó un estudio farmacológicode terpenoides de Helianthus annuus L., optimizando un método deextracción, aislamiento y purificación de dichos metabolitos, para evaluar unaposible actividad farmacológica sobre modelos de inflamación. También se evaluóuna potencial actividad antiinflamatoria utilizando extractos (metanólico y acuoso)de la planta. Se aislaron tres diterpenos, dos kauranos y un traquilobano, mediantetécnicas cromatográficas, identificándose sus estructuras por RMN (1H, 13C) y evaluando su pureza por HPLC. Paralelamente se evaluó la variación estacional delácido grandiflorólico y de la mezcla de ácido kaurenoico y traquilobánico obtenida,en diferentes sumidades de la planta durante su desarrollo, con el fin de determinardónde y cuándo se produce una máxima acumulación del metabolito estudiado,para así obtener una extracción con un mayor rendimiento. Se encontrarondiferencias significativas útiles para el control de calidad de preparados a base deplantas medicinales que contengan algunos de estos metabolitos secundarios. Parael estudio de la actividad farmacológica de los terpenoides y de los extractos, setrabajó sobre dos modelos de inflamación (in vivo e in vitro). En el modelo in vivose evaluó la acción de los compuestos sobre el edema producido por aplicacióntópica de TPA en oreja de ratón, evaluando en paralelo la infiltración leucocitariaen términos de actividad mieloperoxidasa. En este modelo los ácidos kaurenoicoy traquilobánico demostraron actividad antiinflamatoria. En el modelo in vitro seutilizaron cultivos celulares de una línea de macrófagos, evaluando la actividad delos compuestos sobre la liberación de mediadores inflamatorios (NO, PGE2 y TNFa),y sobre la enzima COX, donde se observó que el ácido grandiflorólico y elextracto metanólico mostraron actividad inhibidora sobre la liberación de estosmediadores, además el ácido grandiflorólico mostró actividad inhibidora de laenzima COX. Sin embargo, no se descarta que en las actividades antiinflamatoriasde dichos compuestos estén implicados otros mediadores

Since the dawn of the humanity plants have been a source of interest becauseof their nutritional and medicinal characteristics. For that reason, a pharmacologicstudy of the terpenoids of Helianthus annuus L. was done, optimizing a method ofextraction, isolation and purification of these metabolites in order to evaluate apossible pharmacologic activity in inflammation models. Also, potentialantiinflammatory activity was evaluated using extracts (methanolic and watery) ofthe plant. Three diterpenes, two kauranes and a trachylobane were isolated, bymeans of chromatographic techniques; their structures were identified by RMN(1H, 13C) and their purity was evaluated by HPLC. Parallelly, the seasonal variationof grandiflorolic acid and kaurenoic and the trachylobanic acid mixture obtainedwas evaluated, in different above-ground parts from the plant during itsdevelopment, with the purpose of determining where and when the highestaccumulation of the studied metabolite occurs thus to obtain an extraction withthe greatest yield. Useful significant differences were found for the quality controlof preparations with medicinal plants that contain some of these secondarymetabolites. For the study of the pharmacologic activity of the terpenoids and theextracts, two models of inflammation (in vivo and in vitro) were worked on. In thein vivo model, the action of compounds was evaluated on edema produced by topical application of TPA in mouse ear, evaluating in parallel the leucocitaryinfiltration in terms of mieloperoxidase activity.In this model the kaurenoic and trachylobanic acids demonstratedantiinflammatory activity. In the in vitro model cellular cultures of a line ofmacrophages were used, the activity of compounds on the liberation ofinflammatory mediators (NO, PGE2 and TNF-a), and the COX enzyme wereevaluated, where it was observed that the grandiflorolic acid and the methanolicextract showed inhibiting activity on the liberation of these mediators. Also, thegrandiflorolic acid showed inhibiting activity on the COX enzyme. However, onedoes not rule out other mediators being implicated in the antiinflammatory activities of these said compounds

Acidos grasos esenciales en la producción actual de oleaginosas de la República Argentina: posibilidades futuras de diversificación / Essential fatty acids in the present vegetable oils production of the República Argentina: future possibiities in the diversification trends production

Se presenta un resumen de los logros alcanzados durante casi 50 años en un tema fundamental del conocimiento de las características de composición acídica de aceites vegetales de producción masiva en la república Argentina. Su desarrollo, en parte coincidente con la evolución del conocimiento analítico, ha sido de utilidad a la nutrición, normalización, legislación alimentaria, tecnología, uso y contralor de aceites vegetales y de pulpa de frutos. El progreso observado en los avances de modernas técnicas de la Biotecnología tiende a una apertura en la diversificación de la producción

Acidos grasos esenciales en la producción actual de oleaginosas de la República Argentina: posibilidades futuras de diversificación / Essential fatty acids in the present vegetable oils production of the República Argentina: future possibiities in the diversification trends production

Se presenta un resumen de los logros alcanzados durante casi 50 años en un tema fundamental del conocimiento de las características de composición acídica de aceites vegetales de producción masiva en la república Argentina. Su desarrollo, en parte coincidente con la evolución del conocimiento analítico, ha sido de utilidad a la nutrición, normalización, legislación alimentaria, tecnología, uso y contralor de aceites vegetales y de pulpa de frutos. El progreso observado en los avances de modernas técnicas de la Biotecnología tiende a una apertura en la diversificación de la producción

Absolute configurations of three ent-beyerene derivatives.

(1): 11 beta,17-Bis(4-bromobenzoyloxy)-9 beta-hydroxy-ent-beyerene, C34H38Br2O5, Mr = 686.5, orthorhombic, P2(1)2(1)2(1), a = 6.1686 (12), b = 14.613 (3), c = 32.935 (7) A, V = 2969 (1) A3, Z = 4, Dx = 1.536 g cm-3, lambda(Mo K alpha) = 0.71069 A, mu = 27.43 cm-1, F(000) = 1408, T = 173 K, R = 0.0347 and wR = 0.0358 for 3064 reflections [Io greater than or equal to 3 sigma(Io)]. (2): 7 beta,17-Bis(4-bromobenzoyloxy)-9 beta-hydroxy-ent-beyerene, C34H38Br2O5, Mr = 686.5, monoclinic, P2(1), a = 12.6424 (15), b = 6.8353 (12), c = 18.496 (2) A, beta = 101.901 (9) degrees, V = 1564.0 (4) A3, Z = 2, D chi = 1.458 g cm-3, lambda(Mo K alpha) = 0.71073 A, mu = 26.03 cm-1, F(000) = 704, T = 173 A, R = 0.0336 and wR = 0.0361 for 4610 reflections [Io greater than or equal to 3 sigma(Io)]. (3): 17-(4-Bromobenzoyloxy)-9 beta,11 beta-epoxy-7 beta-hydroxy-ent-beyerene, C27H33BrO4, Mr = 501.5, orthorhombic, P2(1)2(1)2(1), a = 6.1315 (7), b = 18.389 (3), c = 21.109 (3) A, V = 2380.0 (6) A3, Z = 4, D chi = 1.399 g cm-3, lambda(Mo K alpha) = 0.71073 A, mu = 17.38 cm-1, F(000) = 1048, T = 198 K, R = 0.0325 and wR = 0.0344 for 2292 reflections [Io greater than or equal to 3 sigma(Io)].(ABSTRACT TRUNCATED AT 250 WORDS)

Bifunctional lipid-transfer: fatty acid-binding proteins in plants.

A cytosolic protein, able to facilitate intermembrane movements of phospholipids in vitro, has been purified to homogeneity from sunflower seedlings. This protein, which has the properties of a lipid-transfer protein (LTP), is also able to bind oleoyl-CoA, as shown by FPLC chromatography. This finding, in addition to previous observations suggesting that a lipid-transfer protein from spinach leaves can bind oleic acid and that oat seedlings contain a fatty acid-binding protein with similar features than lipid transfer proteins, provides a clear demonstration that plant cells contain bifunctional fatty acid/lipid transfer proteins. These proteins can play an active role in fatty acid metabolism which involves movements of oleyl-CoA between intracellular membranes.

Fructans of Jerusalem artichokes: intestinal transport, absorption, fermentation, and influence on blood glucose, insulin, and C-peptide responses in healthy subjects.

Fructans are naturally occurring plant oligosaccharides with sweetening properties. Fructans (FAs) isolated from Jerusalem artichokes (Helianthus tuberosus) were studied with respect to intestinal handling and influence on blood glucose (BG), insulin, and C-peptide responses in eight healthy subjects. The responses were compared with those for fructose ingestion. The effect of FAs added to a wheat-starch meal was also studied. Standardized breath-hydrogen excretion indicated that FAs were completely malabsorbed and, after a 20-g dose, traces of FA were detected in 24-h urine collections in one subject only. Orocecal transit times were longer for FAs than for lactulose and fructose. The BG and insulin increments were very low after FA ingestion, lower than after fructose ingestion, whereas hydrogen production was much higher. Areas under BG curves tended to be smaller when 10 g FA was added to a 50-g wheat-starch meal, but there was no apparent interference with starch absorption.

Regulatory domains of the Gmhsp17.5-E heat shock promoter of soybean.

Promoter domains required for in vivo transcriptional expression of soybean heat shock gene Gmhsp17.5-E were identified by insertion-deletion mutagenesis with transgenic expression monitored in Agrobacterium tumefaciens-incited tumors of sunflower. Removal of the TATA-distal domain from position -1175 to position -259 had little effect on overall activity. The four regions contributing to promoter activity identified by this study all map within 244 base pairs from the start of transcription. The most distal cis-acting element of major significance was located from -244 to -179 and contains a conserved TATA-dyad motif centered at -220. Sequences from -179 to -40 comprise the TATA-proximal domain and include an AT-rich region and two sites containing heat shock consensus elements (HSEs). Deletion of the HSE centered at -93 (site 2) severely reduced transcriptional activity. Heat-inducible expression was also eliminated by internal deletion of either the TATA motif or the overlapping HSEs at site 1, indicating that each of these regions is also a major determinant of promoter activity.

[Animal experimento-toxicologic studies of protein isolates in sunflower seeds]. / Tierexperimentell-toxikologische Untersuchungen von Proteinisolaten aus Sonnenblumensamen.

Safety evaluations of sunflower protein isolates (SPI) obtained by various processes were performed in subchronic (90-day) feeding studies using male and female rats as experimental animals. General appearance, food consumption and efficiency, haematology, kidney function and urine analysis, serum chemistry including determinations of enzyme activities, organ weights and macro- and microscopic pathology were used as criteria to disclose adverse effects. Feeding graded levels of SPI as supplements up to 75% of the total protein of the diet revealed no morphologic and functional changes attributable to toxic effects of the test product at daily intakes up to 13 g/kg body weight. The evaluations of the SPI-variants tested were similar.

Metabolic changes in healthy men using fat-modified diets. I. Disposition of serum cholesterol.

The effect of typical fat-modified diets on serum lipids, lipoproteins and apolipoproteins, on the intravenous fat-tolerance test and on fecal sterol excretion were observed in a group of men living at home and compared to that of their normal diets. Two 4-week-long diet periods alternated with four periods of 6 weeks' duration during which the men followed their normal dietary habits and accustomed life-styles. According to a randomized cross-over design sunflower oil and corn oil were used as the main fat sources for the fat-modified diets. Both diets lowered total cholesterol considerably acting mainly on LDL cholesterol, without affecting plasma triglycerides significantly. Apolipoprotein A-I and A-II concentrations in serum remained constant, and clearance of triglyceride-rich lipoproteins, as measured by an intravenous fat-tolerance test (Intralipid test), was not significantly affected. While changes of all measured parameters pointed in the same direction, serum total and LDL cholesterol levels were significantly lower with corn oil than with the sunflower oil. Excretion of endogenous sterols (fecal sterol balance) was higher with the fat-modified than with the normal diet. This increase in sterol excretion closely corresponded to the extent of serum cholesterol lowering.

Sesquiterpene lactones and flavonoids from Helianthus species.

From the leaves and the flowers of Helianthus glaucophyllus and Helianthus microcephalus, three new guaianolides were isolated. H. microcephalus afforded another two new guaianolides, the highly unsaturated guaianolide, the flavane, the flavone, and three flavonols. Structures of all the compounds were determined by spectral analysis.

[The quality of protein-enriched products from sunflower seeds. 1. The effect of various production processes on the nutritive value of meals and protein isolates]. / Untersuchungen zur Qualität proteinangereicherter Produkte aus Sonnenblumensamen. 1. Mitt. Einfluss unterschiedlicher Gewinnungsverfahren auf den nutritiven Wert von Mehlen und Proteinisolaten.

Globulin isolates from native sunflower seed and industrial extraction meal obtained by extraction with different electrolyte solutions and subsequent isoelectric precipitation are relatively poor in the essential amino acids lysine, threonine, and methionine as compared to defatted seed meals. On the other hand, albumins separated by means of polyanionic complexing agents (sodium alginate and aluminium potassium sulphate) are relatively rich in these amino acids, and albumin-globulin-co-precipitates have a correspondingly balanced amino-acid composition, being also reflected by nutrition physiological values as BW, NPU, and EAA-index. As compared to seed meals protein isolates are characterized furthermore by a better protein digestibility.

Physicochemical properties of oilseed proteins.

This review attempts to consolidate the information on the physicochemical properties of proteins from groundnut, soybean, sesame seed, mustard seed, rapeseed, sunflower seed, cottonseed, and other oilseeds. It deals with the extraction and characterization of the oilseed proteins and describes the methods for isolation of the various protein fractions and determination of their physicochemical characteristics. Also discussed are the subunit composition of the oligomeric proteins, their hydrodynamic properties, and the effect of denaturants on these proteins. The similarity in the properties of the proteins from various oilseed materials is discussed. The review article aims to indicate the gaps in our knowledge about the physicochemical properties of oilseed proteins and suggests areas for future investigation.

Response of Japanese quail fed seed meal from sunflowers grown on a municipal sludge-amended soil: elevation of cadmium in tissues.

Sunflowers were grown on soil amended with 224 metric tons/ha of municipal sewage sludge from Syracuse, N.Y. The yield of sunflower seeds was reduced by 47.2% by the sludge addition. The harvested seeds contained 1.71 ppm dry weight of cadmium. Deoiled seed meal was incorporated as 25 and 50% of semipurified diet and fed to male and female Japanese quail. The concentrations of cadmium were higher in kidney, liver, muscle, and eggs of birds fed the sludge-grown seed meal as compared to control quail. Tissue concentrations of cadmium increased with increasing dietary levels of sludge-grown seed meal. No significant differences (p greater than 0.05) were observed between dietary treatments in the activity of hepatic microsomal p-nitroanisole O-demethylase or aminopyrine N-demethylase in the male birds. Additionally, no mutagenic activity, either direct or with metabolic activation, was found in quail eggs. No observable changes in tissue ultrastructure were observed under electron microscopy in any of the treatment groups. There were no significant (p greater than 0.05) differences among the dietary treatment groups in feed intake, growth rate, egg production, or egg hatchability.

Determination of fat in vegetable foods.

The fat in vegetable foods--tree nuts, peanuts, sunflower seeds, avocado, and olives--can be determined volumetrically by acid digestion of the material and separation of the fat. The assay can be performed conveniently by using the equipment developed for fat determination of milk (Gerber method). The results agree well with those obtained by Soxhlet extraction. The advantages of using the Gerber method for vegetable foods are simplicity, speed, low operation cost, and elimination of the use of inflammable solvents.

Determination of sterol and triterpene alcohol acetates in natural products by reversed-phase liquid chromatography and gas chromatography-mass spectrometry.

A partial separation of nine sterol acetates and seven triterpene alcohol acetates by reversed-phase liquid chromatography is described. Good results are obtained using acetonitrile-water (90:10, v/v) as mobile phase with an UV detector at 205 nm. The variation in sterol sensitivity shows that this technique is not suitable for quantitative analyses. A combination of this technique for the fractionation of the natural sterol mixture, gas-liquid chromatography for quantitation and gas chromatography-mass spectrometry for identification is necessary for the determination of sterol compounds contained in natural products. An example of the separation, identification and quantitation of sterol acetates from sunflower seed oil is given.

High cadmium and nickel contents in sunflower kernels.

High cadmium and nickel contents in sunflower kernels intended for human consumption are reported. The cadmium contents of 55 samples from North America and Europe were 0.25-0.69 mg/kg with averages from different countries of 0.32-0.54 mg/kg. The contents in kernels from bird seeds (i.e. animal feed) from China and Egypt were much lower. The cadmium content of sunflower kernels for human consumption might pose a risk to human health. Danish authorities recommend the Danish consumers do not eat large amounts of sunflower kernels for a long period of time. The nickel contents of 25 of the samples of kernels for human consumption were 2.3-5.3 mg/kg. This is comparable with that found in different kinds of nuts with high nickel contents.