Analysis of the structure of lignin-carbohydrate complexes by the specific13C tracer method

Xie, Yimin; Yasuda, Sciichi; Wu, Hong; Liu, Huanbin

doi:10.1007/bf00777359

Cited by 70 publications

(56 citation statements)

References 20 publications

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“…This observation supported the data obtained by sugar analysis. Similar results were reported by Xie et al [28] from the study of ginkgo lignin-carbohydrate complexes (LCC). The authors stated that three lignin-carbohydrate linkages (i.e., ether type, ester type, ketal type) were found at the C-a position of the Analysis of Lignins Solubilized 257 side chain of phenylpropane units in ginkgo LCC, and no lignin-carbohydrate bond at the C-b or C-g position of the lignin side chain was observed in the 13 C-NMR spectra of the 13 C-enriched LCCS.…”

Section: Analysis Of Lignins Solubilized 255supporting

confidence: 90%

Analysis of Lignins Solubilized in Two-Stage Organosolv and Alkaline Peroxide Treatments from Haloxylon ammodendron and Elaeagnus angustifolia

Sun

2002

International Journal of Polymer Analysis and Characterization

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Section: Analysis Of Lignins Solubilized 255supporting

confidence: 90%

Analysis of Lignins Solubilized in Two-Stage Organosolv and Alkaline Peroxide Treatments from Haloxylon ammodendron and Elaeagnus angustifolia

Sun

2002

International Journal of Polymer Analysis and Characterization

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“…The aromatic ring primarily responsible for the anti-oxidant properties is shown at the right of each structure benzyl-polysaccharide ether bonds between ferulate derivatives and wall polysaccharides has been suggested to occur (Fig. 7) via quinone methide intermediates-unstable, initial products of oxidative phenolic coupling that may attach via ether bonds to nucleophiles such as the -OH groups of polysaccharides (Tanaka et al 1979;Toikka and Brunow 1999;Xie et al 2000;Kishimoto et al 2002). Such ether-linked phenolics have so far been reported only in lignified walls (Scalbert et al 1985;Wallace et al 1995;Iiyama et al 1994), which are not present in our maize cell cultures.…”

Section: Alkali-lability Of Cross-linksmentioning

confidence: 98%

Extracellular cross-linking of xylan and xyloglucan in maize cell-suspension cultures: the role of oxidative phenolic coupling

Kerr

Fry

2004

Planta

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Cell-suspension cultures of maize ( Zea mays L.) released soluble extracellular polysaccharides (SEPs) into their medium. Some or all of the SEPs had feruloyl ester groups. Pulse-labelling with [(3)H]arabinose was used to monitor changes in the SEPs' M(r) (estimated by gel-permeation chromatography) with time after synthesis. Newly released (3)H-SEPs were 1.3-1.6 MDa, but between 2 days and 3 days after radiolabelling (in one experiment) or between 5 days and 6 days (in another), the (3)H-SEPs abruptly increased to approximately 17 MDa, indicating extensive cross-linking. The cross-linking involved both [(3)H]xylan and [(3)H]xyloglucan components of the SEPs. The cross-links could be cleaved by alkali, returning the SEPs to their original M(r). In 0.1 M NaOH at 37 degrees C, 58% cleavage was effected within 24 h. The requirement for such prolonged alkali treatment indicates that ester-bonded (e.g. diferuloyl) groups were not solely responsible for the cross-linking. Bonds cleaved only by relatively severe alkali could include benzyl ether linkages formed between sugar residues and oxidised phenolics that had quinone methide structures. The ability of alkali to cleave the cross-links was independent of the age of the (3)H-SEP molecules. Cross-linking of (3)H-SEPs in vivo was delayed (up to approx. 7 days after radiolabelling) by exogenous sinapic acid, chlorogenic acid or rutin-agents predicted to compete with the oxidative coupling of feruloyl-polysaccharides. The cross-linking was promoted by exogenous ferulic acid or l-tyrosine, possibly because these compounds acted as precursors for polysaccharide feruloylation, thus providing additional partner substrates for the oxidative coupling of previously formed (3)H-SEPs. The ability of certain phenolics to prevent the cross-linking of (3)H-SEPs supports the idea that the cross-linking involved phenolic oxidation.

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“…Thus, one strategy usually reported in literature, consist in the use of 13 C labelled lignin monomers to increase the sensitivity of the analysis. This was used both in the case of synthetic (Parkas et al 2001) and natural lignin (Terashima et al 2002) and also applied to the investigation of LCC (Xi et al 2000). Solution state 13 C NMR spectra of the ZL and ZT GAX-DHPs reaction obtained from a labelled coniferyl alcohol are reported in Fig.…”

Section: Nmr Analyses Of Zt and Zl Gax-dhpmentioning

confidence: 99%

“…In hydrated media the latter process will be prominent the early stages of lignification. The second process, ubiquitous in all lignified walls, involves the addition of nucleophilic groups on the transient quinone methide (QM) intermediate generated during the oxidative polymerisation of lignin Xi et al 2000;Terashima 2001; Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Studies of xylan interactions and cross-linking to synthetic lignins formed by bulk and end-wise polymerization: a model study of lignin carbohydrate complex formation

Barakat

Winter²,

Rondeau-Mouro

et al. 2007

Planta

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The mechanism of lignin carbohydrate complex formation by addition of polysaccharides on quinone methide (QM) generated during lignin polymerisation was investigated using a model approach. Dehydrogenation polymers (DHPs, lignin model compounds) were synthesized from coniferyl alcohol in the presence of a glucuronoarabinoxylan (GAX) extracted from oat spelts, by Zutropfverfahren (ZT) and Zulaufverfahren (ZL) methods. The methods ZT and ZL differed in their distribution of QM over the reaction period but generated roughly the same QM amount. Steric exclusion chromatography of the ZT and ZL reaction products showed that only the ZT reaction produced high molar mass compounds. Covalent linkages in the ZT reaction involving ether bonds between GAX moiety and alpha carbon of the lignin monomer were confirmed by (13)C NMR and xylanase-based fractionation. The underlying phenomena were further investigated by examining the interactions between GAX and DHP in sorption experiments. GAX and DHPs were shown to interact to form hydrophobic aggregates. In the ZT process, slow addition permitted polymer reorganisation which led to dehydration around the lignin-like growing chains thereby limiting the addition of water on the quinone methide formed during polymerisation and thus favoured lignin-carbohydrate complex (LCC) formation.

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Analysis of the structure of lignin-carbohydrate complexes by the specific13C tracer method

Cited by 70 publications

References 20 publications

Analysis of Lignins Solubilized in Two-Stage Organosolv and Alkaline Peroxide Treatments from Haloxylon ammodendron and Elaeagnus angustifolia

Analysis of Lignins Solubilized in Two-Stage Organosolv and Alkaline Peroxide Treatments from Haloxylon ammodendron and Elaeagnus angustifolia

Extracellular cross-linking of xylan and xyloglucan in maize cell-suspension cultures: the role of oxidative phenolic coupling

Studies of xylan interactions and cross-linking to synthetic lignins formed by bulk and end-wise polymerization: a model study of lignin carbohydrate complex formation

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