Alkylresorcinols of cereal grains — their importance in food and feed

Danuta Boros

d.boros@ihar.edu.pl
Samodzielna 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

The article was created thanks to the co-financing of the Ministry of Agriculture and Rural Development under the Multiannual Program of IHAR-PIB for the years 2015-2020

Keywords:

alkylresorcinols, cereal grains, bioactive properties

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


Published
2015-09-30

Cited by

Boros, D. (2015) “Alkylresorcinols of cereal grains — their importance in food and feed”, Bulletin of Plant Breeding and Acclimatization Institute, (277), pp. 7–20. doi: 10.37317/biul-2015-0007.

Authors

Danuta Boros 
d.boros@ihar.edu.pl
Samodzielna Pracownia Oceny Jakości Produktów Roślinnych, Instytut Hodowli i Aklimatyzacji Roślin — PIB, Radzików Poland

Statistics

Abstract views: 172
PDF downloads: 79


License

Copyright (c) 2015 Danuta Boros

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Upon submitting the article, the Authors grant the Publisher a non-exclusive and free license to use the article for an indefinite period of time throughout the world in the following fields of use:

  1. Production and reproduction of copies of the article using a specific technique, including printing and digital technology.
  2. Placing on the market, lending or renting the original or copies of the article.
  3. Public performance, exhibition, display, reproduction, broadcasting and re-broadcasting, as well as making the article publicly available in such a way that everyone can access it at a place and time of their choice.
  4. Including the article in a collective work.
  5. Uploading an article in electronic form to electronic platforms or otherwise introducing an article in electronic form to the Internet or other network.
  6. Dissemination of the article in electronic form on the Internet or other network, in collective work as well as independently.
  7. Making the article available in an electronic version in such a way that everyone can access it at a place and time of their choice, in particular via the Internet.

Authors by sending a request for publication:

  1. They consent to the publication of the article in the journal,
  2. They agree to give the publication a DOI (Digital Object Identifier),
  3. They undertake to comply with the publishing house's code of ethics in accordance with the guidelines of the Committee on Publication Ethics (COPE), (http://ihar.edu.pl/biblioteka_i_wydawnictwa.php),
  4. They consent to the articles being made available in electronic form under the CC BY-SA 4.0 license, in open access,
  5. They agree to send article metadata to commercial and non-commercial journal indexing databases.