Mapping the Biotransformation of Coumarins through Filamentous Fungi

Natural coumarins are present in remarkable amounts as secondary metabolites in edible and medicinal plants, where they display interesting bioactivities. Considering the wide enzymatic arsenal of filamentous fungi, studies on the biotransformation of coumarins using these microorganisms have great...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-09, Vol.24 (19), p.3531
Main Authors: Nascimento, Jainara Santos do, Núñez, Wilson Elias Rozo, Santos, Valmore Henrique Pereira Dos, Aleu, Josefina, Cunha, Sílvio, Silva, Eliane de Oliveira
Format: Article
Language:English
Subjects:
Biotransformation
Chemical compounds
Chemical reactions
Chromatography, High Pressure Liquid
Coumarin
Coumarins - chemistry
Coumarins - isolation & purification
Coumarins - metabolism
Enzymes
filamentous fungi
Filamentous microorganisms
Fungi
Fungi - metabolism
Herbal medicine
Hydroxylation
Medicinal plants
Metabolites
Microorganisms
Molecular Structure
Pharmaceutical industry
Secondary metabolites
selective hydroxylation
Selectivity
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Summary:Natural coumarins are present in remarkable amounts as secondary metabolites in edible and medicinal plants, where they display interesting bioactivities. Considering the wide enzymatic arsenal of filamentous fungi, studies on the biotransformation of coumarins using these microorganisms have great importance in green chemical derivatization. Several reports on the biotransformation of coumarins using fungi have highlighted the achievement of chemical analogs with high selectivity by using mild and ecofriendly conditions. Prompted by the enormous pharmacological, alimentary, and chemical interest in coumarin-like compounds, this study evaluated the biotransformation of nine coumarin scaffolds using ATCC 10028b and ATCC 16404. The chemical reactions which were catalyzed by the microorganisms were highly selective. Among the nine studied coumarins, only two of them were biotransformed. One of the coumarins, 7-hydroxy-2,3-dihydrocyclopenta[ ]chromen-4(1 )-one, was biotransformed into the new 7,9-dihydroxy-2,3-dihydrocyclopenta[ ]chromen-4(1 )-one, which was generated by selective hydroxylation in an unactivated carbon. Our results highlight some chemical features of coumarin cores that are important to biotransformation using filamentous fungi.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24193531