Bioreduction of Chalcones using
Cereus peruvianus Mill. callus culture
FERRAREZI, A. A.1; SANTOS, R. A. M.1; PORTO, C.1; PILAU, E. J.2;
GONÇALVES, J. E.3; OLIVEIRA, A. J. B.1; GONÇALVES, R. A. C.1
1. Pharmacy Department, State University of Maringá, Maringá-PR, Brazil
2. Chemistry Department, Sate University of Maringá, Maringá-PR, Brazil.
3. UniCesumar- Centro Universitário Cesumar, Maringá-PR, Brazil
*[email protected]
Keywords: Plant cell culture, chalcones, biocatalysis
INTRODUCTION
Nowadays enzymatic reactions have attracted the
chemists’ attention due to its low impacts over the
environment,
low-cost
processes
and
the
enantiomeric purity of the products1. Callus tissue
culture represents an efficient way to replicate plant
cells, especially those with biocatalytic potential.
Cereus peruvianus is a columnar cactus known in
Brazil as “Mandacaru” and provides many
compounds of industrial and pharmacological
interest, furthermore, its callus tissue culture have
great potential as biocatalysts2. Chalcones are α, βunsaturated compounds and exhibits a wide
spectrum of pharmacological properties3. In this
context, the aim of this work was to evaluate the
biotransformantion of chalcones by C. peruvianus
callus tissue through two different approaches: intact
cells and ruptured cells.
RESULTS AND DISCUSSION
The enzymatic reactions were performed using
Chalcone (1) as substrate. During the experiments,
the plant cells were used as intact and cells ruptured
by sonication. Solvent extractions of these cells and
their respective supernatants showed the partial
conversion of compound 1 to 2 (Scheme 1), both in
the cells and supernatant. The conversion mediated
by intact cells was expected according previous
report from our research group4. In addition, analysis
by GC-MS revealed that this conversion occurs
either in cells as well as in the supernatant. In this
point, 2 probably acts as an intermediate for further
reduction, giving compound 3 (Table 1).
Table 1. Conversion of Chalcone.
Source
2 (%)
Intact cells (a)
9.7
Sonicated Cells (b)
11.9
Supernatant from (a)
43.0
Supernatant from (b)
38.6
n.d.= not detected
3 (%)
n.d.
n.d.
18.7
29.3
Thus, there is the combination of one enoate
reductase (ENR) selective for 1, followed by the
action of an alcohol dehydrogenase (ADH), for the
sequential reduction of the carbonyl group of
compound 2. Such behavior was not observed in
intact and ruptured cells, suggesting that the ADH
was released to the aqueous media (supernatant).
Scheme 1. Suggested enzymatic pathway.
Further studies must be done to evaluate the
enantiomeric purity of 3 to obtain enantioenriched
building blocks.
CONCLUSIONS
The exposed results showed that callus culture of C.
peruvianus expresses a combination of two
enzymes:
enoate
reductase
and
alcohol
dehydrogenase, which open new perspectives for
future studies about these enzymes.
ACKNOWLEDGEMENTS
The authors thanks to CNPQ, CAPES, Fundação
Araucária and PPG-UEM.
REFERENCES
1. Gonçalves, C.C.S.; Marsaioli, A.J. Fatos e Tendências da
Biocatálise. Quim. Nova, 2013, 36 (10), 1587-1590.
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de células de Cereus peruvianus. Biochem. and Biotec. Reports,
2013, 2, 118-121.
3. Janeczko, T.; Gładkowski, W.; Kostrzewa-Susłow, E. Microbial
transformations of chalcones to produce food sweetener
derivatives.J. Mol. Catal. B: Enzym, 2013, 98, 55-61.
4. Gonçalves, R. A. C et al.. In: Marsaioli, A. J.; Porto, A. L.; Ed.
Schoba Ltda; Salto-SP; 2010, vol 1, pp 101-157.
VII Workshop on Biocatalysis and Biotransformations and 1o Simposio Latinoamericano de Biocatalisis y Biotransformaciones