Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

The plant phenolic natural products (PNPs) protocatechuic aldehyde, syringaldehyde and vanillin were used as platforms for obtaining four urease inhibitors. Urea (urease substrate) or thiourea (urease inhibitor) core was added to the structure of newly synthesized compounds to provide inhibitors up to 230-fold more active than the PNPs they originated from. The PNP derivatives are mixed inhibitors with higher affinity to urease active site. Two compounds were as efficient as N-(butyl)thiophosphoric triamide (NBPT) toward soil. Overall, PNPs derivatives are promising urease inhibitors for use as additive in urea-based fertilizers formulations.

Keywords:
urea; urease inhibitor; natural product; phenolic aldehyde; fertilizer additive

Authorship

Lívia P. Horta

Grupo de Estudos em Bioquímica de Plantas, GEBioPlan, Departamento de Botânica, ICB, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, BrazilUniversidade Federal de Minas GeraisBrazilBelo Horizonte, MG, BrazilGrupo de Estudos em Bioquímica de Plantas, GEBioPlan, Departamento de Botânica, ICB, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, Brazil

Yane C. C. Mota

Gisele Maria Barbosa

Taniris C. Braga

Grupo de Estudos em Química Orgânica e Biológica, GEQOB, Departamento de Química, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, BrazilUniversidade Federal de Minas GeraisBrazilBelo Horizonte, MG, BrazilGrupo de Estudos em Química Orgânica e Biológica, GEQOB, Departamento de Química, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, Brazil

Ivanildo E. Marriel

Empresa Brasileira de Pesquisa Agropecuária, Centro Nacional de Pesquisas de Milho e Sorgo, EMBRAPA/CNPMS, Sete Lagoas-MG, BrazilEmpresa Brasileira de Pesquisa AgropecuáriaBrazilSete Lagoas, MG, BrazilEmpresa Brasileira de Pesquisa Agropecuária, Centro Nacional de Pesquisas de Milho e Sorgo, EMBRAPA/CNPMS, Sete Lagoas-MG, Brazil

Ângelo de Fátima ^**e-mail: adefatima@qui.ufmg.br, lvmodolo@icb.ufmg.br

Luzia V. Modolo ^**e-mail: adefatima@qui.ufmg.br, lvmodolo@icb.ufmg.br

*e-mail: adefatima@qui.ufmg.br, lvmodolo@icb.ufmg.br

SCIMAGO INSTITUTIONS RANKINGS

Figures | Tables

Figures (4)
Tables (1)

Thumbnail

Figure 1
Design of the urease inhibitors of agricultural interest 2A7, 2A9, 2B10 and 2D2 based on protocatechuic aldehyde (PA), vanilin (VN) or syringaldehyde (SA) structures combined with (thio)urea cores.

Thumbnail

Figure 2
Inhibition of jack bean urease by phenolic aldehydes and its derivatives. The compounds hydroxyurea (HU), protocatechuic aldehyde (PA), syringaldehyde (SA), vanillin (VA), 2A7 and 2B10 (PA derivatives), 2A9 (SA derivative) and 2D2 (VN derivative) were employed at 1.6 mM in reactions containing 10 mmol L^-1 urea and 12.5 mU urease. Results are representative of three independent experiments, each with four replicates. Different letters indicate significant difference (p < 0.05 by contrast analysis) among the compounds.

Thumbnail

Figure 3
Representative Michaelis-Menten hyperbola and Lineweaver-Burk plots for jack bean urease in the presence of phenolic aldehyde derivatives. The compounds 2A7 and 2B10 (PA derivatives), 2A9 (SA derivative) and 2D2 (VN derivative) were employed at different concentrations (0.3 to 1.6 mM) in reactions containing urea ranging from 1 to 32 mmol L^-1 and 12.5 mU urease. A V_oversus urea concentration plot obtained from data of assays with 2A7 is shown to exemplify the Michaelian behavior of urea catalysis.

Thumbnail

Figure 4
Effect of phenolic aldehyde derivatives and NBPT on the activity of soil ureases. The compounds N-(butyl) thiophosphorictriamide (NBPT), 2A7 and 2B10 (PA derivatives), 2A9 (SA derivative) and 2D2 (VN derivative) were applied to soil at 3.2 mM in the presence of 72 mmol L^-1 urea. Results are representative of independent experiments, each with at least five replicates. Distinct letters indicate significant difference (p < 0.05 by contrast analysis) among the compounds.

Thumbnail

Table 1
Inhibition constants for phenolic aldehyde derivatives towards jack bean type III urease

Figure 1 Design of the urease inhibitors of agricultural interest 2A7, 2A9, 2B10 and 2D2 based on protocatechuic aldehyde (PA), vanilin (VN) or syringaldehyde (SA) structures combined with (thio)urea cores.

Figure 2 Inhibition of jack bean urease by phenolic aldehydes and its derivatives. The compounds hydroxyurea (HU), protocatechuic aldehyde (PA), syringaldehyde (SA), vanillin (VA), 2A7 and 2B10 (PA derivatives), 2A9 (SA derivative) and 2D2 (VN derivative) were employed at 1.6 mM in reactions containing 10 mmol L^-1 urea and 12.5 mU urease. Results are representative of three independent experiments, each with four replicates. Different letters indicate significant difference (p < 0.05 by contrast analysis) among the compounds.

Figure 3 Representative Michaelis-Menten hyperbola and Lineweaver-Burk plots for jack bean urease in the presence of phenolic aldehyde derivatives. The compounds 2A7 and 2B10 (PA derivatives), 2A9 (SA derivative) and 2D2 (VN derivative) were employed at different concentrations (0.3 to 1.6 mM) in reactions containing urea ranging from 1 to 32 mmol L^-1 and 12.5 mU urease. A V_oversus urea concentration plot obtained from data of assays with 2A7 is shown to exemplify the Michaelian behavior of urea catalysis.

Figure 4 Effect of phenolic aldehyde derivatives and NBPT on the activity of soil ureases. The compounds N-(butyl) thiophosphorictriamide (NBPT), 2A7 and 2B10 (PA derivatives), 2A9 (SA derivative) and 2D2 (VN derivative) were applied to soil at 3.2 mM in the presence of 72 mmol L^-1 urea. Results are representative of independent experiments, each with at least five replicates. Distinct letters indicate significant difference (p < 0.05 by contrast analysis) among the compounds.

Table 1 Inhibition constants for phenolic aldehyde derivatives towards jack bean type III urease

Inhibitor	K_i / mM	K'_i / mM
2A7	0.23 ± 0.01	1.19 ± 0.07
2A9	3.83 ± 0.84	9.29 ± 3.78
2B10	0.69 ± 0.02	10.71 ± 6.77
2D2	1.26 ± 0.06	11.22 ± 4.57

K_i: equilibrium dissociation constant for urease-phenolic aldehyde derivative complex; K'_i: equilibrium dissociation constant for urease-urea-phenolic aldehyde derivative complex; values are the mean ± standard deviation of triplicate determinations from a representative experiment.

How to cite

copy

Sociedade Brasileira de Química Instituto de Química - UNICAMP, Caixa Postal 6154, 13083-970 Campinas SP - Brazil, Tel./FAX.: +55 19 3521-3151 - São Paulo - SP - Brazil
E-mail: office@jbcs.sbq.org.br

Acompanhe os números deste periódico no seu leitor de RSS

Versão para download de PDF

PDF

Inglês

Versões e tradução automática

Versão original do texto

English

Tradução automática

Google Translator
Microsoft Translator

Como citar

RIS

BIBTEX

Outros formatos de citação e exportação:

SciELO - Scientific Electronic Library Online
Rua Dr. Diogo de Faria, 1087 – 9º andar – Vila Clementino 04037-003 São Paulo/SP - Brasil
E-mail: scielo@scielo.org

Leia a Declaração de Acesso Aberto

Métricas

Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

PlumX

Mensagem

[1] *e-mail: adefatima@qui.ufmg.br, lvmodolo@icb.ufmg.br