Biotransformations of nitro-aromatic compounds to amines and acetamides by tuberous roots of Arracacia xanthorrhiza and Beta vulgaris and associated microorganism (Candida guilliermondii)

Pacheco, Adriana de O.; Kagohara, Edna; Andrade, Leandro H.; Comasseto, J. V.; Crusius, Iracema H. S.; Paula, Claudete Rodrigues; Porto, André Luiz Meleiro

doi:10.1016/j.enzmictec.2007.08.001

Cited by 20 publications

(11 citation statements)

References 23 publications

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“…Type I (oxygen-insensitive) nitroreductases catalyze the sequential transfer of two electrons from NAD(P)H to the nitro groups of nitrosubstituted compounds, in the presence or absence of oxygen, resulting in nitroso and hydroxylamine intermediates and finally primary amines [ 18 , 19 , 20 ]. Many nitroreductases have been reported to possess broad substrate specificity catalyzing the reduction of organic nitroaromatic and nitroheterocyclic compounds [ 17 , 21 , 22 , 23 , 24 ].…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity

Álvarez-Fitz¹,

Álvarez

Marquina

et al. 2012

Molecules

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Biotransformation processes have been successfully utilized to obtain products of pharmaceutical, chemical, food, and agricultural interest, which are difficult to obtain by classic chemical methods. The compound with antituberculous activity, 9-methoxy-tariacuripyrone (1), isolated from Aristolochia brevipes, was submitted to biotransformation with the yeast Saccharomyces cerevisiae under culture, yielding 5-amino-9-methoxy-3,4-dihydro-2H-benzo[h]chromen-2-one (2). The structure of 2 was elucidated on the basis of spectroscopic analyses. The results mainly show the reduction of the double bond and the nitro group of compound 1. Metabolite 2 demonstrated an increase in anti-tuberculous activity (MIC = 3.12 µg/mL) against the drug-sensitive Mycobacterium tuberculosis (H37Rv) strain, with respect to that shown by 1.

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Section: Resultsmentioning

confidence: 99%

Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity

Álvarez-Fitz¹,

Álvarez

Marquina

et al. 2012

Molecules

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“…It was described that the bioreduction of the nitroaromatic substrate, by other organisms [25], is dependent of the electronic characteristic of the rest of the aromaticsubstituents. Herein, it is in general true.…”

Section: Resultsmentioning

confidence: 99%

Anaerobic Biotransformation of Nitro-Compounds to Amines by Bovine Rumen Fluid

Rodríguez¹,

Irazoqui²,

Álvarez³

et al. 2011

GSC

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Microorganims of the bovine rumen fluid biocatalyzed the reduction of nitro-compound substrates to yield the respective amines. This enzymatic process, using ruminal contents, has rarely been reported in associa- tion with the bioreduction of nitro groups. The biotransformation reactions catalyzed by this system were de- pendent of both the electronic characteristics and the area/volume of the nitro-substrates confirming the processes are enzymatic. The semi-preparative scale biotransformation went by in good yield showing the rumen fluid may be employed in the synthesis of amines under very mild conditions and, moreover, it may have application in the bioremediation of nitro-compounds

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“…Finally, the reaction of substrate 3, with the Linum usitatissimum L. seeds, gave rise to 3-amino-acetophenone (3a) and (S)-1-(3-aminophenyl)ethanol (3b) as products, with values of conversion of 21.6% e 40.5%, respectively. The presence of a carbonyl group, above all when it is in para or ortho position, that decreases the electron deficiency in nitroaromatic ring, appears favor the reduction of the nitro group 19 . In addition, we observed low enantioselectivity (8.7%) of the product alcohol (3b) with the S configuration, which is in agreement with Prelog rule 24,26 .…”

Section: Resultsmentioning

confidence: 99%

“…Studies report biotransformation of nitroaromatic compounds using Arracacia xanthorrhiza and Beta vulgaris associated with a microorganism Candida guilliermondii, coconut water which were converted into amines and to the corresponding acetamides. Some plants, as Lens culinaris seeds, are also reported as a biocatalyst for reducing nitro groups [19][20][21] .…”

mentioning

confidence: 99%

Linseed (Linum usitatissimum L.) as a Biocatalyst for Reduction of Nitroaromatic Compounds

Tavares¹,

Lemos²,

Arriaga³

et al. 2014

Orient. J. Chem.

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Biotransformations of nitro-aromatic compounds to amines and acetamides by tuberous roots of Arracacia xanthorrhiza and Beta vulgaris and associated microorganism (Candida guilliermondii)

Cited by 20 publications

References 23 publications

Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity

Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity

Anaerobic Biotransformation of Nitro-Compounds to Amines by Bovine Rumen Fluid

Linseed (Linum usitatissimum L.) as a Biocatalyst for Reduction of Nitroaromatic Compounds

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