Alkylresorcinol

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Arkadiusz Kozubek - One of the best experts on this subject based on the ideXlab platform.

  • Various effects of the photosystem II--inhibiting herbicides on 5-n-Alkylresorcinol accumulation in rye seedlings.
    Pesticide Biochemistry and Physiology, 2014
    Co-Authors: Elżbieta G. Magnucka, Stanislaw J. Pietr, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    Abstract The effect of three PSII-inhibiting herbicides, lenacil, linuron, and pyrazon, on the accumulation of 5- n -Alkylresorcinols in rye seedlings ( Secale cereale L.) grown under various light and thermal conditions was studied. All used chemicals increased resorcinolic lipid content in both green and etiolated plants grown at 29 °C. At 22 °C pyrazon and lenacil decreased the content of Alkylresorcinols in plants kept in the darkness and increased their amount in the light-grown seedlings. In turn, level of resorcinolic lipids was decreased by linuron in both etiolated and green plants. At the lowest tested temperature lenacil enhanced production of Alkylresorcinols only in etiolated rye seedlings, whereas the light-independent stimulatory action of pyrazon on Alkylresorcinol accumulation in rye grown at 15 °C was observed. Additionally, only the latter did not exert a negative effect on rye seedling growth under any of tested conditions. Compared with respective controls, the herbicides used also markedly modified the qualitative pattern of resorcinolic homologs. Interestingly, the observed changes generally favored the enhanced antifungal activity of these compounds. Our study provides novel information on the influence of PSII inhibitors on Alkylresorcinol metabolism in rye seedlings. The unquestionable achievement of this work is the observation that low dose of pyrazon mainly stimulated both growth and Alkylresorcinol synthesis in rye seedlings, a non-target plant. Moreover, our experimental work showed unambiguously that the observed pyrazon-driven accumulation and homolog pattern modification of Alkylresorcinols dramatically improved the resistance of winter rye to infections caused by Rhizoctonia cerealis .

  • Alkylresorcinols in rye (Secale cereale L.) grains. V. Chromatographic analysis of 5-n-alk(en)ylresorcinols during their preparation
    Acta Societatis Botanicorum Poloniae, 2014
    Co-Authors: Arkadiusz Kozubek, Franciszek Tłuścik, Wanda Mejbaum-katzenellenebogen
    Abstract:

    Analysis of 5-n-alk(en)ylresorcinols during the coarse of their preparation from rye grains showed that changes of the composition of 5-n-Alkylresorcinol homologues in acetone oil; raw preparation, and Alkylresorcinol fraiction obtained after chromatography on silica gel, were insignificant. About 20% of alk(en)-ylresorcinals were washed out from acetone oil with pentane. Over 50% of alk(en)ylresorcinols eluted by pentane constituted homologues with unsaturated hydrocarbon chains (5-n-alkenylresorcinols). Preparation obtained after chromatagraphic separation constituted a mixtureof 5-n-alk(en)ylresorcinols width saturated hydrocarbon chains (5-n-Alkylresorcinols).

  • antioxidant activity of rye bran Alkylresorcinols and extracts from whole grain cereal products
    Food Chemistry, 2009
    Co-Authors: Mariola Korycinska, Karolina Czelna, Anna Jaromin, Arkadiusz Kozubek
    Abstract:

    Abstract The antioxidant properties of rye bran Alkylresorcinols (C15:0–C25:0) and extracts from whole-grain cereal products were evaluated using their radical-scavenging activity on DPPH and the chemiluminescence method (CL). DPPH radical reduction varied from ∼10% to ∼60% for the Alkylresorcinol homologues at concentrations from 5 to 300 μM and was not dependent on the length of the alkyl side chain of the particular homologue. Differences in the EC 50 values for the studied compounds were not statistically significant, the values varying from 157 μM for homologue C23:0 to 195 μM for homologue C15:0. Moreover, values of EC 50 for all the Alkylresorcinol homologues were significantly higher than those for Trolox and α-, δ-, and γ-tocopherols, compounds with well-defined antioxidant activity and used as positive controls. CL inhibition was evaluated for all the tested Alkylresorcinol homologues at concentrations of 5 and 10 μM and varied from ∼27% to ∼77%. Similar to the DPPH method, the slight differences in CL inhibition suggest that the length of the alkyl side chain had no major impact on their antioxidant properties. The extracts from whole-grain products were added to the DPPH and CL reaction systems and their antioxidant activities were tested and compared with the total amount of Alkylresorcinols evaluated in the extracts. DPPH radical and CL reduction for the whole-grain products varied from ∼7% to ∼43% and from ∼37% to ∼91%, respectively. A clear relationship between DPPH radical and CL reduction levels and the amount of total Alkylresorcinols was obtained for whole-grain breakfast cereals, in which the reduction level decreased in the order rye > wheat > mixed > barley. Therefore it may be considered that the antioxidant activity of Alkylresorcinols could be of potential importance to the food industry, which is continuously searching for natural antioxidants for the protection of food products during their processing and storage.

  • cycloate an inhibitor of fatty acid elongase modulates the metabolism of very long side chain Alkylresorcinols in rye seedlings
    Pest Management Science, 2009
    Co-Authors: Elżbieta G. Magnucka, Yoshikatsu Suzuki, Stanislaw J. Pietr, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    BACKGROUND: Cycloate inhibits the biosynthesis of very-long-chain fatty acids, the essential constituents of plant waxes and suberin.Fattyacidsalsoserveasprecursorsofaliphaticcarbonchainsinresorcinoliclipids,whichplayafundamentalroleinthe plant defence system against fungal pathogens. In this study, the effect of cycloate on the biosynthesis of 5-n-Alkylresorcinols in rye seedlings (SecalecerealeL.) grown under various light and thermal conditions was examined. RESULTS: The content of Alkylresorcinols biosynthesised in rye was generally increased by the herbicide in both green and etiolatedplants.Thepresenceofcycloate alsoaffected patternsofAlkylresorcinolhomologuesinplantsgrownat15and22 ◦ C; very-long-side-chain compounds were less abundant, whereas both short-chain saturated and unsaturated homologues were generally accumulated. No cycloate-related effects caused by homologue pattern modifications were observed at elevated temperature. CONCLUSION:Thisstudyextendspresentunderstandingofthemodeofactionofthiocarbamateherbicides.Cycloatemarkedly affected the biosynthesis of very-long-side-chain resorcinolic lipids in rye seedlings, confirming the existence of parallels in both fatty acid and Alkylresorcinol biosynthetic pathways. The observed cycloate-driven accumulation of 5-n-Alkylresorcinols may improve the resistance of cereals to infections caused by microbial pathogens. c � 2009 Society of Chemical Industry

  • Alkylresorcinols in selected polish rye and wheat cereals and whole grain cereal products
    Journal of Agricultural and Food Chemistry, 2008
    Co-Authors: Mariola Kulawinek, Anna Jaromin, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    The Alkylresorcinol content and homologue composition in selected Polish rye and wheat cultivars and selected whole-grain cereal products were determined in this study. Cereal grains and whole-grain cereal products were extracted with acetone, whereas bread types were extracted with hot 1-propanol. The average Alkylresorcinol content in tested rye (∼1100 mg/kg DM) and wheat (∼800 mg/kg DM) grains harvested in Poland was within the range previously reported in Swedish and Finnish samples. The total Alkylresorcinol content in tested cereal products available on the Polish market varied from very low levels in barley grain-based foods up to 3000 mg/kg DM in wheat bran. The total Alkylresorcinol content in 14 bread samples extracted with hot 1-propanol varied from ∼100 mg/kg DM in whole bread made with honey up to ∼650 mg/kg DM in whole-rye bread. Calculated ratios of C17:0 to C21:0 homologues, a useful parameter previously used to distinguish between rye and wheat cereals and their derived products, was abou...

Alastair B Ross - One of the best experts on this subject based on the ideXlab platform.

  • Serum Alkylresorcinols as Biomarkers of Dietary Gluten Exposure in Celiac disease
    The FASEB Journal, 2017
    Co-Authors: Alastair B Ross, Eric V Marietta, Rok Seon Choung, Carol T. Van Dyke, Joseph A Murray
    Abstract:

    Background Therapy for celiac disease (CD) mainly relies on following a gluten-free diet (GFD); however, a serum marker for gluten intake has yet to be established. Aims To evaluate the utility of Alkylresorcinol concentrations for detecting gluten intake in studies of human and mouse. Methods Alkylresorcinol concentrations were compared among treated CD patients (n=34), untreated CD patients (n=36), and controls (n=33). Furthermore, 7 additional CD patients whose serum samples were available at diagnosis and after GFD were evaluated. In mice studies, Alkylresorcinol concentrations were compared in the serum of 5 mice fed a regular chow and 10 mice fed lifelong with a gluten-free chow. In addition, the effect of adding gluten on changes of Alkylresorcinol concentrations was also evaluated. Results Total Alkylresorcinol concentrations were significantly lower in treated CD patients (median [IQR], 3 (2–8) nmol/L), compared to untreated CD patients (median [IQR], 32 [11–74] nmol/L; P

  • serum Alkylresorcinols as biomarkers of dietary gluten exposure in coeliac disease
    Alimentary Pharmacology & Therapeutics, 2017
    Co-Authors: Rok Seon Choung, Eric V Marietta, Carol T Van Dyke, Joseph A Murray, Alastair B Ross
    Abstract:

    Therapy for coeliac disease (CD) mainly relies on following a gluten-free diet (GFD); however, a serum marker for gluten intake has yet to be established. Aim: To evaluate the utility of Alkylresorcinol concentrations for detecting gluten intake in studies of human and mouse. Methods: Alkylresorcinol concentrations were compared among treated patients with coeliac disease (n = 34), untreated coeliac disease patients (n = 36) and controls (n = 33). Furthermore, seven additional coeliac disease patients whose serum samples were available at diagnosis and after GFD were evaluated. In mice studies, Alkylresorcinol concentrations were compared in the serum of five mice fed a regular chow and 10 mice fed lifelong with a gluten-free chow. In addition, the effect of adding gluten on changes of Alkylresorcinol concentrations was also evaluated. Results: Total Alkylresorcinol concentrations were significantly lower in treated with coeliac disease [median (IQR), 3 (2–8) nmol/L], compared to untreated patients [median (IQR), 32 (11–74) nmol/L; P < 0.0001] or healthy controls [median (IQR), 54 (23–112) nmol/L; P < 0.0001]. Moreover, Alkylresorcinol concentrations in coeliac disease patients significantly decreased after introduction of a GFD (median, 34 nmol/L at diagnosis vs. 5 nmol/L after GFD, P = 0.02). In the mice, median (IQR) total Alkylresorcinol concentrations in serum samples of mice fed lifelong with a gluten-free chow was 1.8 (1.6–2.3) nmol/L, which was further significantly increased to 16 (11–22) nmol/L after 8 days of feeding with the gluten-free chow that had gluten added to it. (P = 0.008). Conclusion: Serum Alkylresorcinol concentrations could be a useful marker for dietary gluten in coeliac disease.

  • serum Alkylresorcinols as biomarkers of dietary gluten exposure in celiac disease
    The FASEB Journal, 2017
    Co-Authors: Alastair B Ross, Eric V Marietta, Carol T Van Dyke, Rok Seon Choung, Joseph A Murray
    Abstract:

    Background Therapy for celiac disease (CD) mainly relies on following a gluten-free diet (GFD); however, a serum marker for gluten intake has yet to be established. Aims To evaluate the utility of Alkylresorcinol concentrations for detecting gluten intake in studies of human and mouse. Methods Alkylresorcinol concentrations were compared among treated CD patients (n=34), untreated CD patients (n=36), and controls (n=33). Furthermore, 7 additional CD patients whose serum samples were available at diagnosis and after GFD were evaluated. In mice studies, Alkylresorcinol concentrations were compared in the serum of 5 mice fed a regular chow and 10 mice fed lifelong with a gluten-free chow. In addition, the effect of adding gluten on changes of Alkylresorcinol concentrations was also evaluated. Results Total Alkylresorcinol concentrations were significantly lower in treated CD patients (median [IQR], 3 (2–8) nmol/L), compared to untreated CD patients (median [IQR], 32 [11–74] nmol/L; P<.0001) or healthy controls (median [IQR], 54 [23–112] nmol/L; P<.0001). Moreover, Alkylresorcinol concentrations in CD patients significantly decreased after introduction of a GFD (median, 34 nmol/L at diagnosis vs. 5 nmol.L after GFD, p=0.02). In the mice, median (IQR) total Alkylresorcinol concentrations in serum samples of mice fed lifelong with a gluten-free chow was 1.8 (1.6–2.3) nmol/L, which was further significantly increased to 16 (11–22) nmol/L after 8 days of feeding with the gluten free chow that had gluten added to it. (p=.008). Conclusion Serum Alkylresorcinol concentrations could be a useful marker for dietary gluten in CD.

  • a high throughput method for liquid chromatography tandem mass spectrometry determination of plasma Alkylresorcinols biomarkers of whole grain wheat and rye intake
    Analytical Biochemistry, 2016
    Co-Authors: Alastair B Ross, Mads Vendelbo Lind, Cecilia Svelander, Otto Savolainen, Isabelle Breton, Jean Philippe Godin, John P Kirwan, Ann-sofie Sandberg
    Abstract:

    Plasma Alkylresorcinols are increasingly analyzed in cohort studies to improve estimates of whole grain intake and their relationship with disease incidence. Current methods require large volumes of solvent (>10 ml/sample) and have relatively low daily sample throughput. We tested five different supported extraction methods for extracting Alkylresorcinols from plasma and improved a normal-phase liquid chromatography coupled to a tandem mass spectrometer method to reduce sample analysis time. The method was validated and compared with gas chromatography-mass spectrometry analysis. Sample preparation with HybridSPE supported extraction was most effective for Alkylresorcinol extraction, with recoveries of 77-82% from 100 μl of plasma. The use of 96-well plates allowed extraction of 160 samples per day. Using a 5-cm NH2 column and heptane reduced run times to 3 min. The new method had a limit of detection and limit of quantification equivalent to 1.1-1.8 nmol/L and 3.5-6.1 nmol/L plasma, respectively, for the different Alkylresorcinol homologues. Accuracy was 93-105%, and intra- and inter-batch precision values were 4-18% across different plasma concentrations. This method makes it possible to quantify plasma Alkylresorcinols in 100 μl of plasma at a rate of at least 160 samples per day without the need for large volumes of organic solvents.

  • whole grain intake determined by dietary records and plasma Alkylresorcinol concentrations is low among pregnant women in singapore
    Asia Pacific Journal of Clinical Nutrition, 2015
    Co-Authors: Alastair B Ross, Marjorelee Colega, Ai Lin Lim, Irma Silvazolezzi, Katherine Mace, Seangmei Saw, Kenneth Kwek, Peter D Gluckman, Keith M Godfrey, Yapseng Chong
    Abstract:

    Background and Objectives: To quantify whole grain intake in pregnant women in Singapore in order to provide the first detailed analysis of whole grain intake in an Asian country and in pregnant women. Methods and Study Design: Analysis of 24-h diet recalls in a cross-sectional cohort study and analysis of a biomarker of whole grain intake (plasma Alkylresorcinols) in a subset of subjects. The Growing Up in Singapore Towards healthy Outcomes-mother offspring cohort study based in Singapore. 998 pregnant mothers with complete 24-h recalls taken during their 26-28th week of gestation. Plasma samples from a randomly select subset of 100 subjects were analysed for plasma allcylresorcinols. Results: Median (IQR) whole grain intake for the cohort and the 30% who reported eating whole grains were 0 (IQR 0, 9) and 23.6 (IQR 14.6, 44.2) g/day respectively. Plasma Alkylresorcinol concentrations were very low [median (IQR)=9 (3, 15) nmol/L], suggesting low intake of whole grain wheat in this population. Plasma allcylresorcinols were correlated with whole grain wheat intake (Spearman's r=0.35; p<0.01). Conclusions: Whole grain intake among pregnant mothers in Singapore was well below the 2-3 (60-95 g) servings of whole grains per day recommended by the Singapore Health Promotion Board. Efforts to increase whole grain intake should be supported to encourage people to choose whole grains over refined gains in their diet.

Herman Adlercreutz - One of the best experts on this subject based on the ideXlab platform.

  • Plasma Alkylresorcinol Metabolites as Biomarkers for Whole-Grain Intake and Their Association with Prostate Cancer: A Swedish Nested Case–Control Study
    Cancer Epidemiology Biomarkers & Prevention, 2013
    Co-Authors: Isabel Drake, Emily Sonestedt, Elisabet Wirfält, Anders Bjartell, Bo Gullberg, Herman Adlercreutz, Matti J. Tikkanen, Håkan Olsson, Peter Wallström
    Abstract:

    Background:Observational studies have mostly found no association between self-reported whole-grain (WG) intake and prostate cancer (PCa). Plasma Alkylresorcinol metabolites have been suggested as biomarkers for WG intake in free-living populations. Methods:We investigated the major dietary and lifestyle determinants of plasma Alkylresorcinol metabolites in a nested case-control study (1,016 cases and 1817 controls) in the Malmo Diet and Cancer Study. Multivariate adjusted odds ratios (OR) and 95% confidence intervals (95% CI) were estimated to assess the association between plasma Alkylresorcinol metabolites and PCa using logistic regression. Results:WG intake, waist circumference, educational level and smoking status were the main determinants of Alkylresorcinol metabolites. We observed significant correlations between Alkylresorcinol metabolites and WG (r=0.31) and fiber (r=0.27) intake. Metabolite concentration was positively associated with PCa risk (P overall effect = 0.0004) but the association was not linear (P = 0.04). The lowest risk was seen among men with moderate plasma concentrations. The OR for high compared to moderate plasma Alkylresorcinol metabolites was 1.41 (95% CI: 1.10-1.80) for PCa. Conclusions:Results suggest that plasma Alkylresorcinol metabolites are mainly determined by WG intake in this nested-case control study of Swedish men. The increased risk of PCa seen among men with high plasma Alkylresorcinol metabolites requires further study, but residual confounding, detection bias or competing risk of non-PCa related deaths are plausible explanations that could not be ruled out. Impact:We found no evidence of a protective effect of WG on incident PCa. Further validation of Alkylresorcinol metabolites as a biomarker for WG intake is needed.

  • Pharmacokinetics of Alkylresorcinol metabolites in human urine.
    British Journal of Nutrition, 2011
    Co-Authors: Päivi P. Söderholm, Anja Koskela, Johan Lundin, Matti J. Tikkanen, Herman Adlercreutz
    Abstract:

    : Wholegrain cereals are reported to promote beneficial health effects. Wholegrain wheat and rye are almost exclusive sources of Alkylresorcinols, and intact Alkylresorcinols together with their plasma and urinary metabolites, 3-(3,5-dihydroxyphenyl)-1-propanoic acid (DHPPA) and 3,5-dihydroxybenzoic acid (DHBA), have been proposed as biomarkers of the intake of these foods in humans. The pharmacokinetics of Alkylresorcinols and their metabolites in plasma have been determined but not that of the urinary metabolites. We aimed to characterise the urinary pharmacokinetics of Alkylresorcinol metabolites in humans to evaluate their potential as biomarkers of wholegrain wheat and rye. A group of fifteen volunteers followed a low-Alkylresorcinol diet for 2 d before ingesting a single dose of rye bread, containing 100 mg Alkylresorcinols. Urine was collected between baseline (0 h) and 25 h after administration. Thereafter Alkylresorcinol metabolites were quantified by HPLC with coulometric electrode array detection. Maximum excretion rates were observed at 5-6 h for both metabolites, DHPPA being predominant over DHBA and also possessing a greater area under the curve0-25 h. Total urinary recovery between 0 and 25 h yielded 43 % of ingested Alkylresorcinols, and at 25 h significant amounts of metabolites were still retained in the body, suggesting that even a spot urine sample may be sufficient to indicate whether or not wholegrain wheat or rye is a daily dietary component. These results support the use of urinary DHPPA and DHBA as biomarkers of wholegrain wheat and rye and enable new potential for studying the association between wholegrain intake and diseases, even in the absence of dietary data.

  • Plasma pharmacokinetics of Alkylresorcinol metabolites: new candidate biomarkers for whole-grain rye and wheat intake
    The American journal of clinical nutrition, 2009
    Co-Authors: Päivi P. Söderholm, Anja Koskela, Johan Lundin, Matti J. Tikkanen, Herman Adlercreutz
    Abstract:

    Background: Alkylresorcinols are phenolic compounds that are present almost exclusively in rye and wheat fiber. Alkylresorcinols are absorbed and thereafter metabolized to 3,5-dihydroxybenzoic acid (DHBA) and 3-(3,5-dihydroxyphenyl)-1-propanoic acid (DHPPA), which have been detected in human urine and plasma. Objective: The objective was to determine the plasma pharmacokinetics of DHBA and DHPPA in human subjects to estimate whether they show potential as biomarkers for whole-grain rye and/or wheat intake. Design: Fifteen human volunteers followed a low-Alkylresorcinol diet for 2 d before ingesting a single dose of high-fiber rye bread containing 45 mg Alkylresorcinols. Plasma samples were collected for 25 h, and the Alkylresorcinol metabolites were quantified by HPLC with coulometric electrode array detection. Results: Maximum concentrations were reached at ’6 h for both metabolites, although interindividual variation was found. The halflife was significantly (P , 0.0002) longer for DHPPA (16.3 h) than for DHBA (10.1 h). No significant differences were discovered between women and men in the half-life of each metabolite, which, from a pharmacokinetic point of view, is the most important parameter. The area under the curve differed significantly between DHBA and DHPPA (P , 0.0001) and between women and men (P = 0.03 for DHBA and P = 0.01 for DHPPA). However, when corrected for body weight, the difference between sexes was no longer significant. Conclusions: Our results suggest that DHBA and DHPPA are both good candidate biomarkers for whole-grain rye and/or wheat intake; however, DHPPA is the better indicator because of its longer half-life. This could provide a practical tool when investigating the association between diet and diseases. Am J Clin Nutr doi: 10.3945/ajcn. 2009.28290.

  • plasma Alkylresorcinols and urinary Alkylresorcinol metabolites as biomarkers of cereal fiber intake in finnish women
    Cancer Epidemiology Biomarkers & Prevention, 2008
    Co-Authors: Mylene Aubertinleheudre, Anja Koskela, Annukka Marjamaa, Herman Adlercreutz
    Abstract:

    Alkylresorcinols (AR) could be good biomarkers of consumption of fiber-rich cereal products. The aim of this study was to examine the relationship between plasma ARs or urinary AR metabolites and cereal fiber intake in women consuming their habitual diet. Twenty-five postmenopausal and 31 premenopausal women were recruited. The subjects included also vegetarians (n = 20) to obtain a broad range of cereal intake. Dietary intake, plasma ARs, and urinary AR metabolites [3,5-dihydroxybenzoic acid and 3-(3,5-dihydroxyphenyl)-1-propanoic acid] were measured. Pearson's and Partial correlation tests were done between dietary fiber intake and plasma ARs or urinary AR metabolites. Cereal fiber intake correlated significantly with plasma AR C17:0 (r = 0.387), AR C19:0 (r = 0.350), AR C21:0 (r = 0.428), AR C23:0 (r = 0.409), AR C25:0 (r = 0.283), and total AR (r = 0.406) and with urinary AR metabolites DHBA (r = 0.359) and DHPPA (r = 0.402) even after adjustment for body mass index and age, which could be confounding variables. This is the first study to show a significant correlation between plasma ARs or urinary AR metabolites and cereal fiber intake during consumption of a habitual diet. These results indicate that assay of plasma ARs or urinary AR metabolites may be used as biomarkers in epidemiologic studies in free-living populations to evaluate the role of cereal fiber intake in various diseases.

  • Quantities of phenolic compounds and their impacts on the perceived flavour attributes of rye grain
    Journal of Cereal Science, 2008
    Co-Authors: Raija-liisa Heiniö, Kirsi-helena Liukkonen, Olavi Myllymaki, Juha-matti Pihlava, Herman Adlercreutz, Satu-maarit Heinonen
    Abstract:

    Abstract The use of whole grain rye products, beneficial to one's health, could be substantially extended if the typical intensively bitter flavour of rye could be modified without losing the characteristic rye-like flavour. The aim of the study was to evaluate the contribution of non-volatile phenolic compounds on the perceived flavour. Rye grain was milled into five milling fractions. The levels of phenolic compounds, i.e. the phenolic acids, Alkylresorcinols and lignans, of the fractions were analysed and related statistically to sensory flavour profiles by partial least-squares (PLS) regression. The non-bound (free) phenolic acids are suggested to be most flavour-active. Cereal and intense flavour and aftertaste were related to vanillic and veratric acids, Alkylresorcinol C 23:0 , and other lignans except for pinoresinol. The perceived bitterness of the bran fractions was suggested to result from pinoresinol and syringic acid. Sinapic and ferulic acids, Alkylresorcinols, except for Alkylresorcinol C 23:0 , and syringaresinol seemed to cause the germ-like flavour. Phenolic acids, Alkylresorcinols and lignans distributed with a similar pattern in the rye grain as the flavour attributes: the phenolic compounds were clearly located in the outer bran fractions being intense in flavour, but not in the mild-tasting inner layers of the grain.

Robert Zarnowski - One of the best experts on this subject based on the ideXlab platform.

  • Dynamics of Alkylresorcinols during rye caryopsis germination and early seedling growth.
    Zeitschrift für Naturforschung C, 2015
    Co-Authors: Elżbieta G. Magnucka, Stanislaw J. Pietr, Robert Zarnowski
    Abstract:

    : Among secondary metabolites, Alkylresorcinols are considered particularly important for the antimicrobial defense system in cereal grains. Dry rye caryopses and young seedlings contain detectable quantities of resorcinolic lipids. Overall, 11 distinct Alkylresorcinol homologues were identified, which showed variable profiles during rye germination and early seedling development, especially with reference to the production of very long homologues and to side chain saturation. Additionally, changes in the Alkylresorcinol composition during rye seedling growth are presented for the first time.

  • Various effects of the photosystem II--inhibiting herbicides on 5-n-Alkylresorcinol accumulation in rye seedlings.
    Pesticide Biochemistry and Physiology, 2014
    Co-Authors: Elżbieta G. Magnucka, Stanislaw J. Pietr, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    Abstract The effect of three PSII-inhibiting herbicides, lenacil, linuron, and pyrazon, on the accumulation of 5- n -Alkylresorcinols in rye seedlings ( Secale cereale L.) grown under various light and thermal conditions was studied. All used chemicals increased resorcinolic lipid content in both green and etiolated plants grown at 29 °C. At 22 °C pyrazon and lenacil decreased the content of Alkylresorcinols in plants kept in the darkness and increased their amount in the light-grown seedlings. In turn, level of resorcinolic lipids was decreased by linuron in both etiolated and green plants. At the lowest tested temperature lenacil enhanced production of Alkylresorcinols only in etiolated rye seedlings, whereas the light-independent stimulatory action of pyrazon on Alkylresorcinol accumulation in rye grown at 15 °C was observed. Additionally, only the latter did not exert a negative effect on rye seedling growth under any of tested conditions. Compared with respective controls, the herbicides used also markedly modified the qualitative pattern of resorcinolic homologs. Interestingly, the observed changes generally favored the enhanced antifungal activity of these compounds. Our study provides novel information on the influence of PSII inhibitors on Alkylresorcinol metabolism in rye seedlings. The unquestionable achievement of this work is the observation that low dose of pyrazon mainly stimulated both growth and Alkylresorcinol synthesis in rye seedlings, a non-target plant. Moreover, our experimental work showed unambiguously that the observed pyrazon-driven accumulation and homolog pattern modification of Alkylresorcinols dramatically improved the resistance of winter rye to infections caused by Rhizoctonia cerealis .

  • cycloate an inhibitor of fatty acid elongase modulates the metabolism of very long side chain Alkylresorcinols in rye seedlings
    Pest Management Science, 2009
    Co-Authors: Elżbieta G. Magnucka, Yoshikatsu Suzuki, Stanislaw J. Pietr, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    BACKGROUND: Cycloate inhibits the biosynthesis of very-long-chain fatty acids, the essential constituents of plant waxes and suberin.Fattyacidsalsoserveasprecursorsofaliphaticcarbonchainsinresorcinoliclipids,whichplayafundamentalroleinthe plant defence system against fungal pathogens. In this study, the effect of cycloate on the biosynthesis of 5-n-Alkylresorcinols in rye seedlings (SecalecerealeL.) grown under various light and thermal conditions was examined. RESULTS: The content of Alkylresorcinols biosynthesised in rye was generally increased by the herbicide in both green and etiolatedplants.Thepresenceofcycloate alsoaffected patternsofAlkylresorcinolhomologuesinplantsgrownat15and22 ◦ C; very-long-side-chain compounds were less abundant, whereas both short-chain saturated and unsaturated homologues were generally accumulated. No cycloate-related effects caused by homologue pattern modifications were observed at elevated temperature. CONCLUSION:Thisstudyextendspresentunderstandingofthemodeofactionofthiocarbamateherbicides.Cycloatemarkedly affected the biosynthesis of very-long-side-chain resorcinolic lipids in rye seedlings, confirming the existence of parallels in both fatty acid and Alkylresorcinol biosynthetic pathways. The observed cycloate-driven accumulation of 5-n-Alkylresorcinols may improve the resistance of cereals to infections caused by microbial pathogens. c � 2009 Society of Chemical Industry

  • Alkylresorcinols in selected polish rye and wheat cereals and whole grain cereal products
    Journal of Agricultural and Food Chemistry, 2008
    Co-Authors: Mariola Kulawinek, Anna Jaromin, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    The Alkylresorcinol content and homologue composition in selected Polish rye and wheat cultivars and selected whole-grain cereal products were determined in this study. Cereal grains and whole-grain cereal products were extracted with acetone, whereas bread types were extracted with hot 1-propanol. The average Alkylresorcinol content in tested rye (∼1100 mg/kg DM) and wheat (∼800 mg/kg DM) grains harvested in Poland was within the range previously reported in Swedish and Finnish samples. The total Alkylresorcinol content in tested cereal products available on the Polish market varied from very low levels in barley grain-based foods up to 3000 mg/kg DM in wheat bran. The total Alkylresorcinol content in 14 bread samples extracted with hot 1-propanol varied from ∼100 mg/kg DM in whole bread made with honey up to ∼650 mg/kg DM in whole-rye bread. Calculated ratios of C17:0 to C21:0 homologues, a useful parameter previously used to distinguish between rye and wheat cereals and their derived products, was abou...

  • Alkylresorcinols in selected polish rye and wheat cereals and whole grain cereal products
    Journal of Agricultural and Food Chemistry, 2008
    Co-Authors: Mariola Kulawinek, Anna Jaromin, Arkadiusz Kozubek, Robert Zarnowski
    Abstract:

    The Alkylresorcinol content and homologue composition in selected Polish rye and wheat cultivars and selected whole-grain cereal products were determined in this study. Cereal grains and whole-grain cereal products were extracted with acetone, whereas bread types were extracted with hot 1-propanol. The average Alkylresorcinol content in tested rye (approximately 1100 mg/kg DM) and wheat (approximately 800 mg/kg DM) grains harvested in Poland was within the range previously reported in Swedish and Finnish samples. The total Alkylresorcinol content in tested cereal products available on the Polish market varied from very low levels in barley grain-based foods up to 3000 mg/kg DM in wheat bran. The total Alkylresorcinol content in 14 bread samples extracted with hot 1-propanol varied from approximately 100 mg/kg DM in whole bread made with honey up to approximately 650 mg/kg DM in whole-rye bread. Calculated ratios of C17:0 to C21:0 homologues, a useful parameter previously used to distinguish between rye and wheat cereals and their derived products, was about 1.2-1.4 in rye products, about 0.2 in wheat products, and varied between 0.2 and 0.6 in cereal-derived products containing a mixture of whole rye and/or wheat. The data set obtained were subsequently compared using cluster and principal component analysis, which allowed the tested cereal products to be classified into two major groups consisting of whole-rye or whole-wheat products, respectively. On the basis of that approach, mixed cereal products containing rye and wheat bran or whole rye and wheat flour were grouped between those two well-defined clusters. Our work not only provides a detailed examination of Alkylresorcinols in selected Polish rye and wheat cultivars and selected whole-grain cereal products, but also demonstrates that this type of analysis accompanied by the use of proper statistical algorithms offers an objective way to evaluate the quality of whole-grain rye and/or wheat and their derived products.

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  • Dietary intake of whole grains and plasma Alkylresorcinol concentrations in relation to changes in anthropometry: the Danish diet, cancer and health cohort study
    European Journal of Clinical Nutrition, 2017
    Co-Authors: Cecilie Kyro, M U Jakobsen, Hb(as) Bueno-de-mesquita, Jytte Halkjaer, M. Kristensen, Isabelle Romieu, J. Christensen, Anne Tjonneland, Rikard Landberg, A Olsen
    Abstract:

    Background/Objectives: Whole grain intake has been associated with a small but significant lower body weight gain in observational studies, but there is limited knowledge about the associations with specific whole grain types. The objective was to investigate the association between whole grains, different sources of whole grains and biomarkers of whole grain intake (Alkylresorcinols) in relation to subsequent changes in waist circumference (WC) and body weight. Subjects/Methods: Cohort study of 57 053 participants with baseline information on whole grain intake from questionnaires (FFQ) and biomarkers of whole grain rye and wheat intake, plasma Alkylresorcinols, for a subset. WC and body weight were measured at baseline and again at follow-up. The associations were estimated using multiple linear regression analyses and logistic regression. Results: For women, overall whole grain intake was not related to changes in WC or body weight. For men, total whole grain intake was associated with gains in WC (ΔWC per 25 g increment: 0.44 cm, 95% CI: 0.34 cm; 0.54 cm) and body weight (Δweight per 25 g increment: 150 g, 95% CI: 78 g; 222 g), but the results changed to null or changed direction when adjusting for baseline anthropometry. For the different sources of whole grains, rye (women) and crispbread was significantly associated with gains in WC and body weight. Plasma Alkylresorcinol concentration was associated with reduced WC, but not body weight, for women (ΔWC per 50 nmol/l increment: −0.69 cm, 95% CI:−1.26 cm;−0.13 cm), but no association was found for men. Conclusions: Overall, no strong relationship between whole grain intake, measured from questionnaires or using biomarkers was found in relation to changes in body weight and WC.

  • dietary intake of whole grains and plasma Alkylresorcinol concentrations in relation to changes in anthropometry the danish diet cancer and health cohort study
    European Journal of Clinical Nutrition, 2017
    Co-Authors: Cecilie Kyro, M U Jakobsen, Jytte Halkjaer, Isabelle Romieu, J. Christensen, Rikard Landberg, Matilde Bylov Kristensen, H B Buenodemesquita, Anne Tjonneland
    Abstract:

    Whole grain intake has been associated with a small but significant lower body weight gain in observational studies, but there is limited knowledge about the associations with specific whole grain types. The objective was to investigate the association between whole grains, different sources of whole grains and biomarkers of whole grain intake (Alkylresorcinols) in relation to subsequent changes in waist circumference (WC) and body weight. Cohort study of 57 053 participants with baseline information on whole grain intake from questionnaires (FFQ) and biomarkers of whole grain rye and wheat intake, plasma Alkylresorcinols, for a subset. WC and body weight were measured at baseline and again at follow-up. The associations were estimated using multiple linear regression analyses and logistic regression. For women, overall whole grain intake was not related to changes in WC or body weight. For men, total whole grain intake was associated with gains in WC (ΔWC per 25 g increment: 0.44 cm, 95% CI: 0.34 cm; 0.54 cm) and body weight (Δweight per 25 g increment: 150 g, 95% CI: 78 g; 222 g), but the results changed to null or changed direction when adjusting for baseline anthropometry. For the different sources of whole grains, rye (women) and crispbread was significantly associated with gains in WC and body weight. Plasma Alkylresorcinol concentration was associated with reduced WC, but not body weight, for women (ΔWC per 50 nmol/l increment: −0.69 cm, 95% CI:−1.26 cm;−0.13 cm), but no association was found for men. Overall, no strong relationship between whole grain intake, measured from questionnaires or using biomarkers was found in relation to changes in body weight and WC.

  • carotenoids and Alkylresorcinols as objective biomarkers of diet quality when assessing the validity of a web based food record tool and a food frequency questionnaire in a middle aged population
    BMC Nutrition, 2016
    Co-Authors: Sanna Nybacka, Anna Karin Lindroos, Ulrika Ericson, Eva Warensjo Lemming, Elisabet Wirfält, Ingrid Larsson, Per Leanderson, Rikard Landberg, Goran Bergstrom
    Abstract:

    Recently, two web-based dietary assessment tools were developed; a 4-day food record tool (the Riksmaten method), and a food frequency questionnaire (MiniMeal-Q). The aim of this study was to use objective biomarkers to examine the ability of the two methods to capture habitual dietary intake. In total, 200 individuals from the pilot study of the Swedish CArdioPulmonary bioImage Study (SCAPIS) participated. Plasma concentration of carotenoids were determined with high-performance liquid chromatography (HPLC) and used as biomarkers of fruit and vegetable intake. A gas chromatography mass spectrometry (GC-MS) method was used to quantify Alkylresorcinol homologues, which were used as biomarkers of whole grain wheat and rye intake. The correlations between energy-adjusted fruit and vegetable intakes and plasma carotenoid concentrations (except lycopene) were stronger amongst women than men (r = 0.46 and r = 0.20 for the Riksmaten method, and r = 0.50 and r = 0.31 for MiniMeal-Q, respectively). For whole grains, the correlations of energy-adjusted intakes and Alkylresorcinols were higher using the Riksmaten method (r = 0.30 and r = 0.29 for women and men) than the MiniMeal-Q (r = 0.25 and r = 0.20, respectively). In regression analyses between plasma carotenoids (except lycopene) and reported intake of fruits and vegetables, the R2 were 21.6 % and 5.1 % for women and men by the Riksmaten method, and correspondingly, 18.0 % and 6.6 % by the MiniMeal-Q. In the final full models, adjusted for smoking and BMI, all regression models remained statistically significant. The regression analyses of plasma Alkylresorcinols and reported intake of whole grains showed an R2 of 9.4 % and 9.7 % for women and men by the Riksmaten method, and correspondingly, 5.3 % and 8.4 % by the MiniMeal-Q. In the final full models, adjusted for smoking and age, all regression models remained statistically significant, except for women in MiniMeal-Q. Both dietary assessment methods were able to capture dietary intake based on food groups with a similar precision. Agreements with objective biomarkers ranged from low to moderate, depending on sex and diet quality indicator. While the ability to capture whole grain intake was weak for both methods and sexes, the assessment of vegetable and fruit intake performed in a satisfactory manner for women in both methods.

  • simultaneous pharmacokinetic modeling of Alkylresorcinols and their main metabolites indicates dual absorption mechanisms and enterohepatic elimination in humans
    Journal of Nutrition, 2014
    Co-Authors: Matti Marklund, Eric A Stromberg, Afaf Kamaleldin, Andrew C Hooker, Helle Nygaard Lærke, Rikard Landberg, Knud Erik Bach Knudsen
    Abstract:

    BACKGROUND: Alkylresorcinols have proven to be useful biomarkers of whole-grain wheat and rye intake in many nutritional studies. To improve their utility, more knowledge regarding the fate of Alkylresorcinols and their metabolites after consumption is needed.OBJECTIVE: The objective of this study was to develop a combined pharmacokinetic model for plasma concentrations of Alkylresorcinols and their 2 major metabolites, 3,5-dihydroxybenzoic acid (DHBA) and 3-(3,5-dihydroxyphenyl)-propanoic acid (DHPPA).METHODS: The model was established by using plasma samples collected from 3 women and 2 men after a single dose (120 g) of rye bran and validated against fasting plasma concentrations from 8 women and 7 men with controlled rye bran intake (23, 45, or 90 g/d). Alkylresorcinols in the lymph and plasma of a pig fed a single Alkylresorcinol dose (1.3 mmol) were quantified to assess absorption. Human ileostomal effluent and pig bile after high and low Alkylresorcinol doses were analyzed to evaluate biliary Alkylresorcinol metabolite excretion.RESULTS: The model contained 2 absorption compartments: 1 that transferred Alkylresorcinols directly to the systematic circulation and 1 in which a proportion of absorbed Alkylresorcinols was metabolized before reaching the systemic circulation. Plasma concentrations of Alkylresorcinols and their metabolites depended on absorption and formation, respectively, and the mean ± SEM terminal elimination half-life of Alkylresorcinols (1.9 ± 0.59 h), DHPPA (1.5 ± 0.26 h), and DHBA (1.3 ± 0.22 h) did not differ. The model accurately predicted Alkylresorcinol and DHBA concentrations after repeated Alkylresorcinol intake but DHPPA concentration was overpredicted, possibly because of poorly modeled enterohepatic circulation. During the 8 h following administration, <2% of the Alkylresorcinol dose was recovered in the lymph. DHPPA was identified in both human ileostomal effluent and pig bile, indicating availability of DHPPA for absorption and enterohepatic circulation.CONCLUSION: Intact Alkylresorcinols have advantages over DHBA and DHPPA as plasma biomarkers for whole-grain wheat and rye intake because of lower susceptibility to factors other than Alkylresorcinol intake.

  • Simultaneous Pharmacokinetic Modeling of Alkylresorcinols and Their Main Metabolites Indicates Dual Absorption Mechanisms and Enterohepatic Elimination in Humans
    Journal of Nutrition, 2014
    Co-Authors: Matti Marklund, Eric A Stromberg, Afaf Kamal-eldin, Andrew C Hooker, Helle Nygaard Lærke, Knud Erik Bach Knudsen, Rikard Landberg
    Abstract:

    BACKGROUND: Alkylresorcinols have proven to be useful biomarkers of whole-grain wheat and rye intake in many nutritional studies. To improve their utility, more knowledge regarding the fate of Alkylresorcinols and their metabolites after consumption is needed.OBJECTIVE: The objective of this study was to develop a combined pharmacokinetic model for plasma concentrations of Alkylresorcinols and their 2 major metabolites, 3,5-dihydroxybenzoic acid (DHBA) and 3-(3,5-dihydroxyphenyl)-propanoic acid (DHPPA).METHODS: The model was established by using plasma samples collected from 3 women and 2 men after a single dose (120 g) of rye bran and validated against fasting plasma concentrations from 8 women and 7 men with controlled rye bran intake (23, 45, or 90 g/d). Alkylresorcinols in the lymph and plasma of a pig fed a single Alkylresorcinol dose (1.3 mmol) were quantified to assess absorption. Human ileostomal effluent and pig bile after high and low Alkylresorcinol doses were analyzed to evaluate biliary Alkylresorcinol metabolite excretion.RESULTS: The model contained 2 absorption compartments: 1 that transferred Alkylresorcinols directly to the systematic circulation and 1 in which a proportion of absorbed Alkylresorcinols was metabolized before reaching the systemic circulation. Plasma concentrations of Alkylresorcinols and their metabolites depended on absorption and formation, respectively, and the mean ± SEM terminal elimination half-life of Alkylresorcinols (1.9 ± 0.59 h), DHPPA (1.5 ± 0.26 h), and DHBA (1.3 ± 0.22 h) did not differ. The model accurately predicted Alkylresorcinol and DHBA concentrations after repeated Alkylresorcinol intake but DHPPA concentration was overpredicted, possibly because of poorly modeled enterohepatic circulation. During the 8 h following administration,

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