Grasas y Aceites, Vol 66, No 2 (2015)

Nutritional enrichment of vegetable oils with long-chain n-3 fatty acids through enzymatic interesterification with a new vegetable lipase


https://doi.org/10.3989/gya.0715142

J. S. Sousa
Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Biotecnologia Microbiana - Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Bioquímica Nutricional e de Alimentos, Brazil

A. G. Torres
Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Bioquímica Nutricional e de Alimentos, Brazil

D. M.G. Freire
Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Biotecnologia Microbiana, Brazil

Abstract


The aim of the present work was to produce vegetable oils enriched with long-chain n-3 fatty acids of nutraceutical interest, through an enzyme-catalyzed interesterification with a new lipase, from physic nut (Jatropha curcas L.). The Vegetable Lipase Powder (biocatalyst) called VLP, which has never been applied in functional foods, was obtained from the physic nut seed, and efficiently hydrolyzed the 95% of waste fish oil in 24 h. Urea precipitation was used to concentrate polyunsaturated fatty acids (PUFA) and was further interesterified with oils of different sources by means of enzymatic catalysis. After the interesterification reaction, which was also catalyzed by the VLP, the PUFA content in coconut oil increased almost ten-fold from 1.8% to 17.7%. In palm oil, the PUFA content increased two-fold from 10.5% to 21.8%, while in olive oil the level of PUFA increased from 8.6% to 21.3%. The mixture of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) (3.7% to 3.9%) was incorporated into the triacylglycerol fraction of each of the coconut, palm and olive oils. Through the hydroesterification (hydrolysis followed by interesterification) all the interesterified vegetable oils tested presented sufficient EPA and DHA levels to satisfy the levels recommended for intake by human adults in one tablespoon.

Keywords


Interesterification; Jatropha curcas L.; Lipase; Polyunsaturated fatty acids; Structured lipids

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References


Akoh CC. 1995. Structured lipids – Enzymatic approach. Inform 6, 1055–1061.

Auerbach MH, Klemann LP, Heydinger JA. 2001. Reducedenergy lipids, in Structured and Modified Lipids, Gunstone, FD, ed, Marcel Dekker, New York, pp. 485–510.

Brigelius-Flohé R, Traber MG. 1999. Vitamin E: Function and metabolism. Fed. Am. Soc. Exp. Biol. J. 13, 1145–1155.

Cavalcanti EDC, Maciel FM, Villeneuve P, Lago, RCA, Machado OLT, Freire DMG. 2007. Acetone power from dormant seeds of Ricinus communis L. Appl. Biochem. Biotechnol. 137, 57–65. http://dx.doi.org/10.1007/s12010-007-9039-1 PMid:18478376

Connor WE. 2000. Importance of n-3 fatty acids in health and disease. Am. J. Clin. Nutr. 71, 171–175.

Embrandiri A, Ibrahim MH, Singh RP. 2013. Palm Oil Mill Wastes Utilization; Sustainability in the Malaysian Context. IJSRP 3, 1–7.

Fajardo AR, Akoh CC, Lai OM. 2002. Lipase-catalysed incorporation of n-3 PUFA into palm oil. J. Am. Oil Chem. Soc. 80, 1197–1200. http://dx.doi.org/10.1007/s11746-003-0842-6

FAO/WHO. 2008. Interim Summary of Conclusions and Dietary Recommendations on Total Fat & Fatty Acids—From the Joint FAO/WHO Expert Consultation on Fats and Fatty Acids in Human Nutrition, WHO HQ, Geneva, Switzerland.

Foster R, Williamson CS, Lunn J. 2009. Culinary oils and their health effects. Br. Nut. Found. Nut. Bull. 34, 4–47. http://dx.doi.org/10.1111/j.1467-3010.2008.01738.x

Frankel, EN. 2011. Nutritional and Biological Properties of Extra Virgin Olive Oil. J. Agric. Food Chem. 59, 785–792. http://dx.doi.org/10.1021/jf103813t PMid:21210703

Freire DMG, Castilho LC. 2008. Enzimas em Biotecnologia: Produção, aplicação e mercado, Ed. Interciência, Rio de Janeiro, pp. 369–385.

Freire DMG, Teles EMF, Bon EPS, Sant'anna GL. 1997. Lipase production by Penicillium restrictum in a bench-scale fermenter effect of carbon and nitrogen nutrition, agitation and aeration. Appl. Biochem. Biotechnol. 64, 409–421. http://dx.doi.org/10.1007/BF02920442 PMid:18576099

Gámez-Meza N, Noriega-Rodríguez JA, Medina-Juárez LA, Ortega-García J, Monroy-Rivera J, Toro-Vázquez FJ, García HS, Angulo-Guerrero O. 2003. Concentration of eicosapentaenoic acid and docosahexaenoic acid from fish oil by hydrolysis and urea complexation. Food Res. Int. 36, 721–727. http://dx.doi.org/10.1016/S0963-9969(03)00052-8

Goh SH, Choo YM, Ong SH. 1985. Minor constituents of palm oil. J. Am. Oil Chem. Soc. 62, 237–240. http://dx.doi.org/10.1007/BF02541384

Gopala KAG, Gaurav R, Ajit SB, Prasanth KPK, Preeti C. 2010. Coconut Oil: Chemistry, Production and Its Applications - A Review. Indian Cocon. J. 15–27.

Gunstone FD. 1998. Movements towards tailor-made fats. Prog. Lipid Res. 37 (5), 277–305. http://dx.doi.org/10.1016/S0163-7827(98)00012-5

Gunstone FD, Harwood JL, Dijkstra AJ. 2007. The Lipid Handbook - Third Edition CRC Press Taylor & Francis Group. PMid:17761064 PMCid:PMC2151791

Haraldsson GG, Hjaltason B. 2001. Fish oils as sources of important polyunsaturated fatty acids. Structured and Modified Lipids, Gunstone FD, ed.; Dekker: New York, pp. 313–350.

Hee-Guk B, Tae-Kil E, Won-Kyo J, Se-Kwon K. 2007. Lipase catalyzed production of monoacylglycerols by the esterification of fish oil fatty acid with glycerol. Biotechnol. Bioprocess Eng. 12, 484–490.

Hernández-Martín E, Otero C. 2008. Differente enzyme requirements for the syntehesis of biodiesel: Novozym 435 and Lipozyme TM IM. Bioresource Technol. 99, 277–286. http://dx.doi.org/10.1016/j.biortech.2006.12.024 PMid:17321130

Institute of Medicine. 2005. Dietary Reference Intakes for Energy and Macronutrients. Washington, DC: National Academy Press.

Jennings BH, Akoh CC. 2001. Lipase catalyzed modification of fish oil to incorporate capric acid. Food Chem. 72, 273–278. http://dx.doi.org/10.1016/S0308-8146(00)00266-1

Kasai M, Nosaka N, Maki H, Negishi S, Aoyama T, Nakamura M, Suzuki Y, Tsuji H, Uto H, Okazaki M, Kondo K. 2003. Effect of dietary medium and long-chain triacylglycerols (MLCT) on the accumulation of body fat in healthy humans. Asia Pacific J. Clin. Nutr. 12, 151–160. PMid:12810404

Klinkesorn U, H-Kittikun A, Chinachoti P, Sophanodora P. 2004. Chemical transesterification of tuna oil to enriched omega-3 polyunsaturated fatty acids. Food Chem. 87, 415–421. http://dx.doi.org/10.1016/j.foodchem.2003.12.021

Lee DH, Kim JM, Shin HY, Kang SW, Kim SW. 2006. Biodiesel production using a mixture of immobilized Rhizopus oryzae and Candida rugosa lipases. Biotechnol. Bioprocess Eng. 11, 522–525. http://dx.doi.org/10.1007/BF02932077

Lee KT, Akoh CC. 1998. Characterization of Enzymatically Synthesized Structured Lipids Containing Eicosapentaenoic, Docosahexaenoic and Caprylic Acids. J. Am. Oil Chem. Soc. 75, 495–499. http://dx.doi.org/10.1007/s11746-998-0253-y

Lepage G, Roy CC. 1986. Direct transesterification of all classes of lipids in a one-step reaction. J. Lipid Res. 27, 114–120. PMid:3958609

Lucas A, Quinlan P, Abrams S, Ryan S, Meah S, Lucas PJ. 1997. Randomized controlled trial of a synthetic triglyceride milk formula for preterm infants, Archives of Disease in Childhood: Fetal & Neonatal. 77, 128–184.

Macrae AR, Hammond RC. 1985. Present and future applications of lipases. Biotechnol. Genet. Eng. Rev. 3, 193–217. http://dx.doi.org/10.1080/02648725.1985.10647813

Molendi-Coste O, Legry V, Leclercq, IA. 2011. Why and How Meet n-3 PUFA Dietary Recommendations? Gastroenterol. Res. Prac. ID 364040, 11. http://dx.doi.org/10.1155/2011/364040

Mu H, Xu X, Høy CE. 1998. Production of specific structured triacylglycerols by lipase-catalyzed interesterification in a laboratory scale continuous reactor. J. Am. Oil Chem. Soc. 75, 1187–1193. http://dx.doi.org/10.1007/s11746-998-0310-6

Nagao T, Watanabe H, Goto N, Onizawa K, Taguchi H, Matsuo N, Yasukawa T, Tsushima R, Shimasaki H, Itakura H. 2000. Dietary Diacylglycerol Suppresses Accumulation of Body Fat Compared to Triacylglycerol in Men in a Double-Blind Controlled Trial. J. Nutr. 130, 792–797. PMid:10736331

Oh JE, Lee KW, Park HK, Kim JY, Kwon KI, Kim JW, Kim HR, Kim IH. 2009. Lipase Catalyzed Acidolysis of Olive oil with Capric Acid: Effect of Water Activity on incorporation and Acyl Migration. J. Agric. Food Chem. 57 (19), 9280–9283. http://dx.doi.org/10.1021/jf9023245 PMid:19728714

Osborn HT, Akoh CC. 2002. Structured lipids - novel fats with medical, nutraceutical, and food applications. Compr. Rev. Food Sci. Food Safety 1, 93–103. http://dx.doi.org/10.1111/j.1541-4337.2002.tb00010.x

Owen RW, Giacosa A, Hull WE, Haubner R, Wu.rtele G, Spiegelhalder B, Bartsch H. 2000. Olive oil consumption and health: the possible role of antioxidants. Lancet Oncol. 1, 107–112. http://dx.doi.org/10.1016/S1470-2045(00)00015-2

Rao R, Manohar B, Sambaiah K, Lokesh, BR. 2002. Enzymatic acidolysis in hexane to produce n-3 or n-6 FA-enriched structured lipids from coconut oil: Optimization of reactions by response surface methodology. J. Am. Oil Chem. Soc. 79 (9), 885–890. http://dx.doi.org/10.1007/s11746-002-0574-7

Simopoulos AP. 2001. n-3 Fatty acids and human health: Defining strategies for public policy. Lipids 36, 83–89. http://dx.doi.org/10.1007/s11745-001-0687-7

Sousa JS, Cavalcanti EDC, Aranda DAG, Freire, DMG. 2010. Application of lipase from the physic nut (Jatropha curcas L.) to a new hybrid (enzyme/chemical) hydroesterification process for biodiesel production. J. Mol. Catal. B Enzym. 65, 133–137. http://dx.doi.org/10.1016/j.molcatb.2010.01.003

Sreenivasan B. 1978. Interesterification of fats. J. Am. Oil Chem. Soc. 55, 796–805. http://dx.doi.org/10.1007/BF02682651

Stark AH, Madar Z. 2002. Olive oil as a functional food: epidemiology and nutritional approaches. Nutrition Rev. 60, 170–176. http://dx.doi.org/10.1301/002966402320243250 PMid:12078915

Stillwell W. 2006. The role of polyunsaturated lipids in membrane raft function. Scand. J. Food Nutr. 50 (2), 107–113. http://dx.doi.org/10.1080/17482970601066165

Wanasundara UN, Shahidi F. 1999. Concentration of omega 3-polyunsaturated fatty acids of seal blubber oil by urea complexation: optimization of reaction conditions. Food Chem. 65, 41–49. http://dx.doi.org/10.1016/S0308-8146(98)00153-8

Wu JC, Low WR, Leng Y, Chow Y, Li R, Talukder M, Choi WJ. 2006. Ketoprofen resolution by enzymatic esterification and hydrolysis of the ester product. Biotechnol. Bioprocess Eng. 11, 211–214. http://dx.doi.org/10.1007/BF02932032

Yankah VV, Akoh CC. 2000. Lipase catalyzed acidolysis of tristearin with oleic or caprylic acids to produce structured lipids. J. Am. Oil Chem. Soc. 77, 495–500. http://dx.doi.org/10.1007/s11746-000-0079-4




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