Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi

The enantioselective biotransformation of propranolol (Prop) by the endophytic fungi Phomopsis sp., Glomerella cingulata, Penicillium crustosum, Chaetomium globosum and Aspergillus fumigatus was investigated by studying the kinetics of the aromatic hydroxylation reaction with the formation of 4-hydr...

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Main Authors: Keyller Bastos Borges, Pierina Sueli Bonato, Mônica Tallarico Pupo
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2011-01-01
Series:Química Nova
Subjects:
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000800011&lng=en&tlng=en
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author Keyller Bastos Borges
Pierina Sueli Bonato
Mônica Tallarico Pupo
author_facet Keyller Bastos Borges
Pierina Sueli Bonato
Mônica Tallarico Pupo
author_sort Keyller Bastos Borges
collection DOAJ
description The enantioselective biotransformation of propranolol (Prop) by the endophytic fungi Phomopsis sp., Glomerella cingulata, Penicillium crustosum, Chaetomium globosum and Aspergillus fumigatus was investigated by studying the kinetics of the aromatic hydroxylation reaction with the formation of 4-hydroxypropranolol (4-OH-Prop). Both Prop enantiomers were consumed by the fungi in the biotransformation process, but the 4-hydroxylation reaction yielded preferentially (-)-(S)-4-OH-Prop. The quantity of metabolites biosynthesized varied slightly among the evaluated endophytic fungi. These results show that all investigated endophytic fungi could be used as biosynthetic tools in biotransformation processes to obtain the enantiomers of 4-OH-Prop.
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spelling doaj.art-62ee79040cd94ed6bd9ca25ace45ddfe2022-12-21T17:57:00ZengSociedade Brasileira de QuímicaQuímica Nova1678-70642011-01-013481354135710.1590/S0100-40422011000800011S0100-40422011000800011Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungiKeyller Bastos Borges0Pierina Sueli Bonato1Mônica Tallarico Pupo2Universidade de São PauloUniversidade de São PauloUniversidade de São PauloThe enantioselective biotransformation of propranolol (Prop) by the endophytic fungi Phomopsis sp., Glomerella cingulata, Penicillium crustosum, Chaetomium globosum and Aspergillus fumigatus was investigated by studying the kinetics of the aromatic hydroxylation reaction with the formation of 4-hydroxypropranolol (4-OH-Prop). Both Prop enantiomers were consumed by the fungi in the biotransformation process, but the 4-hydroxylation reaction yielded preferentially (-)-(S)-4-OH-Prop. The quantity of metabolites biosynthesized varied slightly among the evaluated endophytic fungi. These results show that all investigated endophytic fungi could be used as biosynthetic tools in biotransformation processes to obtain the enantiomers of 4-OH-Prop.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000800011&lng=en&tlng=enenantioselective biotransformationpropranololendophytic fungi
spellingShingle Keyller Bastos Borges
Pierina Sueli Bonato
Mônica Tallarico Pupo
Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi
Química Nova
enantioselective biotransformation
propranolol
endophytic fungi
title Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi
title_full Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi
title_fullStr Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi
title_full_unstemmed Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi
title_short Enantioselective biotransformation of propranolol to the active metabolite 4-hydroxypropranolol by endophytic fungi
title_sort enantioselective biotransformation of propranolol to the active metabolite 4 hydroxypropranolol by endophytic fungi
topic enantioselective biotransformation
propranolol
endophytic fungi
url http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000800011&lng=en&tlng=en
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AT pierinasuelibonato enantioselectivebiotransformationofpropranololtotheactivemetabolite4hydroxypropranololbyendophyticfungi
AT monicatallaricopupo enantioselectivebiotransformationofpropranololtotheactivemetabolite4hydroxypropranololbyendophyticfungi