biomolecules
Article
Revisiting Jatropha curcas Monomeric Esterase: A Dienelactone
Hydrolase Compatible with the Electrostatic Catapult Model
Marcos Gustavo Araujo Schwarz
1,
* , Deborah Antunes
1
, Gabriela Coelho Brêda
2
, Richard Hemmi Valente
3
and Denise Maria Guimarães Freire
4
Citation: Schwarz, M.G.A.; Antunes,
D.; Brêda, G.C.; Valente, R.H.; Freire,
D.M.G. Revisiting Jatropha curcas
Monomeric Esterase: A Dienelactone
Hydrolase Compatible with the
Electrostatic Catapult Model.
Biomolecules 2021, 11, 1486. https://
doi.org/10.3390/biom11101486
Academic Editor: Umesh R. Desai
Received: 27 July 2021
Accepted: 11 August 2021
Published: 9 October 2021
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1
Laboratório de Genômica Funcional e Bioinformática, Instituto Oswaldo Cruz, Fiocruz,
Rio de Janeiro 21040900, Brazil; deborah.santos@fiocruz.br
2
Laboratório de Microbiologia Molecular e Proteínas, Departamento de Bioquímica, Instituto de Química,
Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941909, Brazil; breda.gabriela@gmail.com
3
Laboratório de Toxinologia, Instituto Oswaldo Cruz, Fiocruz, Rio de Janeiro 21040900, Brazil;
richardhemmi@gmail.com
4
Laboratório de Biotecnologia Microbiana, Departamento de Bioquímica, Instituto de Química, Universidade
Federal do Rio de Janeiro, Rio de Janeiro 21941909, Brazil; freire@iq.ufrj.br
* Correspondence: schwarz@ioc.fiocruz.br; Tel.: +55-21-38658201
Abstract: Jatropha curcas contains seeds with a high oil content, suitable for biodiesel production.
After oil extraction, the remaining mass can be a rich source of enzymes. However, data from the
literature describing physicochemical characteristics for a monomeric esterase from the J. curcas seed
did not fit the electrostatic catapult model for esterases/lipases. We decided to reevaluate this J. curcas
esterase and extend its characterization to check this apparent discrepancy and gain insights into the
enzyme’s potential as a biocatalyst. After anion exchange chromatography and two-dimensional
gel electrophoresis, we identified the enzyme as belonging to the dienelactone hydrolase family,
characterized by a cysteine as the nucleophile in the catalytic triad. The enzyme displayed a basic
optimum hydrolysis pH of 9.0 and an acidic pI range, in contrast to literature data, making it well in
line with the electrostatic catapult model. Furthermore, the enzyme showed low hydrolysis activity
in an organic solvent-containing medium (isopropanol, acetonitrile, and ethanol), which reverted
when recovering in an aqueous reaction mixture. This enzyme can be a valuable tool for hydrolysis
reactions of short-chain esters, useful for pharmaceutical intermediates synthesis, due to both its
high hydrolytic rate in basic pH and its stability in an organic solvent.
Keywords: Jatropha curcas L.; seed; esterase; dienelactone hydrolase
1. Introduction
Jatropha curcas (physic nut)—a plant belonging to the Euphorbiaceae family—has
received attention from the scientific community due to its potential in the biodiesel
production field [1]. Biofuel generation can be achieved through different methods such as
the alkaline transesterification of the seed oil triglycerides with short-chain alcohol (usually
methanol or ethanol) [2]. Such technology is quite advantageous due to the good quality
of the produced biodiesel. Furthermore, J. curcas can be cultivated on nutrient-poor soils,
thus not competing with other crops of agricultural importance [3].
Along with the biodiesel purpose, interest has arisen concerning the remaining mate-
rial after the oil extraction, known as the press cake, mainly to use it as animal food due to
its high protein content [4]. One drawback of such an approach is the presence of different
toxic substances in this material, with phorbol esters being the most harmful for animals [5].
That is why non-toxic J. curcas strains are used for animal feeding purposes. However, this
material can also be a source of several enzymes with interesting features. Such is the case
for the previously described J. curcas lipase, isolated from the press cake and used in a
hybrid (enzymatic/chemical) hydroesterification process for biodiesel production [6].
Biomolecules 2021, 11, 1486. https://doi.org/10.3390/biom11101486 https://www.mdpi.com/journal/biomolecules