Coumarin metabolic routes in Aspergillus spp.

Aguirre-Pranzoni, Celeste; Orden, Alejandro A.; Bisogno, Fabricio R.; Ardanaz, C. E.; Tonn, Carlos E.; Kurina-Sanz, Marcela

doi:10.1016/j.funbio.2010.12.009

Cited by 24 publications

(21 citation statements)

References 20 publications

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“…1). This result is the first report of A. flavus-a fungal strain with probed capability to biotransfom natural products [29,30]-catalyzing an oxidative decarboxylation reaction, which is in agreement with early studies made by Buswell et al for several lignin-degrading white-rot and brown-rot fungi [31,32]. Since A. flavus transformed 4a with growing cultures but not with resting cells, it could be assumed that the oxidative decarboxylation pathway is triggered only under primary metabolism conditions.…”

Section: Microbial Screeningsupporting

confidence: 91%

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Palazzolo

Mascotti

Lewkowicz

et al. 2015

Journal of Industrial Microbiology and Biotechnology

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Aromatic carboxylic acids are readily obtained from lignin in biomass processing facilities. However, efficient technologies for lignin valorization are missing. In this work, a microbial screening was conducted to find versatile biocatalysts capable of transforming several benzoic acids structurally related to lignin, employing vanillic acid as model substrate. The wild-type Aspergillus flavus growing cells exhibited exquisite selectivity towards the oxidative decarboxylation product, 2-methoxybenzene-1,4-diol. Interestingly, when assaying a set of structurally related substrates, the biocatalyst displayed the oxidative removal of the carboxyl moiety or its reduction to the primary alcohol whether electron withdrawing or donating groups were present in the aromatic ring, respectively. Additionally, A. flavus proved to be highly tolerant to vanillic acid increasing concentrations (up to 8 g/L), demonstrating its potential application in chemical synthesis. A. flavus growing cells were found to be efficient biotechnological tools to perform self-sufficient, structure-dependent redox reactions. To the best of our knowledge, this is the first report of a biocatalyst exhibiting opposite redox transformations of the carboxylic acid moiety in benzoic acid derivatives, namely oxidative decarboxylation and carboxyl reduction, in a structure-dependent fashion.

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Section: Microbial Screeningsupporting

confidence: 91%

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Palazzolo

Mascotti

Lewkowicz

et al. 2015

Journal of Industrial Microbiology and Biotechnology

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“…A different strain, A. niger ATCC 11394, reduces coumarin to dihydrocoumarin (3,4-dihydrochromen-2-one, CLXXXVIII) and then either to 6-hydroxy-3,4-dihydrochromen-2-one (CLXXXIX) or to melilotic acid (XXXIX), 3-(2-hydroxyphenyl)propanal (CXC), and 2-(3-hydroxypropyl)phenol (CXCI) (Aguirre-Pranzoni et al 2011b). Dihydrocoumarin (CLXXXVIII), which is widely used as a flavor and fragrance, is transformed by A. niger ATCC 11394 to 2-(3-hydroxypropyl)phenol (CXCI), 6-hydroxy-3,4-dihydrochromen-2-one (CLXXXIX), 4-hydroxycoumarin (XL), and three minor metabolites (Aguirre-Pranzoni et al 2011a).…”

Section: Transformation Of Other Organic Compoundsmentioning

confidence: 99%

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

Parshikov

Woodling

Sutherland

2015

Appl Microbiol Biotechnol

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Many different organic compounds may be converted by microbial biotransformation to high-value products for the chemical and pharmaceutical industries. This review summarizes the use of strains of Aspergillus niger, a well-known filamentous fungus used in numerous biotechnological processes, for biochemical transformations of organic compounds. The substrates transformed include monocyclic, bicyclic, and polycyclic aromatic hydrocarbons; azaarenes, epoxides, chlorinated hydrocarbons, and other aliphatic and aromatic compounds. The types of reactions performed by A. niger, although not unique to this species, are extremely diverse. They include hydroxylation, oxidation of various functional groups, reduction of double bonds, demethylation, sulfation, epoxide hydrolysis, dechlorination, ring cleavage, and conjugation. Some of the products may be useful as new investigational drugs or chemical intermediates.

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“…Physiologically active compounds such as antibiotics, antitumor drugs, antibodies, hypocholesterolemic drugs, anticancer drugs, immunosuppressants, plant hormones, growth promoters for livestock, alkaloids, statins (Vieira et al 2008;Demain 2014;Khan et al 2014), phenolic compounds, terpenes, steroids (Hasnat et al 2015), and antioxidants (Borderes et al 2011) are obtained by fungal culture in bioprocess. Fungi are also recognized by their wide potential in enzyme production of commercial scale (Demain 2014;Hansen et al 2015), biotransformation process (Aguirre-Pranzoni et al 2011), and synthesis of organic acids (Liaud et al 2014).…”

Section: Introductionmentioning

confidence: 99%

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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Natural coumarins and derivatives are compounds that occur naturally in several organisms (plant, bacteria, and fungi) consisting of fused benzene and α-pyrone rings. These compounds show high technological potential applications in agrochemical, food, pharmaceuticals, and cosmetics industries. Therefore, the need for bulk production of coumarins and the advancement of the chemical and pharmaceutical industries led to the development of synthetic coumarin. However, biotransformation process, synthetic bioengineering, metabolic engineering, and bioinformatics have proven effective in the production of natural products. Today, these biological systems are recognized as green chemistry innovation and business strategy. This review article aims to report the potential of fungi for synthesis of coumarin. These microorganisms are described as a source of natural products capable of synthesizing many bioactive metabolites. The features, classification, properties, and industrial applications of natural coumarins as well as new molecules obtained by basidiomycetes and ascomycetes fungi are reported in order to explore a topic not yet discussed in the scientific literature.

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Coumarin metabolic routes in Aspergillus spp.

Cited by 24 publications

References 20 publications

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

Fungi as a source of natural coumarins production

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