Skip to main content
SpringerLink
Log in

Synthesis of flavor esters by a novel lipase from Aspergillus niger in a soybean-solvent system

  • Original Article
  • Published:
3 Biotech Aims and scope Submit manuscript

Abstract

To find a lipase for synthesis of flavor esters in food processing, a total of 35 putative lipases from Aspergillus niger F0215 were heterologously expressed and their esterification properties in crude preparations were examined. One of them, named An-lipase with the highest esterification rate (23.1%) was selected for further study. The purified An-lipase had the maximal activity at 20 °C and pH 6.5 and the specific activity of 1293 U/mg. Sixty percent of the activity was maintained in a range of temperatures of 0–30 °C and pHs of 3.0–8.5. The highest hydrolysis activity of An-lipase was towards pNPC (C8), followed by pNPB (C4) and pNPA (C2), then pNPL (C12). Km, Vmax, kcat, and kcat/Km towards pNPC were 26.7 mmol/L, 129.9 mmol/(L h), 23.2 s−1, and 0.8/mM/s, respectively. The ethyl lactate, butyl butyrate, and ethyl caprylate flavor esters were produced by esterification of the corresponding acids with conversion efficiencies of 15.8, 37.5, and 24.7%, respectively, in a soybean-oil-based solvent system. In conclusion, An lipase identified in this study significantly mediated synthesis of predominant flavor esters (ethyl lactate, butyl butyrate, and ethyl caprylate) in a soybean-oil-lacking other toxic organic solvents, which has potential application in food industries.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Ahmed Al-Tammar K, Omar O, Abdul Murad AM, Abu Bakar FD (2016) Expression and characterization of a cutinase (AnCUT2) from Aspergillus niger. Open Life Sci 11:29–38

    Google Scholar 

  • Brault G, Shareck F, Hurtubise Y, Lépine F, Doucet N (2014) Short-chain flavor ester synthesis in organic media by an Escherichia coli whole-cell biocatalyst expressing a newly characterized heterologous lipase. PLoS ONE 9:1–9

    Article  Google Scholar 

  • Cai Y, Wang L, Liao X, Ding Y, Sun J (2009) Purification and partial characterization of two new cold-adapted lipases from mesophilic Geotrichum sp. SYBC WU-3. Process Biochem 44:786–790

    Article  CAS  Google Scholar 

  • De Barros DPC, Fernandes P, Cabral JMS, Fonseca LP (2011) Synthetic application and activity of cutinase in an aqueous, miniemulsion model system: hexyl octanoate synthesis. Catal Today 173:95–102

    Article  Google Scholar 

  • De Barros DPC, Azevedo AM, Cabral JMS, Fonseca LP (2012) Optimization of flavor esters synthesis by Fusarium solani pisi cutinase. J Food Biochem 36:275–284

    Article  Google Scholar 

  • Duan X, Liu Y, You X, Jiang Z, Yang S, Yang S (2017) High-level expression and characterization of a novel cutinase from Malbranchea cinnamomea suitable for butyl butyrate production. Biotechnol Biofuels 10:233

    Article  Google Scholar 

  • Ghamgui H, Karra-Chaˆbouni M, Gargouri Y (2004) 1-Butyl oleate synthesis by immobilized lipase from Rhizopus oryzae: a comparative study between n-hexane and solvent-free system. Enzyme Microb Technol 35:355–363

    Article  CAS  Google Scholar 

  • Hemamalini R, Khare SK (2016) Purification and characterization of active aggregates of an organic solvent tolerant lipase from Marinobacter sp. EMB5. Insights Enzyme Res 1:1–8

    Google Scholar 

  • Hu K, Jin G-J, Mei W-C, Li T, Tao Y-S (2018) Increase of medium-chain fatty acid ethyl ester content in mixed H. uvarum/S. cerevisiae fermentation leads to wine fruity aroma enhancement. Food Chem 239:495–501

    Article  CAS  Google Scholar 

  • Kim HR, Kim IH, Hou CT, Kwon KI, Shin BS (2010) Production of a novel cold-active lipase from Pichia lynferdii Y-7723. J Agric Food Chem 58:1322–1326

    Article  CAS  Google Scholar 

  • Koutinas M, Yiangou C, Osório NM, Ioannou K, Canet A, Valero F, Ferreira-Dias S (2018) Application of commercial and non-commercial immobilized lipases for biocatalytic production of ethyl lactate in organic solvents. Bioresour Technol 247:496–503

    Article  CAS  Google Scholar 

  • Longo MA, Sanroman MA (2006) Production of food aroma compounds: microbial and enzymatic methodologies. Food Technol Biotechnol 44:335–353

    CAS  Google Scholar 

  • Martins AB, Friedrich JLR, Cavalheiro JC, Garcia-Galan C, Barbosa O, Ayub MAZ, Fernandez-Lafuente R, Rodrigues RC (2013) Improved production of butyl butyrate with lipase from Thermomyces lanuginosus immobilized on styrene-divinylbenzene beads. Bioresour Technol 134:417–422

    Article  CAS  Google Scholar 

  • Mishra S, Sachan A, Sachan SG (2013) Production of natural value-added compounds: an insight into the eugenol biotransformation pathway. J Ind Microbiol Biotechnol 40:545–550

    Article  CAS  Google Scholar 

  • Mishra S, Sachan A, Vidyarthi AS, Sachan SG (2014) Transformation of ferulic acid to 4-vinyl guaiacol as a major metabolite: a microbial approach. Rev Environ Sci Biotechnol 13:377–385

    Article  CAS  Google Scholar 

  • Muhammad A, Ali S, Bokhari I, Ali N, Mukhtar H, Nawaz A, Imran M (2017) Purification and characterization of extracellular lipase by Geotrichum candidum of dairy origin. Pak J Bot 49:757–761

    CAS  Google Scholar 

  • Niu D, Tian X, Mchunu NP, Jia C, Singh S, Liu X, Prior BA, Lu F (2017) Biochemical characterization of three Aspergillus niger β-galactosidases. Electron J Biotechnol 27:37–43

    Article  CAS  Google Scholar 

  • Parra LP, Reyes F, Acevedo JP, Salazar O, Andrews BA, Asenjo JA (2008) Cloning and fusion expression of a cold-active lipase from marine Antarctic origin. Enzyme Microb Technol 42:371–377

    Article  CAS  Google Scholar 

  • Pires EJ, Teixeira JA, Brányik T, Vicente AA (2014) Yeast: the soul of beer’s aroma-a review of flavour-active esters and higher alcohols produced by the brewing yeast. Appl Microbiol Biotechnol 98:1937–1949

    Article  CAS  Google Scholar 

  • Pires-Cabral P, Fonseca MMRD, Ferreira-Dias S (2010) Esterification activity and operational stability of Candida rugosa lipase immobilized in polyurethane foams in the production of ethyl butyrate. Biochem Eng J 48:246–252

    Article  CAS  Google Scholar 

  • Sathish Yadav KN, Adsul MG, Bastawde KB, Jadhav DD, Thulasiram HV, Gokhale DV (2011) Differential induction, purification and characterization of cold active lipase from Yarrowia lipolytica NCIM 3639. Bioresour Technol 102:10663–10670

    Article  CAS  Google Scholar 

  • Sharma P, Sharma N, Pathania S, Handa S (2017) Purification and characterization of lipase by Bacillus methylotrophicus PS3 under submerged fermentation and its application in detergent industry. J Genet Eng Biotechnol 15:369–377

    Article  Google Scholar 

  • Sumby KM, Matthews AH, Grbin PR, Jiranek V (2009) Cloning and characterization of an intracellular esterase from the wine-associated lactic acid bacterium Oenococcus oeni. Appl Environ Microbiol 75:6729–6735

    Article  CAS  Google Scholar 

  • Talon R, Montel MC, Berdague JL (1996) Production of flavor esters by lipases of Staphylococcus warneri and Staphylococcus xylosus. Enzyme Microb Technol 19:620–622

    Article  CAS  Google Scholar 

  • Tamang JP, Holzapfel WH, Watabane K (2016) Review: diversity of microorganisms in global fermented foods and beverages. Front Microbiol 7:377

    PubMed  PubMed Central  Google Scholar 

  • Villanueva-Bermejo D, Reglero G, Fornari T (2017) Recent advances in the processing of green tea biomolecules using ethyl lactate: a review. Trends Food Sci Technol 62:1–12

    Article  CAS  Google Scholar 

  • Wu R, Yu M, Liu X, Meng L, Wang Q, Xue Y, Wu J, Yue X (2015) Changes in flavour and microbial diversity during natural fermentation of suan-cai, a traditional food made in Northeast China. Int J Food Microbiol 211:23–31

    Article  CAS  Google Scholar 

  • Yang J, Sun J, Yan Y (2010) lip2, a novel lipase gene cloned from Aspergillus niger exhibits enzymatic characteristics distinct from its previously identified family member. Biotechnol Lett 32:951–956

    Article  CAS  Google Scholar 

  • Yu H, Lee M-W, Shin H, Park KM, Chang PS (2019) Lipase-catalyzed solvent-free synthesis of erythorbyl laurate in a gas-solid-liquid multiphase system. Food Chem 271:445–449

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was supported by the Intergovernmental International Scientific and Technological Innovation Cooperation Program, MOST, China (Grant No.: 2018YFE0100400) and the Raising Program of Innovation Team for Tianjin Colleges and Universities, Tianjin, China (Grant No.: TD12-5002) to ZXWANG.

Author information

Authors and Affiliations

  1. College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, China

    Shanzi Cong, Xin Zhang & Fuping Lu

  2. Department of Biological Chemical Engineering, College of Chemical Engineering and Materials Science, Tianjin University of Science and Technology, Tianjin, 300457, China

    Shanzi Cong, Kangming Tian & Zheng-Xiang Wang

  3. Department of Biotechnology and Food Technology, Faculty of Applied Sciences, Durban University of Technology, P.O. Box 1334, Durban, 4001, South Africa

    Suren Singh

  4. Department of Microbiology, University of Stellenbosch, Private Bag X1, Matieland, 7602, South Africa

    Bernard Prior

Authors
  1. Shanzi Cong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kangming Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fuping Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Suren Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Bernard Prior
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Zheng-Xiang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Fuping Lu or Zheng-Xiang Wang.

Ethics declarations

Conflict of interest

The authors declare that a Chinese Innovative Patent based on the use of this enzyme or its mutants for improving the flavor of fermented foods is under application.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cong, S., Tian, K., Zhang, X. et al. Synthesis of flavor esters by a novel lipase from Aspergillus niger in a soybean-solvent system. 3 Biotech 9, 244 (2019). https://doi.org/10.1007/s13205-019-1778-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s13205-019-1778-5

Keywords

Search

Navigation