Formation of 4-Vinyl Guaiacol as an Intermediate in Bioconversion of Ferulic Acid bySchizophyllum commune

Abstract

In order to utilize phenolic compounds in unused biomass resources, the metabolic pathway of ferulic acid by way of a white-rot fungus, Schizophyllum commune, was investigated. Ferulic acid was immediately degraded, and the formation of 4-vinyl guaiacol was confirmed by GC-MS analysis. The metabolic test of ferulic acid and its degradation products indicated that S. commune converted ferulic acid into 4-vinyl guaiacol by decarboxylation. This was then oxidized to vanillin and vanillic acid. This result indicates that S. commune distinguished ferulic acid from lignins and metabolized it specifically.

Decarboxylation of Ferulic Acid to 4-Vinyl Guaiacol by Streptomyces setonii

“…These results suggest that S. setonii has a reduction mechanism for vanillin to vanillyl alcohol. A similar tendency was observed with Schizophyllum commune [21], Pycnoporus cinnabarinus [26,27], Sporotrichum pulverulentum [28] and Fomitopsis palustris [29].…”

“…After this threshold, 4VG started to be consumed leading to 679 mg/l of 4VG within 243 h. However, no other metabolites were detected, since the only compound z 100 90 80 70 60 50 40 30 20 10 0 60 80 100 120 140 160 180 200 220 240 260 280 300 320 observed, vanillyl alcohol, only oscillated between 35 to 45 mg/l. Consequently, although 4VG was produced from ferulic acid by certain fungi [2,20,21], yeasts [5,6,14] and bacteria [1,10,13], in our knowledge, 4VG was not identified up to now in the products metabolised by S. setonii. An additional control culture without inoculation of S. setonii, ferulic acid did not decrease, and 4-vinyl guaiacol was not observed (data not shown).…”

Production of cellulolytic enzymes containing cinnamic acid esterase from Schizophyllum commune

“…commune metabolizes ferulic acid specifi cally, converting it into vanillin and vanillic acid via 4-vinyl guaiacol (Tsujiyama and Ueno, 2008). This metabolic pathway has not been reported in other basidiomycetes (Enoki et al, 1981;Falconnier et al, 1994;Gupta et al, 1981;Krings et al, 2001;Münzenberger et al, 2003;Nishida and Fukuzumi, 1978).…”

Bioconversion of ferulic acid to vanillin by combined action of Aspergillus niger K8 and Phanerochaete crysosporium ATCC 24725

“…To fulfill this demand, many biotechnological methods to produce natural vanillin from ferulic acid using fungi have been proposed. For example Schizophyllum commune degraded ferulic acid to 4-vinylguaiacol, then it was oxidized to vanillin and vanillic acid (Tsujiyama and Ueno, 2008). Biotransformation of ferulic acid using Enterobacter sp.…”