PROPERTIES AND BIOTECHNOLOGICAL APPLICATIONS OF LIPASES FROM SEED OILS
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1 PROPERTIES AND BIOTECHNOLOGICAL APPLICATIONS OF LIPASES FROM SEED OILS Adriano Aguiar Mendes Instituto de Química, Universidade Federal de Alfenas Alfenas/MG - Brazil
2 Lipases Hydrolysis of ester bonds in tri-, di-, and monoacylglycerols to glycerol and free fatty acids. Organic media: esterification, transesterification and interesterification. Industrial applications: production of pharmaceuticals, agrochemicals, structured lipids, biolubricants, sugar esters, resolution of racemates, biopolymers, biodiesel, cosmetics and flavors. A.A. Mendes, P.C. Oliveira, H.F. de Castro. J. Mol. Catal. B: Enzym. 78 (2012)
3 Lipases: Interfacial activation R. Fernández-Lafuente. J. Mol. Catal. B: Enzym. 62 (2010)
4 Lipase Sources Microorganisms: bacteria and fungi (filamentous and yeasts). Tissue animals: porcine pancreas. Several plants: seed oils, cereals and latex. The most plant lipases used in biotransformation reactions seed oils and latex. R.W.M. Mounguengui, C. Brunschwig, B. Baréa, P. Villeneuve, J. Blin. Progress Energy Combust. Sci. 39 (2013)
5 Plant lipases Advantages They are available from natural sources (easy accessibility). Low cost and high substrate specificity. No requirement of immobilization step (naturally immobilized onto solid materials from seeds). Interesting alternative for commercial exploitation as industrial enzymes. P. Villeneuve. Eur. J. Lipid Sci. Technol. 105 (2003)
6 Plant Lipases Seed oils: castor bean (Ricinus communis), physic nut (Jatropha curcas L.), Rape (Brassica napus), sunflower (Helianthus annuus) soybean (Glycine max), etc. Cereals: rice bran (Oryza sativa), wheat germ (Triticum aestivum L.), barley (Hordeum vulgare), corn (Zea mays), etc. Latex: papaya (Carica papaya) and babaco (Vasconcellea heilbornii; syn. Carica pentagona). R.W.M. Mounguengui, C. Brunschwig, B. Baréa, P. Villeneuve, J. Blin. Progress Energy Combust. Sci. 39 (2013)
7 Plant Lipases These enzymes are found in dormant and germinated seeds. A.-L. Quettier, P.J. Eastmond. Plant Physiol. Biochem. 47 (2009)
8 Seed oil Lipases: Germination Hydrolytic Activity (IU/g crude extract) Passium fruit Corn Sunflower Castor bean Germination (h) Dormant physic nut Germinated physic nut Zymogram of hydrolysis of ester catalyzed by VEED (lanes 1, 2 and 3) and by VEEG (lines 4, 5 and 6). K.C. Santos, D.M.J. Cassimiro, M.H.M. Avelar, D.B. Hirata, H.F. de Castro, R. Fernández-Lafuente, A. A. Mendes. Ind. Crops Prod. 49 (2013) J.S. Sousa, E.D.C. Oliveira, D.A.G. Aranda, D.M.G. Freire. J. Mol. Catal. B: Enzym. 65 (2010)
9 N.K. Sana, I. Hossin, E.M. Haque, R.K. Shaha. Pakistan J. Biol. Sci. 7 (2004) T.H. Sanders, H.E. Pattee. Lipids 10 (1975) P.P. Gadge, S.D. Madhikar, J.N. Yewle, U.U. Jadhav, A.D. Chougale, V.P. Zambare, M.V. Padul. Am. J. Biochem. Biotechnol. 7 (2011) Seed Oil Lipases ph 100 Lipase from germinated Physic nut seeds: ph 8.0 (Santos et al., 2010). Relative activity (%) Castor bean Sunflower Corn Passion fruit Lipase from germinated rape seeds: ph 7.0 (Sana et al., 2004). Lipase from germinated peanut seeds: ph 8.5 (Sanders and Pattee, 1975). Lipase from germinated soybean seeds: ph 8.0 (Gadge et al., 2011). ph
10 K.C. Santos, D.M.J. Cassimiro, M.H.M. Avelar, D.B. Hirata, H.F. de Castro, R. Fernández-Lafuente, A. A. Mendes. Ind. Crops Prod. 49 (2013) Seed Oil Lipases Temperature Relative activity (%) Corn Castor bean Sunbflower Passion fruit Temperature ( C) Lipase from germinated Physic nut seeds: ph 40 C (Santos et al., 2010). Lipase from germinated rape seeds: 37 C (Sana et al., 2004). Lipase from germinated soybean seeds: 24 C (Gadge et al., 2011).
11 Hydrolytic activity of plant lipases K.C. Santos, D.M.J. Cassimiro, M.H.M. Avelar, D.B. Hirata, H.F. de Castro, R. Fernández-Lafuente, A. A. Mendes. Ind. Crops Prod. 49 (2013)
12 P.J. Eastmond. J. Biol. Chem. 279 (2004) Substrate specificity Castor bean lipase (Hydrolysis)
13 Preparation of Delipidated Extracts Sterilization with 0.5% (v/v) NaClO Ratio 1:2 (%m/v) Endosperm tissue removal Trituration (e.g. knife-mill) Cold acetone (20% m/v) Delipidation with cold acetone Ratio 1:5 (%m/v) Filtration Particle size classification K.C. Santos, D.M.J. Cassimiro, M.H.M. Avelar, D.B. Hirata, H.F. de Castro, R. Fernández-Lafuente, A. A. Mendes. Ind. Crops Prod. 49 (2013)
14 Biotechnological Applications Hydrolysis of Triacylglycerols Free fatty acids (FFA): important class of compounds for the production of esters of industrial interest (biodiesel, biolubricants, sugar esters, plasticizers, flavor esters, additives for diesel fuels, etc.).
15 Hydrolysis of Canola Oil Biocatalyst: 2% m/v of enzymatic crude extract from dormant castor bean seeds. Reaction time: 2 h. Stirring: 1000 rpm (stirred-tank reactor). ph: 4.5 Reaction temperature: 37.5 C. M.H.M. Avelar, D.M.J. Cassimiro, K.C. Santos, R.C.C. Domingues, H.F. de Castro, A. A. Mendes. Ind. Crops Prod. 44 (2013)
16 Hydrolysis of Soybean, Palm and Babassu oils Hydrolysis (%) Babassu oil Palm oil Soybean oil Soybean oil: 44.1% m/m oil:buffer, 37 C, 2.0% m/m of crude lipase extract and 100 mm sodium acetate ph 4.5. Babassu and palm oils: 15.9% m/m oil:buffer, 43.5 C, 3.0% m/m of crude lipase extract and 100 mm sodium acetate ph 4.5. Reaction time (min) K.C. Santos, D.M.J. Cassimiro, M.H.M. Avelar, D.B. Hirata, H.F. de Castro, R. Fernández-Lafuente, A. A. Mendes. Ind. Crops Prod. 49 (2013)
17 Ester synthesis - Hydroesterification Hydrolysis Triacylglicerols + 3 H 2 O 3 FFA + Glycerol Esterification FFA + Alcohol Ester + H 2 O A.P.P. Bressani, K.C.A. Garcia, D.B. Hirata, A.A. Mendes. Bioprocess Biosyst. Eng. 38 (2015) E.C.G. Aguieiras, E.D. C. Oliveira, A.M. de Castro, M.A.P. Langone, D.M.G. Freire. Fuel 135 (2014)
18 A.P.P. Bressani, K.C.A. Garcia, D.B. Hirata, A.A. Mendes. Bioprocess Biosyst. Eng. 38 (2015) Biolubricant Synthesis Hydrolysis Step of Macaw Palm Oil Hydrolysis (%) % m/m 40% m/m 46.8% m/m Reaction time (min) Hydrolysis: 35 C, 6.0% m/m of crude lipase extract from dormant castor bean seeds, ph 4.5 and stirring of 1000 rpm (stirred-tank reactor). Esterification reaction: Esterification of purified FFA with hexanol catalyzed by immobilized Thermomyces lanuginosus lipase on polyhydroxybutyrate particles (conversion 92% after 15 min of reaction).
19 E.C.G. Aguieiras, E.D. C. Oliveira, A.M. de Castro, M.A.P. Langone, D.M.G. Freire. Fuel 135 (2014) Biodiesel Synthesis Hydrolysis Step of Macaw Palm Oil Hydrolysis: Complete hydrolysis of macaw palm oil at 50% m/v after 6 of reaction catalyzed by crude lipase extract from dormant castor bean seeds (7.8 U/g of oil), ph 4, 30 C under continuous stirring. Esterification reaction: Esterification of purified FFA with ethanol (molar ratio ethanol:ffa 2:1) catalyzed by several lipases at 40 C (conversion 91% after 8 h of reaction).
20 Biodiesel Synthesis Hydrolysis Step of Physic Nut Oil Hydrolysis: 97% hydrolysis using 10% m/m of germinated physic nut seeds at ph 8.0, 10% m/m of oil at 40 C after 2 h of reaction. Esterification reaction: Esterification of purified FFA with methanol/ethanol (molar ratio alcohol:ffa 3:1) catalyzed by niobic acid at 200 C (conversion 97% after 2 h of reaction). J.S. Sousa, E.D.C. Oliveira, D.A.G. Aranda, D.M.G. Freire. J. Mol. Catal. B: Enzym. 65 (2010)
21 Esterification Germinated Rape Seeds Flavor and fragrance esters: used in food, beverage, cosmetic, pharmaceutical and personal care industries. Experimental conditions: Esterification reaction at 40 C for 48 h in hexane medium containing 0.25 M of alcohols and 0.25 M caproic acid, and 50 g/l of rape seed lipase (4-6 days of germination). Maximum ester conversion: 1-butanol (88%) isoamyl alcohol (93%) (Z)-3-hexen-1-ol (88%) M. Liaquat. J. Mol. Catal. B: Enzym. 68 (2011)
22 Esterification Castor Bean Lipase Structured Lipids (SLs) Experimental conditions: Reaction temperature of 40 C, reaction time of 4 h, 20% m/m of castor bean lipase (dormant) previously incubated at ph 4.0 by 4 h, and molar ratio glycerol:ffa of 1:3. Maximum ester conversion: 52.37% TAG. Several esters Experimental conditions: 37 C, castor bean lipase (germinated seeds after 1 day), molar ratio alcohol:ffa (2:1) in hexane medium after 6 h of reaction. Maximum ester conversion: 90% using several alcohols (C1-C4) and stearic/oleic acids. M. Tüter. J. Am. Oil Chem. Soc. 75 (1998) E.R. Su, Y. Zhou, P.Y. You, D.Z. Wei. J. Shangai Univ. 1 4 (2010)
23 J.S. Sousa, A.G. Torres, D.M.G. Freire. Grasas y Aceites 66 (2015) e071. Interesterification Germinated Physic Nut Seeds Structured Lipids (SLs): Enriched of vegetable oils with PUFAs (EPA and DHA) from fish oil (acidolysis). Experimental conditions: Reaction temperature of 40 C, reaction time of 24 h, 10% m/m of biocatalyst, molar ratio oil:ffa of 1:3 in hexane medium. ICO: Interesterified coconut oil. IPO: Interesterified palm oil. IOO: Interesterified olive oil.
24 Future Perspectives Extraction, Purification and Immobilization by Different Protocols: Modulation of their catalytic properties (stability, selectivity and catalytic activity). Molecular Genetic Technology: use of bacteria and yeasts as host organisms to provide sufficient amounts of the enzyme.
25 Muchas Gracias s:
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