Alkylresorcinols of cereal grains — their importance in food and feed
Danuta Boros
d.boros@ihar.edu.plSamodzielna Pracownia Oceny Jakości Produktów Roślinnych, Instytut Hodowli i Aklimatyzacji Roślin — PIB, Radzików (Poland)
Abstract
Alkylresorcinols (AR) are a group of phenolics lipids, found in substantial amounts in whole grain of cereals. Rye grain is characterised with the greatest content of these compounds (360–2180 mg/kg), while lower content has been found in triticale (294–1145 mg/kg) and wheat (268–943 mg/kg), and much lower in barley (32–152 mg/kg). In general, alkylresorcinols are not present in oat. In years of the sixties and seventies of the previous century, AR have been assigned a role of antinutrients in animal feeding, which was related to their high content and poor feeding quality of rye grain. The studies of many scientific groups, conducted later on, have shown that low digestibility and availability of all nutrients and in particular the energetic compounds in the intestinal tract of monogastric animals, in diets based on rye grain is a result of very high content of water-soluble fraction of arabinoxylans, that are characterized by a great water holding capacity and high viscosity in the aquatic environment. Nowadays, AR have been arousing again a great interest, as an important bioactive component of food and potential biomarker for consumption of wholegrain products. Due to the differences in the homologue composition between wheat and rye, AR are considered to be used to identify the type of grain consumed. As a group of phenolic compounds the AR are a strong antioxidant, but they have also antibacterial and antimutagenic properties.
Supporting Agencies
Keywords:
alkylresorcinols, cereal grains, bioactive propertiesReferences
Andersson A. A. M, Kamal-Eldin A., Fraś A., Boros D., Åman P. 2008 a. Alkylresorcinols in wheat varieties in the HEALTHGRAIN diversity screen. J. Agric. Food Chem. 56: 9722 — 9725.
Google Scholar
Andersson A. A. M., Lampi A-M., Nyström L., Piironen V., Li L., Ward J., Gebruers K., Courtin C. M., Delcour J. A., Boros D., Fraś A., Dynkowska W., Rakszegi M., Bedo Z., Shewry P. R., Åman P. 2008 b. Phytochemical and Fibre Components in Barley Varieties in the HEALTHGRAIN DIVERSITY SCREEN. J. Agric. Food Chem. 56: 9767 — 9776.
Google Scholar
Annison G., Choct M. 1991. Anti-nutritive activities of cereal non-starch polysaccharides in broiler diets and strategies minimizing their effects. World's Poultry Sci. J. 47: 232 — 242.
Google Scholar
Antoniou T. C., Marquardt R. R. 1981. Influence of rye pentosans on the growth of chicks. Poultry Sci. 60: 1898 — 1904.
Google Scholar
Biskup I., Mizerska A., Fecka I. 2015. Alkilofenole pochodzenia naturalnego — właściwości i perspektywy wykorzystania ich w lecznictwie. Postępy Fitoterapii. 1: 37 — 44.
Google Scholar
Bock H. D., Flamme W., Kesting S. 1981. Preliminary experiments with rats on alkylresorcinols in rye. Die Nahrung. 25 (9): 805 — 810.
Google Scholar
Boros D. 2002. Lepkość rozpuszczalnych arabinoksylanów wskaźnikiem wartości pokarmowej żyta. Monografie i Rozprawy Naukowe IHAR Nr 16,: 1 — 44.
Google Scholar
Boros D., Fraś A., Gołębiewska K., Gołębiewski D., Paczkowska O., Wiśniewska M. 2015. Wartość odżywcza i właściwości prozdrowotne ziarna odmian zbóż i nasion rzepaku zalecanych do uprawy w Polsce. Monografia pod. red. Boros D. i Fraś A. Monografie i Rozprawy Naukowe IHAR — PIB 49: 1 — 119.
Google Scholar
Boros D., Madej L., Jagodzinski J. 1997. Perspectives of selection for better nutritive quality of rye I. Viscosity of grain water extract as an index of nutritive value of rye for broiler chicks. Plant Breed. Seed Sci. 41: 81 — 89.
Google Scholar
Boros D., Rakowska M., Raczyńska-Bojanowska K., Kozaczyński K. 1985. The response of Japanese quails and chicks to the water-soluble antinutritive compounds from rye grain. Nutr. Rep. Inter. 32: 827 — 836.
Google Scholar
Choct M., Annison G. 1992. Anti-nutritive effect of wheat pentosans in broiler chickens: Role of viscosity and gut microflora. Brit. Poultry Sci. 33: 821 — 834.
Google Scholar
Evans L. E., Dedio W., Hill R.D. 1973. Variability in the alkylresorcinol content of rye grain. Can. J. Plant Sci. 53: 485 — 488.
Google Scholar
Fengler A. I., Marquardt R. R., 1988. Water-soluble pentosans from rye: II. Effects on rate of dialysis and on the retention of nutrients by the chick. Cereal Chem. 65: 298 — 302.
Google Scholar
Fernandez R., Lucas E., McGinnis J. 1973. Fractionation of a chick growth depressing factor from rye. Poultry Sci. 52: 2252 — 2259.
Google Scholar
Fraś A. 2011. Analiza zmienności zawartości błonnika pokarmowego i alkilorezorcynoli w ziarnie pszenicy zwyczajnej (Triticum aestivum L.). Rozprawa doktorska IHAR-PIB.: 11 — 144.
Google Scholar
Gajda A., Kulawinek M., Kozubek A. 2008. An improved colorimetric method for the determination of alkylresorcinols in cereals and whole-grain cereal products. J. Food Compos. Anal. 21 (5): 428 — 434.
Google Scholar
Hengtrakul P., Lorenz K., Mathias M. 1990. Alkylresorcinols in U.S. and Canadian wheats and flours. Cereal Chem. 67: 413 — 417.
Google Scholar
Jakubowski S., Stuczyńska J. 1981. Zmienność zawartości 5-alkilorezorcyn (AR) w materiale hodowlanym żyta, pszenicy i pszenżyta oraz metodyka badań. Biul. IHAR 145: 17 — 25.
Google Scholar
Kamal-Eldin A., Pouru A., Eliasson C., Åman P. 2001. Alkylresorcinols as antioxidants: hydrogen donation and peroxyl radical-scavenging effects. J. Sci. Food Agric. 81: 353 — 356.
Google Scholar
Korycińska M., Czelna K., Jaromin A., Kozubek A. 2009. Antioxidant activity of rye bran alkylresorcinols and extracts from whole-grain cereal products. Food Chem. 116: 1013 — 1018.
Google Scholar
Kozubek A., Pietr S., Czerwonka A. 1996. Alkylresorcinols are abundant lipid component in different strains of Azotobacter chroococcum and Pseudomonas spp. J. Bacteriol. 178: 4027 — 4030.
Google Scholar
Kozubek A., Tyman J. H. P. 1995. Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains. Chem. Phys. Lipids. 78: 29 — 35.
Google Scholar
Kozubek A., Tyman J. H. P. 1999. Resorcinolic lipids, the natural non-isoprenoic amphiphiles and their biological activity. Chem. Rev. 99: 1 — 26.
Google Scholar
Kubus G., Tłuścik F. 1983. Alkyl resorcinols in grains from plants from the family Gramineae. Acta Soc. Bot. Polon. 52: 223 — 230.
Google Scholar
Kulawinek M., Kozubek A. 2007. 5-n-alkilorezorcynole ziaren zbóż i pełnoziarnistych produktów spożywczych jako biomarkery zdrowej żywności. Postępy Biochemii. 53: 287 — 296.
Google Scholar
Kulawinek M., Jaromin M., Kozubek A., Żarnowski R. 2008. Alkylresorcinols in selected Polish rye and wheat cereals and whole-grain cereal products. J. Food Agric. Chem. 56: 7236 — 7242.
Google Scholar
Kulawinek M., Kozubek A. 2008. Quantitative determination of alkylresorcinols in cereal grains: indepedence of the length of the aliphatic side chain. J. Food Lipids. 15: 251 — 262.
Google Scholar
Landberg R., Kamal-Eldin A., Salmenkallio-Marttila M., Rouau X., Åman P. 2008. Localization of alkylresorcinols in wheat, rye and barley kernels. J. Cereal Sci. 48: 401 — 406.
Google Scholar
Landberg R., Andersson A. A. M., Åman P. Kamal-Eldin A. 2009. Comparison of GC and colorimetry for the determination of alkylresorcinols homologues in cereal grains and products. Food Chem. 113: 1363 — 1369.
Google Scholar
Liu L., Winter K. M., Stevenson L., Morris C., Leach D. N. 2012. Wheat bran lipophilic compounds with in vitro anticancer effects. Food Chem.130 (1): 156 — 164.
Google Scholar
Liukkonen K.-H., Katina K., Wilhelmsson A., Myllymäki O., Lampi A. M., Kariluoto S., Piironen V., Heinonen S.M., Nurmi T., Adlercreutz H., Peltoketo A., Pihlava J. M., Hietaniemi V., Poutanen K. 2003. Process-induced changes on bioactive compounds in whole grain rye. Proc. Nutr. Soc. 62: 117 — 122.
Google Scholar
Lorenz K., Hengtrakul K. 1990. Alkylresorcinols in cereal grains – nutritional importance and methods of analysis Lebensm.-Wiss. u.-Technol. 23: 208 — 215.
Google Scholar
Mejbaum-Katzenellenbogen W., Tłuścik F., Kozubek A., Sikorski A., Maresz Z. 1975 a. Alkylresorcinols in rye (Secale cereale L.) grains. I. Micromethod for determination of alkyl derivatives of resorcinol in rye grains. Acta Soc. Bot. Polon. 44: 479 — 489.
Google Scholar
Mejbaum-Katzenellenbogen W., Sikorski A.,Tłuścik F. 1975b. Alkylresorcinols in rye (Secale cereale L.) grains. II. Dependence of alkylresorcinols level on weight and specific weight of grains. Acta Soc. Bot. Polon. 44: 597 — 606.
Google Scholar
Mejbaum-Katzenellenbogen W., Tłuścik F., Kozubek A. 1978. Alkylresorcinols in rye (Secale cereale L.) grains. IV. Three step preparation of 5-n-alkylresorcinols. Acta Soc. Bot. Polon. 47: 379 — 389.
Google Scholar
Musehold J. 1974. Zur Methodik der Selektion auf 5-alkyl-resorcin-arme pflanzen beim Roggen. Zeitschrift Pflanzenzuchtg. 71: 124 — 129.
Google Scholar
Nienartowicz B., Kozubek A. 1993. Antioxidant activity of cereal bran resorcinolic lipids. Polish J. Food Nutr. 2: 51 — 60.
Google Scholar
Pawlik J., Kudrewicz-Hubicka Z., Wilusz T. 1976. Wpływ ziarna żyta i zawartości w nim alkilorezorcynoli na wzrost i wydajność rzeźną oraz zachowanie się białek surowicy krwi kurczat brojlerów. Rocz. Nauk. Zootech. 5: 109 — 125.
Google Scholar
Poutanen K. 2012. Past and future of cereal grains as food for health. Trends Food Sci. Technol. 25: 58-62.
Google Scholar
Raczyńska-Bojanowska K., Rakowska M., Wrzesińska K., Zębalska M., Boros D. 1988. Chemical indicators of nutritive value of rye grain. Hod. Rośl. Aklim. Nas. 32: 261 — 263.
Google Scholar
Rakowska M. 1994. Antinutritive compounds in rye grain. Hod. Rośl. Aklim. 38: 21 — 42.
Google Scholar
Rakowska M., Boros D., Tłuścik F., Szkiłłądź W. 1990. Studies on antinutritive components of the rye grain. Part I. Effect of isolated and in situ alkylresorcinols of rye grain on growth of laboratory animals and diet utilization. Acta Alimentaria Polonica, 16/1–2: 53 — 61.
Google Scholar
Ross A. B., Kamal-Eldin A., Jung C., Shepherd M. J., Åman P. 2001. Gas chromatographic analysis of alkylresorcinols in rye (Secale cereale L.) grains. J. Sci. Food Agric. 81: 1405 — 1411.
Google Scholar
Ross A. B. 2003. Alkylresorcinols in cereal grains. Occurrence, absorption, and possible use as biomarkers of whole grain wheat and rye intake. Doctoral Thesis. Swedish University of Agricultural Sciences. Uppsala.
Google Scholar
Ross A. B., Shepherd M. J., Bach Knudsen K. E., Glitsø L. V., Bowey E., Phillips J., Rowland I., Guo Z. X., Massy D. J., Aman P., Kamal-Eldin A. 2003 a. Absorption of dietary alkylresorcinols in ileal-cannulated pigs and rats. Br. J. Nutr. 90: 787 — 794.
Google Scholar
Ross A. B., Shepherd M. J., Schüpphaus M., Sinclair V., Alfaro B., Kamal-Eldin A., Åman P. 2003b. Alkylresorcinols in cerals and cereal products. J. Agric. Food Chem. 51: 4111 — 4118.
Google Scholar
Sałek M. 1978. Oznaczanie zawartości 5-alkilorezorcyn w ziarnie i produktach przemiału żyta. Roczniki PZH. 29: 205 — 211.
Google Scholar
Sampiero D. A., Vattuone M.A., Catalán C.A.N. 2009. A new colorimetric method for determination of alkylresorcinols in ground and whole-cereal grains using the diazonium salt Fast Blue RR. Food Chem. 115: 1170 — 1174.
Google Scholar
Sang S., Ju J., Lambert J. D., Lin Y., Hong J., Bose M., Wang S., Bai N., He K., Reddy B. S., Ho C-T., Li F., Yang C. S. 2006. Wheat bran oil and its fractions inhibit human colon cancer cell growth and intestinal tumorigenesis in Apcmin/+ mice J. Agric. Food Chem. 54: 9792 — 9797.
Google Scholar
Sedlet K., Mathias M., Lorenz K. 1984. Growth-depressing effect of 5-n-pentadecylresorcinol: Model for cereal alkylresorcinols. Cereal Chem. 61: 239 — 241.
Google Scholar
Surget A., Barron C. 2005. Histologie du grain blé. Industries des Céreales. 145: 3 — 7.
Google Scholar
Tłuścik F. 1978. Localization of the alkylresorcinols in rye and wheat caryopses. Acta Soc. Bot. Polon. 44 (4): 211 — 218.
Google Scholar
Tłuścik F., Kozubek A., Mejbaum-Katzenellebogen W. 1981. Alkylresorcinols in rye (Secale cereale L.) grains. VI. Colorimetric micromethod for the determination of alkylresorcinols with the use of diazonium salt, Fast Blue B. Acta Soc. Bot. Polon. 50: 645 — 651.
Google Scholar
Tłuścik F., Kupiec R., Rakowska M. 1990. Studies on antinutritive components of the rye grain. Part II. Balance and metabolism of 5-n-alkylresorcinols isolated from rye grain in rats. Acta Alimentaria Polonica. 16/3: 119 — 127.
Google Scholar
Verdeal K., Lorenz K. 1977. Alkylresorcinols in wheat, rye and triticale. Cereal Chem. 54: 475 — 483.
Google Scholar
Wenkert E., Loeser E. M., Mahapatra N., Schenker F., Wilson E. M. 1964. Wheat grain phenoles. J. Org. Chem. 29: 435 — 439.
Google Scholar
Wieringa G. W. 1967. On occurrence of growth inhibiting substances in rye. Pub. 156. Ins. Storage Proc. Agric. Prod., Wageningen, Netherlands.
Google Scholar
Zhu Y., Conklin D. R., Chen H., Wang L., Sang S. 2011. 5-Alk(en)ylresorcinols as the major active components in wheat bran inhibit human colon cancer cell growth. Bioorg. Med. Chem. 19: 3973 — 3982.
Google Scholar
Żarnowski R., Suzuki Y., Yamaguchi I., Pietr S. 2002. Alkylresorcinols in barley (Hordeum vulgare L. distichon) grain. Z. Naturforsch. 57: 57 — 62.
Google Scholar
Authors
Danuta Borosd.boros@ihar.edu.pl
Samodzielna Pracownia Oceny Jakości Produktów Roślinnych, Instytut Hodowli i Aklimatyzacji Roślin — PIB, Radzików Poland
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