Isolation and structural identification of diarabinosyl 8--4-dehydrodiferulate from maize bran insoluble fibre

Allerdings, Ella; Ralph, John; Schatz, Paul F.; Gniechwitz, Diana; Steinhart, Hans; Bunzel, Mirko

doi:10.1016/j.phytochem.2004.10.026

Cited by 64 publications

(53 citation statements)

References 34 publications

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“…Their structural characterization revealed that 5-5-DFA is indeed attached to arabinoxylans. More recently this was also demonstrated for 8-O-4-DFA and 8-8c-DFA (Allerdings et al 2005;Bunzel et al 2008a) by isolating the 8-O-4-and 8-8c-DFA-saccharides 16-19 shown in Fig. 7 from acidic hydrolysates of maize bran.…”

Section: Other Dehydrodihydroxycinnamatesmentioning

confidence: 60%

Chemistry and occurrence of hydroxycinnamate oligomers

2009

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Hydroxycinnamates such as ferulic acid, sinapic acid and p-coumaric acid ester-linked to plant cell wall polymers may act as cross-links between polysaccharides to each other, but also to proteins and lignin. Although sinapates and p-coumarates also form cell wall cross-links by the formation of radically or photochemically formed dimers, ferulate derivatives are the quantitatively most important cross-links in the plant cell wall. While the first radically generated ferulate dimer was already identified almost 40 years ago, the spectrum of known ferulate dimers was considerably broadened within the last 15 years. Higher ferulate oligomers were generated in model systems, but also isolated from plant materials. Different model systems using either free hydroxycinnamic acids or their esters are reviewed, highlighting a discussion of the relevance of these models for the plant cell wall. The first ferulate trimer from plant material was discovered in 2003 and seven dehydrotrimers of ferulic acid were isolated from maize bran since. Some of these trimers were also identified in other plant materials such as wheat and rye grains, corn stover, sugar beet and asparagus. Formation mechanisms of ferulate trimers and implications for the plant cell wall are discussed. Ferulate tetramers are the highest oligomers isolated from plant materials so far. These compounds can theoretically cross-link up to four polysaccharide chains, assuming all cross-links are formed intermolecularly. Formation of intramolecular versus intermolecular polysaccharide crosslinks is a key question to be answered in the future if we want to judge properly the importance of hydroxycinnamate cross-links in the plant cell wall.

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Section: Other Dehydrodihydroxycinnamatesmentioning

confidence: 60%

Chemistry and occurrence of hydroxycinnamate oligomers

2009

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“…They have been found in a wide range of wall preparations of grasses, including a preparation from maize cell suspension culture that contained only primary walls (Ralph et al 1994), but they almost certainly also occur in secondary walls. Treatment of various grass wall preparations with fungal 'cellulase' or mild acid, as described above, released ferulic acid dehydrodimers that were esterlinked on both ferulic acid residues to arabinosyl residues or oligosaccharides, consistent with them cross linking different GAX molecules (Ishii 1991;Allerdings et al 2005;Bunzel et al 2008). In addition to dehydrodimers, dehydrotrimers and dehydrotetramers of ferulic acid, which probably cross link GAXs, have been identified in wall preparations of maize bran (Bunzel et al 2006).…”

Section: Ferulate Dimers Trimers and Tetramers Also Occur In Grass Cmentioning

confidence: 92%

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

2009

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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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“…1A; for review, see Buanafina, 2009). Dehydrodimers of ferulate (diferulates) form through oxidative coupling likely mediated by peroxidases (Takahama and Oniki, 1994;Bunzel et al, 2008) and cross link adjacent xylan strands to one another (Ishii, 1991;Allerdings et al, 2005). Furthermore, the observation of ether linkages between ferulate and monolignols suggests that FA on GAX may nucleate lignin polymerization (Bunzel et al, 2004).…”

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confidence: 99%

Overexpression of a BAHD Acyltransferase, OsAt10, Alters Rice Cell Wall Hydroxycinnamic Acid Content and Saccharification

et al. 2013

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Grass cell wall properties influence food, feed, and biofuel feedstock usage efficiency. The glucuronoarabinoxylan of grass cell walls is esterified with the phenylpropanoid-derived hydroxycinnamic acids ferulic acid (FA) and para-coumaric acid (p-CA). Feruloyl esters undergo oxidative coupling with neighboring phenylpropanoids on glucuronoarabinoxylan and lignin. Examination of rice (Oryza sativa) mutants in a grass-expanded and -diverged clade of BAHD acyl-coenzyme A-utilizing transferases identified four mutants with altered cell wall FA or p-CA contents. Here, we report on the effects of overexpressing one of these genes, OsAt10 (LOC_Os06g39390), in rice. An activation-tagged line, OsAT10-D1, shows a 60% reduction in matrix polysaccharide-bound FA and an approximately 300% increase in p-CA in young leaf tissue but no discernible phenotypic alterations in vegetative development, lignin content, or lignin composition. Two additional independent OsAt10 overexpression lines show similar changes in FA and p-CA content. Cell wall fractionation and liquid chromatography-mass spectrometry experiments isolate the cell wall alterations in the mutant to ester conjugates of a fivecarbon sugar with p-CA and FA. These results suggest that OsAT10 is a p-coumaroyl coenzyme A transferase involved in glucuronoarabinoxylan modification. Biomass from OsAT10-D1 exhibits a 20% to 40% increase in saccharification yield depending on the assay. Thus, OsAt10 is an attractive target for improving grass cell wall quality for fuel and animal feed.

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Isolation and structural identification of diarabinosyl 8--4-dehydrodiferulate from maize bran insoluble fibre

Cited by 64 publications

References 34 publications

Chemistry and occurrence of hydroxycinnamate oligomers

Chemistry and occurrence of hydroxycinnamate oligomers

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

Overexpression of a BAHD Acyltransferase, OsAt10, Alters Rice Cell Wall Hydroxycinnamic Acid Content and Saccharification

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