Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures

Fry, Stephen C.; Willis, Stephen C.; Paterson, Alice E. J.

doi:10.1007/s004250000330

Cited by 167 publications

(181 citation statements)

References 69 publications

(86 reference statements)

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“…Therefore, we have used both the cell suspension system and the stem internode section system to make predictions. Maize cell culture systems have been used previously to study cell wall cross-linking through ferulic acid or p-coumaric acids (Grabber et al, 1995;Fry et al, 2000;Kerr and Fry, 2004;Grabber et al, 2009), and it will be interesting to pursue such features of cell wall biosynthesis in the switchgrass cell culture system. (A, C, E) Transcript levels of the target genes in the C4H1-, CCR1-, and CCoAOMT-RNAi lines.…”

Section: Biological Systems For Studying Monolignol Biosynthesis In Smentioning

confidence: 99%

A Genomics Approach to Deciphering Lignin Biosynthesis in Switchgrass

et al. 2013

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It is necessary to overcome recalcitrance of the biomass to saccharification (sugar release) to make switchgrass (Panicum virgatum) economically viable as a feedstock for liquid biofuels. Lignin content correlates negatively with sugar release efficiency in switchgrass, but selecting the right gene candidates for engineering lignin biosynthesis in this tetraploid outcrossing species is not straightforward. To assist this endeavor, we have used an inducible switchgrass cell suspension system for studying lignin biosynthesis in response to exogenous brassinolide. By applying a combination of protein sequence phylogeny with whole-genome microarray analyses of induced cell cultures and developing stem internode sections, we have generated a list of candidate monolignol biosynthetic genes for switchgrass. Several genes that were strongly supported through our bioinformatics analysis as involved in lignin biosynthesis were confirmed by gene silencing studies, in which lignin levels were reduced as a result of targeting a single gene. However, candidate genes encoding enzymes involved in the early steps of the currently accepted monolignol biosynthesis pathway in dicots may have functionally redundant paralogues in switchgrass and therefore require further evaluation. This work provides a blueprint and resources for the systematic genome-wide study of the monolignol pathway in switchgrass, as well as other C4 monocot species.

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Section: Biological Systems For Studying Monolignol Biosynthesis In Smentioning

confidence: 99%

A Genomics Approach to Deciphering Lignin Biosynthesis in Switchgrass

et al. 2013

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“…Nevertheless, the formation of higher molecular weight oligomers and polymers from FA is undefined. A recent report indicates that ferulate trimers and larger coupling products are formed in cultured maize cells, where they are believed to tighten the cell wall (19), and higher oligomers of FA have been implicated during polymerization with horseradish peroxidase under weakly basic conditions (pH 8) (11). However, their structures were not characterized, leaving much speculation surrounding their formation.…”

Section: Lignin Peroxidase (Lip)mentioning

confidence: 99%

Initial Steps of Ferulic Acid Polymerization by Lignin Peroxidase

Ward

Hadar²,

Bilkis

et al. 2001

Journal of Biological Chemistry

151

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The major products of the initial steps of ferulic acid polymerization by lignin peroxidase included three dehydrodimers resulting from ␤-5 and ␤-␤coupling and two trimers resulting from the addition of ferulic acid moieties to decarboxylated derivatives of ␤-O-4-and ␤-5-coupled dehydrodimers. This is the first time that trimers have been identified from peroxidase-catalyzed oxidation of ferulic acid, and their formation appears to be favored by decarboxylation of dehydrodimer intermediates. After initial oxidation, the coupling reactions appear to be determined by the chemistry of ferulic acid phenoxy radicals, regardless of the enzyme and of whether the reaction is performed in vitro or in vivo. This claim is supported by our finding that horseradish peroxidase provides a similar product profile. Lignin peroxidase (LIP)1 is considered to be one of the most important enzymes of the extracellular lignin degradation system secreted by the white rot fungus, Phanerochaete chrysosporium (1). Although LIP shares spectral and kinetic features with other peroxidases, the enzyme has several unique characteristics, including a redox potential higher than those of other peroxidases (2, 3). The high redox potential enables LIP to oxidize aromatic compounds with calculated ionization potential (IP) values of up to 9.0 eV (4). This has striking implications when considering the potential applications of peroxidases for useful biotransformations (5-7). LIP can be expected to oxidize a wider range of substrates and therefore have potential applications unsuitable for less potent peroxidases.Phenols are oxidized by peroxidases to generate phenoxy radicals, which couple with other substrate molecules to form dimeric, oligomeric, and polymeric products. This phenomenon can be exploited for the biocatalytic production of useful oligomers and polymers (6, 7), as well as for the treatment of wastewater streams polluted with toxic phenols (8 -10).Ferulic acid (FA), which is an extremely abundant and widespread cinnamic acid derivative (11), was chosen as a model substrate for studying the initial steps of LIP-catalyzed polymerization of phenolic compounds in vitro. In vivo, peroxidasecatalyzed oxidation of FA esterified to primary plant cell wall polysaccharides results in the formation of FA dehydrodimers, believed to enhance the rigidity and strength of the cell wall. A range of regio-isomeric dehydrodimers identified and quantified in several plant cell walls include products of ␤-␤Ј, ␤-5Ј, ␤-O-4Ј, 4-O-5Ј, and 5-5Ј radical coupling (12-15). Such dehydrodimers, along with FA, are also believed to act as nucleation sites in the lignification process, coupling with lignin monomers (16). This clearly indicates that FA dehydrodimers can be further oxidized. Indeed, certain dehydrodimers formed from oxidative coupling of FA have been reported to be more effective antioxidants than FA itself (17, 18). Their antioxidant activity appears to be related to the existence of a full conjugation system in the molecule. Nevertheless, the formati...

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“…These results further confirmed that FA was liberated from the rice hemicellulose by enzymes from the wheat Qu. It has been previously reported that FA was found esterified with polysaccharides, which comprise the hemicellulose of plant cell walls 5,18 . This suggests that the FA linked to the hemicellulose of the cell walls of the rice grains was liberated by the hydrolytic enzymes present in the wheat Qu.…”

Section: Enzymatic Hydrolysis Of Rice Flour By Crude Enzyme Solutionmentioning

confidence: 99%

Ferulic Acid Release and 4-Vinylguaiacol Formation during Chinese Rice Wine Brewing and Fermentation

2010

Journal of the Institute of Brewing

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J. Inst. Brew. 116(3), 304-311, 2010The release of ferulic acid (FA) and the subsequent enzymatic decarboxylation to 4-vinylguaiacol (4-VG) were nearly ubiquitous during the production of Chinese rice wine. To evaluate the release of FA and the transformation to 4-VG, the levels of FA and 4-VG were determined by high performance liquid chromatography (HPLC) and gas chromatography-mass spectrum (GC-MS), respectively. During rice wine brewing, the concentrations of FA and 4-VG increased as fermentation time prolonged, with a rapid rise in days 1 to 5 of the main fermentation and followed by a slower rise from the 6th day post inoculation. FA and 4-VG levels in mashes, fermented by yeast with wheat Qu, were significantly higher than those in mashes fermented by yeast using commercial enzyme additions. The release of FA from rice by wheat Qu involves an enzymatic release mechanism. The levels of FA and 4-VG from rice flour by wheat Qu rose gradually during the first 24 h and then tended to stabilize. The capacity of yeasts to decarboxylate phenolic acids (Pof + phenotype) was absent in most rice wine brewing yeasts. These results suggest that the production of FA and 4-VG originated from materials in the wheat Qu rather than by the yeast during Chinese rice wine brewing and fermentation.

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Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures

Cited by 167 publications

References 69 publications

A Genomics Approach to Deciphering Lignin Biosynthesis in Switchgrass

A Genomics Approach to Deciphering Lignin Biosynthesis in Switchgrass

Initial Steps of Ferulic Acid Polymerization by Lignin Peroxidase

Ferulic Acid Release and 4-Vinylguaiacol Formation during Chinese Rice Wine Brewing and Fermentation

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