Comparative electrochemical study on monolignols and dimers relevant for the comprehension of the lignification process

Cottyn, Betty; Rivard, Michaël; Majira, Amel; Beauhaire, Josiane; Allais, Florent; Martens, Thierry; Baumberger, Stéphanie; Ducrot, Paul‐Henri

doi:10.1016/j.phytol.2015.07.002

Cited by 12 publications

(4 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…hirsuta laccases on the basis of oxidation rates of model lignin compounds. It is remarkable that middle-redox potential laccases SbL and JnL showed comparable to high-redox potential laccases ThL and CcL catalytic efficiency of pinoresinol oxidation, whose potential of oxidation is 1670 mV [ 42 ]. Furthermore, the catalytic efficiency of JnL ( E 0 T1 = 610 mV) towards pinoresinol was a bit higher than that of CcL ( E 0 T1 = 780 mV).…”

Section: Discussionmentioning

confidence: 99%

White-rot basidiomycetes Junghuhnia nitida and Steccherinum bourdotii: Oxidative potential and laccase properties in comparison with Trametes hirsuta and Coriolopsis caperata

et al. 2018

View full text Add to dashboard Cite

White-rot basidiomycetes from the poorly studied residual polyporoid clade of Polyporales order Junghuhnia nitida (Pers.) Ryvarden and Steccherinum bourdotii Saliba & A. David grow as secondary xylotrohps on well decomposed woody materials. The main objective of the current study was to compare oxidative potential, growth, production of oxidative enzymes and laccase properties of J. nitida and S. bourdotii with that of typical primary xylotrohps Trametes hirsuta (Wulfen) Lloyd and Coriolopsis caperata (Berk.) Murrill, belonging to the core polyporoid clade. For the first time we report species J. nitida and S. bourdotii as active laccase producers. New laccases from J. nitida and S. bourdotii were purified and characterized. They had an identical molecular weight of 63 kDa and isoelectric points of 3.4 and 3.1, respectively. However, the redox potential of the T1 copper site for both J. nitida (610 mV) and S. bourdotii (640 mV) laccases was lower than those for T. hirsuta and C. caperata laccases. The new laccases showed higher temperature optima and better thermal stability than T. hirsuta and C. caperata laccases. Their half-lives were more than 40 min at 70 °C. The laccases from J. nitida and S. bourdotii showed higher affinity to syringyl-type phenolic compounds than T. hirsuta and C. caperata laccases. The oxidative potential of studied fungi as well as the properties of their laccases are discussed in terms of the fungal life-style.

show abstract

Section: Discussionmentioning

confidence: 99%

White-rot basidiomycetes Junghuhnia nitida and Steccherinum bourdotii: Oxidative potential and laccase properties in comparison with Trametes hirsuta and Coriolopsis caperata

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Recently, Forsythe et al have described an interesting route to obtain controlled oligomers containing , (β-5), and (β-O-4) linkages but always without functionalization of the side chain (Forsythe et al, 2013). In previous works, we have synthesized model compounds with elaborated side chains to (1) conduct electrochemical study (Cottyn et al, 2015), (2) develop analytical method and immunohistochemistry approaches (Mouterde et al, 2013), or (3) unveil the chemical reactivity of lignosulfonates (Broussard et al, 2016). Such models can be used for numerous applications such as determining energetic level for electronic excitation (e.g., photochemistry), determining preferential pathways of (de)lignification, or estimating the required energy to break specific C-C bonding and release monomers from lignin.…”

Section: Introductionmentioning

confidence: 99%

First Total Synthesis of (β-5)-(β-O-4) Dihydroxytrimer and Dihydrotrimer of Coniferyl Alcohol (G): Advanced Lignin Model Compounds

et al. 2019

Self Cite

View full text Add to dashboard Cite

To investigate lignin degradation, scientists commonly use model compounds. Unfortunately, these models are most of the time simple β-O-4 dimers and do not sufficiently mimic the wide complexity of lignin structure (i.e., aliphatic side chains and robust C-C bonds). Herein, we present a methodology to access advanced lignin models through the first synthesis of two trimers of monolignol G-possessing side-chains and both robust β-5 bond and labile β-O-4 bond-via a chemo-enzymatic pathway. Key steps were (1) the C-C coupling via laccase-mediated oxidation, (2) the C-O coupling via a simple S N2 between a phenolate and a bromoketoester, and (3) a modified Upjohn dihydroxylation or a palladium-catalyzed hydrogenation. (β-5)-(β-O-4) dihydroxytrimer and dihydrotrimer of coniferyl alcohol (G) were obtained in good global yield, 9 and 20%, respectively, over nine steps starting from ferulic acid.

show abstract

“…27,28 This technique has been previously applied in the field of patrimony conservation. 29,30 Much polyphenolic compounds in wood can produce a well-defined electrochemistry in solution-phase, from lignins [31][32][33] to flavonoids, flavones, etc. [34][35][36][37] and solid state.…”

Section: Introductionmentioning

confidence: 99%

Identification of vegetal species in wooden objects using in situ microextraction-assisted voltammetry of microparticles

Doménech‐Carbó

Ferragud-Adam

et al. 2017

Anal. Methods

View full text Add to dashboard Cite

show abstract

Comparative electrochemical study on monolignols and dimers relevant for the comprehension of the lignification process

Cited by 12 publications

References 47 publications

White-rot basidiomycetes Junghuhnia nitida and Steccherinum bourdotii: Oxidative potential and laccase properties in comparison with Trametes hirsuta and Coriolopsis caperata

White-rot basidiomycetes Junghuhnia nitida and Steccherinum bourdotii: Oxidative potential and laccase properties in comparison with Trametes hirsuta and Coriolopsis caperata

First Total Synthesis of (β-5)-(β-O-4) Dihydroxytrimer and Dihydrotrimer of Coniferyl Alcohol (G): Advanced Lignin Model Compounds

Identification of vegetal species in wooden objects using in situ microextraction-assisted voltammetry of microparticles

Contact Info

Product

Resources

About