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The distribution of ester-linked ferulic acid in the cell walls of angiosperms

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Abstract

Ester-linked ferulic acid occurs in the cell walls of two major groups of angiosperms, the commelinid monocotyledons and the ‘core’ Caryophyllales, at concentrations >3.5 mg g−1 cell walls, and has been detected in primary cell walls by its autofluorescence using ultraviolet fluorescence microscopy. Both of these groups are resolved as monophyletic clades in phylogenetic trees constructed using gene sequences. In the primary cell walls of the commelinid monocotyledons, including the grasses (family Poaceae), the ferulic acid is ester-linked to the non-cellulosic polysaccharide glucuronoarabinoxylan. In contrast, in the ‘core’ Caryophyllales, the ferulic acid is ester-linked to the side chain arabinans and galactans of the pectic polysaccharide rhamnogalacturonan-1, at least in the family Amaranthaceae. In the walls of both angiosperm groups, a range of dehydrodiferulates have also been found. These are formed oxidatively via radical coupling and result in the cross linking of the polysaccharides to which they are attached. Much lower concentrations of ester-linked ferulic acid have been found in cell walls isolated from other angiosperms, although physiological stress conditions may cause increases in these concentrations. The polysaccharides to which the ferulic acid is attached to in the cell walls of these other angiosperms is unknown.

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Abbreviations

FAXX:

[5-O-E-Feruloyl]-α-l-Araf-(1 → 3)-β-d-Xylp-(1 → 4)-d-Xylp

GAX:

Glucuronoarabinoxylan

UV:

Ultraviolet

References

  • Allerdings E, Ralph J, Schatz PF et al (2005) Isolation and structural identification of diarabinosyl 8-O-4-dehydrodiferulate from maize bran insoluble fibre. Phytochemistry 66:113–124

    Article  CAS  PubMed  Google Scholar 

  • Allerdings E, Ralph J, Steinhart H et al (2006) Isolation and structural identification of complex feruloylated heteroxylan side-chains from maize bran. Phytochemistry 67:1276–1286

    Article  CAS  PubMed  Google Scholar 

  • APG II (2003) An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II. Bot J Linn Soc 141:399–436

    Article  Google Scholar 

  • Bacic A, Harris PJ, Stone BA (1988) Structure and function of plant cell walls. In: Preiss J (ed) The biochemistry of plants. Academic Press, San Diego, pp 297–371

    Google Scholar 

  • Bunzel M, Ralph J, Steinhart H (2005) Association of non-starch polysaccharides and ferulic acid in grain amaranth (Amaranthus caudatus L.) dietary fiber. Mol Nutr Food Res 49:551–559

    Article  CAS  PubMed  Google Scholar 

  • Bunzel M, Ralph J, Brünning P et al (2006) Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fiber. J Agric Food Chem 54:6409–6418

    Article  CAS  PubMed  Google Scholar 

  • Bunzel M, Allerdings E, Ralph J et al (2008) Cross-linking of arabinoxylans via 8–8-coupled diferulates as demonstrated by isolation and identification of diarabinosyl 8–8(cyclic)-dehydrodiferulate from maize bran. J Cereal Sci 47:29–40

    Article  CAS  Google Scholar 

  • Carnachan SM, Harris PJ (2000a) Polysaccharide compositions of primary cell walls of the palms Phoenix canariensis and Rhopalostylis sapida. Plant Physiol Biochem 38:699–708

    Article  CAS  Google Scholar 

  • Carnachan SM, Harris PJ (2000b) Ferulic acid is bound to the primary cell walls of all gymnosperm families. Biochem Syst Ecol 28:865–879

    Article  CAS  PubMed  Google Scholar 

  • Chase MW, Soltis DE, Olmstead RG et al (1993) Phylogenetics of seed plants: an analysis of nucleotide sequences from the plastid gene rbcL. Ann Mo Bot Gard 80:528–580

    Article  Google Scholar 

  • Chase MW, Fay MF, Devey DS et al (2006) Multigene analyses of monocot relationships: a summary. Aliso 22:63–75

    Google Scholar 

  • Chen F, Reddy MSS, Temple S et al (2006) Multi-site genetic modulation of monolignol biosynthesis suggests new routes for formation of syringyl lignin and wall bound ferulic acid in alfalfa (Medicago sativa L.). Plant J 48:113–124

    Article  CAS  PubMed  Google Scholar 

  • Colquhoun IJ, Ralet M-C, Thibault J-F et al (1994) Structure and identification of feruloylated oligosaccharides from sugar-beet pulp by NMR spectroscopy. Carbohydr Res 263:243–256

    Article  CAS  PubMed  Google Scholar 

  • Cronquist A (1968) Evolution and classification of flowering plants. Nelson, London

    Google Scholar 

  • Cuénoud P, Savolainen V, Chatrou LW et al (2002) Molecular phylogenetics of Caryophyllales based on nuclear 18S rDNA and plastid rbcL, atpB, and matK DNA sequences. Am J Bot 89:132–144

    Article  Google Scholar 

  • Dahlgren RMT, Clifford HT, Yeo PF (1985) The families of the monocotyledons. Springer-Verlag, New York

    Google Scholar 

  • Derikvand MM, Sierra JB, Ruel K et al (2008) Redirection of the phenylpropanoid pathway to feruloyl malate in Arabidopsis mutants deficient for cinnamoyl-CoA reductase 1. Planta 227:943–956

    Article  Google Scholar 

  • Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085–1097

    Article  CAS  PubMed  Google Scholar 

  • Donaldson LA (2001) Lignification and lignin topochemistry—an ultrastructural view. Phytochemistry 17:859–873

    Article  Google Scholar 

  • Ferguson LR, Lim IF, Pearson AE et al (2003) Bacterial mutagenesis by hydroxycinnamic acids from plant cell walls. Mutat Res 542:49–58

    CAS  PubMed  Google Scholar 

  • Franke R, Fry SC, Kauss H (1998) Low-molecular-weight precursors for defense-related cell wall hydroxycinnamoyl esters in elicited parsley suspension cultures. Plant Cell Rep 17:379–383

    Article  CAS  Google Scholar 

  • Fry SC (1979) Phenolic components of the primary cell wall and their possible role in the hormonal control of growth. Planta 146:343–351

    Article  CAS  Google Scholar 

  • Fry SC (1982) Phenolic components of the primary cell wall. Feruloylated disaccharides of d-galactose and l-arabinose from spinach polysaccharide. Biochem J 203:493–504

    CAS  PubMed  Google Scholar 

  • Gou J-Y, Park S, Yu X-H et al (2008) Compositional characterization and imaging of “wall-bound” acylesters of Populus trichocarpa reveal differential accumulation of acyl molecules in normal and reactive woods. Planta 229:15–24

    Article  CAS  PubMed  Google Scholar 

  • Harris PJ (2000) Compositions of monocotyledon cell walls: implications for biosystematics. In: Wilson KL, Morrison DA (eds) Monocots: systematics and evolution. CSIRO, Melbourne, pp 114–126

    Google Scholar 

  • Harris PJ (2005) Diversity in plant cell walls. In: Henry RJ (ed) Plant diversity and evolution: genotypic and phenotypic variation in higher plants. CAB International Publishing, Wallingford, pp 201–227

    Chapter  Google Scholar 

  • Harris PJ, Hartley RD (1976) Detection of bound ferulic acid in cell walls of the Gramineae by ultraviolet fluorescence microscopy. Nature 259:508–510

    Article  CAS  Google Scholar 

  • Harris PJ, Hartley RD (1980) Phenolic constituents of the cell walls of monocotyledons. Biochem Syst Ecol 8:153–160

    Article  CAS  Google Scholar 

  • Harris PJ, Stone BA (2008) Chemistry and molecular organization of plant cell walls. In: Himmel ME (ed) Biomass recalcitrance: deconstructing the plant cell wall for bioenergy. Blackwell, Oxford, pp 61–93

    Google Scholar 

  • Harris PJ, Hartley RD, Lowry KH (1980) Phenolic constituents of mesophyll and non-mesophyll cell walls from leaf laminae of Lolium perenne. J Sci Food Agric 31:959–962

    Article  CAS  Google Scholar 

  • Harris PJ, Kelderman MR, Kendon MF et al (1997) Monosaccharide composition of unlignified cell walls of monocotyledons in relation to the occurrence of wall-bound ferulic acid. Biochem Syst Ecol 25:167–179

    Article  CAS  Google Scholar 

  • Hartley RD (1987) HPLC for the separation and determination of phenolic compounds in plant cell walls. In: Linskens HF, Jackson JF (eds) High performance liquid chromatography in plant sciences. Springer-Verlag, Berlin, pp 92–103

    Google Scholar 

  • Hartley RD, Harris PJ (1981) Phenolic constituents of the cell walls of dicotyledons. Biochem Syst Ecol 9:189–203

    Article  CAS  Google Scholar 

  • Hartley RD, Jones EC (1976) Diferulic acid as a component of cell walls of Lolium multiflorum. Phytochemistry 15:1157–1160

    Article  CAS  Google Scholar 

  • Hartley RD, Morrison WH (1991) Monomeric and dimeric phenolic acids released from cell walls of grasses by sequential treatment with sodium hydroxide. J Sci Food Agric 55:365–375

    Article  CAS  Google Scholar 

  • Hartley RD, Whatley FR, Harris PJ (1988) 4,4’-Dihydroxytruxillic acid as a component of cell walls of Lolium multiflorum. Phytochemistry 27:349–351

    Article  CAS  Google Scholar 

  • Higuchi T, Ito Y, Kawamura I (1967) p-Hydroxyphenylpropane component of grass lignin and role of tyrosine-ammonia lyase in its formation. Phytochemistry 6:875–881

    Article  CAS  Google Scholar 

  • Ishii T (1991) Isolation and characterization of a diferuloyl arabinoxylan hexasaccharide from bamboo shoot cell-walls. Carbohydr Res 219:15–22

    Article  CAS  PubMed  Google Scholar 

  • Ishii T (1994) Feruloyl oligosaccharides from cell walls of suspension-cultured spinach cells and sugar beet pulp. Plant Cell Physiol 35:701–704

    CAS  PubMed  Google Scholar 

  • Ishii T (1997) Structure and function of feruloylated polysaccharides. Plant Sci 127:111–127

    Article  CAS  Google Scholar 

  • Ishii T, Hiroi T (1990) Isolation and characterization of feruloylated arabinoxylan oligosaccharides from bamboo shoot cell-walls. Carbohydr Res 196:175–183

    Article  CAS  PubMed  Google Scholar 

  • Ishii T, Tobita T (1993) Structural characterization of feruloyl oligosaccharides from spinach-leaf cell walls. Carbohydr Res 248:179–190

    Article  CAS  PubMed  Google Scholar 

  • Ishii T, Hiroi T, Thomas JR (1990) Feruloylated xyloglucan and p-coumaroyl arabinoxylan oligosaccharides from bamboo shoot cell-walls. Phytochemistry 29:1999–2003

    Article  CAS  PubMed  Google Scholar 

  • Jung H-JG (2003) Maize stem tissues: ferulate deposition in developing internode cell walls. Phytochemistry 63:543–549

    Article  CAS  PubMed  Google Scholar 

  • Kang Y-H, Parker CC, Smith AC et al (2008) Characterization and distribution of phenolics in carrot cell walls. J Agric Food Chem 56:8558–8564

    Article  CAS  PubMed  Google Scholar 

  • Kato Y, Nevins DJ (1985) isolation and identification of O-(5-O-feruloyl-α-l-arabinofuranosyl)-(1 → 3)-O-β-d-xylopyranosy-(1 → 4)-d-xylopyranose as a component of Zea shoot cell-walls. Carbohydr Res 137:139–150

    Article  CAS  Google Scholar 

  • Kato A, Azuma J, Koshijima T (1983) A new feruloylated trisaccharide from bagasse. Chem Lett 13:7–140

    Google Scholar 

  • Levigne SV, Ralet M-C, Quéméner BC et al (2004a) Isolation from sugar beet cell walls of arabinan oligosaccharides esterified by two ferulic acid monomers. Plant Physiol 134:1173–1180

    Article  CAS  PubMed  Google Scholar 

  • Levigne S, Ralet M-C, Quéméner B et al (2004b) Isolation of diferulic acid bridges ester-linked to arabinan in sugar beet cell walls. Carbohydr Res 339:2315–2319

    Article  CAS  PubMed  Google Scholar 

  • Mabberley DJ (2008) Mabberley’s plant book: a portable dictionary of plants, their classification and uses. Cambridge University Press, Cambridge

    Google Scholar 

  • Mohnen D (2008) Pectin structure and biosynthesis. Curr Opin Plant Biol 11:266–277

    Article  CAS  PubMed  Google Scholar 

  • Mueller-Harvey I, Hartley RD, Harris PJ et al (1986) Linkage of p-coumaroyl and feruloyl groups to cell-wall polysaccharides of barley straw. Carbohydr Res 148:71–85

    Article  CAS  Google Scholar 

  • Ng A, Harvey AJ, Parker ML et al (1998) Effect of oxidative coupling on the thermal stability of texture and cell wall chemistry of beet root (Beta vulgaris). J Agric Food Chem 46:3365–3370

    Article  CAS  Google Scholar 

  • Ng A, Parker ML, Parr AJ et al (2000) Physicochemical characteristics of onion (Allium cepa L.) tissues. J Agric Food Chem 48:5612–5617

    Article  CAS  PubMed  Google Scholar 

  • Parker ML, Ng A, Smith AC et al (2000) Esterified phenolics of the cell walls of chufa (Cyperus esculentus L.) tubers and their role in texture. J Agric Food Chem 48:6284–6291

    Article  CAS  PubMed  Google Scholar 

  • Parker CC, Parker ML, Smith AC et al (2003) Thermal stability of texture in Chinese water chestnut may be dependent on 8,8’-diferulic acid (aryltetralyn form). J Agric Food Chem 51:2034–2039

    Article  CAS  PubMed  Google Scholar 

  • Parr AJ, Waldron KW, Ng A et al (1996) The wall-bound phenolics of Chinese water chestnut (Eleocharis dulcis). J Sci Food Agric 71:501–507

    Article  CAS  Google Scholar 

  • Parr AJ, Ng A, Waldron KW (1997) Ester-linked phenolic components of carrot cell walls. J Agric Food Chem 45:2468–2471

    Article  CAS  Google Scholar 

  • Ralph J, Quideau S, Grabber JH et al (1994) Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J Chem Soc Perkin Trans 1:3485–3498

    Article  Google Scholar 

  • Ralph J, Grabber JH, Hatfield RD (1995) Lignin-ferulate cross-links in grasses: active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr Res 275:167–178

    Article  CAS  Google Scholar 

  • Ralph J, Bunzel M, Marita JM et al (2004a) Peroxidase-dependent cross-linking reactions of p-hydroxycinnamates in plant cell walls. Phytochem Rev 3:79–96

    Article  CAS  Google Scholar 

  • Ralph J, Lundquist K, Brunow G et al (2004b) Lignins: natural polymers from oxidative coupling of 4-hydroxyphenyl-propanoids. Phytochem Rev 3:29–60

    Article  CAS  Google Scholar 

  • Ralph J, Kim H, Lu F et al (2008) Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency). Plant J 53:368–379

    Article  CAS  PubMed  Google Scholar 

  • Renard CMGC, Champenois Y, Thibault J-F (1993) Characterisation of the extractable pectins and hemicelluloses of the cell walls of glasswort, Salicornia ramosissima. Carbohydr Polym 22:239–245

    Article  CAS  Google Scholar 

  • Renard CMGC, Wende G, Booth E (1999) Cell wall phenolics and polysaccharides in different tissues of quinoa (Chenopodium quinoa Willd). J Sci Food Agric 79:2029–2034

    Article  CAS  Google Scholar 

  • Rodríguez R, Jarmillo S, Guillén R et al (2005) Cell wall phenolics of white and green asparagus. J Sci Food Agric 85:971–978

    Article  Google Scholar 

  • Rodríguez-Arcos RC, Smith AC, Waldron KW (2002) Effect of storage on wall-bound phenolics in green asparagus. J Agric Food Chem 50:3197–3203

    Article  PubMed  Google Scholar 

  • Rodríguez-Arcos RC, Smith AC, Waldron KW (2004) Ferulic acid crosslinks in asparagus cell walls in relation to texture. J Agric Food Chem 52:4740–4750

    Article  PubMed  Google Scholar 

  • Rombouts FM, Thibault JF (1986) Feruloylated pectic substances from sugar-beet pulp. Carbohydr Res 154:177–187

    Article  CAS  Google Scholar 

  • Rudall PJ, Caddick LR (1994) Investigation of the presence of phenolic compounds in monocotyledonous cell walls, using UV fluorescence microscopy. Ann Bot 74:483–491

    Article  CAS  Google Scholar 

  • Rudall P, Chase MW (1996) Systematics of Xanthorrhoeaceae sensu lato: evidence for polyphyly. Telopea 6:629–647

    Google Scholar 

  • Saarela JM, Rai HS, Doyle JA et al (2007) Hydatellaceae identified as a new branch near the base of the angiosperm phylogenetic tree. Nature 446:312–315

    Article  CAS  PubMed  Google Scholar 

  • Saulnier L, Vigouroux J, Thibault J-F (1995) Isolation and partial characterization of feruloylated oligosaccharides from maize bran. Carbohydr Res 272:241–253

    Article  CAS  PubMed  Google Scholar 

  • Schatz PF, Ralph J, Lu F et al (2006) Synthesis and identification of 2,5-bis-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuran-3,4-dicarboxylic acid, an unanticipated ferulate 8–8-coupling product acylating ceral plant cell walls. Org Biomol Chem 4:2801–2806

    Article  CAS  PubMed  Google Scholar 

  • Smith BG, Harris PJ (1995) Polysaccharide composition of unlignified cell walls of pineapple [Ananas comosus (L.) Merr.] fruit. Plant Physiol 107:1399–1409

    Article  CAS  PubMed  Google Scholar 

  • Smith BG, Harris PJ (1999) The polysaccharide composition of Poales cell walls: Poaceae cell walls are not unique. Biochem Syst Ecol 27:33–53

    Article  CAS  Google Scholar 

  • Smith BG, Harris PJ (2001) Ferulic acid is esterified to glucuronoarabinoxylans in pineapple cell walls. Phytochemistry 56:513–519

    Article  CAS  PubMed  Google Scholar 

  • Soltis PS, Brockington SF, Yoo M-J et al (2009) Floral variation and floral genetics in basal angiosperms. Am J Bot 96:110–128

    Article  Google Scholar 

  • Suzuki K, Kitamura S, Kato Y et al (2000) Highly substituted glucuronoarabinoxylans (hsGAXs) and low-branched xylans show a distinct localization pattern in the tissues of Zea mays L. Plant Cell Physiol 41:948–959

    Article  CAS  PubMed  Google Scholar 

  • Trethewey JAK, Campbell LM, Harris PJ (2005) (1 → 3),(1 → 4)-β-d-Glucans in the cell walls of the Poales (sensu lato): an immunogold labelling study using a monoclonal antibody. Am J Bot 92:1669–1683

    Article  Google Scholar 

  • Waldron KW, Ng A, Parker ML et al (1997) Ferulic acid dehydrodimers in the cell walls of Beta vulgaris and their possible role in texture. J Sci Food Agric 74:221–228

    Article  CAS  Google Scholar 

  • Wende G, Fry SC (1997a) O-Feruloylated, O-acetylated oligosaccharides as side chains of grass xylans. Phytochemistry 44:1011–1018

    Article  CAS  PubMed  Google Scholar 

  • Wende G, Fry SC (1997b) 2-O-β-d-xylopyranosyl-(5-O-feruloyl)-l-arabinose, a widespread component of grass cell walls. Phytochemistry 44:1019–1030

    Article  CAS  Google Scholar 

  • Yang J-G, Uchiyama T (2000) Hydroxycinnamic acids and their dimers involved in the cessation of cell elongation in Mentha suspension culture. Biosci Biotechnol Biochem 64:1572–1579

    Article  CAS  PubMed  Google Scholar 

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  1. School of Biological Sciences, The University of Auckland, Private Bag 92019, Auckland, New Zealand

    Philip J. Harris

  2. AgResearch Ltd, Lincoln Research Centre, Private Bag 4749, Christchurch, New Zealand

    Jason A. K. Trethewey

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Harris, P.J., Trethewey, J.A.K. The distribution of ester-linked ferulic acid in the cell walls of angiosperms. Phytochem Rev 9, 19–33 (2010). https://doi.org/10.1007/s11101-009-9146-4

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