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Marine Biotechnology

, Volume 21, Issue 3, pp 430–439 | Cite as

Hydrogenation of Halogenated 2′-Hydroxychalcones by Mycelia of Marine-Derived Fungus Penicillium raistrickii

  • Iara Lisboa de Matos
  • Marcia Nitschke
  • André Luiz Meleiro PortoEmail author
Original Article

Abstract

This study describes the chemoselective hydrogenation reaction of halogenated 2′-hydroxychalcones by the marine-derived fungus Penicillium raistrickii CBMAI 931. Initially, 2′-hydroxychalcone was utilized as a model for the selection of the appropriate conditions to perform the biotransformation reactions. The best results were obtained using mycelia and filtered culture broth, and this condition was chosen for the biotransformation reaction of 2′-hydroxychalcones substituted with methoxy and halogen groups. Experiments performed with 2′-hydroxychalcones dissolved in 600 μL-DMSO were more effective than those performed using 300 μL-DMSO, once solubility of the compounds influenced conversion rate in the liquid medium. The halogenated 2′-hydroxy-dihydrochalcones were obtained in good conversions (78–99%) and moderate isolated yields (31–65%). All biotransformation reactions using the marine-derived fungus P. raistrickii CBMAI 931 showed regioselective and chemoselective control for the formation of 2′-hydroxy-dihydrochalcones.

Keywords

Biotransformation Marine-derived fungus Chemoselectivity Biohydrogenation 2′-hydroxychalcones Penicillium raistrickii 

Notes

Acknowledgements

The authors would also like to acknowledge Prof. R.G.S. Berlinck (Instituto de Química de São Carlos – USP) for providing the marine fungal strains.

Funding Information

The authors would like to acknowledge the Fundação de Amparo a Pesquisa do Estado de São Paulo (FAPESP process no. 2013/21642-0) for the financial support provided to this research. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001. Iara Lisboa de Matos is indebt to CAPES for the provision of the scholarship (CAPES process no 1313652).

Compliance with Ethical Standards

Conflict of Interest

The authors declare that they have no conflict of interest.

Supplementary material

10126_2019_9893_MOESM1_ESM.doc (7.6 mb)
ESM 1 (DOC 7800 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Iara Lisboa de Matos
    • 1
  • Marcia Nitschke
    • 2
  • André Luiz Meleiro Porto
    • 1
    Email author
  1. 1.Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São CarlosUniversidade de São PauloSão CarlosBrazil
  2. 2.Laboratório de Biotecnologia Microbiana, Instituto de Química de São CarlosUniversidade de São PauloSão CarlosBrazil

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