Abstract
The wild strain Amycolatopsis sp. ATCC 39116 was explored in ferulic acid-based media to produce naturally the aroma components of the cured vanilla pod, namely vanillin, vanillic acid, and vanillyl alcohol. Other phenolic compounds (4-vinyl guaiacol, guaiacol, and protocatechuic acid) were also evaluated. The influence of medium composition, fermentation technology (batch or fed-batch), supplementation with vanillic acid, and inoculum concentration on ferulic acid biotransformation were evaluated. The results postulate the initial concentration of cell mass as the variable with the strongest impact on ferulic acid metabolization under the studied conditions. The highest amounts of vanillin and vanillic acid were achieved at intermediate values of cell mass. Vanillyl alcohol and protocatechuic acid were more closely linked to high cell mass concentrations. Conversely, 4-vinyl guaiacol reached its highest amount at the lowest amount of cell mass. Guaiacol was not detected in any case. Therefore, the initial cell concentration must be considered a critical parameter when using Amycolaptosis sp. ATCC 39116 for the production of vanillin and related compounds.
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References
Asaff Torres A, De la Torre Martínez M, Macias Ochoa RM (2008) Proceso para producir vainillina a partir de microorganismos inmovilizados por cultivo de superficie. Patent WO 2008/130210, 30th October 2008
Converti A, Aliakbarian B, Domínguez JM, Bustos Vázquez G, Perego P (2010) Microbial production of biovanillin. Braz J Microbiol 41:519–530. doi: 10.1590/S1517-83822010000300001
De Paiva LB, Goldbeck R, Dantas W, Squina FM (2013) Ferulic acid and derivatives: molecules with potential application in the pharmaceutical field. Braz J Pharmacol Sci 49:396–411. doi: 10.1590/S1984-82502013000300002
Fleige C, Steinbüchel A (2014) Construction of expression vectors for metabolic engineering of the vanillin-producing actinomycete Amycolatopsis sp. ATCC 39116. Appl Microbiol Biotechnol 98:6387–6395. doi:10.1007/s00253-014-5724-5
Fleige C, Hansen G, Kroll J, Steinbüchel A (2013) Investigation of the Amycolatopsis sp. strain ATCC 39116 vanillin dehydrogenase and its impact on the biotechnical production of vanillin. Appl Environ Microbiol 79:81–90. doi:10.1128/AEM.02358-12
Ghosh S, Sachan A, Sen SK, Mitra A (2007) Microbial transformation of ferulic acid to vanillic acid by Streptomyces sannanensis MTCC 6637. J Ind Microbiol Biotechnol 34:131–138. doi:10.1007/s10295-006-0177-1
Hua D, Ma C, Song L, Lin S, Zhang Z, Deng Z, Xu P (2007) Enhanced vanillin production from ferulic acid using adsorbent resin. Appl Microbiol Biotechnol 74:783–790. doi:10.1007/s00253-006-0735-5
Iwagami SG, Yang K, Davies J (2000) Characterization of the protocatechuic acid catabolic gene cluster from Streptomyces sp. strain 2065. Appl Environ Microbiol 66:1499–1508. doi:10.1128/AEM.66.4.1499-1508.2000
Kaur B, Chakraborty D (2013) Biotechnological and molecular approaches for vanillin production: a review. Appl Biochem Biotechnol 169:1353–1372. doi:10.1007/s12010-012-0066-1
Ma X, Daugulis AJ (2014a) Effect of bioconversion conditions on vanillin production by Amycolatopsis sp. ATCC 39116 through an analysis of competing by-product formation. Bioprocess Biosyst Eng 37:891–899. doi:10.1007/s00449-013-1060-x
Ma XK, Daugulis AJ (2014b) Transformation of ferulic acid to vanillin using a fed-batch solid–liquid two-phase partitioning bioreactor. Biotechnol Prog 30:207–214. doi:10.1002/btpr.1830
Martínez-Cuesta MDC, Payne J, Hanniffy SB, Gasson MJ, Narbad A (2005) Functional analysis of the vanillin pathway in a vdh-negative mutant strain of Pseudomonas fluorescens AN103. Enzym Microb Technol 37:131–138. doi:10.1016/j.enzmictec.2005.02.004
Mathew S, Abraham TE, Sudheesh S (2007) Rapid conversion of ferulic acid to 4-vinyl guaiacol and vanillin metabolites by Debaryomyces hansenii. J Mol Catal B Enzym 44:48–52. doi:10.1016/j.molcatb.2006.09.001
Max B, Carballo J, Cortés S, Domínguez JM (2012a) Decarboxylation of ferulic acid to 4-vinyl guaiacol by Streptomyces setonii. Appl Biochem Biotechnol 166:289–299. doi:10.1007/s12010-011-9424-7
Max B, Tugores F, Cortés-Diéguez S, Domínguez JM (2012b) Bioprocess design for the microbial production of natural phenolic compounds by Debaryomyces hansenii. Appl Biochem Biotechnol 168:2268–2284. doi:10.1007/s12010-012-9935-x
Muheim A, Lerch K (1999) Towards a high-yield bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol 51:456–461. doi:10.1007/s002530051416
Muheim A, Müller B, Münch T, Wetli M (1988) Process for the production of vanillin. Patent EP 0885968 A1, 12 June 1998
Ou S, Kwok K-C (2004) Ferulic acid: pharmaceutical functions, preparation and applications in foods. J Sci Food Agric 84:1261–1269. doi:10.1002/jsfa.1873
Plaggenborg R, Overhage J, Loos A, Archer JAC, Lessard P, Sinskey AJ, Steinbüchel A, Priefert H (2006) Potential of Rhodococcus strains for biotechnological vanillin production from ferulic acid and eugenol. Appl Microbiol Biotechnol 72:745–755. doi:10.1007/s00253-005-0302-5
Priefert MH (2001) Biotechnological production of vanillin. Appl Microbiol Biotechnol 56:296–314. doi:10.1007/s002530100687
Priefert H, Rabenhorst J, Steinbüchel A (2001) Biotechnological production of vanillin. Appl Microbiol Biotechnol 56:296–314. doi:10.1007/s002530100687
Priefert H, Achterholt S, Steinbüchel A (2002) Transformation of the Pseudonocardiaceae Amycolatopsis sp. strain HR167 is highly dependent on the physiological state of the cells. Appl Microbiol Biotechnol 58:454–460. doi:10.1007/s00253-001-0920-5
Rabenhorst J, Hopp R (1997) Process for the preparation of vanillin and suitable microorganisms. Patent US6133003 A, 17th October 2000
Rao SR, Ravishankar GA (2000) Review Vanilla flavour: production by conventional and biotechnological routes. J Sci Food Agric 304:289–304. doi:10.1002/1097-0010(200002)80:3<289::AID-JSFA543>3.0.CO;2-2
Sarangi PK, Sahoo HP (2009) Standardization of cultural conditions for maximum vanillin production through ferulic acid degradation. Rep Opin 1:49–51. doi: 10.1007/s13205-014-0262-5
Sova M (2012) Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini-Rev Med Chem 12:749–767. doi:10.2174/138955712801264792
Sutherland JB, Crawford DL, Pometto AL III (1983) Metabolism of cinnamic, p-coumaric, and ferulic acids by Streptomyces setonii. Can J Microbiol 29:1253–1257. doi:10.1139/m83-195
Tilay A, Bule M, Annapure U (2010) Production of biovanillin by one-step biotransformation using fungus Pycnoporous cinnabarinus. J Agric Food Chem 58:4401–4405. doi:10.1021/jf904141u
Tripathi U, Rao SR, Ravishankar GA (2002) Biotransformation of phenylpropanoid compounds to vanilla flavor metabolites in cultures of Haematococcus pluvialis. Process Biochem 38:419–426. doi:10.1016/S0032-9592(02)00135-8
Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochemistry 63:505–515. doi:10.1016/S0031-9422(03)00149-3
Zamzuri NA, Abd-Aziz S (2013) Biovanillin from agro wastes as an alternative food flavour. J Sci Food Agric 93:429–438. doi:10.1002/jsfa.5962
Acknowledgments
We are grateful to the Spanish Ministry of Science and Innovation for the financial support of this work (project CTQ2011-28967), which has partial financial support from the FEDER funds of the European Union and to the Spanish Ministry of Education, Culture and Sports for Pérez-Rodríguez’s FPU. We are also grateful to the Brazilian research funding institution CAPES for Prof. J. M. Domínguez’s fellowship as Special Visiting Researcher (Science without Borders Program, project no. 88881.062223/2014-01).
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This study was funded by the Spanish Ministry of Science and Innovation for the financial support of this work (project CTQ2011-28967), which has partial financial support from the FEDER funds of the European Union.
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The authors declare that they have no competing interests.
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This article does not contain any studies with human participants or animals performed by any of the authors.
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Pérez-Rodríguez, N., Pinheiro de Souza Oliveira, R., Torrado Agrasar, A.M. et al. Ferulic acid transformation into the main vanilla aroma compounds by Amycolatopsis sp. ATCC 39116. Appl Microbiol Biotechnol 100, 1677–1689 (2016). https://doi.org/10.1007/s00253-015-7005-3
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DOI: https://doi.org/10.1007/s00253-015-7005-3