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PubMed1988

Immunological properties of chemically produced fragments of rye grass pollen extract.

Two fragment pools, one of MW greater than 10,000 and the other of MW between 1,000 and 10,000, were prepared by the sequential treatment of rye grass pollen extract with cyanogen bromide (cleavage at Met-X) and 2-nitro-5-thiocyanobenzoic acid (cleavage at X-Cys). Electrophoretic analysis of the two pools showed that none of the major components of the whole extract remained intact. Characterisation of the two fragment pools by radioimmunoassay showed that whilst they both lost the ability to bind to human anti-rye IgE antibodies, they largely retained their reactivity towards both human and mouse anti-rye IgG antibodies. In addition, the higher molecular weight pool retained its ability to stimulate extract-specific T cells, after accessory cell processing. This separation of the immunological properties of rye grass pollen extract by chemical cleavage is seen as a basis for the development of novel immunotherapy agents.

Animals↗
PubMed2005

Effects of yeasts and bacteria on the levels of folates in rye sourdoughs.

Fermentation of rye dough is often accompanied with an increase in folate content. In this study, three sourdough yeasts, Candida milleri CBS 8195, Saccharomyces cerevisiae TS 146, and Torulaspora delbrueckii TS 207; a control, baker's yeast S. cerevisiae ALKO 743; and four Lactobacillus spp., L. acidophilus TSB 262, L. brevis TSB 307, L. plantarum TSB 304, and L. sanfranciscensis TSB 299 originally isolated from rye sourdough were examined for their abilities to produce or consume folates. The microorganisms were grown in yeast extract-peptone-d-glucose medium as well as in small-scale fermentations that modelled the sourdough fermentation step used in rye baking. Total folate contents were determined using Lactobacillus rhamnosus (ATCC 7469) as the growth indicator organism. The microorganisms studied did not excrete folates into the media in significant amounts. Yeasts increased the folate contents of sterilised rye flour-water mixtures from 6.5 microg/100 g to between 15 and 23 microg/100 g after 19-h fermentation, whereas lactic acid bacteria decreased it to between 2.9 and 4.2 microg/100 g. Strains of Lactobacillus bulgaricus, L. casei, L. curvatus, L. fermentum, L. helveticus, Pediococcus spp., and Streptococcus thermophilus that were also tested gave folate contents after fermentation that varied between 2 and 10.4 microg/100 g. Although the four Lactobacillus spp. from sourdough consumed folates their effect on folate contents in co-cultivations was minimal. It was concluded that the increase of folate content during fermentation was mainly due to folate synthesis by yeasts. Fermentation of non-sterilised flour-water mixtures as such resulted in three-fold increases in the folate contents. Two folate producing bacteria were isolated from the non-sterilised flour and identified as Enterobacter cowanii and Pantoea agglomerans.

Bread↗
PubMed1992

Calorimetric and x-ray diffraction studies of rye glucocerebroside mesomorphism.

Glucocerebrosides (GlcCer) isolated from the leaves of winter rye (Secale cereale L. cv Puma) differ from the more commonly investigated natural and synthetic cerebrosides, in that greater than 95% of the fatty acids are saturated and monounsaturated hydroxy fatty acids. Isomers of the trihydroxy long chain base hydroxysphingenine (t1(8:18 cis or trans)) and isomers of sphingadienine (d18:2(4trans, 8 cis or trans)) comprise 77% and 17%, respectively, of the total long chain bases. The phase behavior of fully hydrated and dry rye leaf GlcCer was investigated using differential scanning calorimetry (DSC) and x-ray diffraction. On initial heating, aqueous dispersions of GlcCer exhibit a single endothermic transition at 56 degrees C and have an enthalpy (delta H) of 46 J/g. Cooling to 0 degrees C is accompanied by a small exothermic transition (delta H = -8 J/g) at 8 degrees C. On immediate reheating, a broad exothermic transition (delta H = -39 J/g) is observed between 10 and 20 degrees C in addition to a transition at 56 degrees C. These transitions are not reversible, and the exothermic transition rapidly diminishes when the sample is held at low temperature. Using x-ray diffraction, it was determined that the endotherm at 56 degrees C represents a transition from a highly ordered lamellar crystalline phase (Lc) with a d-spacing of 57 A and a series of wide-angle reflections in the 3-10 A range, to a lamellar liquid crystalline (L alpha) phase having a d-spacing of 55 A and a diffuse wide-angle scattering peak centered at 4.7 A. Cooling leads to the formation of a metastable gel phase (L beta) with a d-spacing of 64.0 A and a single broad reflection at 4.28 A. Subsequent warming to above 15 degrees C restores the original Lc phase. Thus, rye GlcCer in excess water exhibit a series of irreversible transitions and gel phase metastability. Dry GlcCer undergo an initial heating endothermic transition at 130 degrees C, which is ascribed to a transformation into the HII phase from a two phase state characterized by the coexistence of phases with disordered (alpha) and helical (delta) type chain conformations but of unknown lattice identity: An exotherm at 67.5 degrees C observed upon subsequent cooling is of unknown origin. Since an undercooled HII phase persists down to 19 degrees C, the exotherm may derive in part from an alpha-to-delta type chain packing conformational change especially under slow cooling conditions. Upon reheating from low temperatures to 65 degrees C, a phase with a two-dimensional, primitive rectangular lattice and delta-like chain packing (R8 phase) in coexistence with the HI, phase emerges. With continued heating to 90 degrees C these coexisting phases give way to a phase with a two-dimensional, centered rectangular lattice and delta-like chain packing (P8phase) which again coexists with the HI, phase. Above 130 degrees C, the Pb phase disappears and the sample converts completely to the HI, phase as observed upon initial heating. These results indicate that the mesomorphic behavior of rye leaf GIcCer is distinct from that of other cerebrosides.

Biophysical Phenomena↗
PubMed2001

The ABC-like vacuolar transporter for rye mesophyll flavone glucuronides is not species-specific.

In many cases, the vacuolar uptake of secondary metabolites has been demonstrated to be strictly specific for a given compound and plant species. While most plants contain glycosylated secondary substances, few cases are known where flavonoids may also carry negative charges, e.g. as glucuronide conjugates. Vacuolar transport of glucosylated phenylpropanoid derivatives has been shown to occur by proton substrate antiport mechanisms (Klein, M., Weissenböck. G., Dufaud, A., Gaillard, C., Kreuz, K., Martinoia, E., 1996. Different energization mechanisms drive the vacuolar uptake of a flavonoid glucoside and a herbicide glucoside. J. Biol. Chem. 271, 29,666-29,671). In contrast, flavone glucuronides appearing specifically in rye mesophyll vacuoles are taken up by direct energisation utilising MgATP, strongly arguing for the presence of an ATP-binding cassette (ABC) transporter belonging to the subfamily of multidrug resistance-associated proteins (MRP) on the rye vacuolar membrane (Klein, M., Martinoia, E., Hoffmann-Thoma, G., Weissenböck, G., 2000. A membrane-potential dependent, ubiquitous ABC-like transporter mediates the vacuolar uptake of rye flavone glucuronides regulation of glucturonide uptake by glutathione and its conjugates. Plant Journal 21, 289-304). MRPs are known to transport negatively charged organic anions. Results presented here suggest that the vacuolar directly energised MRP-like glucuronate pump for plant-specific flavone glucuronides is ubiquitously present in diverse plant species since rye flavone glucuronides are taken up into vacuoles isolated from the barley mesophyll or from the broccoli stalk parenchyma representing two species which do not synthesise glucuronidated secondary compounds. According to the transport characteristics and inhibition profile observed we propose the existence of a high-capacity, uncoupler-insensitive vacuolar ABC transporter for flavone glucuronides and possibly other negatively charged organic compounds -- plant-born or xenobiotic -- irrespective of the plant's capability to endogenously produce glucuronidated compounds.

ATP-Binding Cassette Transporters↗
PubMed2007

Metabolic profiling of liver from hypercholesterolemic pigs fed rye or wheat fiber and from normal pigs. High-resolution magic angle spinning 1H NMR spectroscopic study.

This study presents the first application of a high-resolution magic angle spinning 1H NMR approach to elucidate the metabolic effects of a hypercholesterolemic condition and two high-fiber diets based on rye and wheat bread, respectively, in intact pig liver biopsy samples. Standard 1D and spin-echo 1H spectra were acquired on a total of 20 biopsy samples, and 2D total correlation spectroscopy experiments were carried out on selected samples for assignment of the observed resonances. Principal component analyses and partial least-squares regression discriminant analysis revealed differences in the hepatic lipid content and choline-containing compounds between normal and hypercholesterolemic pigs. In addition, the results demonstrated that the liver metabolite profile of hypercholesterolemic pigs fed a high-fiber rye bread differed from that of pigs fed high-fiber wheat bread with respect to both the lipoprotein fractions and the choline-containing compounds. These findings suggest that earlier reports on high-fiber rye diet-induced effects on plasma HDL/LDL content partially can be ascribed to effects on liver cholesterol metabolism and that the hepatic phospholipase pathways of phosphatidylcholine breakdown are affected by the high-fiber rye diet.

Animal Feed↗
PubMed2006

Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts.

Growing cereals (especially rye), which are incorporated into the soil to increase soil fertility or organic matter content, is a common practice in crop rotation. The additional sanitizing effect of this incorporation has often been appreciated and is said to be due to leaching of benzoxazinones and subsequent formation of benzoxazolinones. In this study wheat (Stakado) and rye (Hacada) sprouts were incorporated into soil in amounts that simulated agricultural practice. By extraction and subsequent LC-MS analysis the disappearance and appearance of benzoxazinones, benzoxazolinones, and phenoxazinones in soil were followed. In the wheat experiments 6-methoxybenzoxazolin-2-one (MBOA) was detected as the main compound. 2-Hydroxy-7-methoxy-1,4-benzoxazin-3-one (HMBOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) were detected as well. No phenoxazinones were detected. For the rye experiment the picture was more complex. In the first 2 days of incubation MBOA and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected as the main allelochemicals along with HBOA, HMBOA, and benzoxazolin-2-one (BOA), in decreasing order. Later in the incubation period some 2-amino-3H-phenoxazin-3-one (APO) was detected and the amount of HBOA increased considerably and decreased again. The profiling of the benzoxazinone metabolites and their derivates in soil was dynamic and time-dependent. The highest concentrations of most of the compounds were seen at day 1 after incorporation. A maximum concentration was reached at day 4 for a few of the compounds. This study is the first of its kind that shows the dynamic pattern of biologically active benzoxazinone derivates in soil after incorporation of wheat and rye sprouts. Methods for organic synthesis of HBOA and HMBOA were developed as part of the study.

Benzoxazines↗
PubMed1999

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.

Aminopeptidases↗
PubMed1998

Comparative analysis of the nucleosomal structure of rye, wheat and their relatives.

Analysis of the structure of chromatin in cereal species using micrococcal nuclease (MNase) cleavage showed nucleosomal organization and a ladder with typical nucleosomal spacing of 175-185 bp. Probing with a set of DNA probes localized in the authentic telomeres, subtelomeric regions and bulk chromatin revealed that these chromosomal regions have nucleosomal organization but differ in size of nucleosomes and rate of cleavage between both species and regions. Chromatin from Secale and Dasypyrum cleaved more quickly than that from wheat and barley, perhaps because of their higher content of repetitive sequences with hairpin structures accessible to MNase cleavage. In all species, the telomeric chromatin showed more rapid cleavage kinetics and a shorter nucleosome length (160 bp spacing) than bulk chromatin. Rye telomeric repeat arrays were shortest, ranging from 8 kb to 50 kb while those of wheat ranged from 15 kb up to 175 kb. A gradient of sensitivity to MNase was detected along rye chromosomes. The rye-specific subtelomeric sequences pSc200 and pSc250 have nucleosomes of two lengths, those of the telomeric and of bulk nucleosomes, indicating that the telomeric structure may extended into the chromosomes. More proximal sequences common to rye and wheat, the short tandem-repeat pSc119.2 and rDNA sequence pTa71, showed longer nucleosomal sizes characteristic of bulk chromatin in both species. A strictly defined spacing arrangement (phasing) of nucleosomes was demonstrated along arrays of tandem repeats with different monomer lengths (118, 350 and 550 bp) by combining MNase and restriction enzyme digestion.

Base Composition↗
PubMed2001

Winter rye antifreeze activity increases in response to cold and drought, but not abscisic acid.

Antifreeze activity increases in winter rye (Secale cereale L.) during cold acclimation as the plants accumulate antifreeze proteins (AFPs) that are similar to glucanases, chitinases and thaumatin-like proteins (TLPs) in the leaf apoplast. In the present work, experiments were conducted to assess the role of drought and abscisic acid (ABA) in the regulation of antifreeze activity and accumulation of AFPs. Antifreeze activity was detected as early as 24 h of drought treatment at 20 degrees C and increased as the level of apoplastic proteins increased. Apoplastic proteins accumulated rapidly under water stress and reached a level within 8 days that was equivalent to the level of apoplastic proteins accumulated when plants were acclimated to cold temperature for 7 weeks. These drought-induced apoplastic proteins had molecular masses ranging from 11 to 35 kDa and were identified as two glucanases, two chitinases, and two TLPs, by using antisera raised against cold-induced rye glucanase, chitinase, and TLP, respectively. Apoplastic extracts obtained from plants treated with ABA lacked the ability to modify the growth of ice crystals, even though ABA induced the accumulation of apoplastic proteins within 4 days to a level similar to that obtained when plants were either drought-stressed for 8 days or cold-acclimated for 7 weeks. These ABA-induced apoplastic proteins were identified immunologically as two glucanases and two TLPs. Moreover, the ABA biosynthesis inhibitor fluridone did not prevent the accumulation of AFPs in the leaves of cold-acclimated rye plants. Our results show that cold acclimation and drought both induce antifreeze activity in winter rye plants and that the pathway regulating AFP production is independent of ABA.

Journal Article↗
PubMed2000

Similar responses in hemostatic factors after consumption of wholemeal rye bread and low-fiber wheat bread.

OBJECTIVE: Both epidemiological and experimental evidence suggests a protective effect of dietary fiber against disease, such as cancer and cardiovascular disease. The effects of fiber on lipoproteins are modest, indicating that other mechanisms may be involved. As the hemostatic effects of different types of fiber are poorly known, we compared the effects of wholemeal rye bread and low-fiber wheat bread on factors related to coagulation, fibrinolysis and platelet function. DESIGN: Subjects consumed rye and wheat bread as part of their habitual diet in a cross-over manner for 4 weeks, with a 4 week washout period between the diet periods. SUBJECTS: Forty healthy subjects (18 men, 22 women), aged 43+/-2 y. RESULTS: Mean daily intake of fiber during the rye bread period was 31 g for men and 26 g for women, while the respective figures for the wheat bread period were 15 g and 12 g. However, no significant differences between the two periods were seen in factor VII coagulant activity (FVIIc), fibrinogen, prothrombin fragments 1+2 (F1+2), tissue plasminogen activator (tPA) plasminogen activator inhibitor 1 (PAI-1) or 2,3,-dinor-thromboxane B2. Fibrin degradation products, D-dimers, were slightly lower after the wheat period (P=0.046). CONCLUSIONS: The results indicate that wheat and rye bread do not differ in their effects on coagulation, fibrinolysis or platelet function. SPONSORSHIP: Fazer Bakeries Ltd, Lahti Finland; Vaasan & Vaasan Ltd, Helsinki, Finland.

Adult↗
PubMed2000

A membrane-potential dependent ABC-like transporter mediates the vacuolar uptake of rye flavone glucuronides: regulation of glucuronide uptake by glutathione and its conjugates.

In this paper we present results on the vacuolar uptake mechanism for two flavone glucuronides present in rye mesophyll vacuoles. In contrast to barley flavone glucosides (Klein et al. (1996) J. Biol. Chem. 271, 29666-29671), the flavones luteolin 7-O-diglucuronyl-4'-O-glucuronide (R1) and luteolin 7-O-diglucuronide (R2) were taken up into vacuoles isolated from rye via a directly energized mechanism. Kinetic studies suggested that the vacuolar glucuronide transport system is constitutively expressed throughout rye primary leaf development. Competition experiments argued for the existence of a plant MRP-like transporter for plant-specific and non-plant glucuronides such as beta-estradiol 17-(beta-D-glucuronide) (E217G). The interaction of ATP-dependent vacuolar glucuronide uptake with glutathione and its conjugates turned out to be complex: R1 transport was stimulated by dinitrobenzene-GS and reduced glutathione but was inhibited by oxidized glutathione in a concentration-dependent manner. In contrast, R2 uptake was not increased in the presence of reduced glutathione. Thus, the transport system for plant-derived glucuronides differed from the characteristic stimulation of vacuolar E217G uptake by glutathione conjugates but not by reduced glutathione (Klein et al. (1998) J. Biol. Chem. 273, 262-270). Using tonoplast vesicles isolated with an artificial K+ gradient, we demonstrate for the first time for plant MRPs that the ATP-dependent uptake of R1 is membrane-potential dependent. We discuss the kinetic capacity of the ABC-type glucuronide transporter to explain net vacuolar flavone glucuronide accumulation in planta during rye primary leaf development and the possibility of an interaction of potential substrates at both the substrate binding and allosteric sites of the MRP transporter regulating the activity towards a certain substrate.

ATP-Binding Cassette Transporters↗
PubMed2005

Whole-grain rye and wheat alkylresorcinols are incorporated into human erythrocyte membranes.

Alkylresorcinols (AR), a group of phenolic lipids, exist in the human diet in whole-grain rye and wheat. They are absorbed by humans and have been quantified in plasma. In this 2-week study we assessed AR incorporation into human erythrocyte membranes. Nine subjects attended the study; four avoided whole-grain products for 1 week and then included whole-grain rye and wheat bread in the diet for the second week, four included whole-grain rye and wheat products in the diet during the whole follow-up and one followed a gluten-free diet. Plasma and erythrocyte membrane AR were analysed after weeks 1 and 2. Erythrocyte membrane AR concentrations increased an average of 231 nmol/l of packed erythrocytes (P=0.036) after consumption of whole-grain rye and wheat products. Plasma AR levels increased an average of 175 nmol/l (P=0.058). When intake of whole-grain products was constant, erythrocyte membrane and plasma AR levels remained stable. Long-chain AR were incorporated into erythrocyte membranes in a higher proportion compared to shorter-chain AR. This preliminary study shows that AR are incorporated into human erythrocyte membranes in vivo.

Bread↗
PubMed1983

Improvement of the nutritive value of rye for broiler chickens by gamma irradiation-induced viscosity reduction.

A study was undertaken with chickens to determine the effect of irradiation treatment on the viscosity-inducing properties of polysaccharide components of rye. Three-week body weight, food utilisation, fat retention, and bone ash of chicks were substantially improved by irradiating rye (0 to 10 Mrad) and were maximal at 6 Mrad. Irradiation of the entire diet resulted in no further improvement over irradiating the rye fraction alone. The improved performance coincided with radiation-induced damage to rye polysaccharides, as indicated by reduced viscosity and increased concentrations of reducing sugars.

Animals↗
PubMed1997

Interactions between dietary fat type and xylanase supplementation when rye-based diets are fed to broiler chickens. 1. Physico-chemical chyme features.

1. The interactions between fat type and xylanase supplementation of rye-based diets were investigated using a 2 x 2 factorial design in which a rye-based diet (610 g rye/kg) was combined with 100 g/kg of soya oil or beef tallow, with and without xylanase supplementation at 3000 IU/kg, and fed to 1-d-old male broilers. Food passage time, viscosity of digesta supernatant, xylanase activity and pH in different segments of the digestive tract were examined. 2. Food passage throughout the digestive tract was accelerated by enzyme addition regardless of fat type. The time taken for 50% of the marker to be excreted was reduced from 8.4 to 6.7 h in animals receiving the rye-soya oil diets and from 8.0 to 6.9 h with the rye-tallow diets. 3. Viscosity in the supernatant of the jejunal and ileal digesta was markedly decreased after enzyme addition. Viscosities were generally higher in the ileal than in the jejunal supernatant, and fell as the birds aged from 14 to 28 d. The effect of enzyme was also reduced in older chicks. There was not a clear effect of the fat source on viscosity. 4. Xylanase activity was still found at the end of the ileum in digesta of birds fed on the enzyme-supplemented diets but not in control animals. Xylanase activity was also detected in the caeca of all groups. 5. Significantly lower pH values were found in tallow-fed birds in some segments of the digestive tract. A significant increase in pH after enzyme addition was detected in the proximal ileum; this was independent of fat source.

Animal Feed↗
PubMed1986

Low glycemic response to traditionally processed wheat and rye products: bulgur and pumpernickel bread.

To look at the effect of processing wheat and rye on blood glucose responses with special reference to bulgur and pumpernickel bread, groups of 9-12 Noninsulin-dependent (NIDDM) and 5-6 Insulin-dependent diabetic volunteers (IDDM) were fed test meals containing 50 g carbohydrate portions of four wheat and three rye products. Glycemic indices for IDDM and NIDDM combined, calculated as the incremental area under the blood glucose response curve, where white bread = 100, demonstrated values of 96 +/- 5 for wholemeal wheat bread, 89 +/- 6 for wholemeal rye bread, 78 +/- 3 for pumpernickel bread, 65 +/- 4 for bulgur, 63 +/- 6 for whole wheat kernels and 48 +/- 5 for whole rye kernels. Results for IDDM and NIDDM were similar (r = 0.96, p less than 0.01). It is concluded that traditional processing of cereals, such as parboiling (bulgur) or the use of wholegrains in bread (pumpernickel) may result in the low GI value associated with the unmilled cereal. Cereal foods processed in these ways may form a useful part of the diet where a reduction in postprandial glycemia is required.

Aged↗
PubMed2000

Rye bread improves bowel function and decreases the concentrations of some compounds that are putative colon cancer risk markers in middle-aged women and men.

Cereal fiber may reduce the risk of colorectal cancer by diluting colonic contents due to increased fecal output, by accelerating intestinal transit, by increasing fecal frequency and by altering bacterial metabolism. The effects of whole-meal rye bread on some putative colon cancer risk markers were investigated in 17 healthy Finnish subjects using a randomized crossover trial with two 4-wk bread consumption periods and a 4-wk washout period between the bread periods. White wheat bread was used as a control. Test breads covered a minimum of 20% of the daily energy intake (range, 4330-14, 033 kJ/d). Intestinal transit time, stool weight, fecal bacterial enzyme activities and short-chain fatty acid, ammonia, diacylglycerol (DAG) and bile acid concentrations in feces (expressed per gram wet feces) were measured. Whole-meal rye bread significantly increased fecal output and fecal frequency and shortened mean intestinal transit time compared with wheat bread in both women and men. Activities of beta-glucuronidase and beta-glucosidase (expressed per gram wet feces) were significantly lower in men and urease activity significantly higher in women during the rye bread period (RBP). Fecal butyrate concentration was higher during the RBP in men. Fecal ammonia and DAG concentrations did not differ between bread periods. Fecal total and secondary bile acid concentrations were significantly lower during RBP in both women and men. This study shows that whole-meal rye bread significantly improves bowel function in healthy adults and may decrease the concentration of some compounds that are putative colon cancer risk markers.

Adult↗
PubMed2003

Rye bread in the diet of pigs enhances the formation of enterolactone and increases its levels in plasma, urine and feces.

To obtain new insight into the quantitative and qualitative metabolism of rye and wheat lignans, we performed three series of experiments with catheterized pigs. Two diets with similar levels of dietary fiber and macronutrients but with contrasting levels of plant lignans (isolariciresinol, lariciresinol, matairesinol, pinoresinol, secoisolariciresinol and syringaresinol) were prepared from rye (high in lignans) and wheat (low in lignans) soft and crisp breads. In two series of experiments we quantified the uptake from the gut of enterolactone in four pigs fitted with catheters in the portal vein and mesenteric artery and with an ultrasonic flow probe attached to the portal vein to monitor the blood flow. In a third study with six pigs, we quantified the bioavailability of the plant lignans that can be converted to enterolactone (lariciresinol, matairesinol, pinoresinol, secoisolariciresinol and syringaresinol) and the concentration in the peripheral blood. Plant and mammalian lignans in diets and stool were analyzed by isotope dilution gas chromatography-mass spectrometry and enterolactone in plasma and urine determined by time-resolved fluoroimmunoassay. There was a significantly higher formation of enterolactone in pigs fed the rye diet, and higher fecal and urinary excretion and circulating levels of mammalian lignans than in pigs fed the wheat diet. The conversion of mammalian lignan precursors to enterolactone was 48% with the wheat diet and 60% with the rye diet. Mammalian lignans are absorbed by passive diffusion from the large intestine and a substantial fraction of the absorbed mammalian lignans undergoes enterohepatic circulation, resulting in low diurnal variation in plasma levels of enterolactone.

4-Butyrolactone↗
PubMed2006

Human plasma kinetics and relative bioavailability of alkylresorcinols after intake of rye bran.

Alkylresorcinols (ARs) are phenolic lipids present in whole grain and bran of wheat and rye. Chemically, they comprise 1,3- dihydroxy-5-alkylbenzene homologs with odd-numbered, mainly saturated hydrocarbon side chains in the range of 17-25 carbon atoms. ARs are evaluated both for physiological effects and for their potential use as biomarkers of whole-grain wheat and rye intake. In this study, plasma kinetics and relative bioavailability of ARs in humans were investigated after a single intake of rye bran 120 g (190 mg ARs). The shapes of plasma concentration time curves were similar in the subjects (n = 6) with 2 peaks at approximately 2.8 and 6.5 h and maximum concentrations (mean +/- SEM) of 1253 +/- 125 and 3365 +/- 309 nmol/L, respectively. The relative bioavailability of different homologs increased with increasing length of the AR side chain (r = 0.97, P < 0.001), indicating differences in metabolism. The apparent half-lives were rather short, approximately 5 h for all homologs, which suggests that the AR concentration in plasma could be used as a short- to medium-term biomarker of regular intake of whole-grain wheat and rye.

Absorption↗