Enzymic feruloylation of arabinoxylan-trisaccharide by feruloyl-CoA:arabinoxylan-trisaccharide O -hydroxycinnamoyl transferase from Oryza sativa

Yoshida-Shimokawa, Tomoko; Yoshida, Shigeki; Kakegawa, Koichi; Ishii, Tadashi

doi:10.1007/s004250000490

Cited by 52 publications

(29 citation statements)

References 24 publications

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“…This radioactive precursor can be covalently linked to the polysaccharides and oxidative coupled only after its hydroxylation and activation within the cell. In the presence of trans-[U-14 C]cinnamic acid a great proportion of the ethanol soluble pool was associated with low-M r compounds which could represent hydroxycinnamoyl precursors (hydroxycinnamoyl-CoA thioesters or hydroxycinnamoyl-sugar esters), which provide a steady supply of activated hydroxycinnamoyl groups to be transferred to the nascent polysaccharides (Yoshida-Shimokawa et al 2001;Obel et al 2003). Our data are in agreement with those reported in spinach (Fry 1984) and maize (Fry et al 2000;Lindsay and Fry 2008) cell cultures that rapidly incorporated 14 C from radioactive [ 14 C]cinnamic acid into presumed hydroxycinnamoyl-CoA derivatives and then into polysaccharide-bound phenolic residues.…”

Section: Discussionmentioning

confidence: 97%

Evidence for intra- and extra-protoplasmic feruloylation and cross-linking in wheat seedling roots

Mastrangelo

Lenucci

Piro

et al. 2008

Planta

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The sub-cellular feruloylation and oxidative coupling sites of cell wall polysaccharides were investigated in planta by monitoring the kinetics of appearance of arabinosyl- and feruloyl-radiolabelled polysaccharides in the protoplasmic compartment and their secretion in the wall either in the presence or absence of brefeldin A (BFA). By using root apical segments excised from wheat seedlings (Triticum durum Desf.), incubated with trans-[U-(14)C]cinnamic acid, we demonstrated that [14C]ferulate, likely [14C]diferulate, as well as trimers and larger products of ferulate are incorporated into the protoplasmic polysaccharides very rapidly within 1-3 min of [14C]cinnamate feeding. This agrees with the assumption that (glucurono)arabinoxylans [(G)AX] feruloylation and oxidative coupling occur intracellularly, likely in the Golgi apparatus. Simultaneously, polymer bound radioactive hydroxycinnamic acids appeared to be incorporated into the cell wall of root apical segments as early as 2 min after trans-[U-(14)C]cinnamic acid feeding. On the contrary, starting from L-[1-(14)C]arabinose as tracer, the secretion of the pentose-containing polymers into the wall was between 5 to 10 min. These results indicated that (G)AX feruloylation and oxidative coupling occur both intra-protoplasmically and in muro. The occurrence of in muro feruloylation and oxidative coupling was confirmed by the use of BFA a well known inhibitor of secretion. The drug caused a strong inhibition of the synthesis and secretion into the wall of the 14C-pentosyl-labelled polymers as well as of 14C-feruloyl-polymers. In spite of this, the total amount of 14C-feruloyl-polymers incorporated into the wall was only slightly affected by BFA. This indicates the existence of a mechanism involved into secretion of the activated hydroxycinnamoyl precursors to the wall, alternative to that involved in polysaccharide secretion.

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Section: Discussionmentioning

confidence: 97%

Evidence for intra- and extra-protoplasmic feruloylation and cross-linking in wheat seedling roots

Mastrangelo

Lenucci

Piro

et al. 2008

Planta

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“…By structural elucidation of feruloyl-oligosaccharides released by mild acid and enzymic hydrolysis, it has been shown that the feruloyl residues are ester-linked to a-L-Ara and b-D-Xyl residues of arabinoxylans and xyloglucans respectively (Kato and Nevins 1985;Ishii 1997;Wende and Fry 1996;Saulnier et al 1995). The process of polysaccharide feruloylation occurs within the protoplast, probably in the Golgi apparatus (Myton and Fry 1994;Fry et al 2000;Obel et al 2003), with feruloyl-CoA (Meyer et al 1991;Yoshida-Shimokawa et al 2001) or feruloyl glucosyl ester (Obel et al 2003) being the most likely substrates for the feruloyltransferase activity.…”

Section: Introductionmentioning

confidence: 96%

Oxidative coupling of a feruloyl-arabinoxylan trisaccharide (FAXX) in the walls of living maize cells requires endogenous hydrogen peroxide and is controlled by a low-Mr apoplastic inhibitor

Encina

Fry

2005

Planta

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Feruloyl-polysaccharides can be oxidatively coupled in isolated cell walls by peroxidase plus exogenous H(2)O(2) in vitro, but the extent to which similar reactions may occur in the apoplast in vivo was unclear. Numerous cellular factors potentially control feruloyl coupling in vivo, and their net controlling influence is not readily studied in vitro. Therefore, we have monitored apoplastic feruloyl coupling in cultured maize cells in vivo using a radiolabelled model substrate, 5-O-feruloyl-alpha-L: -arabinofuranosyl-(1-->3)-beta-D: -xylopyranosyl-(1-->4)-D: -xylose (FAXX). FAXX was expected to permeate the wall and to undergo reactions analogous to those normally exhibited by apoplastic feruloyl-polysaccharides in vivo. Little difference was found between the fates of [feruloyl-(14)C]FAXX and [pentosyl-(3)H]FAXX, indicating negligible apoplastic hydrolase or transferase activities. Very little radioactivity entered the protoplasm. Maize cells that had recently been washed in fresh medium were able to bind most of the FAXX (90%) in their cell walls, regardless of the age of the culture. During wall-binding, the [(14)C]feruloyl groups were converted to [(14)C]dehydrodiferulates and larger coupling products, as revealed by TLC after alkaline hydrolysis. As expected for an oxidative reaction, wall-binding was delayed by added anti-oxidants (ascorbate, ferulate, sinapate, chlorogenate or rutin). It was also completely inhibited by iodide, an H(2)O(2)-scavenger, indicating a role for peroxidase rather than oxidase. The observations indicate that oxidative coupling of feruloyl groups occurred within the cell wall, dependent on endogenous apoplastic H(2)O(2) and wall-localised peroxidase, in vivo. Cells that had not recently been washed in fresh medium were much less able to bind FAXX, indicating the presence in the apoplast of an endogenous inhibitor of oxidative coupling. This inhibitor was of low M(r), was destroyed by heating, and remained in the aqueous phase (pH approximately 3.5) when shaken with ethyl acetate. Its effectiveness was not altered by ascorbate oxidase. It is thus a small, heat-labile, hydrophilic inhibitor (not ascorbate) which we suggest plays a natural role in the control of wall cross-linking, and thus potentially in the control of cell growth.

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“…Although studies have identified key enzymes that are involved in hydroxycinnamoyl-AX synthesis, including xylosyl transferase from barley (Urahara et al 2004), arabinosyl transferase from wheat (Porchia et al 2002), and feruloyl transferase from parsley, Festuca arundinacea, and rice (Meyer et al 1991;Myton and Fry 1994;Yoshida-Shimokawa et al 2001), the genes encoding these enzymes are still unknown. Using public EST databases for cereals and dicots, Mitchell et al (2007) proposed candidate genes for xylan synthase, arabinosyl transferase, feruloyl transferase, and acyltransferase, of which several genes encoding glycosyl transferase (GT) 61 family were experimentally shown to be responsible for the activity of arabinosyl transferase and xylosyl transferase (Anders et al 2012;Chiniquy et al 2012).…”

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confidence: 99%

Transcription profiling identifies candidate genes for secondary cell wall formation and hydroxycinnamoyl-arabinoxylan biosynthesis in the rice internode

Nakano

Nishikubo

Sato-Izawa

et al. 2013

Plant Biotechnology

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Microarray analysis was used to identify candidate genes that are involved in the formation of secondary cell walls and hydroxycinnamoyl-arabinoxylan (AX) in rice. In order to identify genes involved in secondary cell wall formation, gene expression was compared between wild-type whole internodes that contain cells with thickened secondary cell walls, such as vascular and cortical fiber cells, and wild-type internode parenchyma cells without secondary cell walls. In addition, gene expression was compared between the internode parenchyma of Fukei71 (F71), a rice dwarf mutant that accumulates large amounts of hydroxycinnamoyl-AX in pith parenchyma cells, and wild-type pith parenchyma cells to identify hydroxycinnamoyl-AX-related genes. To address the significant expression of candidate genes, gene lists were prepared for the phenylpropanoid pathway, major carbon metabolism, and cell wall biosynthesis, which is a useful platform to analyze cell wall formation in rice. The data indicated that a number of rice genes are potentially associated with secondary cell wall formation, such as the up-regulation of genes encoding cellulose synthase subunit A and ferulate 5-hydroxylase in wild-type whole internodes. Similarly, for hydroxycinnamoyl-AX synthesis, the expression of several genes changed, such as the downregulation of genes encoding cinnamoyl-CoA reductase and the up-regulation of the phosphoenolpyruvate carboxykinase gene in F71 pith parenchyma.

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Enzymic feruloylation of arabinoxylan-trisaccharide by feruloyl-CoA:arabinoxylan-trisaccharide O -hydroxycinnamoyl transferase from Oryza sativa

Cited by 52 publications

References 24 publications

Evidence for intra- and extra-protoplasmic feruloylation and cross-linking in wheat seedling roots

Evidence for intra- and extra-protoplasmic feruloylation and cross-linking in wheat seedling roots

Oxidative coupling of a feruloyl-arabinoxylan trisaccharide (FAXX) in the walls of living maize cells requires endogenous hydrogen peroxide and is controlled by a low-Mr apoplastic inhibitor

Transcription profiling identifies candidate genes for secondary cell wall formation and hydroxycinnamoyl-arabinoxylan biosynthesis in the rice internode

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