Vanillin as a product of ferulic acid biotransformation by the white-rot fungus Pycnoporus cinnabarinus I-937: Identification of metabolic pathways

Falconnier, B.; Lapierre, Catherine; Lesage‐Meessen, Laurence; Yonnet, G.; Brunerie, Pascal; Colonna-Ceccaldi, Benoît; Corrieu, Georges; Asther, Michèle

doi:10.1016/0168-1656(94)90003-5

Cited by 132 publications

(77 citation statements)

References 15 publications

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“…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). Furthermore, S. commune transformed p-coumaric acid into p-hydroxybenzaldehyde and accumulated it in the cultures (Nimura et al, 2010).…”

mentioning

confidence: 99%

Production of cellulolytic enzymes containing cinnamic acid esterase from Schizophyllum commune

Tsujiyama

Ueno

2011

J. Gen. Appl. Microbiol.

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confidence: 99%

Production of cellulolytic enzymes containing cinnamic acid esterase from Schizophyllum commune

Tsujiyama

Ueno

2011

J. Gen. Appl. Microbiol.

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“…5B and 5C). The order of formation of these compounds is different to that seen in Pycnoporus cinnabarinus (Estrada Alvarado et al, 2001;Falconnier et al, 1994;Krings et al, 2001). During the metabolism of these compounds, P. cinnabarinus forms benzoic acids before forming benzaldehydes.…”

Section: Discussionmentioning

confidence: 78%

“…However, the fungus hydrogenated the double bond fi rst in p-coumaric acid (Fig. 5B).Reduction of p-coumaric and ferulic acids by whiterot fungi has been reported previously; for example, the reduction of the carboxyl group at the γ-position (Enoki et al, 1981;Estrada Alvarado et al, 2001Falconnier et al, 1994;Gupta et al, 1981;Krings et al, 2001;Lapadatescu et al, 2000;Nishida and Fukuzumi, 1978) and the hydrogenation of C α -C β double bond (Enoki et al, 1981;Estrada Alvarado et al, 2001;Gupta et al, 1981). This study demonstrates that S. commune reduced the side chain of p-coumaric acid but not that of ferulic acid ( Fig.…”

mentioning

confidence: 97%

Bioconversion of cinnamic acid derivatives by Schizophyllum commune

Nimura

Tsujiyama

Ueno

2010

J. Gen. Appl. Microbiol.

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To investigate the production of useful phenols from plant resources, we examined the metabolism of cinnamic acid derivatives by a wood-rotting fungus, Schizophyllum commune. Four cinnamic acid derivatives (cinnamic, p-coumaric, ferulic, and sinapic acids) were tested as substrates. Two main reactions, reduction and cleavage of the side chain, were observed. Reduction of the side chain was confi rmed in cinnamic acid and p-coumaric acid metabolism. The side chain cleavage occurred in p-coumaric acid and ferulic acid metabolism but the initial reactions of these acids differed. Sinapic acid was not metabolized by S. commune. p-Hydroxybenzaldehyde accumulation was observed in the culture to which p-coumaric acid was added. This suggests that S. commune is a useful agent for transforming p-coumaric acid into p-hydroxybenzaldehyde. S. commune has the potential to release and metabolize cinnamic acid derivatives esterifi ed or etherifi ed to plant cell walls. It is a white-rot fungus and enables the release of etherifi ed cinnamic acid derivatives during lignin degradation by ligninolytic enzymes such as laccase and peroxidases. It produces ferulic acid esterase (MacKenzie and Bilous, 1988) and p-coumaric acid esterase (unpublished data), and releases cinnamic acid derivatives esterifi ed to xylans in plant cell walls. Furthermore, it secretes highly active extracellular cellulolytic and xylanolytic enzymes during plant biomass degradation (Haltrich and Steiner, 1994) and it has the ability to enhance the accessibility of ligninolytic enzymes and cinnamic acid esterases to plant cell walls. Thus, S. commune is expected to independently convert the cinnamic acid derivatives bound to plant cell walls. KeyVarious kinds of cinnamic acid derivatives are found in plant biomass. To use S. commune for the bioconversion of these acid derivatives, it is necessary to study its metabolic potential. In this study, we investigated the metabolic mechanism of 4 cinnamic acid derivatives by identifying their metabolic products. Materials and MethodsStrain and cultivation methods. Schyzopyllum commune (Kyoto Prefectural University Forestry Collection (KPUF) 0588) was used in this study. The basal medium was prepared according to Kirk et al. (1978) and contained 1% glucose and 1 mM ammonium tartrate as carbon and nitrogen sources, respectively.Conversion test. S. commune was inoculated onto agar culture containing Kirk s basal media, 1% glucose and 1 mM ammonium tartrate in a 90-mm petri dish and cultivated at 28 C for 1 week. A mycelium plug (6 mm in diameter) was inoculated with 30 ml of liquid medium in 100 ml Erlenmeyer fl asks and incubated (stationary) at 28 C. S. commune culture was incubated for 3 days before adding 3 cinnamic acid derivatives, namely p-coumaric acid, ferulic acid, and sinapic acid, and for 5 days when cinnamic acid was added. The cinnamic acid derivatives were aseptically added to the liquid cultures (fi nal concentration: 1.0 mM). The cinnamic acid derivatives tested were cinnamic acid, p-coumaric acid (4-hyd...

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“…Vanillic acid (4-hydroxy-3-methoxybenzoic acid, Figure 1) is a dietary phenolic compound found in plants and fruits (Duke, 1992) and an intermediate in the production of vanillin from ferulic acid (Lesage-Meessen, 1996;Civolani, 2000). Additionally, vanillic acid is a metabolic product of caffeic acid that is found in the urine of humans after consuming coffee, chocolate or green tea (Falconnier et al, 1994) and it can exhibit antioxidant, antimicrobial and antimalarial activity (Rechner et al, 2001;Yemis et al, 2011). It is a key component of the vanilla plant and in recent years, it has been used as a preservative and antiseptic agent in the food, pharmaceutical and cosmetic industries (Boyce et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Genotoxic and Anti-Genotoxic Effects of Vanillic Acid Against Mitomycin C-Induced Genomic Damage in Human Lymphocytes In Vitro

Erdem¹,

Çinkılıç²,

Vatan³

et al. 2012

Asian Pacific Journal of Cancer Prevention

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Vanillic acid, a vegetable phenolic compound, is a strong antioxidant. The aim of the present study was to determine its effects on mitomycin C-induced DNA damage in human blood lymphocyte cultures in vitro, both alone and in combination with mitomycin C (MMC). The cytokinesis block micronucleus test and alkaline comet assay were used to determine genotoxic damage and anti-genotoxic effects of vanillic acid at the DNA and chromosome levels. MMC induced genotoxicity at a dose of 0.25 µg/ml. Vanillic acid (1 µg/ml) significantly reduced both the rates of DNA damaged cells and the frequency of micronucleated cells. A high dose of vanillic acid (2 µg/ml) itself had genotoxic effects on DNA. In addition, both test systems showed similar results when tested with the negative control, consisting of dimethyl sulfoxide (DMSO) in combination with vanillic acid (1 µg/ml)+MMC. In conclusion, vanillic acid could prevent oxidative damage to DNA and chromosomes when used at an appropriately low dose.

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Vanillin as a product of ferulic acid biotransformation by the white-rot fungus Pycnoporus cinnabarinus I-937: Identification of metabolic pathways

Cited by 132 publications

References 15 publications

Production of cellulolytic enzymes containing cinnamic acid esterase from Schizophyllum commune

Production of cellulolytic enzymes containing cinnamic acid esterase from Schizophyllum commune

Bioconversion of cinnamic acid derivatives by Schizophyllum commune

Genotoxic and Anti-Genotoxic Effects of Vanillic Acid Against Mitomycin C-Induced Genomic Damage in Human Lymphocytes In Vitro

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