Synthesis of monoacylglycerol containing pinolenic acid via stepwise esterification using a cold active lipase

Biotechnology Progress

Volumn 28, Issue 5, 2012, Pages 1218-1224

  Pyo, Young Gil ^a   Hong, Seung In ^a   Kim, Yangha ^b   Kim, Byung Hee ^c   Kim, In Hwan ^a  

^a Korea University   (South Korea)

^b Ewha Womans University   (South Korea)

^c Chung Ang University   (South Korea)

Author keywords

Diacylglycerol; Esterification; Glycerol; Monoacylglycerol; Penicillium camembertii; Pinolenic acid

Indexed keywords

COLD-ACTIVE; DIACYLGLYCEROL; EFFECTS OF TEMPERATURE; ENZYME LOADING; ESTERIFICATION ACTIVITIES; HIGH PURITY; LIPASE-CATALYZED; MOLAR RATIO; MONOACYLGLYCEROL; NUT OIL; OPTIMUM TEMPERATURE; PENICILLIUM CAMEMBERTII; SUB-ZERO TEMPERATURES;

CURRICULA; ENZYMES; ESTERIFICATION; ESTERS; GLYCEROL; LIPIDS; POLYUNSATURATED FATTY ACIDS; REACTION RATES; TEMPERATURE; VACUUM;

LOADING;

5,9,12 OCTADECATRIENOIC ACID; 5,9,12-OCTADECATRIENOIC ACID; FUNGAL PROTEIN; LINOLENIC ACID; MONOACYLGLYCEROL; TRIACYLGLYCEROL LIPASE; VEGETABLE OIL;

ARTICLE; BIOCATALYSIS; CHEMISTRY; COLD; ENZYMOLOGY; ESTERIFICATION; NUT; PENICILLIUM; PINE; SYNTHESIS;

BIOCATALYSIS; COLD TEMPERATURE; ESTERIFICATION; FUNGAL PROTEINS; LINOLENIC ACIDS; LIPASE; MONOGLYCERIDES; NUTS; PENICILLIUM; PINUS; PLANT OILS;

ARACHIS; PENICILLIUM; PENICILLIUM CAMEMBERTI;

EID: 84867403114     PISSN: 87567938     EISSN: 15206033     Source Type: Journal    
DOI: 10.1002/btpr.1596     Document Type: Article

References (32)

1. Takagi T, Itabashi Y. cis-5-olefinic unusual fatty acids in seed lipids of gymnospermae and their distribution in triacylglycerols. Lipids. 1982; 17: 716-723.
2. Wolff RL, Marpeau AM. Δ5-Olefinic acids in the edible seeds of nut pines (Pinus cembroides edulis) from the United States. J Am Oil Chem Soc. 1997; 74: 613-614.
3. Imbs AB, Nevshupova NV, Pham LQ. Triacylglycerol composition of Pinus koraiensis seed oil. J Am Oil Chem Soc. 1998; 75: 865-870.
4. Wolff RL, Comps B, Deluc LG, Marpeau AM. Fatty acids of the seeds from pine species of the Ponderosa-Banksiana and Halepensis sections. The peculiar taxonomic position of Pinus pinaster. J Am Oil Chem Soc. 1998; 75: 45-50.
5. Asset G, Bauge E, Wolff RL, Fruchart JC, Dallongeville J. Pinus pinaster oil affects lipoprotein metabolism in apolipoprotein E-deficient mice. J Nutr. 1999; 129: 1972-1978.
6. Pasman WJ, Heimerikx J, Rubingh CM, van den Berg R, O'Shea M, Gambelli L, Hendriks HFJ, Einerhand AW, Scott C, Keizer HG, Mennen LI. The effect of Korean pine nut oil on in vitro CCK release, on appetite sensations and on gut hormones in post-menopausal overweight women. Lipids Health Dis. 2008; 7: 10.
7. Hughes GM, Boyland EJ, Williams NJ, Mennen L, Scott C, Kirkham TC, Harrold JA, Keizer HG, Halford JC. The effect of Korean pine nut oil (PinnoThin) on food intake, feeding behaviour and appetite: a double-blind placebo-controlled trial. Lipids Health Dis. 2008; 7: 6.
8. Scott C, Pasman W, Heimerikx J, Rubingh C, van den Berg R, O'Shea M, Gambelli L, Hendriks H, Mennen L, Einerhand A. Pinnothin™ suppresses appetite in overweight women. Appetite. 2007; 49: 330-330.
9. Chen S, Hsu C, Li C, Lu J, Chuang L. Pinolenic acid inhibits human breast cancer MDA-MB-231 cell metastasis in vitro. Food Chem. 2011; 126: 1708-1715.
10. Ghamgui H, Miled N, Rebaï A, Karra-chaâbouni M, Gargouri Y. Production of mono-olein by immobilized Staphylococcus simulans lipase in a solvent-free system: optimization by response surface methodology. Enzyme Microb Technol. 2006; 39: 717-723.
11. Zhang Z, Goff HD. On fat destabilization and composition of the air interface in ice cream containing saturated and unsaturated monoglyceride. Int Dairy J. 2005; 15: 495-500.
12. Damstrup ML, Jensen T, Sparsø FV, Kiil SZ, Jensen AD, Xu X. Solvent optimization for efficient enzymatic monoacylglycerol production based on a glycerolysis reaction. J Am Oil Chem Soc. 2005; 82: 559-564.
13. Bornscheuer UT. Lipase-catalyzed syntheses of monoacylglycerols. Enzyme Microb Technol. 1995; 17: 578-586.
14. Fiametti KG, Rovani S, de Oliveira D, Corazza ML, Treichel H, Oliveira JV. Assessment of variable effects on solvent-free monoacylglycerol enzymatic production in AOT surfactant. Eur J Lipid Sci Technol. 2008; 110: 510-515.
15. Lauridsen JB. Food emulsifiers: surface activity, edibility, manufacture, composition, and application. J Am Oil Chem Soc. 1976; 53: 400-407.
16. Sonntag NOV. New developments in the fatty acid industry in America. J Am Oil Chem Soc. 1984; 61: 229-232.
17. Esmelindro ÂFA, Fiametti KG, Ceni G, Corazza ML, Treichel H, de Oliveira D, Oliveira JV. Lipase-catalyzed production of monoglycerides in compressed propane and AOT surfactant. J Supercrit Fluids. 2008; 47: 64-69.
18. Watanabe Y, Shimada Y, Yamauchi-Sato Y, Kasai M, Yamamoto T, Tsutsumi K, Tominaga Y, Sugihara A. Synthesis of MAG of CLA with Penicillium camembertii lipase. J Am Oil Chem Soc. 2002; 79: 891-896.
19. Chojnacka A, Gladkowski W, Kielbowicz G, Wawrzenczyk C. Enzymatic enrichment of egg-yolk phosphatidylcholine with alpha-linolenic acid. Biotechnol Lett. 2009; 31: 705-709.
20. Xu X, Mu H, Skands ARH, Høy CE, Adler-Nissen J. Parameters affecting diacylglycerol formation during the production of specific-structured lipids by lipase-catalyzed interesterification. J Am Oil Chem Soc. 1999; 76: 175-181.
21. Dudal Y, Lortie R. Influence of water activity on the synthesis of triolein catalyzed by immobilized Mucor miehei lipase. Biotechnol Bioeng. 1995; 45: 129-134.
22. Watanabe Y, Yamauchi-Sato Y, Nagao T, Yamamoto T, Ogita K, Shimada Y. Production of monoacylglycerol of conjugated linoleic acid by esterification followed by dehydration at low temperature using Penicillium camembertii lipase. J Mol Catal B: Enzym. 2004; 27: 249-254.
23. Lee SB, Kim K-J. Effect of water activity on enzyme hydration and enzyme reaction rate in organic solvents. J Ferment Bioeng. 1995; 79: 473-478.
24. Han JJ, Rhee JS. Lipase-catalyzed synthesis of lysophosphatidic acid in a solvent free system. Biotechnol Lett. 1995; 17: 531-536.
25. Rosu R, Iwasaki Y, Shimidzu N, Doisaki N, Yamane T. Enzymatic synthesis of glycerides from DHA-enriched PUFA ethyl ester by glycerolysis under vacuum. J Mol Catal B Enzym. 1998; 4: 191-198.
26. Adlercreutz P, Lyberg A, Adlercreutz D. Enzymatic fatty acid exchange in glycero-phospholipids. Eur J Lipid Sci Technol. 2003; 105: 638-645.
27. Xu X. Engineering of enzymatic reactions and reactors for lipid modification and synthesis. Eur J Lipid Sci Technol. 2003; 105: 289-304.
28. Dordick JS. Enzymatic catalysis in monophasic organic solvents. Enzyme Microb Technol. 1989; 11: 194-211.
29. Feller G, Thiry M, Gerday C. Nucleotide sequence of the lipase gene lip2 from the Antarctic psychrotroph Moraxella TA144 and site-specific mutagenesis of the conserved serine and histidine residues. DNA Cell Biol. 1991; 10: 381-388.
30. Russell NJ. Molecular adaptations in psychrophilic bacteria: potential for biotechnological applications. Adv Biochem Eng Biotechnol. 1998; 61: 1-21.
31. Rashid N, Shimada Y, Ezaki S, Atomi H, Imanaka T. Low-temperature lipase from psychrotrophic Pseudomonas sp. strain KB700A. Appl Environ Microbiol. 2001; 67: 4064-4069.
32. Cabot MC, Lumb RH. The activity of a low temperature lipase in the larvae of Sarcophaga bullata (Diptera:Sarcophagidae). Comp Biochem Physiol B. 1981; 68: 325-328.