Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties

The contents of pnenolic acids and ferulic acid dehydrodimers were quantified by HPLC analysis after alkaline hydrolysis in kernels of 17 rye (Secale cereale L.) varieties grown in one location in Denmark during 1997 and 1998. Significant variations (P < 0.05) with regard to the concentration of the analyzed components were observed among the different rye varieties and also between different harvest years. However, the content of phenolic acids in the analyzed rye varieties was narrow compared to cereals such as wheat and barley. The concentration of ferulic acid, the most abundant phenolic acid ranged from 900 to 1170 microgram g(-1) dry matter. The content in sinapic acid ranged from 70 to 140 microgram g(-1) dry matter, p-coumaric acid ranged from 40 to 70 microgram g(-1) dry matter, and caffeic, p-hydroxybenzoic, protocatechuic, and vanillic acids were all detected in concentrations less than 20 microgram g(-1) dry matter. The most abundant ferulic acid dehydrodimer 8-O-4 -DiFA was quantified in concentrations from 130 to 200 microgram g(-1) dry matter followed by 8,5 -DiFA benzofuran form (50-100 microgram g(-1) dry matter), 5,5 -DiFA (40-70 microgram g(-1) dry matter), and 8,5 -DiFA (20-40 microgram g(-1) dry matter).     

Regrowth in barley (Hordeum vulgare L.) and rye (Secale cereale L.)

Regrowth after cutting at four development stages, from heading to grain maturity, was investigated in a pot experiment containing three rye and four barley varieties. Regrowth in the barley varieties decreased strongly from heading to grain maturity. Rye generally showed stronger regrowth than barley after late cutting, but only the perennial variety ‘Soperta’ regenerated as many tillers at cutting as formed when harvested at the ripe grain stage. In both species, significant differences were found between varieties. The level of soluble carbohydrates reached a maximum between heading and maturity, but differences in regrowth could not be explained by such differences. Total N decreased from heading to maturity, except for perennial rye, where an increase was observed towards ripening. It is, however, uncertain whether this was an effect rather than a cause of the regrowth.     

Proteolytic activities in dormant rye (Secale cereale L.) grain.

Endoproteolytic, exoproteolytic, carboxypeptidase, aminopeptidase, and N-alpha-benzoyl-arginine-p-nitroanilide hydrolyzing activities were detected in 0.05 M sodium acetate buffer (pH 5.0) extracts of whole meal of the rye (Secale cereale L.) varieties Amando, Halo, and Humbolt. The proteolytic enzymes of Humbolt, the variety with the highest proteolytic activity, optimally hydrolyzed hemoglobin around pH 3.5 and 40-45 degrees C. In the different milling fractions of Humbolt, azocasein and hemoglobin hydrolytic activities were especially found in the bran and shorts. Proteolytic enzymes in the bran extract were concentrated in the 35-60% ammonium sulfate precipitate. Pepstatin A, an inhibitor of aspartic proteases, reduced approximately 88 and approximately 75% of the hemoglobin and azocasein hydrolyzing activities of this precipitate, respectively. Phenylmethanesulfonyl fluoride, an inhibitor of serine proteases, inhibited approximately 33% of both cited activities. Both rye and wheat storage proteins were degraded by Humbolt rye whole meal enzyme extract and the above-mentioned ammonium sulfate rye bran fraction in vitro. With the latter fraction digestion was more pronounced.     

Cultivar and year-to-year variation of phytosterol content in rye (Secale cereale L.)

Intake of phytosterols (and -stanols) has been shown to decrease the level of low-density lipoprotein cholesterol and thus protect against development of cardiovascular diseases. Therefore, studies on the cultivar and year-to-year variation in phytosterol content in rye grains have been performed. The phytosterol content and composition of different rye cultivars, grown under identical conditions on the same field in three consecutive years, were analyzed. Both cultivar and year-to-year variation in sterol content were statistically significant (p < 0.0001). The total sterol content varied from 1007 +/- 21 mg/kg in the highest yielding cultivar, Tsulpan 3, to 761 +/- 10 mg/kg in the lowest yielding cultivar (Amando in the 1999 harvest). Because the meteorological conditions varied substantially between the different years, it was possible to deduce the impact of varying weather conditions on phytosterol content in the different cultivars. The studied cultivars had all the lowest phytosterol contents in the dry and warm harvest season of 1999. Although there were statistically significant cultivar and year-to-year variations in the sterol composition (p < 0.0001), these were only between 2 and 4% of the total sterol content.     

Amplified fragment length polymorphism-based genetic diversity among cultivated and weedy rye (Secale cereale L.) accessions

Amplified fragment length polymorphism markers were evaluated to determine the genetic diversity and relationships among cultivated and weedy ryes (Secale cereale L.) using a large global set of accessions. On the basis of 395 polymorphic bands resulted from nine PstI-MseI primer combinations, cultivated rye exhibited higher average genetic diversity (H_t?=?0.34) than that of the weedy rye (H_t?=?0.27), however, it had lower genetic differentiation (F_st?=?0.16). The average genetic diversity of cultivated rye varied from region to region ranging from 0.21 to 0.31. As expected, all cultivated accessions clustered together both in dendrogram and principal coordinate diagram indicating common breeding program selection criteria based on similar value-added agronomic characteristics. A clustering of cultivated rye accessions into groups based strictly on geographical origin was not found. The relationships among cultivated, weedy and wild ryes were discussed.     

Phosphate sorption by Egyptian,Ethiopian and German soils and P uptake by rye (Secale cereale L.) seedlings

Phosphate sorption was studied in samples (0 - 20 cm depth) of five soils from Egypt (pH 7.4 - 8.7), four soils from Ethiopia (pH 3.9 - 5.3) and six soils from Germany (pH 3.3 - 7.2). Sorption parameters were calculated according to Pagel and Van Huay (1976) and according to Langmuir (Syers et al., 1973). Phosphate sorption parameters and oxalate extractable Fe and Al (Fe_ox, Al_ox) were related to the phosphate uptake by young rye plants in Neubauer pot experiments. P sorption parameter after Pagel and Van Huay (A) correlated significantly positively with the Fe_ox and Al_ox content in acid (r = 0.73) as well as in calcareous soils (r = 0.89) if the whole equilibrium concentration range (0 - 14 mg P/L) was considered. The relations calculated after Langmuir (B) were similar. P uptake by rye in acid soils was negatively correlated with the affinity constant n (r = ?0.76, (A)). In calcareous soils, a negative correlation between P uptake and affinity constant was calculated in the lower P equilibrium range (0 - 2.8 mg P/L) only for (B). Thus, P uptake decreased with increasing strength of P bonding to soil. From these results it is concluded that phosphate sorbed to Fe/Al oxides is an important P source for plants in acid and calcareous soils.     

Grain characteristics, chemical composition, and functional properties of rye (Secale cereale L.) as influenced by genotype and harvest year

Grain characteristic, chemical composition, and functional properties of rye were measured in 19 different cultivars grown in one location in up to 3 years. The cultivars included 8 adapted hybrids, 7 adapted population cultivars, and 4 nonadapted population cultivars. The results showed a significant influence of both harvest year and genotype on grain characteristics, chemical composition, and functional properties of the grain. Multivariate data analysis confirmed that the variations in the data were explained by yearly and genotype differences. Calculations of variance components showed that the variations in plant height, harvest yield, and protein content were mainly due to genotype differences and to a lesser extent to differences among harvest years. The kernel weight, hardness index, and content of dietary fiber components, however, were more strongly influenced by the harvest year than by the genotype. Differences in starch properties measured by falling number (FN), amylograph peak viscosity, and temperature at peak viscosity were more strongly influenced by harvest year. The water absorption was strongly influenced by genotype effects, compared to yearly differences. FN and amylograph peak temperature were positively correlated (r = 0.94). No correlation was found between the water absorption and the relative proportion of water-extractable arabinoxylan (AX) compared to the total AX content. However, the degree of ferulic acid cross-linking showed a negative correlation (r = -0.70) with the water absorption.     

An interim report on a long term storage experiment on rye (Secale cereale L.) under a range of temperatures and atmospheres

A long term seed storage experiment with rye was started in 1978 in the Gatersleben genebank. Seeds of 3.7 and 5.5% moisture content were kept at –15, 0 and 10 °C in hermetically sealed glasses filled with air, CO₂, N₂, and also evacuated. The initial germination was 72% and germination was tested after 1, 5, 15 and 17 years of storage. After 17 years at –15 °C the smallest losses in germination and smallest interactions with the gas atmosphere were observed. At 0 and 10 °C there were greater, but variable losses in germination and inconsistent interactions with the gas atmosphere. Generally, air promoted and N₂ reduced germination loss.     

Studies on rye (Secale cereale L.) lines exhibiting a range of extract viscosities. 1. Composition, molecular weight distribution of water extracts, and biochemical characteristics of purified water-extractable arabinoxylan

Five rye lines exhibiting a wide range of extract viscosities, along with commercial cultivars of rye and wheat, were compared with respect to their physical and chemical properties. Rye wholemeals contained significantly higher concentrations of total and soluble dietary fiber (TDF and SDF, respectively), total and water-extractable arabinoxylan (TAX and WEAX, respectively), and beta-glucan than did wheat. Significant positive correlations were obtained between rye wholemeal extract viscosity and SDF content (r = 0.90, p < 0.05) and WEAX content (r = 0.89, p < 0.05). Gel permeation chromatography (GPC) of water extracts of rye wholemeals revealed the presence of a high molecular weight fraction (HMWF), which was found in higher concentration in the ryes than in wheat. A significant positive correlation (r = 0.84, p < 0.05) was observed between HMWF content (expressed as a proportion of the total carbohydrate in water extracts) and extract viscosity of rye wholemeals. Treatment of a rye wholemeal extract with xylanase, followed by GPC, indicated that the HMWF consisted primarily of WEAX. Successive treatment of a rye wholemeal extract with alpha-amylase, lichenase, protease, and xylanase confirmed that the viscosity of the extract was primarily related to its content of WEAX. WEAX was isolated from high, intermediate, and low extract viscosity ryes. Structural differences were observed among the three arabinoxylans using H NMR and high-pressure size exclusion chromatography with triple detection. The WEAX from high extract viscosity rye was a higher molecular weight macromolecule exhibiting a higher intrinsic viscosity, a larger radius of gyration, a larger hydrodynamic radius, and a lower degree of branching compared to WEAX from low and intermediate extract viscosity ryes.     

Concentrations and allelopathic effects of benzoxazinoid compounds in soil treated with rye (Secale cereale) cover crop

The concentration of benzoxazinoids (BX) was measured in field soils at selected intervals after rye residue was either incorporated or left on the soil surface. The spectrum of compounds arising in the soil persisted approximately two weeks and was dominated by methoxy containing BX compounds, which were only minor components of the rye foliage. Growth assays with lettuce and smooth pigweed species showed inhibition when treated soils were tested during the first two weeks after rye applications; however, there were no sufficient concentrations of any one BX compound in the soil to explain these affects. Solution applications of two pure BX compounds, benzoxazolin-2(3H)-one (BOA) and 6-methoxy-benzoxazolin-2(3H)-one (MBOA), to the surface of soils revealed that movement into the soil column was minimal (greater than 70% BOA and 97% MBOA remained in the top 1-cm of soil profiles) and that the time course for their complete dissipation was less than 24 h.     

Studies on rye (Secale cereale L.) lines exhibiting a range of extract viscosities. 2. Rheological and baking characteristics of rye and rye/wheat blends and feeding value for chicks of wholemeals and breads

Five rye lines exhibiting a wide range of extract viscosities were evaluated for the rheological and baking properties of their flours, individually and in blends with hard red spring wheat flour. Commercial cultivars of rye and triticale were included in the study as controls. Extract viscosities of rye flours were higher than those of corresponding wholemeals, indicating shifting of water-extractable arabinoxylan into flour during roller milling. Falling numbers of the rye flours correlated positively with their extract viscosities in the presence (r = 0.73, p < 0.05) or absence (r = 0.65, p < 0.05) of an enzyme inhibitor. Farinograms revealed the weakness of rye and triticale flours compared to wheat flour. Extract viscosities of rye flours were negatively correlated (r = -0.65, p < 0.05) with mixing tolerance index and positively correlated (r = 0.64, p < 0.05) with dough stability, suggesting a positive impact of extract viscosity on dough strength. Extract viscosity was negatively correlated (r = -0.74, p < 0.05) with loaf volume and specific volume (r = -0.73, p < 0.05) and positively correlated (r = 0.73, p < 0.05) with loaf weight of rye/wheat bread. Overall, the results indicated that 30% of flour from high or low extract viscosity rye could be incorporated into rye/wheat breads without seriously compromising bread quality. Inclusion of rye, particularly high extract viscosity rye, in chick diets seriously impeded growth performance and feed efficiency. Part of the arabinoxylan survived bread-making and exerted an effect on chicks, although substantially lower digesta viscosities were observed in chicks fed rye bread diets than in those fed rye wholemeals.     

Variation of agronomic and qualitative traits and local adaptation of mountain landraces of winter rye (Secale cereale L.) from Val Venosta/Vinschgau (South Tyrol)

Landraces are thought to be well adapted to the environmental conditions of the region where they have evolved and to be highly tolerant to biotic and abiotic stress. There is indeed experimental evidence of that for several cereal species, but to our knowledge only scarce data is available on rye and none on rye landraces from South Tyrol in particular. For this region, assumptions rely mainly on historic documents or reports from the owners of the landraces. In a 3-year field experiment we described 13 landraces from Val Venosta/Vinschgau (South Tyrol, Italy), along with six modern population cultivars (CUL), at a mountain location. Depending on the available passport data, the landraces were assigned to two variety types: well documented landrace status (DLS) and uncertain landrace status (ULS). 14 traits concerning phenology, agronomy, indirect milling and baking quality as well as seed colour were investigated. Most of the traits representing the usual target of modern breeding were found to be dependent on the variety type. The results reflect well the expected differences between CUL and DLS, while ULS had an intermediate character. Winter hardiness and ripening time of both DLS and ULS, however, were found to be affected by the altitude of the site at which the landraces were collected, suggesting a certain adaptation of the landraces to the climatic conditions at the sites of origin.     

Phenotypic Variation and Relationships in Landraces and Improved Varieties of Rye (Secale cereale L.) from Northern Europe

Phenotypic diversity for agronomic characteristics was determined in an experiment with 29 landraces and 14 improved varieties of rye from the Nordic area, Germany and Poland. The accessions were scored for 12 characters. Effects of the location, year, type, and country of origin for landraces were investigated with analysis of variance. Phenotypic variations for the traits were estimated using the Shannon–Weaver diversity index. The genetic variation was high, with an average of H ₀ = 0.566. The landraces from Norway, Sweden and Finland showed the highest variation, whereas the improved varieties had the lowest. The German material also had low variation but the status of this material is uncertain. The genetic diversity showed that 70% of the variation was found within the accessions. A cluster analysis was carried out to identify the relationship between the accessions. The material grouped into eight clusters, where clusters I to V included landraces from Sweden, Finland and Norway, except for cluster III, which included one improved variety from Denmark. Cluster VI comprised a single Swedish landrace from Gotland. Most of the improved varieties were in cluster VII and the last cluster contained accessions from Germany and Sweden.     

4-hydroxycinnamic ethyl ester derivatives and related dehydrodimers: Relationship between oxidation potential and protective effects against oxidation of low-density lipoproteins

The electrochemical oxidation potential of a series of monomeric and dimeric 4-hydroxycinnamic ethyl ester derivatives has been compared with their antioxidant activity toward copper-catalyzed human low-density lipoproteins (LDL) oxidation. Within the series of monomeric hydroxycinnamate derivatives, both oxidation potential and IC50 values decreased in the following order: sinapate > ferulate > p-coumarate. Among the 4-hydroxycinnamate dehydrodimer derivatives, noncyclized 8-8 diphenol dehydrodimers followed the same aforementioned sequence order and were found to be better antioxidants than their monomer counterparts. A good correlation between the inhibitory concentration and the oxidation potential was established among all these derivatives. However, a significantly deviating behavior was observed with the 8-5 dihydrobenzofuran and the 8-8 dihydronaphthol cyclic dehydrodimers, which showed lower activities toward copper-catalyzed human LDL, although their oxidation potentials remained very close to those of the noncyclized 8-8 dehydrodimers. Conversely, in the Trolox equivalent antioxidant capacity (TEAC) assay system, the 8-8 dihydronaphthol dehydrodimers were found to be the most efficient free-radical scavengers. Finally, in the series of dehydrodimers studied, it could be concluded that, whatever the in vitro test system used, (a) all dehydrodimer derivatives tested could contribute efficiently to the overall intake of antioxidants in the diet and (b) a low oxidation potential value was in favor of a satisfactory antioxidant activity.     

Vermicompost from municipal sewage sludge affects growth and mineral nutrition of winter rye (Secale cereale) plants

The aim of the study was to investigate sewage sludge vermicompost application effects on growth and mineral nutrition of winter rye (Secale cereale L.) plants as compared to two initial levels of mineral nutrient availability, pure sand and sand enriched with inorganic nutrients at the optimal level. Addition of sewage sludge vermicompost significantly inhibited rye seed germination at 20 to 50% sand substitution independently on mineral nutrient supplement. Growth inhibition was evident at early stages of plant development. However, at the later stages, sewage sludge vermicompost acted both as mineral fertilizer and plant growth-promoting agent. Significant stimulation of mineral uptake was seen only at high rates of vermicompost substitution (40 and 50%) already causing decrease in shoot dry matter accumulation. Vermicompost substitution resulted in a significant increase of leaf chlorophyll content. Beneficial effect of sewage sludge vermicompost in conditions of optimal mineral supply can result mainly from plant growth-promoting activity.     

Antioxidant capacity and phenolic content in leaf extracts of tree spinach (Cnidoscolus spp.)

Total phenolic content and antioxidant capacity of two tree spinach species (Cnidoscolus chayamansa McVaugh and C. aconitifolius Miller.) were determined in raw and cooked leaf extracts. Antioxidant capacity was assessed by the oxygen radical absorbance capacity (ORAC) assay, and flavonoid glycoside composition was quantified by HPLC and identified by GC. Total phenolics and antioxidant capacity were higher in raw than in cooked leaf extracts. The ORAC values were strongly correlated with total phenolic content (r = 0.926) in all leaf extracts. The major flavonoids isolated from the leaf extracts were kaempferol-3-O-glycosides and quercetin-3-O-glycosides. C. aconitifolius leaves contained more varieties of the flavonoid glycosides than C. chayamansa. Cooking reduced antioxidant activity and phenolic content and resulted in losses of some kaempferol glycoside and quercetin glycoside residues in leaf extracts. The results of this study indicate that tree spinach leaves are a rich source of natural antioxidants for foods.     

Antioxidant effects of water extracts from barley (Hordeum vulgare L.) prepared under different roasting temperatures

The antioxidant effects of water extracts of roasted barley (WERB) were investigated under different roasting temperatures and compared with those of the water extracts of unroasted barley (WEUB). It was found that the Maillard reaction products increased upon increasing the roasting temperatures. Both WERB and WEUB exhibited significant antioxidant activities in linoleic acid and liposome model systems. Although WERB and WEUB afforded considerable protection against the damage of deoxyribose and proteins, the antioxidant efficiency of roasted samples was weaker than that of unroasted samples because of the reduction of antioxidant components (catechin, tocopherol, and lutein) with increasing roasting temperature. Unroasted samples were more effective in reducing power, quenching free radical, hydroxyl radical, and chelating iron than the roasted samples. The different antioxidant activity among roasted and unroasted barley samples may be partly attributed to the changes in catechin, tocopherol, and lutein contents.     

Antioxidant capacity of oat (Avena sativa L.) extracts. 1. Inhibition of low-density lipoprotein oxidation and oxygen radical absorbance capacity

Milled oat groat pearlings, trichomes, flour, and bran were extracted with methanol and the fractions tested in vitro for antioxidant capacity against low-density lipoprotein (LDL) oxidation and R-phycoerythrin protein oxidation in the oxygen radical absorbance capacity (ORAC) assay. The oxidative reactions were generated by 2,2'-azobis(2-amidinopropane) HCl (AAPH) or Cu(2+) in the LDL assay and by AAPH or Cu(2+) + H(2)O(2) in the ORAC assay and calibrated against a Trolox standard to calculate Trolox equivalents (1 Trolox equivalent = 1 TE = activity of 1 micromol of Trolox). The antioxidant capacity of the oat fractions was generally consistent with a potency rank of pearlings (2.89-8.58 TE/g) > flour (1.00-3.54 TE/g) > trichome (1.74 TE/g) = bran (1.02-1.62 TE/g) in both LDL and ORAC assays regardless of the free radical generator employed. A portion of the oat antioxidant constituents may be heat labile as the greatest activity was found among non-steam-treated pearlings. The contribution of oat tocols from the fractions accounted for <5% of the measured antioxidant capacity. AAPH-initiated oxidation of LDL was inhibited by the oat fractions in a dose-dependent manner, although complete suppression was not achieved with the highest doses tested. In contrast, Cu(2+)-initiated oxidation of LDL stimulated peroxide formation with low oat concentrations but completely inhibited oxidation with higher doses. Thus, oats possess antioxidant capacity most of which is likely derived from polar phenolic compounds in the aleurone.     

Antioxidant capacity of oat (Avena sativa L.) extracts. 2. In vitro antioxidant activity and contents of phenolic and tocol antioxidants

Oat milling fractions were examined for concentrations of total phenolics, tocols, and phenolic acids and in vitro antioxidant activity to determine their potential as dietary antioxidants. Methanolic extracts of pearling fractions, flour and aspirations from flaking, and trichomes had high, intermediate, and low antioxidant activities, respectively, evaluated by the beta-carotene bleaching method. Pearling fractions were also highest in total phenolics and tocols. p-Hydroxybenzoic acid, vanillic acid, caffeic acid, vanillin, p-coumaric acid, and ferulic acid were identified and quantified by HPLC. Three avenanthramides and an unidentified ferulate derivative were also detected. Total phenolic content was significantly correlated with antioxidant activity, and regression equations that predicted antioxidant activity from phenolic and tocol concentrations were calculated. Antioxidant activity, evaluated by beta-carotene bleaching, was correlated with measures of oxygen radical absorbance capacity and low-density lipoprotein oxidation. These data indicate a potential for oat products, especially those enriched in outer layers of the groat, to contribute to dietary intakes of antioxidant phytonutrients.     

铝胁迫下黑麦根尖分泌有机酸和钾离子的研究

采用药理学研究方法,研究了几种抑制剂和脱落酸对铝诱导黑麦根尖分泌有机酸和钾离子的影响。结果表明,在铝(100、200、300μmol/L AlCl3)胁迫下,根尖分泌柠檬酸、苹果酸和钾离子,且随着铝处理浓度的增加其分泌量显著增加。阴离子通道抑制剂苯甲酰甲醛(0.1、0.2 mmol/L)抑制根尖在铝(200μmol/L AlCl3)胁迫下分泌有机酸的同时,也抑制根尖分泌钾离子;钾离子通道抑制剂四乙基铵(20、40 mmol/L)和铯(10、20 mmol/L CsCl)在抑制根尖分泌钾离子的同时,也抑制铝诱导的有机酸分泌。25、50μmol/L的ABA处理后,铝诱导的有机酸分泌和钾离子的分泌均显著增加。但是,铝诱导的有机酸分泌在受到阴离子通道抑制剂尼氟灭酸(0.4、0.8 mmol/L)处理抑制后,钾离子的分泌并不减少;铝胁迫下根尖分泌的钾离子在ATP酶抑制剂钒酸钠(0.25、0.50、2.00 mmol/L)处理后受阻的同时,有机酸的分泌却显著增加。这些结果说明,钾离子是铝诱导黑麦根尖分泌有机酸的陪伴离子,而并非有机酸分泌的调控因子。