Abstract
Abstract
In the present study, we demonstrated the use of molecular docking as an efficient in silico screening tool for lipase–triglyceride interactions. Computational simulations using the crystal structures from Burkholderia cepacia lipase (BCL), Thermomyces lanuginosus lipase (TLL), and pancreatic porcine lipase (PPL) were performed to elucidate the catalytic behavior with the majority triglycerides present in Licuri oil, as follows: caprilyl–dilauryl–glycerol (CyLaLa), capryl–dilauryl–glycerol (CaLaLa), capryl–lauryl–myristoyl–glycerol (CaLaM), and dilauryl–myristoyl–glycerol (LaLaM). The computational simulation results showed that BCL has the potential to preferentially catalyze the major triglycerides present in Licuri oil, demonstrating that CyLaLa, (≈25.75% oil composition) interacts directly with two of the three amino acid residues in its catalytic triad (Ser87 and His286) with the lowest energy (–5.9 kcal/mol), while other triglycerides (CaLaLa, CaLaM, and LaLaM) interact with only one amino acid (His286). In one hard, TLL showed a preference for catalyzing the triglyceride CaLaLa also interacting with His286 residue, but, achieving higher binding energies (−5.3 kcal/mol) than found in BCL (–5.7 kcal/mol). On the other hand, PPL prefers to catalyze only with LaLaM triglyceride by His264 residue interaction. When comparing the computational simulations with the experimental results, it was possible to understand how BCL and TLL display more stable binding with the majority triglycerides present in the Licuri oil, achieving conversions of 50.86 and 49.01%, respectively. These results indicate the production of fatty acid concentrates from Licuri oil with high lauric acid content. Meanwhile, this study also demonstrates the application of molecular docking as an important tool for lipase screening to reach a more sustainable production of fatty acid concentrates from vegetable oils.
Graphic abstract
Similar content being viewed by others
References
Bauer LC, Damásio JMA, do, da Silva MV et al (2013) Caracterização química dos óleos prensado e refinado do licuri (Syagrus coronata). Acta Sci Technol 35:771–776. https://doi.org/10.4025/actascitechnol.v35i4.20251
Lisboa MC, Wiltshire FMS, Fricks AT et al (2020) Oleochemistry potential from Brazil northeastern exotic plants. Biochimie 178:96–104. https://doi.org/10.1016/j.biochi.2020.09.002
Crepaldi IC, De A-M, Rios MDG et al (2001) Composição nutricional do fruto de licuri (Syagrus coronata (Martius) Beccari). Rev Bras Botânica 24:155–159. https://doi.org/10.1590/s0100-84042001000200004
da Silva T, de La Salles K, Meneghetti SMP, Ferreira de La Salles W et al (2010) Characterization of Syagrus coronata (Mart.) Becc. oil and properties of methyl esters for use as biodiesel. Ind Crops Prod 32:518–521. https://doi.org/10.1016/j.indcrop.2010.06.026
Iha OK, Alves FCSC, Suarez PAZ et al (2014) Physicochemical properties of Syagrus coronata and Acrocomia aculeata oils for biofuel production. Ind Crops Prod 62:318–322. https://doi.org/10.1016/j.indcrop.2014.09.003
de Albuquerque UP, de Medeiros PM, de Almeida ALS et al (2007) Medicinal plants of the caatinga (semi-arid) vegetation of NE Brazil: a quantitative approach. J Ethnopharmacol 114:325–354. https://doi.org/10.1016/j.jep.2007.08.017
Leal LB, Sousa GD, Seixas KB et al (2013) Determination of the critical hydrophile-lipophile balance of licuri oil from Syagrus coronata: application for topical emulsions and evaluation of its hydrating function. Brazilian J Pharm Sci 49:167–173. https://doi.org/10.1590/S1984-82502013000100018
Pereira RAG, Oliveira CJB, Medeiros AN et al (2010) Physicochemical and sensory characteristics of milk from goats supplemented with castor or licuri oil. J Dairy Sci 93:456–462. https://doi.org/10.3168/jds.2009-2315
Sheldon RA, Woodley JM (2018) Role of biocatalysis in sustainable chemistry. Chem Rev 118:801–838. https://doi.org/10.1021/acs.chemrev.7b00203
Tavares F, Petry J, Sackser PR et al (2018) Use of castor bean seeds as lipase source for hydrolysis of crambe oil. Ind Crops Prod. https://doi.org/10.1016/j.indcrop.2018.06.073
Ferreira MM, de Oliveira GF, Basso RC et al (2019) Optimization of free fatty acid production by enzymatic hydrolysis of vegetable oils using a non-commercial lipase from Geotrichum candidum. Bioprocess Biosyst Eng 42:1647–1659. https://doi.org/10.1007/s00449-019-02161-2
Hasan F, Shah AA, Hameed A (2006) Industrial applications of microbial lipases. Enzyme Microb Technol 39:235–251. https://doi.org/10.1016/j.enzmictec.2005.10.016
Sarmah N, Revathi D, Sridhar S et al (2017) Recent advances on sources and industrial applications of lipases. Biotechnol Prog 53:112–119. https://doi.org/10.1002/btpr
Kapoor M, Gupta MN (2012) Lipase promiscuity and its biochemical applications. Process Biochem 47:555–569. https://doi.org/10.1016/j.procbio.2012.01.011
Arana-Peña S, Carballares D, Berenguer-Murcia Á et al (2020) One pot use of combilipases for full modification of oils and fats: multifunctional and heterogeneous substrates. Catalysts 10:605
Lerin LA, Loss RA, Remonatto D et al (2014) A review on lipase-catalyzed reactions in ultrasound-assisted systems. Bioprocess Biosyst Eng. https://doi.org/10.1007/s00449-014-1222-5
Ramani K, Saranya P, Jain SC, Sekaran G (2013) Lipase from marine strain using cooked sunflower oil waste: production optimization and application for hydrolysis and thermodynamic studies. Bioprocess Biosyst Eng. https://doi.org/10.1007/s00449-012-0785-2
Kamal MZ, Barrow CJ, Rao NM (2015) A computational search for lipases that can preferentially hydrolyze long-chain omega-3 fatty acids from fish oil triacylglycerols. Food Chem 173:1030–1036. https://doi.org/10.1016/j.foodchem.2014.10.124
Bisht M, Mondal D, Pereira MM et al (2017) Long-term protein packaging in cholinium-based ionic liquids: improved catalytic activity and enhanced stability of cytochrome c against multiple stresses. Green Chem. https://doi.org/10.1039/c7gc02011b
Islam MT, Biswas S, Bagchi R et al (2019) Ponicidin as a promising anticancer agent: Its biological and biopharmaceutical profile along with a molecular docking study. Biotechnol Appl Biochem. https://doi.org/10.1002/bab.1740
Hanke AT, Klijn ME, Verhaert PDEM et al (2016) Prediction of protein retention times in hydrophobic interaction chromatography by robust statistical characterization of their atomic-level surface properties. Biotechnol Prog. https://doi.org/10.1002/btpr.2219
Weiser D, Sóti PL, Bánóczi G et al (2016) Bioimprinted lipases in PVA nanofibers as efficient immobilized biocatalysts. Tetrahedron 72:7335–7342. https://doi.org/10.1016/j.tet.2016.06.027
Almeida LC, Barbosa MS, de Jesus FA et al (2020) Enzymatic transesterification of coconut oil by using immobilized lipase on biochar: an experimental and molecular docking study. Biotechnol Appl Biochem. https://doi.org/10.1002/bab.1992
Van der Borght J, Soetaert W, Desmet T (2012) Engineering the acceptor specificity of trehalose phosphorylase for the production of trehalose analogs. Biotechnol Prog 28:1257–1262. https://doi.org/10.1002/btpr.1609
Barbosa MS, Freire CCC, Almeida LC et al (2019) Optimization of the enzymatic hydrolysis of Moringa oleifera Lam oil using molecular docking analysis for fatty acid specificity. Biotechnol Appl Biochem 66:823–832. https://doi.org/10.1002/bab.1793
Andrade Mota D, dos Santos BM, Kleveston Schneider J et al (2021) Potential use of crude coffee silverskin oil in integrated bioprocess for fatty acids production. JAOCS, J Am Oil Chem Soc. https://doi.org/10.1002/aocs.12472
Chen Y, Cheong LZ, Zhao J et al (2019) Lipase-catalyzed selective enrichment of omega-3 polyunsaturated fatty acids in acylglycerols of cod liver and linseed oils: Modeling the binding affinity of lipases and fatty acids. Int J Biol Macromol 123:261–268. https://doi.org/10.1016/j.ijbiomac.2018.11.049
Brandão LM, d. S, Barbosa MS, Souza RL, et al (2020) Lipase activation by molecular bioimprinting: the role of interactions between fatty acids and enzyme active site. Biotechnol Prog. https://doi.org/10.1002/btpr.3064
Bhutada PR, Jadhav AJ, Pinjari DV et al (2016) Solvent assisted extraction of oil from Moringa oleifera Lam seeds. Ind Crops Prod 82:74–80. https://doi.org/10.1016/j.indcrop.2015.12.004
Nadkarni R (2007) Guide to ASTM test methods for the analysis of petroleum products and lubricants, 2nd edn. ASTM International, West Conshohocken
Schrag JD, Li Y, Cygler M et al (1997) The open conformation of a Pseudomonas lipase. Structure 5:187–202. https://doi.org/10.1016/S0969-2126(97)00178-0
Brzozowski AM, Savage H, Verma CS et al (2000) Structural origins of the interfacial activation in Thermomyces (Humicola) lanuginosa lipase. Biochemistry. https://doi.org/10.1021/bi0013905
Hermoso J, Pignol D, Kerfelec B et al (1996) Lipase activation by nonionic detergents. The crystal structure of the porcine lipase-colipase-tetraethylene glycol monooctyl ether complex. J Biol Chem. https://doi.org/10.1074/jbc.271.30.18007
Berman HM, Battistuz T, Bhat TN et al (2002) The protein data bank. Acta Crystallogr Sect D Biol Crystallogr 58:899–907. https://doi.org/10.1107/S0907444902003451
BIOVIA DS, (2016) Discovery studio modeling environment, release 2017. Dassault Systèmes, San Diego
Morris GM, Huey R, Lindstrom W et al (2009) AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 30:2785–2791. https://doi.org/10.1002/jcc
Trott O, Olson AJ (2010) Software news and update Autodock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455–461. https://doi.org/10.1002/jcc
Rooney D, Weatherley LR (2001) The effect of reaction conditions upon lipase catalysed hydrolysis of high oleate sunflower oil in a stirred liquid-liquid reactor. Process Biochem 36:947–953. https://doi.org/10.1016/S0032-9592(01)00130-3
Teixeira LF, Bôas RV, Oliveira PC, De Castro HF (2014) Effect of natural antioxidants on the lipase activity in the course of batch and continuous glycerolysis of babassu oil. Bioprocess Biosyst Eng. https://doi.org/10.1007/s00449-014-1144-2
Karmakar G, Ghosh P, Sharma B (2017) Chemically modifying vegetable oils to prepare green lubricants. Lubricants 5:44. https://doi.org/10.3390/lubricants5040044
Gomna A, N’Tsoukpoe KE, Le Pierrès N, Coulibaly Y (2019) Review of vegetable oils behaviour at high temperature for solar plants: stability, properties and current applications. Sol Energy Mater Sol Cells. https://doi.org/10.1016/j.solmat.2019.109956
Negi S (2019) Green bio-processes. Springer, Singapore
Melani NB, Tambourgi EB, Silveira E (2020) Lipases: from production to applications. Sep Purif Rev. https://doi.org/10.1080/15422119.2018.1564328
Javed S, Azeem F, Hussain S et al (2018) Bacterial lipases: a review on purification and characterization. Prog Biophys Mol Biol 132:23–34. https://doi.org/10.1016/j.pbiomolbio.2017.07.014
Segall SD, Artz WE, Raslan DS et al (2004) Ouricuri (Syagrus coronata) triacylglycerol analysis using HPLC and positive ion electrospray tandem MS. JAOCS 81:143–149. https://doi.org/10.1007/s11746-004-0872-0
Sánchez DA, Tonetto GM, Ferreira ML (2018) Burkholderia cepacia lipase: a versatile catalyst in synthesis reactions. Biotechnol Bioeng 115:6–24. https://doi.org/10.1002/bit.26458
Casas-Godoy L, Gasteazoro F, Duquesne S et al (2018) Lipases: an overview. Methods Mol Biol 1835:3–38
Ramos-de-la-Peña AM, Aguilar O (2020) High pressure processing of lipase (Thermomyces lanuginosus): kinetics and structure assessment. Eur J Lipid Sci Technol. https://doi.org/10.1002/ejlt.201900289
Eremeev LN, Zaitsev SY (2016) Porcine pancreatic lipase as a catalyst in organic synthesis. Mini Rev Org Chem 13:78–85. https://doi.org/10.2174/1570193x13666160225000520
Acknowledgements
The authors thank Dr. Adriano Aguiar Mendes from Departamento de Química, Universidade Federal de Alfenas, for help next step after this work. This study was financed in part by Coordenação de Aperfeiçoamento de Pessoal de Nível Superior [CAPES], Finance Code 001; Conselho Nacional de Desenvolvimento Científico e Tecnológico [CNPq]; and Fundação de Apoio à Pesquisa e à Inovação Tecnológica do Estado de Sergipe [FAPITEC/SE].
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
All the authors declare that there is no conflict of interest.
Ethical statement
The authors declare that there are no studies conducted with human participants or animals.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
de A. Rodrigues, C., Barbosa, M.S., dos Santos, J.C.B. et al. Computational and experimental analysis on the preferential selectivity of lipases for triglycerides in Licuri oil. Bioprocess Biosyst Eng 44, 2141–2151 (2021). https://doi.org/10.1007/s00449-021-02590-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00449-021-02590-y