Degradation of trimeric lignin model compounds, arylglycerol-.BETA.-syringaresinol ethers, by Fusarium solani M-13-1.

Abstract

Trimeric lignin model compounds, arylglycerol-/?-syringaresinol ethers, were incubated with Fusarium solani M-1 3-1 in basal salts mediumwith shaking. From the culture filtrates, degradation products were isolated and characterized spectroscopically. Based on the degradation products of guaiacylglycerol-/?-syringaresinol ether (II), the following reactions were found to occur; 1) oxidation of benzylic position (a") and subsequent ring opening of the syringaresinol side chain, 2) cleavage of alkyl-aryl CC bonds (Ca-C1 and Ca-CrO of both arylglycerol and syringaresinol portions, and 3) splitting of the alkyl-aryl ether bond (C^-O-C^). In the case of syringlyglycerol-/?syringaresinol ether (III), preferential oxidation of benzylic position (a) of the arylglycerol moiety was seen. The former two reactions were found to be catalyzed by the fungal phenol oxidizing enzymes.

Transformation of 3,5‐dimethoxy,4‐hydroxy cinnamic acid by polyphenol oxidase from the fungus Trametes versicolor: Product elucidation studies

“…The MS fragmentation patterns indicated that compounds I and II were fairly symmetrical, showing the most abundant mass fragment at m/z 181. This fragment was assigned to the 3,5-dimethoxy,4-hydroxy-␣-ketone moiety (Iwahara, 1983;Kamaya et al, 1983). In addition, the appearance of fragments of 44, 402, and 358 in the mass spectra suggested a presence of one and two decarboxylated molecules, respectively.…”

Compositional Changes in Compost during Composting and Growth of Agaricus bisporus

“…These oxidative changes in compost lignins may be catalyzed by mushroom laccase through a hydroxyl radical mechanism, probably a one-electron oxidation (11,53). In vitro experiments using lignin model compounds have shown that fungal laccase catalyzes certain degradation reactions (61), particularly with syringyl compounds (30,32,33,43), and can also cause C.-C,3 cleavage in phenolic syringyl units to produce benzoic acid structures (35).…”

Synthèse d’Oligolignols de Type β–0–4

“…Les premieres etudes de modelisation de la lignine effectuees ä partir d'oligolignols sont relativement recentes (Kamaya et al 1983). Par leur developpement des informations complementaires devraient etre apportees ä celles obtenues essentiellement ä partir de monomeres et de dimeres mais qui sont representatifs d'une seule unite structurale de base du biopolymere.…”