Lapachol biotransformation by filamentous fungi yields bioactive quinone derivatives and lapachol-stimulated secondary metabolites

Lapachol is a natural naphthoquinone with a range of biological effects, including anticancer activity. Microbial transformations of lapachol can lead to the formation of new biologically active compounds. In addition, fungi can produce secondary metabolites that are also important for drug discover...

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Bibliographic Details
Published in:Preparative biochemistry & biotechnology 2019-05, Vol.49 (5), p.459-463
Main Authors: Barbosa Coitinho, Luciana, Fumagalli, Fernando, da Rosa-Garzon, Nathália Gonsales, da Silva Emery, Flavio, Cabral, Hamilton
Format: Article
Language:English
Subjects:
Anticancer properties
Antioxidants
Antitumor activity
Aquatic life
Bioactive compounds
Biocatalysts
Biological activity
Biological effects
Biotransformation
Derivatives
Fungi
gas chromatography
lapachol
mass spectrometry
Metabolites
Microorganisms
Phenols
Pyrazine
Quinones
Secondary metabolites
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Summary:Lapachol is a natural naphthoquinone with a range of biological effects, including anticancer activity. Microbial transformations of lapachol can lead to the formation of new biologically active compounds. In addition, fungi can produce secondary metabolites that are also important for drug discovery. The goal of this study was to evaluate the ability of filamentous fungi to biotransform lapachol into biologically active compounds and identify secondary metabolites produced in the presence of lapachol. Seven out of nine strains of filamentous fungi tested exhibited the ability to biotransform or biodegrade lapachol. The bioactive derivatives norlapachol and isolapachol were identified among biotransformation products. Moreover, lapachol stimulated the production of pyrrolo-[1,2-a] pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl) and phenol-2,4-bis-(1,1-dimethylethyl), secondary metabolites already known to have antimicrobial and antioxidant activities. These results open the perspective of using these strains of filamentous fungi for lapachol biotransformation and efficient production of several biologically active compounds.
ISSN:1082-6068
1532-2297
DOI:10.1080/10826068.2019.1591991