Skip to main content
SpringerLink
Log in

Lens culinaris: A new biocatalyst for reducing carbonyl and nitro groups

  • Research Paper
  • Published:
Biotechnology and Bioprocess Engineering Aims and scope Submit manuscript

Abstract

A series of aliphatic and aromatic aldehydes and ketones, as well as some nitrocompounds were reduced using whole plant cells from Lens culinaris seeds. In addition, we also investigated the possibility of enzymatic ester hydrolysis to explore the potential of these seeds. The reduced ketones products were obtained in yields of 8 ∼ 82% and enantiomeric excess of 39 ∼ 75%. Aldehydes were more reactive than ketones with high chemical yield (95→99%), whereas the aromatic nitrocompounds showed low (2%) to high (> 99%) conversion depending upon the nature and position of the aromatic ring substituents. Ester hydrolysis by the Lens culinaris was quite effective with the ester p-nitrophenyl acetate (> 99% conversion).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Moran, P. J. S., R. De Conti, and J. A. R. Rodrigues (2001) Biocatálise: Avanços recentes. Quím. Nova. 24: 672–675.

    Article  Google Scholar 

  2. Veit, T. (2004) Biocatalysis for the production of cosmetic ingredients. Eng. Life Sci. 4: 508–511.

    Article  CAS  Google Scholar 

  3. Shaw, N. M., K. T. Robins, and A. Kiene (2003) Lonza: 20 years of biotransformations. Adv. Synth. Catal. 345: 425–435.

    Article  CAS  Google Scholar 

  4. Reinhard, E. and A. W. Alfermann (1980) Biotransformation by plant cell culture. Adv. Biochem. Eng. 16: 49–83.

    CAS  Google Scholar 

  5. Machado, L. L., J. S. N. Souza, M. C. Matos, S. Sakata, G. A. Cordell, and T. L. G. Lemos (2006) Bioreduction of aldehydes and ketones using Manihot species. Phytochem. 67: 1637–1643.

    Article  CAS  Google Scholar 

  6. Assunção, J. C. C., L. L. Machado, T. L. G. Lemos, G. A. Cordell, and F. J. Q. Monte (2008) Sugar cane juice for the bioreduction of carbonyl compouds. J. Mol. Catal. B: Enzym. 52–53: 194–198.

    Article  Google Scholar 

  7. Machado, L. L., F. J. Q. Monte, M. C. F. Oliveira, M. C. Mattos, T. L. G. Lemos, V. Gotor-Fernández, G. Gonzalo, and V. Gotor (2008) Bioreduction of aromatic aldehydes and ketones by fruits’ barks of Passiflora edulis. J. Mol. Catal. B: Enzym. 54: 103–106.

    Article  Google Scholar 

  8. Fonseca, A. M., F. J. Q. Monte, M. C. F. Oliveira, M. C. Mattos, G. A. Cordell, R. Braz-Filho, and T. L. G. Lemos (2009) Coconut water (Cocos nucifera L.) — A new biocatalyst system for organic synthesis. J. Mol. Catal. B: Enzym. 57: 78–82.

    Article  CAS  Google Scholar 

  9. Bizerra, A. M. C., G. Gonzalo, I. Lavandera, V. Gotor-Fernández, M. C. Mattos, M. C. F. Oliveira, T. L. G. Lemos, and V. Gotor (2010) Reduction process biocatalyzed by Vigna unguiculata. Tetrahed. Asymm. 21: 566–570.

    Article  CAS  Google Scholar 

  10. Breuer, M., K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. Sturmer, and T. Zelinski (2004) Industrial methods for the production of optically active intermediates. Angew. Chem. Int. Ed. 43: 788–824.

    Article  CAS  Google Scholar 

  11. Peng, F. Z. and Z. H. Shao (2008) Advances in asymmetric organocatalytic reactions catalyzed by chiral primary amines. J. Mol. Catal. A: Chem. 285: 1–13.

    Article  CAS  Google Scholar 

  12. Melchiorre, P., M. Marigo, A. Carlone, and G. Bartoli (2008) Asymmetric aminocatalysis-gold rush in organic chemistry. Angew. Chem. Int. Ed. 47: 6138–6171.

    Article  CAS  Google Scholar 

  13. Noronha, R. G., C. C. Romão, and A. C. Fernandes (2009) Highly chemo- and regioselective reduction of aromatic nitro compounds using the system Silane/Oxo-rhenium complexes. J. Org. Chem. 74: 6960–6964.

    Article  Google Scholar 

  14. Li, B. and Z. Xu (2009) A nonmetal catalyst for molecular hydrogen activation with comparable catalytic hydrogenation capability to noble metal catalyst. J. Am. Chem. Soc. 131: 16380–16382.

    Article  CAS  Google Scholar 

  15. Spencer, J., R. P. Rathnam, H. Patel, and N. Anjum (2008) Microwave mediated reduction of heterocycle and fluorine containing nitroaromatics with Mo(CO)6 and DBU. Tetrahed. 64: 10195–10200.

    Article  CAS  Google Scholar 

  16. MacLaughlin, M. A. and D. M. Barnes (2006) A practical and selective reduction of nitroarenes using elemental sulfur and mild base. Tetrahed. Lett. 47: 9095–9097.

    Article  Google Scholar 

  17. Iqbal, A., I. A. Khalil, N. Ateeq, and M. S. Khan (2006) Nutritional quality of important food legumes. Food Chem. 97: 331–335.

    Article  CAS  Google Scholar 

  18. Tharanathan, R. N. and S. Mahadevamma (2003) Grain legumes: A boon to human nutrition. Trends Food Sci. Technol. 14: 507–518.

    Article  CAS  Google Scholar 

  19. Padovani, R. M., D. M. Lima, F. A. B. Colugnati, and D. B. Rodriguez- Amaya (2007) Comparison of proximate, mineral and vitamin composition of common Brazilian and US food. J. Food Comp. Anal. 20: 733–738.

    Article  CAS  Google Scholar 

  20. Shons, P. F., P. F. Leite, D. Novello, D. M. Bernardi, P. N. Morato, L. M. Rocha, S. M. P. M. Reis, and C. K. Miyasaka (2009) Eficiência protéica da lentilha (Lens culinaris) no desenvolvimento de ratos wistar. Alim. Nutr. Araraquara. 20: 255–260.

    CAS  Google Scholar 

  21. Marks, D. L., R. Buchnsbaum, and T. Swain (1985) Measurement of total protein in plant samples in the presence of tannins. Anal. Biochem. 147: 136–143.

    Article  CAS  Google Scholar 

  22. Matto, R. L., M. Ishaq, and M. Sallemuddin (1987) Protein assay by coomassie brilliant blue g-250-binding method is unsuitable for plant tissues rich in phenols and phenolases. Anal. Biochem. 163: 376–384.

    Article  Google Scholar 

  23. Zaia, D. A. M., C. T. B. V. Zaia, and J. Lichtig (1998) Determinação de proteínas totais via espectrofometria: Vantagens e desvantagens dos métodos existentes. Quím. Nova. 21: 787–793.

    Article  CAS  Google Scholar 

  24. Nassar, N. M. A. (1986) Genetic variation of wild manihot species Native to brazil and its potential for Cassava improvement. Field Crops Res. 13: 177–184.

    Article  Google Scholar 

  25. Allinger, N. L., M. P. Cava, D. C. Jongh, C. R. Johnson, N. A. Lebel, and C. L. Stevens (1978) Química Orgânica. 2nd ed., p. 961. Livros Técnicos e Ciêntíficos Editora, RJ, Brazil.

    Google Scholar 

  26. Suárez-Franco, G., T. Hernández-Quiroz, A. Navarro-Ocaña, R. M. Oliart-Ros, and G. Valerio-Alfaro (2010) Plants as a green alternative for alcohol preparation from aromatic aldehydes. Biotechnol. Bioproc. Eng. 15: 441–445.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratório de Biotransformações e Produtos Naturais (LBPN), Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Ceará, 60451-970, Brazil

    Daniele Alves Ferreira, Robério Costa da Silva, Marcos Carlos de Mattos, Telma Leda Gomes de Lemos & Francisco José Queiroz Monte

  2. Departamento de Química e Meio Ambiente, Instituto Federal de Educação, Ciência e Tecnologia do Ceará, Ceará, 63900-000, Brazil

    João Carlos da Costa Assunção

Authors
  1. Daniele Alves Ferreira
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Robério Costa da Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. João Carlos da Costa Assunção
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marcos Carlos de Mattos
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Telma Leda Gomes de Lemos
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Francisco José Queiroz Monte
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Francisco José Queiroz Monte.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ferreira, D.A., da Silva, R.C., da Costa Assunção, J.C. et al. Lens culinaris: A new biocatalyst for reducing carbonyl and nitro groups. Biotechnol Bioproc E 17, 407–412 (2012). https://doi.org/10.1007/s12257-011-0509-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12257-011-0509-5

Keywords

Search

Navigation