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...

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Published inJournal of the Brazilian Chemical Society Vol. 27; no. 8; pp. 1512 - 1519
Main Authors Horta, Lívia, Mota, Yane, Barbosa, Gisele, Braga, Taniri, Marriel, Ivanildo, de Fátima, Ângelo, Modolo, Luzia
Format Journal Article
LanguageEnglish
Published Sociedade Brasileira de Química 01.08.2016
Subjects
CHEMISTRY, MULTIDISCIPLINARY
phenolic aldehyde
urease inhibitor
natural product
urea
fertilizer additive
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Abstract 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.
AbstractList 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.
Author Horta, Lívia
de Fátima, Ângelo
Barbosa, Gisele
Marriel, Ivanildo
Modolo, Luzia
Mota, Yane
Braga, Taniri
AuthorAffiliation Universidade Federal de Minas Gerais
Empresa Brasileira de Pesquisa Agropecuária
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Issue 8
Keywords phenolic aldehyde
urease inhibitor
natural product
urea
fertilizer additive
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References Voet, D.; Voet, J. 2011
Artola, E.; Cruchaga, S.; Ariz, I.; Moran, J. F.; Garnica, M.; Houdusse, F.; Mina, J. M. G.; Irigoyen, I.; Lasa, B.; Aparicio-Tejo, P. M. 2011; 63
Byrnes, B. H.; Freney, J. R. 1995; 42
Oliveira, F. M.; Barbosa, L. C. A.; Demuner, A. J.; Maltha, C. R. A.; Pereira, S. R.; Horta, L. P.; Modolo, L. V. 2014; 23
Bayless, A. V.; Miliner, O. E. 1980
Kandeler, E.; Gerber, H. 1988; 6
Ngan, L. T. M.; Moon, J. K.; Shibamoto, T.; Ahn, Y. J. 2012; 60
Ge, H. M.; Huang, B.; Tan, S. H.; Shi, D. H.; Song, Y. C.; Tan, R. X. 2006; 69
Wu, D.; Yu, X.; Xie, J.; Su, Z.; Su, J.; Tan, L.; Huang, X. Q.; Chen, J. N.; Su, Z. R. 2013; 91
Araujo, D. P.; Morais, V. S. S.; de Fatima, . A.; Modolo, L. V. 2015; 5
Tan, L.; Su, J.; Wu, D.; Yu, X.; Su, Z.; He, J.; Wu, X.; Kong, S.; Lai, X.; Lin, Ji.; Su, Z. 2013; 2013
Krajewska, B.; Ciurli, S. 2005; 43
Cameron, K. C.; Di, H. J.; Moir, J. L. 2013; 162
Easterby, J. S. 2003
Roscoe, R.; Vasconcellos, C. A.; Furtini, A. E.; Guedes, G. A. A.; Fernandes, L. A. 2000; 32
da Silva, D. L.; Fernandes, S. A.; Sabino, A. A.; de Fátima, A. 2011; 52
Krajewska, B. 2009; 59
Shin, J. E.; Kim, J. M.; Bae, E. A.; Hyun, Y. J.; Kim, D. H. 2005; 71
Canfield, D. E.; Glazer, A. N.; Falkowski, P. G. 2010; 330
Brito, T. O.; Souza, A. X.; Mota, Y. C. C.; Morais, V. S. S.; Souza, L. T.; de Fatima, A.; Macedo, ., F. C.; Modolo, L. V. 2015; 5
Antisari, L. V.; Marzadori, C.; Gioacchine, P.; Ricci, S.; Gessa, C. 1996; 22
Galloway, J. N. 1998; 102
Domínguez, M. J.; Sanmartín, C.; Font, M.; Palop, J. A.; San, S.; Urrutia, O.; Houdusse, F.; García-Mina, J. M. 2008; 56
Cesareo, S. D.; Langton, S. R. 1992; 99
Hendrickson, L. L.; Douglass, E. A. 1993; 25
Espindula, M. C.; Rocha, V. S.; Souza, M. A.; Campanharo, M.; Paula, G. S. 2013; 73
Watson, C. J.; Miller, H.; Poland, P.; Kilpatrick, D. J.; Allen, M. D. B.; Garret, M. K.; Christianson, C. B. 1994; 26
Fetzner, S.; Doelle, H. W.; Rokem, S.; Berovic, M. 2002; X
Junejo, N.; Khanif, M. Y.; Hanfi, M. M.; Yunus, W. M. Z. W.; Dharejo, K. A. 2011; 10
Rashid, U.; Batool, I.; Wadood, A.; Khan, A.; ul-Haq, Z.; Chaudhary, M. I.; Ansari, F. 2013; 43
Gill, J. S.; Bijay-Singh,; Khind, C. S.; Yadvinder-Singh 1999; 53
Carmona, G.; Christianson, C. B.; Byrnes, B. H. 1990; 22
Modolo, L. V.; Souza, A. X.; Horta, L. P.; Araujo, D. P.; de Fatima, A. 2015; 6
Creason, G. L.; Schmitt, M. R.; Douglass, E. A.; Hendrickson, L. L. 1990; 22
Dixon, N. E.; Gazzola, C.; Watters, J. J.; Blakeley, R. L.; Zerner, B. 1975; 97
Cantarella, H.; Trivelin, P. C. O.; Contin, T. L. M.; Dias, F. L. F.; Rossetto, R.; Marcelino, R.; Coimbra, R. B.; Quaggio, J. A. 2008; 65
2013
Rawluk, C. D. L.; Grant, C. A.; Racz, G. J. 2001; 81
Weatherburn, M. W. 1967; 39
Perveen, S.; El-Shafae, A. M.; Al-Taweel, A.; Fawzy, G. A.; Malik, A.; Afza, N.; Latifc, M.; Iqbalc, L. 2011; 13
da Silva, D. L.; Reis, F. S.; Muniz, D. R.; Ruiz, A. L. T. G.; Carvalho, J. E.; Sabino, A. A.; Modolo, L. V.; de Fátima, A. 2012; 20
Grisi, B.; Grace, C.; Brookes, P. C.; Benedetti, A.; dell'Abate, M. T. 1998; 30
Segel, I. H. 1975
References_xml – volume: 42
  start-page: 251
  year: 1995
  publication-title: Fert. Res.
– volume: 39
  start-page: 971
  year: 1967
  end-page: 971
  publication-title: Anal. Chem.
– volume: 30
  start-page: 1309
  year: 1998
  end-page: 1309
  publication-title: Soil Biol. Biochem.
– volume: 65
  start-page: 397
  year: 2008
  end-page: 397
  publication-title: Sci. Agric.
– volume: 53
  start-page: 203
  year: 1999
  end-page: 203
  publication-title: Nutr. Cycling Agroecosyst.
– volume: 71
  start-page: 197
  year: 2005
  end-page: 197
  publication-title: Planta Med.
– volume: 330
  start-page: 192
  year: 2010
  end-page: 192
  publication-title: Science
– year: 1975
  publication-title: Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems
– volume: 26
  start-page: 1165
  year: 1994
  end-page: 1165
  publication-title: Soil Biol. Biochem.
– volume: 10
  start-page: 3504
  year: 2011
  end-page: 3504
  publication-title: Afr. J. Biotechnol.
– volume: 81
  start-page: 239
  year: 2001
  publication-title: Can. J. Soil Sci.
– volume: 25
  start-page: 1613
  year: 1993
  end-page: 1613
  publication-title: Soil Biol. Biochem.
– volume: 22
  start-page: 196
  year: 1996
  end-page: 196
  publication-title: Biol. Fertil. Soils
– volume: X
  year: 2002
  publication-title: Biotechnology, Environmental Biotechnology-Socio-Economic Strategies for Sustainability, Encyclopedia of Life Support Systems (EOLSS)
– volume: 69
  start-page: 1800
  year: 2006
  end-page: 1800
  publication-title: J. Nat. Prod.
– volume: 5
  start-page: 28814
  year: 2015
  end-page: 28814
  publication-title: RSC Adv.
– year: 2003
  publication-title: Hyper32; Version of Hyper for 32 Bit Operating Systems: Hyperbolic Regression Analysis of Enzyme Kinetic Data
– volume: 43
  start-page: 651
  year: 2005
  end-page: 651
  publication-title: Plant Physiol. Biochem.
– volume: 97
  start-page: 4131
  year: 1975
  end-page: 4131
  publication-title: J. Am. Chem. Soc.
– volume: 59
  year: 2009
  end-page: 9
  publication-title: J. Mol. Catal. B: Enzym.
– volume: 2013
  start-page: 1
  year: 2013
  end-page: 1
  publication-title: Sci. World J
– volume: 20
  start-page: 2645
  year: 2012
  end-page: 2645
  publication-title: Bioorg. Med. Chem.
– volume: 56
  start-page: 3721
  year: 2008
  end-page: 3721
  publication-title: J. Agric. Food Chem.
– volume: 5
  start-page: 44507
  year: 2015
  end-page: 44507
  publication-title: RSC Adv.
– volume: 99
  start-page: 15
  year: 1992
  end-page: 15
  publication-title: FEMS Microbiol. Lett.
– year: 1980
  publication-title: US pat. 4,242,325
– volume: 22
  start-page: 209
  year: 1990
  end-page: 209
  publication-title: Soil Biol. Biochem.
– volume: 22
  start-page: 933
  year: 1990
  end-page: 933
  publication-title: Soil Biol. Biochem.
– volume: 13
  start-page: 799
  year: 2011
  end-page: 799
  publication-title: J. Asian Nat. Prod. Res.
– volume: 23
  start-page: 5174
  year: 2014
  end-page: 5174
  publication-title: Med. Chem. Res.
– volume: 43
  start-page: 47
  year: 2013
  end-page: 47
  publication-title: J. Mol. Graphics Modell.
– volume: 32
  start-page: 52
  year: 2000
  end-page: 52
  publication-title: Biol. Fertil. Soils
– volume: 91
  start-page: 60
  year: 2013
  end-page: 60
  publication-title: Fitoterapia
– volume: 63
  start-page: 73
  year: 2011
  end-page: 73
  publication-title: Plant Growth Regul.
– volume: 60
  start-page: 9062
  year: 2012
  end-page: 9062
  publication-title: J. Agric. Food Chem.
– volume: 52
  start-page: 6328
  year: 2011
  end-page: 6328
  publication-title: Tetrahedron Lett.
– year: 2013
  publication-title: World Population Prospects: The 2012 Revision, Key Findings and Advance Tables
– volume: 162
  start-page: 145
  year: 2013
  end-page: 145
  publication-title: Ann. Appl. Biol.
– volume: 6
  start-page: 68
  year: 1988
  end-page: 68
  publication-title: Biol. Fertil. Soils
– year: 2011
  publication-title: Biochemistry
– volume: 102
  start-page: 15
  year: 1998
  end-page: 15
  publication-title: Environ. Pollut.
– volume: 6
  start-page: 35
  year: 2015
  end-page: 35
  publication-title: J. Adv. Res.
– volume: 73
  start-page: 160
  year: 2013
  end-page: 160
  publication-title: Chil. J. Agr. Res.
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Title Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes
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