Enzymatische Versuche zur Entstehung des Lignins, IV. Mitteil.: Dehydrierungen in der Guajacolreihe

Richtzenhain, Hermann

doi:10.1002/cber.19490820602

Cited by 42 publications

(10 citation statements)

References 4 publications

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“…Ferulic acid (FA) was identified and quantified using authentic FA (Wako Pure Chemical Industries, Ltd., Osaka, Japan). The peaks of diferulic acid (DFA) isomers were identified and quantified using 5-5 DFA, which had been synthesized by the method of Richtzenhain (1949), and published spectra and response factors reported by Waldron et al (1996).…”

Section: Determination Of Cell Wall-bound Ferulatesmentioning

confidence: 99%

Phenylalanine ammonia-lyase and cell wall peroxidase are cooperatively involved in the extensive formation of ferulate network in cell walls of developing rice shoots

Wakabayashi

Soga

Hoson

2012

Journal of Plant Physiology

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Section: Determination Of Cell Wall-bound Ferulatesmentioning

confidence: 99%

Phenylalanine ammonia-lyase and cell wall peroxidase are cooperatively involved in the extensive formation of ferulate network in cell walls of developing rice shoots

Wakabayashi

Soga

Hoson

2012

Journal of Plant Physiology

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“…Fry et al (2000). Non-radioactive 5-5'-diferulic acid, synthesised by the method of Richtzenhain (1949), was kindly donated by Prof. S.C. Fry (The University of Edinburgh).…”

Section: Chemicals and Radiochemicalsmentioning

confidence: 99%

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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“…L-[1-3 H]Arabinose (148 TBq/mol) was custom-synthesised by Amersham International. Non-radioactive 5,5¢-diferulic acid, synthesised by the method of Richtzenhain (1949), was kindly donated by Dr G. Wallace (The University of Edinburgh). Non-radioactive feruloyl-CoA was synthesised and kindly donated by Dr K.E.…”

Section: Chemicalsmentioning

confidence: 99%

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

Fry

Willis

Paterson

2000

Planta

167

158

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Maize (Zea mays L.) cell cultures incorporated radioactivity from [14C]cinnamate into hydroxycinnamoyl-CoA derivatives and then into polysaccharide-bound feruloyl residues. Within 5-20 min, the CoA pool had lost its 14C by turnover and little or no further incorporation into polysaccharides then occurred. The system was thus effectively a pulse-chase experiment. Kinetics of radiolabelling of diferulates (also known as dehydrodiferulates) varied with culture age. In young (1-3 d) cultures, polysaccharide-bound [14C]feruloyl- and [14C]diferuloyl residues were both detectable within 1 min of [14C]cinnamate feeding. Thus, feruloyl residues were dimerised < 1 min after their attachment to polysaccharides. For at least the first 2.3 h after [14C]cinnamate feeding, polysaccharide-bound [14C]diferuloyl residues remained almost constant at approximately 7% of the total polysaccharide-bound [14C]ferulate derivatives. Since feruloyl residues are attached to polysaccharides < 1 min after the biosynthesis of the latter, and > 10 min before secretion, the data show that extensive feruloyl coupling occurred intra-protoplasmically. Exogenous H2O2 (1 mM) caused little additional feruloyl coupling; therefore, wall-localised coupling may have been peroxidase-limited. In older (e.g. 4 d) cultures, less intraprotoplasmic coupling occurred: during the first 2.5 h, polysaccharide-bound [14C]diferuloyl residues were a steady 1.4% of the total polysaccharide-bound [14C]ferulate derivatives. In contrast to the situation in younger cultures, exogenous H2O2 induced a rapid 4- to 6-fold increase in all coupling products, indicating that coupling in the walls was H2O2-limited. In both 2- and 4-d-old cultures, polysaccharide-bound 14C-trimers and larger coupling products exceeded [14C]diferulates 3- to 4-fold, but followed similar kinetics. Thus, although all known dimers of ferulate can now be individually quantified, it appears to be trimers and larger products that make the major contribution to cross-linking of wall polysaccharides in cultured maize cells. We argue that feruloyl arabinoxylans that are cross-linked before and after secretion are likely to loosen and tighten the cell wall, respectively. The consequences for the control of cell expansion and for the response of cell walls to an oxidative burst are discussed.

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Enzymatische Versuche zur Entstehung des Lignins, IV. Mitteil.: Dehydrierungen in der Guajacolreihe

Cited by 42 publications

References 4 publications

Phenylalanine ammonia-lyase and cell wall peroxidase are cooperatively involved in the extensive formation of ferulate network in cell walls of developing rice shoots

Phenylalanine ammonia-lyase and cell wall peroxidase are cooperatively involved in the extensive formation of ferulate network in cell walls of developing rice shoots

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

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

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