Alkylresorcinol Content Research Articles

Solid‐state fermentation by Aspergillus niger and Lactobacillus plantarum improved the nutritional and physicochemical properties of wheat bran and whole wheat bread

SummarySolid‐state fermentation (SSF) is an economically viable processing technique to improve the bioactive content from agricultural by‐products. The impacts of SSF by Aspergillus niger (AN) and Lactobacillus plantarum (LP) on the physicochemical and functional properties of wheat bran and whole wheat bread were investigated in this study. Compared with unfermented wheat bran, the pH of fermented wheat bran decreased significantly, and the titrated acidity increased significantly. The water absorption index, water solubility index and swelling capacity of wheat bran were significantly increased after fermentation. Besides, the free‐radical scavenging activities for DPPH, ABTS and the total antioxidant capacity of wheat bran were notably increased after SSF. Moreover, the content of alkylresorcinols (ARs), total phenolics and flavonoids compounds in wheat bran were enhanced by 137.85%, 52.87% and 95.6%, respectively, after fermentation. The content of aflatoxin B1, deoxynivalenol, zearalenone and ochratoxin A were decreased by 76.34%, 18.67%, 34.48% and 20.46%, respectively. SSF enhanced the content of ARs, total phenols and flavonoids in the reconstituted whole wheat bread by 136.55%, 54.55% and 97.74%, respectively. Whereas, the hardness and chewiness of the bran‐rich bread were decreased by 75.2% and 92.41%, respectively. Additionally, the sensory evaluation score, specific volume and the overall score of reconstituted bread were significantly improved. Taken together, SSF by AN and LP could improve the processing value of wheat bran and might be a feasible solution to upgrade whole wheat product quality.

Influence of Nitrogen Fertilisation Level and Weather Conditions on Yield and Quantitative Profile of Anti-Nutritional Compounds in Grain of Selected Rye Cultivars

Cultivar, habitat conditions and agrotechnology have an influence on the yield and chemical composition of rye grain. The main anti-nutritional substances present in rye grain include alkylresorcinols, water-soluble pentosans and trypsin inhibitors. The aim of this study was to determine the variability in yield and the concentration of anti-nutritional compounds in the grain of selected winter rye cultivars in relation to nitrogen fertilisation levels and weather conditions. Field studies were conducted at the Experimental Station of IUNG-PIB in Osiny (Poland) in two growing seasons (2018/2019 and 2019/2020). The experiment was located on pseudo-polylic soil using the randomised sub-block method in three replications. The first factor of the experiment was the level of nitrogen fertilisation (0, 70 and 140 kg N∙ha−1) and the second was the population (Dańkowskie Skand, Piastowskie) and hybrid (KWS Vinetto, SU Performer) winter rye cultivars. The study showed that the yield of winter rye depended on the genotype and the level of nitrogen fertilisation. The hybrid cultivars yield ed 17.9% higher in relation to the population cultivars. The content of anti-nutritional compounds in rye grain depended significantly on genotype, level of nitrogen fertilisation and weather conditions. The reason for the higher synthesis of anti-nutrients in rye grain was the stressful weather conditions occurring in the 2019/2020 season. Nitrogen fertilisation influenced the content of alkylresorcinols, water-soluble pentosans and trypsin inhibitor activity in grain. The interaction of cultivar and fertilisation was also found to shape the content of the aforementioned anti-nutrients.

Alkylresorcinols as a New Type of Gut Microbiota Regulators Influencing Immune Therapy Efficiency in Lung Cancer Treatment

Background. Alkylresorcinols (ARs) are polyphenolic compounds of microbial origin with a wide spectrum of biological activities and are potentially involved in host immune functioning. The present study is aimed at evaluating alterations in AR content in blood serum and faeces from healthy donors and patients with lung cancer in connection with response to immune checkpoint inhibitor (ICI) therapy to estimate the regulatory potential of AR. Methods. Quantitative analysis of AR levels, as well as other microbial metabolites in blood serum and faeces, was performed using gas chromatography with mass spectrometric detection; estimation of lymphocyte subsets was performed by flow cytometry; faecal microbiota transplantation (FMT) from lung cancer patients after ICI therapy to germ-free mice was performed to explore whether the intestinal microbiota could produce AR molecules. Results. AR concentrations in both faeces and serum differ dramatically between healthy and lung cancer donors. The significant increase in AR concentrations in mouse faeces after FMT points to the microbial origin of ARs. For several ARs, there were strong positive and negative correlations in both faeces and serum with immune cells and these interrelationships differed between the therapy-responsive and nonresponsive groups. Conclusions. The content of ARs may influence the response to ICI therapy in lung cancer patients. ARs may be considered regulatory molecules that determine the functioning of antitumor immunity.

Genome-wide association study of alkylresorcinols content in 161 wheat cultivars

Alkylresorcinols (ARs), a group of phenolic lipids exclusively found in wheat, rye and barley among daily foods, are considered to be biomarkers for whole wheat grain intake. Recent studies have gradually revealed their functions and benefits for human health. However, the natural variation of ARs contents (ARC) in bread wheat cultivars in China has not been revealed. This study assayed grain ARC in a panel of 161 wheat cultivars grown in five environments in China and reports significant genotypic and environmental variation. Grain ARC ranged from 321 to 972 μg/g. Cultivars such as Yumai 18 and Yumai 2 had high ARC and thousand kernel weight (TKW) and can be utilized for production of ARs-fortified foods and as parents for breeding. Genome-wide association analysis with high-density single nucleotide polymorphism (SNP) arrays identified 24 and 32 stable loci associated with total ARC and thousand kernel ARC (TKAC), respectively. Loci on chromosome arms 3BL and 7BL, were significant for both ARC and TKAC. This study firstly revealed the extensive variation and genetic architecture of ARC in Chinese bread wheat, providing a theoretical basis for future high-ARC genetic improvement.

Comparative analysis of the qualitative characteristics of formaldehyde and acetaldehyde resins based on styrene-modified oil shale alkylresorcinols

Reducing the amount of volatile compounds in alkylresorcinol-aldehyde resins, reducing the impact of their components on the environment, and improving their performance can be achieved by replacing formaldehyde with acetaldehyde and by preliminary aralkylation of the resorcinol components of the raw material. To prove this, a comparative analysis of the properties of resins synthesized based on oil shale alkylresorcinols pre-treated with styrene, formaldehyde, or acetaldehyde was carried out. The effects of the molar ratio of feedstock/aldehyde and the amount of catalyst on the yield and characteristics of the resins were considered. Both individual alkylresorcinols (R, 5-MR, 2.5-DMR) and industrial fractions (REZOL, HONEYOL) were used as the raw materials. The following indicators were used to compare the obtained resins: softening point, ash content, coke number, moisture content, volatile substances, and solubility in organic solvents. The thermal properties of the resins were studied by TG/DTG/DTA in inert and oxidative atmosphere. Qualitative and quantitative analyses of resins and distillates for the content of unreacted resorcinol, individual alkylresorcinols, and styrene were carried out using iodometry, thin-layer chromatography (TLC), and gas chromatography (GC). It has been shown that the use of acetaldehyde makes it possible to obtain resins with the stated characteristics. The formaldehyde (SF) and acetaldehyde (SAc) resins obtained consist of oligomers with different chain lengths. Synthesized SAc resins are solids with a softening point of 51 °C–103 °C. Resins are soluble in acetone, EtOH, acetonitrile, and THF, and insoluble in benzene. SAc resins contain 3–4 times less unreacted original resorcinol components compared to SF resins. The conversion of styrene in the synthesis of Rez100SF resins was 42 wt%, Rez100SAc and Hon100SAc are 98 and 97 wt%, respectively. A comparative analysis of resins synthesized using acetaldehyde instead of formaldehyde helped identify both the advantages and disadvantages of the proposed synthesis variation.

Study on the spatio-temporal variation of arabinoxylan and alkylresorcinol in wheat grains

The purpose of this study was to clarify the spatio-temporal variation of arabinoxylan (AX) and alkylresorcinol (AR) in wheat. The total arabinoxylan (TOT-AX), water-extractable arabinoxylan (WE-AX), and AR contents of wheat from the main wheat producing areas of China were investigated. The effects of the geographical origin, variety, harvest year, their interactions, and irrigation frequency on the content and structure vibrations of AX and AR in wheat grains were studied based on the field experiment combined with one-way and multi-way analysis of variance. The results showed that the TOT-AX, WE-AX, and AR contents of wheat from the main wheat producing areas of China were 27.03–64.16 mg/g, 3.81–9.70 mg/g and 275.6–661.7 µg/g, respectively. Except for the irrigation, other factors had significant effects on the AX and AR contents of wheat, and the variety had the greatest effect. Xiaoyan 22, Xinmai 18, and Hengguan 35 had the highest TOT-AX, WE-AX and AR contents, respectively. The O-H stretching vibration of AX and AR and the skeleton vibrations of the aromatic ring of AR was mainly affected by the variety. This study indicated that Xiaoyan 22, Xinmai 18, and Hengguan 35 can be used for producing foods with high TOT-AX, WE-AX, and AR contents, respectively.

The Influence of Farming Systems, Genotype and Their Interaction on Bioactive Compound, Protein and Starch Content of Bread and Spelt Wheat.

An increase in the production and consumption of spelt products can be associated with positive effects on human health, which are attributed to bioactive compounds present in the grain. The basic success of spelt wheat in organic farming might be explained by the fact that spelt wheat belongs to the group of hulled wheat where the presence of a husk protects the seed from abiotic and biotic stress factors, thus demanding less chemical protection. The goal of this study was to investigate the variations in the bioactive compound (alkylresorcinol, arabinoxylan, β-glucan), protein, starch and fructan content of bread and spelt wheat under different farming systems (conventional and organic). The results showed higher protein and alkylresorcinol but lower fructan content in spelt wheat. Organic spelt had significantly higher starch, fiber and alkylresorcinol content but lower β-glucan and protein content than conventionally grown spelt. The spelt variety 'Oberkulmer-Rotkorn' was characterized by the highest values for the majority of analyzed traits under both farming systems. Overall, the environmental conditions (Hungary and Serbia), farming systems (conventional and organic) and wheat species (bread and spelt) contributed to the variations of the compositional traits in different manners.

Environmental and cultivar variability in composition, content and biological activity of phenolic acids and alkylresorcinols of winter wheat grains from a multi-site field trial across Europe

Different factors such as the genotype, environmental conditions, temperature stress, solar radiation and others can influence the phytochemical status of plants. The concentration of phenolic acids and alkylresorciols (ARs) as well as their chemical composition and biological activity have been determined in twelve winter wheat cultivars grown at eight European locations. This was the first winter wheat multi-location field trial of the European Consortium for Open Field Experimentation (ECOFE). Extracts from grain were analyzed using a UPLC-PDA-ESI-MS system (phenolic acids), UPLC-PDA-MS/MS (alkylresorcinols) and TLC-DPPH• test with ImageJ program (antiradical activity). The phenolic acid profile consisted of five hydroxybenzoic acid and four hydroxycinnamic acid derivatives, among which ferulic and sinapic acids were predominated. The ARs profile consisted of nine AR derivatives, among which 5-n-heneicosylresorcinol (C21:0) and 5-n-nonadecanylresorcinol (C19:0) were predominated. Our study showed significant differences in phenolic acids and AR content between wheat cultivars, as well as between locations. We observed a positive correlation between the biological activity of extracts and the total amount of phenolic acids and ARs. Two cultivars, Chambo and Julius (average of all sites) and samples from the Spanish site (average of all cultivars) showed the highest content and composition of nutritional substances.

Impact of Genotype, Weather Conditions and Production Technology on the Quantitative Profile of Anti-Nutritive Compounds in Rye Grains

The main anti-nutritive substances present in rye grains include alkylresorcinols, water-soluble pentosans, and trypsin inhibitors. The content of these compounds in the grains can be influenced by genetic factors, habitat conditions and the crop management technology used in cultivation. The aim of the study was to determine the variability of the concentration of anti-nutritive compounds in rye grains depending on the variety, weather conditions and production technology. The field research was conducted at the IUNG-PIB Experimental Station in Osiny (Poland) in three growing seasons 2010/2011, 2011/2012 and 2012/2013. The experiment was located on lessive soil, on plots of 45 m2 in three replications. The first factor was the type of production technology (integrated and intensive), while the second was a variety of winter rye. Two hybrid varieties (Brasetto, Visello) and two population varieties (Dańkowskie Diament, Kier) were included. The research showed that the content of anti-nutritive compounds in rye grains depended significantly on the genotype and weather conditions. Stress conditions during the rye growing season in 2011 and 2013 were the cause of higher synthesis of alkylresorcinols, soluble pentosans and trypsin inhibitors in rye grains. The content of alkylresorcinols and water-soluble pentosans also depended significantly on the intensity of the production technology. The higher content of these compounds was found in rye grains from intensive technology. The production technology had no significant impact on the activity of trypsin inhibitors.

Distribution of free and bound phenolic compounds, and alkylresorcinols in wheat aleurone enriched fractions

Several companies have focused their attention on the development of technologies able to enrich/isolate the wheat aleuronic layer because it is a source of bioactive compounds. In this work two different wheat bran fractions enriched in aleurone (AF1, 55–70% aleurone and AF2, 75–90% aleurone) were obtained by a dry fractionation based on air classification. Free and bound phenolic compounds, and alkylresorcinols were determined in the two fractions by HPLC-DAD-ESI-TOF-MS and GC–MS, respectively. To our knowledge, feruloyl di-hexoside was described for the first time in wheat aleurone and flavonoids were quantified for the first time in this fraction. The results have shown that the most concentrated free phenolic compounds were flavonoids, and AF1 was the fraction that presented the highest flavonoid content; whereas trans ferulic acid was the most abundant bound phenolic acid, which highest content was obtained in AF2. Besides, total content of ferulic acid monomers in AF2 was 33.63% higher than in AF1, whereas total content of ferulic acid dimers/trimers in AF1 was 33.9% higher than in AF2. The highest content of alkylresorcinols was obtained in AF1 and it was 10.30% higher than the obtained in AF2. Therefore, it can be stated that this green technology could be used to produce enriched aleurone fractions as source of phenolic and alkylresorcinol compounds. These fractions could be of great interest for the formulation of enriched foods.

Benzoxazinoid and alkylresorcinol content, and their antioxidant potential, in a grain of spring and winter wheat cultivated under different production systems

The health-promoting properties of the grains of common wheat (Triticum aestivum L.) are associated with the presence of unique phytochemicals. This study determines the profile of alkylresorcinols (ARs) and benzoxazinoids (BXs) in T. aestivum spring and winter cultivars grown in Poland under the two different production systems: conventional and organic. Wheat grain extracts were subjected to qualitative and quantitative UPLC-UV-MS/MS analyses. The ARs profile consisted of five 5-n-alkylresorcinol derivatives, among which 5-n-heneicosylresorcinol (C21:0) and 5-n-nonadecanylresorcinol (C19:0) predominated; while six different BXs were determined in hydrothermally treated grains. Our research shows significant differences in the contents of ARs and BXs among wheat cultivars, as well as the two production systems used. Organically grown varieties had their total contents of ARs and BXs significantly higher than those grown conventionally. Another aim of the study was to determine the antioxidant capacity of alkylresorcinol extracts from tested wheat cultivars. The quantitative TLC-DPPH• method for determining the antiradical capacity of wheat ARs extracts was developed. We observed a positive relationship between the free radical scavenging activity of extracts and the total amount of ARs. The biological activity research is important for developing value-added wheat cultivars, having an improved profile and composition of nutritional substances.

Solid state fermentation by Fomitopsis pinicola improves physicochemical and functional properties of wheat bran and the bran-containing products

Wheat bran was solid state fermented by Fomitopsis pinicola. The results showed that the processing properties were increased by fermentation and the content of total phenol and alkylresorcinols was 5.91 and 1.55 times of the unfermented bran respectively by the 6th day. The total antioxidant capacity was 5.73 times of the unfermented sample by the 4th day. Electronic nose analysis showed that the fermented wheat bran had a special flavor. GC–MS analysis found that 4-ethyl-2-methoxy-phenol was the main flavor substance, which was sharply increased during the fermentation. Furthermore, the textural properties of the dough and bread containing fermented bran were significantly improved. The content of phytic acid in the bread was significantly decreased, while the protein, total phenol and alkylresorcinols contents were significantly increased. Results suggest that solid state fermentation by Fomitopsis pinicola is a promising way to improve wheat bran to a nutritious and flavorful cereal food ingredient.

Effect of different heat treatment on alkylresorcinol contents of wheat bran

The influence of different heat treatment levels on the contents of alkylresorcinol and homologues (ARs) was evaluated using wheat bran from two different wheat cultivars. The ARs in the wheat bran were destroyed by all heat treatments investigated in this study (oven treatment, microwave treatment, autoclave treatment, and extrusion treatment). The results showed that the loss rate of ARs by different heat treatment was oven treatment > autoclave treatment > extrusion treatment > microwave treatment, indicating that microwave treatment was more suitable for stabilizing wheat bran than the other three heat treatments. Both temperature and time of heat treatment had effects on the ARs of wheat bran. Higher temperatures and longer times of the treatment resulted in higher loss rates of ARs of wheat bran. The thermal stability of ARs homologues was different between wheat varieties, which may result from the variance of their structure and other components in wheat bran.

Stone Milling versus Roller Milling in Soft Wheat: Influence on Products Composition

Wholegrain wheat flours are in great demand from consumers worldwide because they are considered healthier then refined flours. They can be obtained by either stone milling, which is experiencing a revival in Europe, or roller milling. In order to study compositional differences due to the milling technology and to explore the possibility of a better qualification of wholegrain flours by means of nutritionally oriented quality parameters, eight mixes of soft wheat grains were stone milled and roller milled and the milling products were analyzed for their protein, ash, lipids, total dietary fibre, total polyphenols and alkylresorcinols content. A wholegrain flour milled with a laboratory disk mill was used as a comparison and a set of seven wholegrain flours purchased on themarket were also analyzed and compared. The particle size distribution of stone milled and recombined roller milled flour was also studied. Considering the above mentioned parameters, we found that there is no compositional difference between a stone milled or a roller milled flour if, in this latter one, the milling streams are all recombined, but the particle size distribution was different. This might have an impact on the technological quality of flours and on the bioavailability of components.

Low molecular phytochemicals of Indian dwarf (Triticum sphaerococcum Percival) and Persian wheat (T. carthlicum Nevski) grain

Ancient wheat grain is considered by consumers to be more natural, pro-healthy and better tolerated, so these genotypes are being steadily reintroduced to cultivation. This study presents the content and composition of phenolic acids, alkylresorcinols, sterols, tocols and carotenoids in the grain of Indian dwarf and Persian wheats, extended by characteristics of their kernels (weight, dimensions and colour). To compare these features, four other wheat species (bread, spelt, durum and einkorn wheats) were used. It was found that the grain of Indian dwarf and Persian wheat is similar in weight and dimensions to grain of einkorn wheat, while in colour to bread wheat. Among the tested samples, grain of both new genotypes was the richest source of total low molecular phytochemicals, especially phenolic acids and alkylresorcinols, while being the weakest source of carotenoids. For these wheats, an enhanced share of ferulic acid (93–95%) was found, accompanied by higher quantitative and qualitative variability of homologues within sterols, tocols and carotenoids. In turn, the alkylresorcinol composition was related to wheat ploidy level.

Transformation of polyphenols found in pigmented gluten-free flours during in vitro large intestinal fermentation

In this work, 18 gluten-free flours (prepared from cereals, pseudocereals and legumes), differing in pigmentation, were screened for their phenolic profiles, cooked and, then, subjected to digestion and large intestinal fermentation in vitro. A combined targeted/untargeted metabolomic approach was used to elucidate the microbial biotransformation processes of polyphenols following digestion. This preliminary work demonstrated an increase in 3,5-dihydroxybenzoic acid (on average from 0.67 up to 1.30 μmol/g dry matter) throughout large intestinal fermentation of pseudocereals (esp. quinoa), due to their high alkylresorcinol contents. Isoflavones were converted into equol- or O-desmethylangolensin- derivatives, whereas anthocyanins were degraded into lower-molecular-weight phenolics (i.e., protocatechuic aldehyde and 4-hydroxybenzoic acid, with the latter exhibiting the highest increase over time). A decreasing trend was observed for antioxidant activities (i.e., FRAP and ORAC values) moving from digested to faecal fermented samples. These findings highlight that gluten-free flours are able to deliver bioaccessible polyphenols to the colon.

Non-Destructive Determination of Alkylresorcinol (ARs) Content on Wheat Seed Surfaces and Prediction of ARs Content in Whole-Grain Flour.

Alkylresorcinols (ARs) are beneficial for human health and can be used as biomarkers for whole-grain cereal intake. In previous studies, ARs content in whole-grain flour was determined by milling the seeds into powder, thus destroying their structure. In this paper, we adopted a non-destructive extraction approach. Chloroform and ethyl acetate extraction methods were carried out to extract lipids from the seed surface and whole-grain flour of 36 wheat varieties in China, respectively. GC-MS analysis identified chemical compounds in which ARs were the major compounds for all the samples. The average total content of ARs (624.223 µg/g) in whole grains was much higher than that on seed surfaces (4.934 µg/g), with a positive correlation (r = 0.863, p < 0.001) between these two parameters. The results suggested that the total ARs content on the seed surface can be used to predict their content in whole-grain flour. Without affecting the seed germination rate and damaging seed structure, we demonstrate that a non-destructive extraction approach is an appropriate and useful method, facilitating the development of rapid screening methods suitable for use in wheat breeding.

Alkylresorcinols and fatty acids in primitive wheat populations of Italian and Black sea region countries origin

Alkylresorcinols, fatty acid content, and antioxidant activity were analysed in Triticum monococcum, T. dicoccum, T. timopheevi, T. palaeo-colchicum and T. macha accessions from Turkey, Georgia, Armenia, Bulgaria and Italy, also including modern durum wheat (T. durum) and bread wheat (T. aestivum) varieties as controls, grown in a common environment. Total alkylresorcinol content ranged between 478.3 and 1153.9 mg kg−1 dm, with the highest contents detected in T. aestivum, T. macha and some T. monococcum accessions. All alkylresorcinol homologues effectively contributed at genotype discrimination. Hexaploid wheats showed higher A19 (23.3–27.5%) and lower A23 (14.0–15.9%) and A25 (4.3–8.1%) relative contents, with respect to other species. C18:2 (50.4–62.3%), C18:1 (14.5–25.8%) and C16 (13.3–16.7%) were the most abundant fatty acid compounds in all accessions. PUFA/MUFA, C18:1/C16 and C18:1/C18:2 ratios significantly differed among genotypes, with special respect to T. monococcum, T. aestivum and T. macha. Significant differences were also observed for protein and total phenolic content, and antioxidant activity. The data indicate that some genotypes could represent interesting sources of specific compounds, with a potential use either as promising material for the selection of improved varieties or raw materials to manufacture foods with naturally enhanced content of health promoting compounds.

Retention of alkylresorcinols, antioxidant activity and fatty acids following traditional hulled wheat processing

This study compared alkylresorcinols, fatty acids and antioxidant activity retention following hulled wheat processing by traditional and modern plants. Glume removal and kernel crushing were considered as characterising steps.Samples were collected from two traditional einkorn wheat bulgur processing plants in Turkey, one emmer wheat processing plant in Armenia and a modern two stage processing plant in Italy, also including pearling.Whole kernels showed higher alkylresorcinol contents (759–1037 mg kg−1 dm) and antioxidant activity with respect to the correspondent crushed products. Following crushing a decrease of total alkylresorcinol content was observed, with lowest amounts detected in the semolina-like fractions. Pearling did not determine a significant decrease of alkylresorcinols of the pearled output. However the waste obtained from pearling, mainly composed of bran parts, showed the highest alkylresorcinol amount (1493 mg kg−1 dm) and antioxidant activity. The waste from pearling resulted also the richest fraction of unsaturated alkylresorcinol homologues and unsaturated fatty acids. Among fatty acids, C18:2, C18:1 and C16 resulted the most abundant compounds in all fractions.All the plants showed similar performance, with higher alkylresorcinol decreases due to the loss of specific parts of kernel, such as germ and bran.

Identification and quantification of even and odd chained 5-n alkylresorcinols, branched chain-alkylresorcinols and methylalkylresorcinols in Quinoa (Chenopodium quinoa).

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.