Comprehensive analysis of oat avenanthramides using hybrid quadrupole-Orbitrap mass spectrometry: Possible detection of new compounds

. 2020 May 30 ; 34 (10) : e8718.

Jazyk angličtina Země Velká Británie, Anglie Médium print

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid31896159

Grantová podpora
RO0419 Ministry of Agriculture of the Czech Republic
NAZV QK1810102 National Agency for Agricultural Research of the Ministry of Agriculture of the Czech Republic
6.2.5/51834/2017-MZE-17253 Ministry of Agriculture of the Czech Republic, Subsidy Programme-The National Program for the Conservation and Use of Plant Genetic Resources and Agrobiodiversity

RATIONALE: Avenanthramides (AVNs) are constituents unique to oats and have many outstanding health benefits. AVNs are antioxidants and possess anti-inflammatory, antifungal and antibacterial activity. The number of known AVNs increased recently because of the latest developments in high-resolution tandem mass spectrometry (HRMS/MS) techniques. METHODS: Oat seed extract from 10 oat cultivars was analysed using ultra-high-performance liquid chromatography (UHPLC) and Q Exactive hybrid quadrupole-Orbitrap mass spectrometry (HRMS/MS) with positive heated electrospray ionization. RESULTS: Thirty-five AVNs were identified and characterized in seed extracts, and the structures of 10 novel AVNs were tentatively elucidated, among which were AVNs bearing a cinamoyl or sinapoyl moiety. These AVNs are reported in oats for the first time. The method was validated using AVN standards (AVNs 2c, 2f and 2p), with limits of detection and quantitation at low picomole levels. Recovery of AVN standards varied from 83% to 106%, and relative standard deviations ranged from 2% to 9%. The total AVNs in the selected oat varieties ranged from 36.0 to 302.5 μg/g (dry weight), with AVN 2c, AVN 2f and AVN 2p representing approximately 65%-70% of that total. CONCLUSIONS: Our comprehensive method for detecting the full avenanthramide spectrum can contribute to better understanding the chemical and biological properties of individual AVNs for utilization in developing new oat cultivars and novel functional foods.

Zobrazit více v PubMed

Matz SA. Oats. In: The Chemistry and Technology of Cereals as Food and Feed. 2nd ed. New York: An Avi Book. Van Nostrand Reinhold; 1991:107-134.

FAOSTAT. Crops. URL http://www.fao.org/faostat/en/#data/QC (accessed August 22, 2019).

Jones JM, Sheats DB. Consumer Trends in Grain Consumption. St. Paul, MN, USA: Elsevier Ltd; 2016.

Gorash A, Armoniene R, Fetch JM, Liatukas Ž, Danyté V. Aspects in oat breeding: Nutrition quality, nakedness and disease resistance, challenges and persectives. Ann Appl Biol. 2017;171:281-302.

Redaelli R, Dimberg L, Germeier CU, Berardo N, Locatelli S, Guerrini L. Variability of tocopherols, tocotrienols and avenanthramides contents in European oat germplasm. Euphytica. 2016;207(2):273-292. https://doi.org/10.1007/s10681-015-1535-8

Sang S, Chu YF. Whole grain oats, more than just a fiber: Role of unique phytochemicals. Mol Nut Food Res. 2017;61(7):600715.

Wu W, Tang Y, Yang J, Idehen E, Sang S. Avenanthramide aglycones and glucosides in oat bran: Chemical profile, levels in commercial oat products, and cytotoxicity to human colon cancer cells. J Agric Food Chem. 2018;66(30):8005-8014.

Zwer P. Oats: characteristics and quality requirements. In: Wrigley CW, Batey IL, eds. Cereal Grains. Assessing and Managing Quality. Cambridge: Woodhead Publishing Limited; 2010.

Chen C-YO, Milbury PE, Collins FW, Blumberg JB. Avenanthramides are bioavailable and have antioxidant activity in humans after acute consumption of an enriched mixture from oats. J Nutr. 2007;137(6):1375-1382.

Meydani M. Potential health benefits of avenanthramides of oats. Nutr Rev. 2009;67(12):731-735.

Sur R, Nigam A, Grote D, Liebel F, Southall MD. Avenanthramides, polyphenols from oats, exhibit anti-inflammatory and anti-itch activity. Arch Dermatol Res. 2008;300(10):569-574.

Thomas M, Kim S, Guo W, Collins FW, Wise ML, Meydani M. High levels of avenanthramides in oat-based diet further suppress high fat diet-induced atherosclerosis in Ldlr−/− mice. J Agric Food Chem. 2018;66(2):498-504.

Schär M, Corona G, Soycan G, et al. Excretion of avenanthramides, phenolic acids and their major metabolites following intake of oat bran. Mol Nutr Food Res. 2018;62(2):1700499.

Walsh J, Haddock J, Blumberg JB, et al. Identification of methylated metabolites of oat avenanthramides in human plasma using UHPLC QToF-MS. Int J Food Sci Tech. 2018;69(3):377-383.

Wise ML. Avenanthramides: Chemistry and biosynthesis. In: Chu Y, ed. Oats Nutrition and Technology. Hoboken, NJ: John Wiley & Sons. Ltd; 2014:195-226.

de Bruijn WJC, van Dinteren S, Gruppen H, Vincken J-P. Mass spectrometric characterisation of avenanthramides and enhancing their production by germination of oat (Avena sativa). Food Chem. 2019;277:682-690.

Collins FW. Oat phenolics: Avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls. J Agric Food Chem. 1989;37:60-66.

Xie Z, Mui T, Sintara M, et al. Rapid quantitation of avenanthramides in oat-containing products by high-performance liquid chromatography coupled with triple quadrupole mass spectrometry (HPLC-TQMS). Food Chem. 2017;224:280-288.

Jastrebova J, Skoglund M, Nilsson J. Selective and sensitive LC-MS determination of avenanthramides in oats. Chromatographia. 2006;63(9-10):419-423.

Collins FW, McLachlan DC, Blackwell BA. Oat phenolics: Avenalumic acids, a new group of bound phenolic acids from oat groats and hulls. Cereal Chem. 1991;68(2):184-189.

Dimberg LH, Theander O, Lingert H. Avenanthramides-a group of phenolic antioxidants in oats. Cereal Chem. 1993;70(6):637-641.

Bratt K, Sunnerheim K, Bryngelsson S, et al. Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationship. J Agric Food Chem. 2003;51(3):594-600.

Emmons CL, Peterson DM, Paul GL. Antioxidant capacity of oat (Avena sativa L.) extracts. 2. in vitro antioxidant activity and contents of phenolic and tocol antioxidants. J Agric Food Chem. 1999;47(12):4894-4898.

Ishihara A, Kojima K, Fujita T, Yamamoto Y, Nakajima H. New series of avenanthramides in oat seed. Biosci Biotech Biochem. 2014;78(12):1975-1983.

Pridal AA, Böttger W, Ross AB. Analysis of avenanthramides in oat products and estimation of avenanthramide intake in humans. Food Chem. 2018;253:93-100.

Multari S, Pihlava J-M, Ollennu-Chuasam P, Hietaniemi V, Yang B, Suomela J-P. Identification and quantification of avenanthramides and free and bound phenolic acids in eight cultivars of husked oat (Avena sativa L) from Finland. J Agric Food Chem. 2018;66:2900-2908.

Mattila P, Pihlava J-M, Hellström J. Contents of phenolic acids, alkyl- and alkenylresorcinols, and avenanthramides in commercial grain products. J Agric Food Chem. 2005;53(21):8290-8295.

Lucci P, Sauina J, Núñez O. Trends in LC-MS and LC-HRMS analysis and characterization of polyphenols in food. TRAC-Trends Anal Chem. 2017;88:1-24.

Koistinen VM, Hanhineva K. Mass spectrometry-based analysis of whole-grain phytochemicals. Crit Rev Food Sci Nutr. 2017;57(8):1688-1709.

Wise ML. Effect of chemical systemic acquired resistance elicitors on avenanthramide biosynthesis in oat (Avena sativa). J Agric Food Chem. 2011;59(13):7028-7038.

Cai S, Huang C, Ji B, et al. In vitro antioxidant activity and inhibitory effect, on oleic acid-induced hepatic steatosis, of fractions and subfractions from oat (Avena sativa L.) ethanol extract. Food Chem. 2011;124(3):900-905.

Chu Y-F, Wise ML, Gulvady AA, et al. In vitro antioxidant capacity and anti-inflammatory activity of seven common oats. Food Chem. 2013;139(1):426-431.

Varga M, Jójárt R, Fónad P, Mihály R, Palágyi A. Phenolic composition and antioxidant activity of colored oats. Food Chem. 2018;268:153-161.

Maliarova M, Mrazova V, Havrlentova M, Sokol J. Optimization of parameters for extraction of avenanthramides from oat (Avena sativa L.) grain using response surface methodology (RSM). J Braz Chem Soc. 2015;26(11):2369-2378.

Kakegawa H, Mitsuo N, Matsumoto H, Satch T, Akagi M, Tasaka K. Hyaluronidase-inhibitory and anti-allergic activities of the photo-irradiated products of Tranilast. Chem Pharm Bull. 1985;33:3738-3744.

Okazaki Y, Ishihara A, Nishioka T, Iwamura H. Identification of a dehydrodimer of avenanthramide phytoalexin in oats. Tetrahedron. 2004;60(22):4765-4771.

Giancotti V, Medana C, Aigotti R, Pazzi M, Baiocchi C. LC-high-resolution multiple stage spectrometric analysis of diuretic compounds. Unusual mass fragmentation pathways. J Pharm Biomed Anal. 2008;48:462-466.

Nuñez A, Sapozhnikova Y, Lehotay SJ. Characterization of MS/MS product ions for the differentiation of structurally isomeric pesticides by high-resolution mass spectrometry. Toxics. 2018;6(4):59.

Niessen WMA, Correa CRA. Interpretation of MS-MS mass spectra of drugs and pesticides. In: Desiderio MD, Loo JA, eds. Wiley Series on Mass Spectrometry. Hoboken, NJ: John Wiley & Sons, Inc.; 2017.

Tsipi D, Botitsi H, Economou A. Mass spectrometry for the analysis of pesticide residues and their metabolites. In: Desiderio MD, Loo JA, eds. Wiley Series on Mass Spectrometry. Hoboken, NJ: John Wiley & Sons, Inc.; 2015.

Chen C, Wang L, Wang R, et al. Phenolic contents, cellular antioxidant activity and antiproliferative capacity of different varieties of oats. Food Chem. 2018;239:260-267.

Dimberg LH, Gissen C, Nilsson J. Phenolic compounds in oat grains (Avena Sativa L.) extracts grown in conventional and organic systems. Ambio. 2005;34(4-5):331-337.

Li X-P, Li M-Y, Ling AJ, et al. Effects of genotype and environment on avenanthramides and antioxidant activity of oats grown in northwestern China. J Cereal Sci. 2017;73:130-137.

Peterson DM, Hahn M, Emmons CL. Oat avenanthramides exhibit antioxidant activities in vitro. Food Chem. 2002;79:473-478.

Fagerlund A, Sunnerheim K, Dimberg LH. Radical-scavenging exhibit antioxidant activities in vitro. Food Chem. 2009;113:550-556.

Kulichová K, Sokol J, Maliarová M. Štúdium avenantramidov ako významných biologicky aktívnych látok fenolového charakteru. Chem Listy. 2018;112:848-854.

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