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Rikard Landberg - One of the best experts on this subject based on the ideXlab platform.
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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, 2017Co-Authors: C Kyrø, Rikard Landberg, M Kristensen, M U Jakobsen, J Halkjær, Hb(as) Bueno-de-mesquita, J Christensen, I Romieu, A Tjønneland, A OlsenAbstract: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.
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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, 2016Co-Authors: Sanna Nybacka, Rikard Landberg, Elisabet Wirfält, Anna Karin Lindroos, Per Leanderson, Ulrika Ericson, Ingrid Larsson, Eva Warensjo Lemming, Goran BergstromAbstract: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.
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Alkylresorcinols in adipose tissue biopsies as biomarkers of whole grain intake an exploratory study of responsiveness to advised intake over 12 weeks
European Journal of Clinical Nutrition, 2015Co-Authors: H Wu, Rikard Landberg, Kaisa Poutanen, Marjukka Kolehmainen, Hannu Mykkanen, Matti Uusitupa, Ursula Schwab, Alicja WolkAbstract:Alkylresorcinols in adipose tissue biopsies as biomarkers of whole-grain intake: an exploratory study of responsiveness to advised intake over 12 weeks
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determination of Alkylresorcinols and their metabolites in biological samples by gas chromatography mass spectrometry
Journal of Chromatography B, 2015Co-Authors: Roksana Wierzbicka, Rikard Landberg, Afaf Kamaleldin, Huaxing Wu, Milan FranekAbstract:Abstract High throughput GC–MS methods for quantification of Alkylresorcinols (AR), biomarkers of whole grain wheat and rye intake, in plasma and adipose tissue and their metabolites in urine were developed and optimised. Alkylresorcinols in plasma (200 μL) and adipose tissues (10–50 mg) were extracted with diethyl ether, whereas main AR metabolites such as DHBA and DHPPA and newly identified metabolites in urine (50 μL) were extracted with ethyl acetate after enzymatic deconjugation. All extracts were purified on OASIS-MAX solid phase extraction cartridges. Plasma and adipose tissue sample extracts were then derivatised with trifluoroacetic anhydride and reconstituted in undecane, whereas AR metabolites in urine samples were derivatised with BSTFA + TMCS (99:1, v/v, 100 μL). Prepared samples were quantified by GC–MS (EI-SIM). Analysis of all compounds in the different matrices showed good selectivity, sensitivity, linearity, precision (
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simultaneous pharmacokinetic modeling of Alkylresorcinols and their main metabolites indicates dual absorption mechanisms and enterohepatic elimination in humans
Journal of Nutrition, 2014Co-Authors: Matti Marklund, Rikard Landberg, Eric A Stromberg, Helle Nygaard Laerke, Knud Erik Bach Knudsen, Afaf Kamaleldin, Andrew C HookerAbstract: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.
Arkadiusz Kozubek - One of the best experts on this subject based on the ideXlab platform.
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Isolation of Alkylresorcinols: Classical and supercritical CO2 extraction methods
2020Co-Authors: José Da Cruz Francisco, Bengt Danielsson, Arkadiusz KozubekAbstract:This chapter focuses on the use of different methods for isolation of Alkylresorcinols. Alkylresorcinols are members of a lipid group called non-isoprenoid phenolic lipids. Different aspects of the extraction by classical methods and supercritical CO2 are discussed. Supercritical CO2 extraction of Alkylresorcinols from rye bran is discussed for the first time. As compared to the classical extraction methods, supercritical CO2 gives higher yields and it allows the separation of the crude extrac into long- and short-chain alkylresorcinol homologues.
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Alkylresorcinols in the family Fabaceae
Acta Societatis Botanicorum Poloniae, 2020Co-Authors: R. Zarnowski, E. D. Zarnowska, Arkadiusz KozubekAbstract:The Fabaceae are a large family, members occurence of which is very common at various latitudes. The characteristic feature of this plant family is the symbiosis with the bacteria genus Rhizobium and Bradyrhizobium . The analysis of acetone extracts from dried seeds of the subfamily Papilinioideae revealed the occurrence of Alkylresorcinols in about 85% of the examined samples. Unfortunately, it was not possible to verify this observation in the second subfamily of Fabaceae-Caesalpinioideae . It was partly because there is merely one species belonging to this subfamily, in Poland.In reference to the common occurence of Alkylresorcinols in Papilinioideae some interspecific differences were indicated. This survey is a basis for further studies on the Fabaceae family.
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Various effects of the photosystem II--inhibiting herbicides on 5-n-alkylresorcinol accumulation in rye seedlings.
Pesticide Biochemistry and Physiology, 2014Co-Authors: Elżbieta G. Magnucka, Arkadiusz Kozubek, Stanislaw J. Pietr, Robert ZarnowskiAbstract: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 .
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antioxidant activity of rye bran Alkylresorcinols and extracts from whole grain cereal products
Food Chemistry, 2009Co-Authors: Mariola Korycinska, Karolina Czelna, Anna Jaromin, Arkadiusz KozubekAbstract: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.
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cycloate an inhibitor of fatty acid elongase modulates the metabolism of very long side chain Alkylresorcinols in rye seedlings
Pest Management Science, 2009Co-Authors: Elzbieta G Magnucka, Yoshikatsu Suzuki, Arkadiusz Kozubek, Stanislaw J. Pietr, Robert ZarnowskiAbstract: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
Alastair B. Ross - One of the best experts on this subject based on the ideXlab platform.
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Serum Alkylresorcinols as Biomarkers of Dietary Gluten Exposure in Celiac disease
The FASEB Journal, 2020Co-Authors: Alastair B. Ross, Rok Seon Choung, Eric V Marietta, Carol T Van Dyke, Joseph A MurrayAbstract: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
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identification and quantification of even and odd chained 5 n Alkylresorcinols branched chain Alkylresorcinols and methylAlkylresorcinols in quinoa chenopodium quinoa
Food Chemistry, 2017Co-Authors: Alastair B. Ross, Cecilia Svelander, Goran Karlsson, Otto SavolainenAbstract:Quinoa is a pseudocereal grown in the Andean region of South America that is of increasing interest worldwide as an alternative staple food. We have detected a complex mixture of both odd- and even-alkyl chain Alkylresorcinols (AR), branched-chain Alkylresorcinols (bcAR) and methylAlkylresorcinols (mAR) in ethyl acetate extracts of quinoa. We quantified the content of AR in 17 commercial samples of quinoa, and found that the mean±SD content of AR was 58±16μg/g, bcAR was 182±52μg/g, and mAR was 136±40μg/g. AR from quinoa could also be detected in plasma after eating quinoa, indicating that some of these unique AR could be used as biomarkers of quinoa intake in humans. Further work is required to understand the role of these ARs in the quinoa plant and whether any of the novel ARs may be of particular interest in human nutrition.
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serum Alkylresorcinols as biomarkers of dietary gluten exposure in coeliac disease
Alimentary Pharmacology & Therapeutics, 2017Co-Authors: Rok Seon Choung, Eric V Marietta, Carol T Van Dyke, Joseph A Murray, Alastair B. RossAbstract: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.
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serum Alkylresorcinols as biomarkers of dietary gluten exposure in celiac disease
The FASEB Journal, 2017Co-Authors: Alastair B. Ross, Rok Seon Choung, Eric V Marietta, Carol T Van Dyke, Joseph A MurrayAbstract: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.
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a high throughput method for liquid chromatography tandem mass spectrometry determination of plasma Alkylresorcinols biomarkers of whole grain wheat and rye intake
Analytical Biochemistry, 2016Co-Authors: Alastair B. Ross, Mads Vendelbo Lind, Cecilia Svelander, Otto Savolainen, John P Kirwan, Isabelle Breton, Jean Philippe Godin, Annsofie SandbergAbstract: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.
Per Aman - One of the best experts on this subject based on the ideXlab platform.
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an update on Alkylresorcinols occurrence bioavailability bioactivity and utility as biomarkers
Journal of Functional Foods, 2014Co-Authors: Matti Marklund, Rikard Landberg, Afaf Kamaleldin, Per AmanAbstract:Abstract Alkylresorcinols (AR) with alkyl chains in the range of C15 to C25 are phenolic lipids particularly abundant in the outer parts of wheat and rye kernels and in food products containing these parts. The content in whole grain and bran products is high (200–4000 μg/g), whereas only trace-levels are detected in refined products. Alkylresorcinols are absorbed in humans in proportion to intake and have therefore been suggested and evaluated as biomarkers for whole grain wheat and rye intake. In humans, plasma AR concentrations reach micromolar concentrations immediately after whole grain wheat and rye product consumption and nano-molar levels at fasting conditions. Results from different model studies have indicated that AR may have some bioactivities including enzyme inhibition, suppression of adipocyte lipolysis and inhibition of colon cancer tumor growth but it is currently unknown whether AR bioactive in vivo or not. This chapter details the recent research findings on Alkylresorcinols with emphasis on their occurrence, bioavailability, bioactivity and utility as biomarkers.
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An update on Alkylresorcinols – Occurrence, bioavailability, bioactivity and utility as biomarkers
Journal of Functional Foods, 2014Co-Authors: Rikard Landberg, Afaf Kamal-eldin, Matti Marklund, Per AmanAbstract:Abstract Alkylresorcinols (AR) with alkyl chains in the range of C15 to C25 are phenolic lipids particularly abundant in the outer parts of wheat and rye kernels and in food products containing these parts. The content in whole grain and bran products is high (200–4000 μg/g), whereas only trace-levels are detected in refined products. Alkylresorcinols are absorbed in humans in proportion to intake and have therefore been suggested and evaluated as biomarkers for whole grain wheat and rye intake. In humans, plasma AR concentrations reach micromolar concentrations immediately after whole grain wheat and rye product consumption and nano-molar levels at fasting conditions. Results from different model studies have indicated that AR may have some bioactivities including enzyme inhibition, suppression of adipocyte lipolysis and inhibition of colon cancer tumor growth but it is currently unknown whether AR bioactive in vivo or not. This chapter details the recent research findings on Alkylresorcinols with emphasis on their occurrence, bioavailability, bioactivity and utility as biomarkers.
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plasma Alkylresorcinols biomarkers of whole grain wheat and rye intake and incidence of colorectal cancer
Journal of the National Cancer Institute, 2014Co-Authors: Cecilie Kyro, Per Aman, Rikard Landberg, Anja Olsen, Guri Skeie, Steffen Loft, Max Leenders, Peter D Siersema, Tobias PischonAbstract:Methods The association between Alkylresorcinols, biomarkers of whole-grain rye and wheat intake, and colorectal cancer incidence were investigated using prediagnostic plasma samples from colorectal cancer case patients and matched control subjects nested within the European Prospective Investigation into Cancer and Nutrition. We included 1372 incident colorectal cancer case patients and 1372 individual matched control subjects and calculated the incidence rate ratios (IRRs) for overall and anatomical subsites of colorectal cancer using conditional logistic regression adjusted for potential confounders. Regional differences (Scandinavia, the Mediterranean, Central Europe) were also explored. Results High plasma total alkylresorcinol concentration was associated with lower incidence of distal colon cancer; the adjusted incidence rate ratio of distal colon cancer for the highest vs lowest quartile of plasma total Alkylresorcinols was 0.48 (95% confidence interval [CI] = 0.28 to 0.83). An inverse association between plasma total alkylresorcinol concentrations and colon cancer was found for Scandinavian participants (IRR per doubling = 0.83; 95% CI = 0.70 to 0.98). However, plasma total alkylresorcinol concentrations were not associated with overall colorectal cancer, proximal colon cancer, or rectal cancer. Plasma Alkylresorcinols concentrations were associated with colon and distal colon cancer only in Central Europe and Scandinavia (ie, areas where alkylresorcinol levels were higher). Conclusions High concentrations of plasma Alkylresorcinols were associated with a lower incidence of distal colon cancer but not with overall colorectal cancer, proximal colon cancer, and rectal cancer.
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long term reproducibility of plasma Alkylresorcinols as biomarkers of whole grain wheat and rye intake within northern sweden health and disease study cohort
European Journal of Clinical Nutrition, 2013Co-Authors: Rikard Landberg, Per Aman, Goran Hallmans, Ingegerd JohanssonAbstract:BACKGROUND/OJBECTIVES: Alkylresorcinols (AR) have been suggested as specific biomarkers of whole-grain (WG) and bran intake from wheat and rye. Before using plasma AR as biomarkers in prospective c ...
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Comparison of GC and colorimetry for the determination of alkylresorcinol homologues in cereal grains and products
Food Chemistry, 2009Co-Authors: Rikard Landberg, Per Aman, Annica A.m. Andersson, Afaf Kamal-eldinAbstract:Abstract Cereal Alkylresorcinols (ARs), a group of phenolic lipids mainly found in the outer parts of wheat and rye kernels, are currently being studied for possible use as biomarkers of intake of whole grain wheat and rye foods. Several different techniques have been used for quantitative AR analysis over the years, but with limited attempts to compare them. In this present study, two commonly used methods, gas chromatography and colorimetry, were evaluated and compared. Gas chromatographic and the colorimetric methods showed good agreement. The GC-method provides the total amount of AR and relative homologue composition, whereas the colorimetric method, which is based on azo-coupling of a Fast Blue salt to the hydroxyl group(s) in the alkylresorcinol molecule, only provides the total amount, but is much faster and does only requires a UV-spectrophotometer.
Robert Zarnowski - One of the best experts on this subject based on the ideXlab platform.
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Dynamics of Alkylresorcinols during rye caryopsis germination and early seedling growth.
Zeitschrift für Naturforschung C, 2015Co-Authors: Elżbieta G. Magnucka, Stanislaw J. Pietr, Robert ZarnowskiAbstract:: 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.
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Various effects of the photosystem II--inhibiting herbicides on 5-n-alkylresorcinol accumulation in rye seedlings.
Pesticide Biochemistry and Physiology, 2014Co-Authors: Elżbieta G. Magnucka, Arkadiusz Kozubek, Stanislaw J. Pietr, Robert ZarnowskiAbstract: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 .
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cycloate an inhibitor of fatty acid elongase modulates the metabolism of very long side chain Alkylresorcinols in rye seedlings
Pest Management Science, 2009Co-Authors: Elzbieta G Magnucka, Yoshikatsu Suzuki, Arkadiusz Kozubek, Stanislaw J. Pietr, Robert ZarnowskiAbstract: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
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Alkylresorcinols in selected polish rye and wheat cereals and whole grain cereal products
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Mariola Kulawinek, Arkadiusz Kozubek, Anna Jaromin, Robert ZarnowskiAbstract: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...
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5 n Alkylresorcinols from grains of winter barley hordeum vulgare l
Zeitschrift für Naturforschung C, 2004Co-Authors: Robert Zarnowski, Yoshikatsu SuzukiAbstract:: The resorcinolic lipid content and homologue composition of winter barley grains harvested at two field locations were evaluated. Depending on the crop location, the predominant Alkylresorcinols identified were 1,3-dihydroxy-5-n-heneicosylbenzene or 1,3-dihydroxy-5-n-pentacosylbenzene. Both resorcinol concentration and their homologue profiles were diverse in samples harvested at different fields indicating a prevailing role of the environment upon the alkylresorcinol biosynthesis in cereals.
