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.

Secoisolariciresinol and matairesinol of sea buckthorn (Hippophaë rhamnoides L.) berries of different subspecies and harvesting times.

Sea buckthorn (Hippophaë rhamnoides) seeds, berries, and berry fractions are often used as sources of bioactive ingredients for health products. The aim of the present study was to analyze lignans in these fractions of sea buckthorn. Secoisolariciresinol and matairesinol in seeds, fruit pulp/peel, and whole berries of sea buckthorn of three subspecies were analyzed by isotope dilution gas chromatography-mass spectrometry. The total content of the two lignans secoisolariciresinol and matairesinol varied widely from 8 to 139 microg/100 g in fresh berries and from 51 to 319 microg/100 g in dry berries. The content of secoisolariciresinol varied in the range of 34-313 microg/100 g of dry mass in the fruit pulp/peel and 93-355 microg/100 g in dry seeds. The content of matairesinol fell within the range of 3-25 microg/100 g in dry pulp/peel and 1-13 microg/kg in dry seeds. Wild H. rhamnoides ssp. sinensis contained a significantly higher total level of secoisolariciresinol and matairesinol in dry seeds, dry berries, and fresh berries compared with wild ssp. rhamnoides (253 vs 135 microg/100 g, P < 0.01, in seeds; 224 vs 153 microg/100 g, P < 0.05, in dry berries; 71 vs 29 g/100 g, P < 0.01, in fresh berries) and the cultivar of ssp. mongolica (253 vs 112 microg/100 g in seeds, 71 vs 9 microg/100 g in fresh berries). Harvesting dates had a significant influence on the content of the two lignans in seeds, fruit pulp/peel, and whole berries. This is the first report of lignans in sea buckthorn.

Kinetics of the appearance of cereal alkylresorcinols in pig plasma.

Alkylresorcinols (AR) are phenolic lipids found in high amounts in wholegrain wheat and rye. They may be important as bioactive components and/or biomarkers of wholegrain wheat and rye intake. AR absorption was studied with pigs during a habitual diet and after a single meal of AR-rich diet. In study 1, four pigs were fed wholegrain rye (RD) and white wheat bread (WD) for 1 week in a cross-over design. Arterial and venous AR concentrations were determined over 540 min after feeding on days 5 and 7. In study 2, four pigs were fed a synthetic, starch-based diet for 5 d, and arterial and venous AR concentrations were determined over 960 min after feeding a single meal of RD. In study 1, plasma AR concentrations after consuming RD peaked at 120 min, remained elevated between 120 and 420 min, and were re-elevated on refeeding at 480 min. In study 2, AR appeared in the plasma after 60 min, peaked at 180-240 min, and remained elevated after 960 min. The apparent elimination half-life was 3.93 h, and the maximum plasma concentration was 666 (sem 35) nmol/l. Arterial and venous plasma AR concentrations were similar, suggesting that AR are absorbed via the lymphatic system. AR concentrations in pig plasma increase rapidly after a meal containing AR, and persist in plasma for at least 5 d, indicating that AR may be a useful biomarker of wholegrain wheat and rye intake.

Whole-grain rye bread consumption by women correlates with plasma alkylresorcinols and increases their concentration compared with low-fiber wheat bread.

Whole-grain rye and wheat products are rich in lignans, the precursors of enterolactone (ENL) and alkylresorcinols (ARs), which are phenolic lipids. In this crossover trial, we examined the effect of whole-grain rye bread compared with low-fiber wheat bread on plasma AR levels. Women (n = 39) aged 59 +/- 0.94 y (mean +/- SEM) were advised to consume rye (214 +/- 7.1 g/d) or wheat (178 +/- 6.5 g/d) bread (20% of total daily energy intake) in random order for 8 wk. The test periods were separated by an 8-wk washout period. ARs with different homologues and ENL were measured in plasma collected at the beginning (habitual diet) and end of the test bread periods. AR concentrations were higher (P < 0.001) after the rye bread (352 +/- 24.7 nmol/L) and habitual diet (97.7 +/- 12.1 and 88.3 +/- 8.7 nmol/L) periods than after the wheat bread period (36.6 +/- 4.2 nmol/L). Plasma AR concentrations were correlated with intake of rye bread (r = 0.34, P = 0.037), and with insoluble fiber from the whole diet during the rye (r = 0.39, P = 0.013) and wheat (r = 0.32, P = 0.047) bread periods. The plasma AR 17:0/21:0 ratio differed after the rye (0.84 +/- 0.04) and wheat (0.53 +/- 0.08) bread diet periods (P < 0.001). These data strongly suggest that plasma ARs could be used as specific biomarkers for whole-grain rye intake, and their homologue pattern could be used as an indicator of the bread type consumed.

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.

Gas chromatographic-mass spectrometric method for the determination of alkylresorcinols in human plasma.

Alkylresorcinols can be found in high amounts in whole grain cereals, especially in rye. Previously it has not been possible to measure alkylresorcinols in plasma. In this paper a validated gas chromatographic-mass spectrometric method for the quantitative determination of alkylresorcinols with chain lengths of C15:0, C17:0, C19:0, C21:0, and C23:0 in human plasma samples is presented. Other alkylresorcinols may be measured with the method as well, but their assay was not validated in this work. In this work also the amount of alkylresorcinol C25:0 was measured. The pretreatment of plasma samples consists of a simple incubation, an extraction with diethyl ether and a chromatographic purification before the GC-MS analysis. As internal standard an alkylresorcinol C20:0 was used. The validation of the method showed that it fulfilled the reliability criteria. Calibration graphs were linear over the range of 4.1-660pg per injection. The mean recovery percentage was 112+/-10.8%. Our results show that the alkylresorcinols are found in plasma in the same ratio, as found in rye grains, according to literature. The alkylresorcinols were in the unconjugated form. The total amounts of alkylresorcinols in two plasma samples analyzed here were 333 and 381nmol/L.