Natural Vanillin Production from Isoeugenol by Using Pseudomonas putida in Biphasic Bioconversion Medium

Year 2022, Volume: 28 Issue: 3, 423 - 429, 05.09.2022

Hüseyin Karakaya Murat Yılmaztekin

https://doi.org/10.15832/ankutbd.866426

Abstract

Vanillin, is one of the most demanded flavoring agents in the world. Because of insufficient supply of natural vanillin, market demand is usually supplied by synthetic ones. In this study, it was investigated possibility of usage biphasic system in bioconversion of isoeugenol to vanillin by Pseudomonas putida (HUT 8100). Organic phase was composed of isoeugenol while biocatalyst, P. putida culture, was dispersed in aqueous phosphate solution. Isoeugenol was used as sole carbon source in concentrations ranging between 50-600 g L-1. Incubation was performed at 28 ○C, at pH 6.3 and 180 rpm shaking. Effect of initial substrate concentration and bioconversion time were investigated. Isoeugenol and vanillin amounts in medium were simultaneously analyzed in HPLC system. After 120 h incubation, vanillin reached the its highest level when 400 g L-1 isoeugenol was applied in medium. In specified conditions, it was achieved to produce 11.95 g L-1 vanillin with 6.2% molar yield within 15 days of bioconversion. It is thought that, obtained result by using biphasic system is very important for the industrial applications in production of natural vanillin via bioconversion.

Keywords

Bioconversion, Biphasic system, Isoeugenol, Natural flavor, Vanillin

Project Number

2015/17

References

• Ashengroph M, Nahvi I, Zarkesh-Esfahani H & Momenbeik F (2011). Use of growing cells of Pseudomonas aeruginosa for synthesis of the natural vanillin via conversion of isoeugenol. Iranian Journal of Pharmaceutical Research 10(4): 749-757
• Ashengroph M & Amini J (2017). Bioconversion of isoeugenol to vanillin and vanillic acid using the resting cells of Trichosporon asahii. 3 Biotech 7: 358
• Bicas J L, Fontanille P, Pastore G M & Larroche C (2010). A bioprocess for the production of high concentrations of R-(+)-a-terpineol from R-(+)-limonene. Process Biochemistry 45: 481-486
• Boccia F, Covino D, Sarnacchiaro P (2018). Genetically modified foods versus knowledge and fear: A numeric approach for consumer behavior. Food Research International 111: 682-688
• Carreno D M P, Quinones O M R, Calvo J R V & Ochoa S H (2014). Bioconversion of (+)-nootkatone by Botryodiplodia theobromae using a membrane aerated biofilm reactor. Revista Mexicana de Ingenieria Quimica 13(3): 757-764
• Castro P S, Soares F, Santos P M (2021). Current advances in the bacterial toolbox for the biotechnological production of monoterpene-based aroma compounds. Molecules 26(91): 1-31
• Chreptowicz K & Mierzejewska J (2018). Enhanced bioproduction of 2-phenylethanol in a biphasic system with rapeseed oil. New Biotechnology 42: 56-61
• Di Gioia D, Luziatelli F., Negroni A, Ficca A G, Fava F, Ruzzi M (2011). Metabolic engineering of Pseudomonas fluorescens for the production of vanillin from ferulic acid. Journal of Biotechnology 156: 309-316
• Eloff J N (1998). A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Medica 64: 711-713.
• Franco A, De S, Balu A M, Romero A A & Luque R (2017). Selective oxidation of isoeugenol to vanillin over mechanochemically synthesized aluminosilicate supported transition metal catalysts. ChemistrySelect 2: 9546-9551
• Hansen E H, Moller B L, Kock G R, Bünner C M, Kristensen C, Jensen O R, Okkels F T, Olsen C E, Motawia M S & Hansen J (2009). De novo biosynthesis of vanillin in fission yeast (Schizosaccharomyces pombe) and baker's yeast (Saccharomyces cerevisiae). Applied and Environmental Microbiology 75(9): 2765-2774
• Hua D, Ma C, Lin S, Song L, Deng Z, Maomy Z, Zhang Z, Yu B & Xu P (2007). Biotransformation of isoeugenol to vanillin by a newly isolated Bacillus pumilus strain: identification of major metabolites. Journal of Biotechnology 130: 463-470
• HUT (2015). Medeum. Retrieved in June, 11, 2015 from https://home.hiroshima-u.ac.jp/hut/mideum.html
• Julsing M K, Kuhn D, Schmid A & Bühler B (2012). Resting cells of recombinant E. coli show high epoxidation yields on energy source and high sensitivity to product inhibition. Biotechnology and Bioengineering 109(5): 1109-1119
• Karakaya H & Yılmaztekin M (2020). Pseudomonas putida ile izoöjenolden doğal vanilin üretiminde bazı ortam koşullarının molar verim üzerine etkisi. Gıda 45(1): 9-19
• Li Y H, Sun Z H & Zheng P (2004). Determination of vanillin, eugenol and isoeugenol by RP-HPLC. Chromatographia 60: 709-713
• Luziatelli F, Brunetti L, Ficca A G & Ruzzi M (2019). Maximizing the efficiency of vanillin production by biocatalyst enhancement and process optimization. Frontiers in Bioengineering and Biotechnology 7: 279
• Muheim A & Lerch K (1999). Towards a high-yield bioconversion of ferulic acid to vanillin. Applied Microbiology and Biotechnology 51: 456-461
• Nouri M, Shahriari S & Pazuki G (2019). Increase of vanillin partitioning using aqueous two phase system with promising nanoparticles. Scientific Reports 9: 19665
• Overhage J, Priefert H, Rabenhorst J & Steinbüchel A (1999). Biotransformation of eugenol to vanillin by a mutant of Pseudomonas sp. strain HR199 constructed by disruption of the vanillin dehydrogenase (vdh) gene. Applied Microbiology and Biotechnology 52: 820-828
• Shimoni E, Baasov T, Ravid U & Shoham Y (2003). Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants. Journal of Biotechnology 105: 61-70
• Sigma-Aldrich (2015). Isoeugenol. Retrieved in August, 24, 2015 from https://www.sigmaaldrich.com/catalog/product/sial/w246830?lang=en&region=TR
• Singh B, Khan S, Pandey S S Singh M, Banerjee S, Kitamura Y & ur Rahman L (2015). Vanillin production in metabolically engineered Beta vulgaris hairy roots through heterologous expression of Pseudomonas fluorescens HCHL gene. Industrial Crops and Products 74: 839-848
• Tang P L & Hassan O (2020). Bioconversion of ferulic acid attained from pineapple peels and pineapple crown leaves into vanillic acid and vanillin by Aspergillus niger I‑1472. BMC Chemistry 14: 7
• van Leeuwen K A, Prenzler P D, Ryan D, Paolini M & Camin F (2018). Differentiation of wood‐derived vanillin from synthetic vanillin in distillates using gas chromatography/combustion/isotope ratio mass spectrometry for δ13C analysis. Rapid Communication in Mass Spectrometry 32: 311-318
• Wang Z, Zhao F, Chen D & Li D (2006). Biotransformation of phytosterol to produce androsta-diene-dione by resting cells of Mycobacterium in cloud point system. Process Biochemistry 41: 557-561
• Wang Q, Wu X, Lu X, He Y, Ma B & Xu Y (2021). Efficient biosynthesis of vanillin from isoeugenol by recombinant isoeugenol monooxygenase from Pseudomonas nitroreducens Jin1. Applied Biochemistry and Biotechnology, Published online: 07.01.2021
• Yamada M, Okada Y, Yoshida T & Nagasawa T (2007). Biotransformation of isoeugenol to vanillin by Pseudomonas putida IE27 cells. Applied Microbiology and Biotechnology 73: 1025-1030
• Yamada M, Okada Y, Yoshida T & Nagasawa T (2008). Vanillin production using Escherichia coli cells over-expressing isoeugenol monooxygenase of Pseudomonas putida. Biotechnology Letters 30: 665-670
• Zhang C, Xu Q, Hou H, Wu J, Zheng Z & Ouyang J (2020). Efficient biosynthesis of cinnamyl alcohol by engineered Escherichia coli overexpressing carboxylic acid reductase in a biphasic system. Microbial Cell Factories 19: 163
• Zhao L Q, Sun Z H, Zheng P & Zhu L L (2005). Biotransformation of isoeugenol to vanillin by a novel strain of Bacillus fusiformis. Biotechnology Letters 27: 1505-1509
• Zhao L Q, Sun Z H, Zheng P & He J Y (2006). Biotransformation of isoeugenol to vanillin by Bacillus fusiformis CGMCC1347 with the addition of resin HD-8. Process Biochemistry 41: 1673-1676
• Zhao L, Xie Y, Chen L, Xuefeng X, Zhao C X & Cheng F (2018). Efficient biotransformation of isoeugenol to vanillin in recombinant strains of Escherichia coli by using engineered isoeugenol monooxygenase and sol-gel chitosan membrane. Process Biochemistry 71: 76-81
• Zhu Y, Liu J, Liao Y, Lv W, Ma L & Wang C (2018). Degradation of vanillin during lignin valorization under alkaline oxidation. Topics in Current Chemistry 376: 29