Microbial production of biovanillin

Brazilian Journal of Microbiology

Volumn 41, Issue 3, 2010, Pages 519-530

  Converti, A ^a   Aliakbarian, B ^a   Dominguez J M ^b   Vázquez, G Bustos ^c   Perego, P ^a  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF VIGO   (Spain)

^c UNIVERSIDAD AUTÓNOMA DE TAMAULIPAS   (Mexico)

Author keywords

Bioconversion; Escherichia coli; Ferulic acid; Review; Vanillin

Indexed keywords

ESCHERICHIA COLI;

EID: 77954265696     PISSN: 15178382     EISSN: 16784405     Source Type: Journal    
DOI: 10.1590/S1517-83822010000300001     Document Type: Review

References (89)

1. Andreoni, V.; Bemasconi, S.; Bestetti, G. (1995). Biotransformation of ferulic acid and related compounds by mutant strains of Pseudomonas fluorescens. Appl. Microbiol. Biotechnol. 42, 830-835.
2. Aono, R. (1998). Improvement of organic solvent tolerance level of Escherichia coli by overexpression of stress-responsive genes. Extremophiles 2, 239-248.
3. Barghini, P.; Di Gioia, D.; Fava, F.; Ruzzi, M. (2007). Vanillin production using metabolically engineered Escherichia coli under non-growing conditions. Microb Cell Fact. 6, 13-23.
4. Barghini, P.; Montebove, F.; Ruzzi, M.; Schiesser, A. (1998). Optimal conditions for bioconversion of ferulic acid into vanillic acid by Pseudomonas fluorescens BF13 cells. Appl. Microbiol. Biotechnol. 49, 309-314.
5. Barraclough, A.J.; Cheetham, P.S.J.; Westcott, R.J. (1994). Production of vanillin. World Pat. 9413614.
6. Bengtson, G., Böddeker, K.W. (1995). Extraction of bioproducts with homogeneous membranes. In: Éitiévant, P.; Schreier, P. (eds.). Biovanillin, INRA Ed., Paris, p. 393-403.
7. Betts, W.B.; Dart, R.K. (1988). Screening of fungi and bacteria for their ability to degrade insoluble, lignin-related aromatic compounds. Microbios 55, 85-93.
8. Blatny, J.M.; Brautaset, T.; Winther-Larsen, H.C.; Haugan, K.; Valla, S. (1997). Construction and use of a versatile set of broad-host-range cloning and expression vectors based on the RK2 replicon. Appl. Environ. Microbiol. 63, 370-379.
9. Böddeker, K.W.; Bengtson, G.; Bode, E. (1990). Pervaporation of low volatility aromatics from water. J. Membrane Sci. 53, 143-158.
10. Böddeker, K.W.; Gatfield, I.L.; Jahnig, J.; Schorm, C. (1997). Pervaporation at the vapor pressure limit: vanillin. J. Membrane Sci. 137, 155-158.
11. Bonnin, E.; Brunel, M.; Gouy, Y.; Lesage-Meessen, L.; Asther, M.; Thibault, J-F. (2001). Aspergillus niger I-1472 and Pycnoporus cinnabarinus MUCL39533, selected for the biotransformation of ferulic acid to vanillin, are also able to produce cell wall polysaccharide-degrading enzymes and feruloyl esterases. Enzyme Microb. Technol. 28, 70-80.
12. Borges da Silva, E.A.; Zabkova, M.; Araújo, J.D.; Cateto, C.A.; Barreiro, M.F.; Belgacem, M.N.; Rodrigues, A.E. (2009). An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin. Chem. Eng. Res. Des. 87, 1276-1292.
13. Brock, T.D.; Madigan, M.D.; Martinko, J.M.; Parker, J. (1995). Microbiologia. Città Studi Edizioni, Milan.
14. Burri, J.; Graf, M.; Lambelet, P.; Löiger, J. (1989). Vanillin: more than a flavouring agent-a potent antioxidant. J. Sci. Food Agric. 48, 49-56.
15. Cheetham, P.S.J. (1993). The use of biotransformation for the production of flavours and fragrances. Trends Biotechnol. 11, 478-488.
16. Ciftci, C.; Constantinides, A.; Wang, S.S (1983). Optimization of conditions and cell feeding procedures for alcohol fermentation. Biotechnol. Bioeng. 25, 2007-2023.
17. Clark, G.S. (1990). Vanillin. Perf. Flavor 15, 45-54.
18. Converti, A. (2008). Recupero di prodotti biotecnologici. In: Donadio, S.; Marino, G. (eds). Biotecnologie Microbiche. Casa Editrice Ambrosiana, Milan, Italy, p. 413-445.
19. Converti, A. (2009). Aprovechamiento de residuos agroindustriales para la generacion de aditivos alimentarios: Tratamiento de las materias primas y estudios metabólicos. Vigo, Spain, 240p. (PhD Dissertation. Faculty of Sciences. Universidade de Vigo).
20. Converti, A.; De Faveri, D.; Perego, P.; Barghini, P.; Ruzzi, M.; Sene L. (2003). Vanillin production by recombinant strains of Escherichia coli. Braz. J. Microbiol. 34(suppl.), 108-110.
21. Converti, A.; Perego, P.; Del Borghi, M.; Parisi, F.; Ferraiolo, G. (1986). Kinetic considerations about the study of alcoholic fermentations of starch hydrolysate. Biotechnol. Bioeng. 28, 711-717.
22. Coulson, J.M.; Richardson, J.F. (1991). Chemical Engineering, Vol. 2, 4th Edn. Pergamon, Oxford, UK.
23. Davidson, P.M.; Naidu. A.S. (2000). Phyto-phenols. In: Naidu A.S. (ed.). Natural Food Antimicrobial Systems. CRC Press LLC, Boca Raton, London, p. 265-294.
24. De Faveri, D.; Torre, P.; Aliakbarian, B.; Domínguez, J.M.; Perego, P.; Bustos, G., Converti A. (2008). Conversión microbiana de ácido ferúlico a vainillina, In: Bustos Vázquez, G.; Velázquez de la Cruz, E.; Rangel Torres, E.; Compeán Ramírez, E.; Campos Leal, J.R. (eds.). Aprovechamiento Biotecnológico de Productos Agropecuarios II. Plaza y Valdés, S.A. de C.V., México, p.181-203.
25. Di Gioia, D.; Sciubba, L.; Setti, L.; Luziatelli, F.; Ruzzi, M.; Zanichelli, D.; Fava, F. (2007). Production of biovanillin from wheat bran, Enzyme Microb. Technol. 41, 498-505.
26. FAO-STAT (2010). FAO Statistical Database, http://www.fao.org. Accessed 17 February 2010.
27. Faulds, C.B.; Mandatari, G.; Lo Curto, R.B.; Bisognano, G.; Waldron, K.W. (2004). Arabinoxylan and mono- and dimeric ferulic acid release from brewer's and wheat bran by feruloyl esterases and glycosyl hydrolases from Humicolar insolens. Appl. Microbiol. Biotechnol. 64, 644-650.
28. Gould, G.W. (1996). Industry perspectives on the use of natural antimicrobials and inhibitors for food applications. J. Food Prot. suppl.59, 82-86.
29. Gräfe V. (1904). Untersuchungen uber die Holzsubstanz von chemischphysiologischen Standpunkte. Monatsh. Chem. Wissen. 25, 987.
30. Gunnarsson, N.; Palmqvist, E.A. (2006). Influence of pH and carbon source on the production of vanillin from ferulic acid by Streptomyces setonii ATCC 39116. Develop. FoodSci. 43, 73-76.
31. Gurujeyalakshmi, G.; Mahadevan, A. (1987). Dissimilation of ferulic acid by Bacillus subtilis. Curr. Microbiol. 16, 69-73.
32. Hagedorn, S.; Kaphammer, B. (1994). Microbial biocatalysis in the generation of flavour and fragrance chemicals. Annu. Rev. Microbiol 48, 773-800.
33. Hausler, A.; Munch, T. (1997). Microbial production of natural flavours, ASM News 63, 551-559.
34. Hibbert, H.; Tomlinson Jr, G.H. (1936). Manufacture of vanillin from waste sulfite pulp liquor. U.S. Patent 2 069 185.
35. Hocking, M.B. (1997). Vanillin: synthetic flavouring from spent sulfite liquor. J. Chem. Educ. 74, 1055-1059.
36. Howard, G.C. (1925). U.S. Patent 1 551 882.
37. Jadhav, D.; Rekha, B.N.; Gogate, P.R.; Rathod, V.K. (2009). Extraction of vanillin from vanilla pods: A comparison study of conventional soxhlet and ultrasound assisted extraction. J. Food Eng. 93, 421-426.
38. Jönsson, A.S.; Nordin, A.K.; Wallberg, O. (2008). Concentration and purification of lignin in hardwood kraft pulping liquor by ultrafiltration and nanofiltration. Chem. Eng. Res. Des. 86, 1271-1280.
39. st Ed. Editora Edgard Blücher, São Paulo, Brazil, p. 493.
40. Kirk, T.K. (1971). Effects of microorganisms on lignin. Annu. Rev. Phytopatol. 9, 185-210.
41. Knuth, M.E.; Sahai, O.P. (1991). Flavour composition and method. World Pat. 8900820.
42. Krings, U.; Berger, R.G. (1998). Biotechnological production of flavours and fragrances. Appl. Microbiol. Biotechnol. 49, 1-8.
43. Labuda, I.M.; Goers, S.K.; Keon, K.A. (1992). Bioconversion process for the production of vanillin. U.S. Pat. 5128253.
44. Lesage-Meessen, L.; Lomascolo, A.; Bonnin, E.; Thibault, J.F.; Buleon, A.; Roller, M.; Asther, M.; Record, E.; Ceccaldi, B.C.; Asther, M. (2002). A biotechnological process involving filamentous fungi to produce natural crystalline vanillin from maize bran. Appl. Biochem. Biotechnol. 102-103, 141-153.
45. Li, K.; Frost, J.W. (1998). Synthesis of vanillin from glucose, J. Am. Chem. Soc. 120, 10545-10546.
46. Lomascolo, A.; Stentelaire, C.; Asther, M.; Lesage-Meessen, L. (1999). Basidiomycetes as new biotechnological tools to generate natural aromatic flavours for the food industry. Trends Biotechnol. 17, 282-289.
47. Muheim, A.; Lerch, K. (1999). Towards a high-yield bioconversion of ferulic acid to vanillin. Appl. Microbiol. Biothechnol. 51, 456-461.
48. Miiller, B.; Munch, T.; Muheim, A.; Wetli, M. (1998). A process for the production of vanillin. European Patent 0885968.
49. Narbad, A.; Gasson, M.J. (1998). Metabolism of ferulic acid to vanillin using a novel CoA-dependent pathway in a newly-isolated strain of Pseudomonas fluorescens. Microbiology 144, 1397-1405.
50. Overhage, J.; Priefert, H.; Steinbüchel, A. (1999). Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl. Environ. Microbiol. 65, 4837-4847.
51. Overhage, J.; Steinbüchel, A.; Priefert, H. (2003). Highly efficient biotransformation of eugenol to ferulic acid and further conversion to vanillin in recombinant strains of Escherichia coli. Appl. Environ. Microbiol. 69, 6569-6576.
52. Overhage, J.; Steinbuchel, A.; Priefert, H. (2006). Harnessing eugenol as a substrate for production of aromatic compounds with a recombinant strains of Amycolatopsis sp. HR167. J. Biotechnol. 125, 369-376.
53. Pak, F.E.; Gropper, S.; Dai, W.D.; Havkin-Frenkel, D.; Belanger, F.C. (2004). Characterization of a multifunctional methyltransferase from the orchid Vanilla planifolia. Plant Cell Rep. 22, 959-966.
54. Priefert, H.; Rabenhorst, J.; Steinbüchel, A. (2001). Biotechnological production of vanillin. Appl. Microbiol. Biotechnol. 56, 296-314.
55. Rabenhorst, J. (1996). Production of methoxyphenol-type natural aroma chemicals by biotransformation of eugenol with a new Pseudomonas sp. Appl. Microbiol. Biotechnol. 46, 470-474.
56. Rabenhorst, J.; Hopp, R. (2000). Process for the preparation of vanillin and suitable microorganisms. US. Pat. 6133003.
57. Raffellini, S; Guerrero, S.; Alzadora, S.M. (2004). Efecto del pH sobre la cinética de inactivación de Escherichia coli por peróxido de oxígeno. XIII Seminario Latinoamericano y del Caribe Ciencia & Tecnología de Alimentos. VII Jornadas Uruguayas. II Feria Especializada de Ingredientes y Aditivos, Envases, Equipos y Servicios, Montevideo, Uruguay.
58. Ramachandra Rao, S.; Ravishankar, G.A. (2000). Vanilla flavour: production by conventional and biotechnological routes. J. Sci. Food. Agric. 80, 289-304.
59. Rito-Palomares M. (2004). Practical application of aqueous two-phase partition to process development for the recovery of biological products. J. Chrom. B 807, 3-11.
60. Rivas Torres, B.; Aliakbarian, N.; Torre, P.; Perego, P.; Domínguez, J.M.; Zilli, M., Converti A. (2009). Vanillin bioproduction from alkaline hydrolyzate of corn cob by Escherichia coli JM109/pBB1. Enzyme Microb.Tech. 44, 154-158.
61. Rosazza, J.P.N.; Huang, Z.; Dostal, L.; Volm, T.; Rosseau, B. (1995). Biocatalytic transformations of ferulic acid; an abundant aromatic natural product. J. Ind. Microbiol. Biotechnol. 15, 457-471.
62. Salter, G.J.; Kell, D.B. (1995). Solvent selection for whole cell biotransformations in organic media. Crit. Rev. Biotechnol. 15, 139-177.
63. Schlegel, H.G. (1996). Microbiologia, Zanichelli, Milan.
64. Schmid, A.; Kollmer, A.; Mathys, R.G.; Witholt, B. (1998).Developments toward large-scale bacterial processes in the presence of bulk amounts of organic solvents. Extremophiles 2, 249-256.
65. Schreier, P. (1992). Bioflavours: an overview. In: Patterson, R.L.S.; Charlwood, B.V.; MacLeo, G.; Williams, A.A. (eds.). Biotrasformation of Flavours. Cambridge, UK. The Royal Society of Chemistry, p. 1.
66. Sciubba, L.; Di Gioia, D.; Fava, F.; Gostoli, C. (2009). Membrane-basedsolvent extraction of vanillin in hollow fiber contactors. Desalination 241, 357-364.
67. Serra, S.; Fuganti, C.; Brenna, E. (2005). Biocatalytic preparation of natural flavours and fragrances. Trends Biotechnol. 23, 193-198.
68. Shin, H.D.; Chen, R.R. (2006). Production and characterization of a type B feruloyl esterase from Fusarium proliferatum NRRL 26517. Enzyme Microb. Technol. 38, 478-485.
69. Stentelaire, C.; Lesage-Meessen, L.; Delattre, M.; Haon, M.; Sgoilot, J.C.; Colonna Cecaldi, B.; Asther, M. (1998). By-passing of unwanted vanillyl alcohol formation using selective adsorbents to improve vanillin production with Phanerochaete chrysosporium. World J. Microbiol. Biotechnol. 14, 285-287.
70. Suresh, G.A.; Ravishankar (2005). Methyl jasmonate modulated biotrasformation of phenyl propanoids to vanillin related metabolites using Capsicum frutescens root cultures. Plant Physiol. Biochem. 43 (2) 125-131.
71. Sutherland, J.B.; Crawford, D.L.; Pometto III, A.L. (1983). Metabolism of cinnamic, p-coumaric and ferulic acids by Streptomyces setonii. Can. J. Microbiol. 29, 1253-1257.
72. Thibault, J.; Micard, V.; Renard, C.; Asther, M.; Delattre, M.; Lesage-Meessen, L.; Faulds, C.; Kroon, P.; Williamson, G.; Duarte, J.; Duarte, J.C.; Ceccaldi, B.C.; Tuohy, M.; Couteau, D.; Van Hulle, S.; Heldt-Hansen, H.-P. (1998). Fungal bioconversion of agricultural by-products to vanillin. LWT-Food Sci. Technol. 31, 530-536.
73. Tomlinson, G.H.; Ibbert, H. (1936). Studies on lignin and related compounds. XXIV. The formation of vanillin from waste sulfite liquor. J. Am. Chem. Soc. 58, 345-348.
74. Torre, P.; Aliakbarian, B.; Rivas, B.; Domínguez, J.M.; Converti, A. (2008). Release of ferulic acid from corn cobs by alkaline hydrolysis. Biochem. Eng. J. 40, 500-506.
75. Torre, P., De Faveri, D., Perego, P., Converti, A., Barghini, P., Ruzzi, M., Faria, F.P. (2004). Selection of co-substrate and aeration conditions for vanillin production by E. coli JM109/pBB1. Food Technol. Biotechnol. 42, 193-196.
76. Torre, P., De Faveri, D., Perego, P., Ruzzi, M., Barghini, P., Gandolfi, R., Converti, A. (2004). Bioconversion of ferulate into vanillin by Escherichia coli strain JM109/pBB1 in an immobilized-cell reactor. Ann. Microbiol. 54, 517-527.
77. Torre, P.; Guarino, C.; Converti, A.; Barghini, P.; Ruzzi, M.; Sato, S. (2003). Effects of temperature and starting substrate concentration on ferulate-to-vanillin bioconversion by Escherichia coli JM109(pBB1). Farmácia & Química 36 (3), 39-42.
78. Vaithanomsat, P.; Apiwatanapiwat, W. (2009). Feasibility study on vanillin production from Jatropha curcas stem using steam explosion as a pretreatment. Int. J. Chem. Biomolec. Eng. 2 (4), 211-214.
79. Van den Heuvel, R.R.H.; Fraaije, M.W.; Laane, C.; Van Berkel, W.J.H. (2001). Enzymatic synthesis of vanillin. J. Agric. Food Chem. 49, 29542958.
80. Vane, L.M. (2005). A review of pervaporation for product recovery from biomass fermentation processes. J. Chem. Technol. Biotechnol. 80, 603-629.
81. Vega, J. (1993). Transformatión de materiales lígnicos a compuestos de alto valor agregado. Seminario de Licenciatura, San José, CR, Laboratorio de Polímeros, Universidad de Costa Rica.
82. Walton, N.J.; Mayer, M.J.; Narbad, A. (2003). Vanillin. Phytochemistry 63, 505-515.
83. Walton, N.J.; Narbad, A.; Faulds, C.B.; Williamson, G. (2000). Novel approaches to the biosynthesis of vanillin. Curr. Opin. Biotechnol. 11, 490-496.
84. Williamson, G.; Kroon, P.A.; Faulds, C.B. (1998). Hairy plant polysaccharides: a close shave with microbial esterases. Microbiology 144, 2011-2023.
85. Yoon, S.H.; Li, C.; Kim, J.-E.; Lee, S.-H.; Yoon, J.-Y.; Choi, M.-S.; Seo, W.-T.; Yang, J.-K.; Kim, J.-Y.; Kim S.-W. (2005). Production of vanillin by metabolically engineered Escherichia coli. Biotechnol. Lett. 27, 18291832.
86. Zabkova, M.; da Silva, E.A.B.; Rodrigues, A.E. (2007). Recovery of vanillin from lignin/vanillin mixture by using tubular ceramic ultrafiltration membranes. J. Membr. Sci. 301, 221-237.
87. Zhang, Q.F., Jiang, Z.T., Gao, H.J., Li, R. (2008). Recovery of vanillin from aqueous solutions using macroporous adsorption resins. Eur. Food Res. Technol. 226, 377-383.
88. Zheng, L.; Zheng, P.; Sun, Z.; Bai, Y.; Wang, J.; Guo X. (2007). Production of vanillin from waste residue of rice bran oil by Aspergillus niger and Pycnoporus cinnabarinus. Bioresour. Technol. 98, 1115-1119.
89. Zucchi, G.; Khan, J.A.; Vulfson, E.N. (1998). Could organic solvents be used for the alteration of flux of hydrophobic intermediates through a metabolic pathway in microorganisms? J. Microbiol. Biotechnol. 8, 719722.