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

Abstract

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.

Keywords:

• Biocatalysts
• fungi
• gas chromatography
• lapachol
• mass spectrometry

Acknowledgments

We are also grateful to Izabel Cristina Casanova Turatti and Prof. Dr. Norberto Peporine Lopes (FCFRP-USP) for their help with GC-MS analysis.

Disclosure statement

The authors declare that they have no conflict of interests.

Additional information

Funding

The authors wish to thank Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) for the financial support (fellowship N° 2014/01497-9 and grant N^o 2012/24703-8).