Effect of barley variety and growth year on ferulic and para-coumaric acids, and their ratio in the seed and hull

Abstract

Complex cell walls of barley hulls contain phenolic constituents — hydroxycinnamic acids, mainly ferulic acid (3-methoxy-4-hydroxy-cinnamic acid, FA) and para-coumaric acid (4-hydroxycinnamic acid, PCA). Ferulic acid is produced via the phenylpropanoid biosynthetic pathway and is covalently cross-linked to polysaccharides by ester bonds and to components of lignin mainly by ether bonds. Various studies have consistently indicated that FA is among the factors most inhibitory to the biodegradability of plant cell wall polysaccharides. PCA is also covalently linked to polysaccharides (minor) and lignin (major), but PCA does not form the inhibitory cross-linkages as FA does. It is considered to represent plant cell wall lignification. The objective of this study was to determine the genotypic variation and magnitude of difference in the concentration of the hydroxycinnamic acids in terms of FA and PCA as well as their ratios in barley hull and seeds in sixteen varieties of barley collected during three years. These data will be correlated to barley nutrient availability in future study. The barley varieties included CDC Cowboy, Valier, TR251, Newdale, RCSL97, KXN/TLN-147 (AU), WABAR2160 (AU), Harrington, CDC Copeland, CDC Kendall, AC Metcalfe, CDC Dolly, McLeod, CDC Bold, CDC Helgason and CDC Trey. The focus of this study was on ferulic acid because of its inhibitory effect on rumen degradation and digestion which are highly related to nutrient availability in animals. The results showed significant differences (P < 0.01) a mong the barley varieties in ferulic acid and p-coumaric acid and their ratio. Whole barley seed contained higher (P<0.05) ferulic acid concentration than p-coumaric acid, ranging from 509 to 679 μg/g DM for ferulic acid and 131 to 345 μg/g DM for p-coumaric acid. The ratios of ferulic acid to p-coumaric acid ranged from 1.8 to 3.9. The ferulic acid concentration in hull was higher (P < 0.05) than that in whole seed, ranging from 2,320 to 4,206 μg/g DM. Percentage of ferulic acid content in hull and dehulled seed ranged from 38 to 70% and 30 to 62%, respectively. Growth year affect affected the hydroxycinnamic acid profiles in barley seed and hull. In conclusion, there were large differences in the ferulic acid and para-coumaric acid among the barley varieties indicating genotypic variation. Harrington contained highest and Valier contained lowest FA in whole seed. Barley TR251 contained lowest % of FA content in the hull and highest % of FA content in the dehulled seed. Future study is needed to understand the relationship between the hydroxycinnamic acid profile in barley seeds and hull and nutrient utilization and availability of barley in animals.

References

  1. Akin, D.E. 1986. Interactions of ruminal bacteria and fungi with southern forages. J. Anim. Sci. 63:965–977.

    Article  Google Scholar 

  2. Andreasen, M.F., Christensen, L.P., Meyer, A.S., Hansen, A. 2000. Ferulic acid dehydrodimers in rye (Secale cereale L.). J. Cereal Sci. 31:303–307.

    CAS  Article  Google Scholar 

  3. Bartolomé, B., Faulds, C.B., Kroon, P.A., Waldron, K., Gilbert, H.J., Hazlewood, G., Williamson, G. 1997a. An Aspergillus nigeresterase (ferulic acid esterase III) and a recombinant Pseudomonas fluorescens subsp. cellulosa esterase (XylD) from barley and wheat cell walls. Appl. Environ. Microbiol. 63:208–212.

    PubMed  PubMed Central  Google Scholar 

  4. Bartolomé, B., Faulds, C.B., Williamson, G. 1997b. Enzymic release of ferulic acid from barley spent grain. J. Cereal Sci. 25:285–288.

    Article  Google Scholar 

  5. Bohn, P.J., Fales, S.L. 1989. Cinnamic acid-carbohydrate esters: An evaluation of a model system. J. Sci. Food Agric. 48:1–7.

    CAS  Article  Google Scholar 

  6. Borneman, W.S., Ljungdahl, L.G., Hartley, R.D., Akin, D.E. 1991. Isolation and characterization of p-coumaroyl esterase from the anaerobic fungus Neocallimastix strain MC-2. Appl. Environ. Microbiol. 57:2337–2344.

    CAS  PubMed  PubMed Central  Google Scholar 

  7. Brézillon, C., Kroon, P.A., Faulds, C.B., Brett, G.M., Williamson, G. 1996. Novel ferulic acid esterases are induced by growth of Aspergillus nigeron sugar-beet pulp. Appl. Microbiol. Biotechnol. 45:371–376.

    Article  Google Scholar 

  8. EBC. 1998. European Brewery Convention (EBC) Analysis Committee. Analytica, 4th ed. Verlag Hans Carl Getränke Fachverlag, Nürnberg, Germany.

    Google Scholar 

  9. Eraso, F., Hartley, R.D. 1990. Monomeric and dimeric phenolic consituents of plant cell walls — possible factors influencing wall biodegradability. J. Sci. Food Agric. 51:163–170.

    CAS  Article  Google Scholar 

  10. Faulds, C.B., Williamson, G. 1991. The purification and characterization of 4-hydroxy-3-methoxycinnamic (ferulic) acid esterase from Streptomyces olivochromogenes. J. General Microbiol. 137:2339–2345.

    CAS  Article  Google Scholar 

  11. Faulds, C.B., Williamson, G. 1999. Effect of hydroxycinnamates and benzoates on the production of feruloyl esterases by Aspergillus niger. J. Sci. Food Agric. 79:450–452.

    CAS  Article  Google Scholar 

  12. Grabber, J.H., Ralph, J., Lapierre, C., Barriere, Y. 2004. Genetic and molecular basis of grass cell-wall degradability. I. Lignin-cell wall matrix interactions. C. R. Biologies. 327:455–465.

    CAS  Article  Google Scholar 

  13. Graham, H., Åman, P. 1984. Acomparison between degradation in vitro and in sacco of constituents of untreated and ammonia treated barley straw. Anim. Feed Sci. Technol. 10:199–211.

    CAS  Article  Google Scholar 

  14. Hartley, R.D. 1981. Chemical constitution, properties and processing of lignocellulosic wastes in relation to nutritional quality for animals. Agric. Enviro. 6:91–113.

    CAS  Article  Google Scholar 

  15. Hartley, R.D., Morrison, W.H., Himmelsbach, D.S., Borneman, W.S. 1990. Cross-linking of cell wall arabinoxylans in graminaceous plants. Phytochem. 12:3705–3709.

    Article  Google Scholar 

  16. Hernanz, D., Nunez, V., Sancho, A., Faulds, C.B., Williamson, G., Bartolome, B., Carmen, G.C. 2001. Hydroxycinnamic acids and ferulic acid dehydrodimers in barley and processed barley. J. Agric. Food Chem. 49:4884–4888.

    CAS  Article  Google Scholar 

  17. Hotekjolen, A.K., Kinitz, C., Knutsen, S.H. 2006. Flavanol and bound phenolic acid content in different barley varieties. J. Agric. Food Chem. 54:2253–2260.

    Article  Google Scholar 

  18. Iiyama, K., Lam, T.B.T., Stone, B.A. 1994. Covalent cross-links in the cell wall. Plant Physiol. 104:315–320.

    CAS  Article  Google Scholar 

  19. Iiyama, K., Lam, T.B.T. 2001. Structural characteristics of cell walls of forage grasses — Their nutritional evaluation for ruminants — Review. Asian-Aust. J. Anim. Sci. 14:862–879.

    CAS  Article  Google Scholar 

  20. Jung, H.G., Deetz, D.A. 1993. Cell wall lignification and degradability. In: Forage cell wall structure and digestibility. ASA-CSSA-SSSA, Madison, WI, USA. pp. 315–346.

    Google Scholar 

  21. Jung, H.G., Allen, M.S. 1995. Characteristics of plant cell walls affecting intake and digestibility of forages by ruminants. J. Anim. Sci. 73:2774–2790.

    CAS  Article  Google Scholar 

  22. Kroon, P.A., Faulds, C.B., Williamson, G. 1996. Purification and characterization of a novel esterase induced by growth of Aspergillus niger on sugar-beet pulp. Biotechnol. Appl. Biochem. 23:255–262.

    CAS  PubMed  Google Scholar 

  23. Kroon, P.A., Williamson, G. 1999. Hydroxycinnamates in plants and food: Current and future perspectives. J. Sci. Food Agric. 79:355–336.

    CAS  Article  Google Scholar 

  24. Moore, K.J., Jung, H.J.G. 2001. Lignin and fiber digestion. J. Range Manage 54:420–430.

    Article  Google Scholar 

  25. Morrison, T.A., Jung, H.G., Buxton, D.R., Hatfield, R.D. 1998. Cell wall composition of maize internodes of varying maturity. Crop Sci. 38:455–460.

    CAS  Article  Google Scholar 

  26. Nordkvist, E., Salomonsson, A., Aman, P. 1984. Distribution of insoluble bound phenolic acids in barley grain. J. Sci. Food Agric. 35:657–661.

    CAS  Article  Google Scholar 

  27. Olkowski, A.A., Amarowicz, R., Yu, P., McKinnon, J.J., Maenz, D.D. 2003. A rapid HPLC method for determination of major phenolic acids in plant material. Polish J. Food Nutri. Sci. 12:53–57.

    CAS  Google Scholar 

  28. Ralph, J., Grabber, J.H., Hatfield, R.D. 1995. Lignin-ferulate crosslinks in grasses: Active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr. Res. 275:167–178.

    CAS  Article  Google Scholar 

  29. Ralet, M.C., Faulds, C.B., Williamson, G., Thibault, J.F. 1994. Degradation of feruloylated oligosaccharides from suger-beet pulp and wheat bran by ferulic acid esterase from Aspergillus niger. Carbohydr. Res. 263:257–269.

    CAS  Article  Google Scholar 

  30. Statistical Analysis System (SAS). 2003. User’s Guide statistics, Version 9.1.3. SAS Institute Inc., Cary, NC, USA.

    Google Scholar 

  31. Sun, R., Sun, X.F., Wang, S.Q., Zhu, W., Wang, X.Y. 2002. Ester and ether linkages between hydroxycinnamic acids and lignins from wheat, rice, rye, and barley straws, maize stems, and fast-growing poplar wood. Ind. Crop. Prod. 15:179–188.

    CAS  Article  Google Scholar 

  32. Yu, P., Maenz, D.D., McKinnon, J.J., Racz, V.J., Christensen, D.A. 2002a. Release of ferulic acid from oat hulls by Aspergillus ferulic acid esterase and Trichoderma xylanase. J. Agric. Food Chem. 50:1625–1630.

    CAS  Article  Google Scholar 

  33. Yu, P., McKinnon, J.J., Maenz, D.D., Racz V.J., Christensen, D.A. 2002b. The interactive effects of enriched sources of Aspergillus ferulic acid esterase and Trichoderma xylanase on the quantitative release of hydroxycinnamic acids from oat hulls. Can. J. Anim. Sci. 82:251–257.

    CAS  Article  Google Scholar 

  34. Yu, P., McKinnon, J.J., Christensen, D.A. 2005. Hydroxycinnamic acids and ferulic acid esterase in relation to biodegradation of complex plant cell walls. Review. Can. J. Anim. Sci. 85:255–267.

    CAS  Article  Google Scholar 

  35. Zupfer, J.M., Churchill, K.E., Rasmusson, D.C., Fulcher, R.G. 1998. Variation in ferulic acid concentration among diverse barley cultivars measured by HPLC and microspectrophotometry. J. Agric. Food Chem. 46:1350–1354.

    CAS  Article  Google Scholar 

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Du, L., Yu, P. Effect of barley variety and growth year on ferulic and para-coumaric acids, and their ratio in the seed and hull. CEREAL RESEARCH COMMUNICATIONS 38, 521–532 (2010). https://doi.org/10.1556/CRC.38.2010.4.9

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Keywords

  • hydroxycinnamic acids
  • ferulic acid
  • para-coumaric acid
  • barley varieties
  • hull