Enrichment of pinolenic acid from pine nut oil via lipase-catalyzed ethanolysis with an immobilized Candida antarctica lipase

Biocatalysis and Biotransformation

Volumn 29, Issue 4, 2011, Pages 155-160

  Lee, Bo Mi ^a   Choi, Jong Hun ^a   Hong, Seung In ^a   Yoon, Sung Won ^a   Kim, Byung Hee ^b   Kim, Chong Tai ^c   Kim, Chul Jin ^c   Kim, Yangha ^d   Kim, In Hwan ^a  

^a Korea University   (South Korea)

^b Chung Ang University   (South Korea)

^c Korea Food Research Institute   (South Korea)

^d Ewha Womans University   (South Korea)

Author keywords

Candida antartica; Ethanolysis; Fatty acid ethyl ester; Lipase; Pine nut oil; Pinolenic acid

Indexed keywords

ANTARTICA; ETHANOLYSIS; FATTY ACID ETHYL ESTER; NUT OIL; PINOLENIC ACID;

BATCH REACTORS; CANDIDA; CATALYSIS; ESTERIFICATION; ESTERS; ETHANOL; GLYCEROL; ISOMERS; POLYUNSATURATED FATTY ACIDS; YEAST;

FATTY ACIDS;

FATTY ACID ESTER; FUNGAL ENZYME; PINOLENIC ACID; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VEGETABLE OIL;

ARTICLE; BIOCATALYST; CANDIDA ANTARCTICA; CATALYSIS; ENZYME SPECIFICITY; NUT; PINE NUT;

CANDIDA; CANDIDA ANTARCTICA;

EID: 79960769710     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242422.2011.590983     Document Type: Article

References (33)

1. Asset G, Staels B, Wolff RL, Bauge E, Madj Z, Fruchart JC, Dallongeville J. 1999. Effects of Pinus pinaster and Pinus koraiensis seed oil supplementation on lipoprotein metabolism in the rat. Lipids 34:39-44. (Pubitemid 29098309)
2. Asset G, Leroy A, Bauge E, Wolff RL, Fruchart JC, Dallongeville J. 2000. Effects of dietary maritime pine ( Pinus pinaster )-seed oil on high-density lipoprotein levels and in vitro cholesterol effl ux in mice expressing human apolipoprotein A-I. Br J Nutr 84: 353-360.
3. Destaillats F, Angers P, Wolff RL, Arul J. 2001. Regiospecifi c analysis of conifer seed triacylglycerols by gas-liquid chromatography with particular emphasis on delta5-olefi nic acids. Lipids 36:1247-1254. (Pubitemid 34007979)
4. Gunstone FD. 1999. Enzymes as biocatalysts in the modifi cation of natural lipids. J Sci Food Agric 79:1535-1549. (Pubitemid 29429066)
5. 13C nuclear magnetic resonance spectroscopy. J Am Oil Chem Soc 73:1611-1613. (Pubitemid 126525448)
6. Gunstone FD, Seth S, Wolff RL. 1995. The distribution of à 5 polyene acids in some pine seed oils between the à-and â-chains by 13 C-NMR spectroscopy. Chem Phys Lipids 78: 89-96.
7. Hughes GM, Boyland EJ, Williams NJ, Mennen L, Scott C, Kirkham TC, Harrold JA, Keizer HG, Halford JC. 2008. The effect of Korean pine nut oil (PinnoThin™ ) on food intake, feeding behaviour and appetite: a double-blind placebo-controlled trial. Lipids Health Dis 7:6.
8. Ikeda I, Oka T, Koba K, Sugano M, Lie Ken Jie MS. 1992. 5 c ,11 c ,14 c -Eicosatrienoic acid and 5 c ,11 c ,14 c ,17 c -eicosatetraenoi acid of Biota orientalis seed oil affect lipid metabolism in the rat. Lipids 27:500-504.
9. Irimescu R, Furihata K, Hata K, Iwasaki Y, Yamane T. 2001. Utilization of reaction medium-dependent regiospecifi city of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryloyl- 2-docosahexaenoyl (or eicosapentaenoyl) glycerol. J Am Oil Chem Soc 78:285-290.
10. Irimescu R, Iwasaki Y, Hou CT. 2002. Study of TAG ethanolysis to 2-MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG. J Am Oil Chem Soc 79:879-883.
11. Iwasaki Y, Yamane T. 2000. Enzymatic synthesis of structured lipids. J Mol Catal B: Enym 10:129-140. (Pubitemid 30479829)
12. Lee JW, Lee KW, Lee SW, Kim IH, Rhee C. 2004. Selective increase in pinolenic acid (all- cis -5,9,12-18:3) in Korean pine nut oil by crystallization and its effect on LDL-receptor activit .Lipids 39:383-387. (Pubitemid 38971752)
13. Luddy FE, Barford RA, Herb SF, Magidman P, Riemenschneider RW. 1964. Pancreatic lipase hydrolysis of triglycerides by a semimicro technique. J Am Oil Chem Soc 41:693-696.
14. Namal Senanayake SPJ, Shahidi F. 1999. Enzymatic incorporation of docosahexaenoic acid into borage oil. J Am Oil Chem Soc 76:1009-1015. (Pubitemid 30503493)
15. Namal Senanayake SPJ, Shahidi F. 2002. Lipase-catalyzed incorporation of docosahexaenoic acid (DHA) into borage oil: optimization using response surface methodology. Food Chem 77: 115-123. (Pubitemid 34230394)
16. Pasman WJ, Heimerikx J, Rubingh CM, van den Berg R, O'Shea M, Gambelli L, Hendriks HF, Einerhand AW, Scott C, Keizer HG, Mennen LI. 2008. 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 7:10
17. Piyatheerawong W, Iwasaki Y, Yamane T. 2005. Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography. J Chromatogr A 1068:243-248. (Pubitemid 40354187)
18. Rogalska E, Cudrey C, Ferrato F, Verger R. 1993. Stereoselective hydrolysis of triglycerides by animal and microbial lipases. Chirality 5:24-30. (Pubitemid 23123047)
19. Seriburi V, Akoh C. 1998. Enzymatic transesterifi cation of triolein and stearic acid and solid fat content of their products. J Am Oil Chem Soc 75:511-516. (Pubitemid 128562387)
20. Shimada Y, Ogawa J, Watanabe Y, Nagao T, Kawashima A, Kobayashi T, Shimizu S. 2003. Regiospecifi c analysis by ethanolysis of oil with immobilized Candida antarctica lipase. Lipids 38:1281-1286. (Pubitemid 38129775)
21. Skakovskii ED, Tychinskaya LY, Gaidukevich OA. Klyuev AY, Kulakova AN, Petlitskaya NM, Rykove SV. 2007. NMR analysis of oils from pine nuts ( Pinus sibirica ) and seeds of common pine ( Pinus silvestris L.). J Appl Spectrosc 74:584-588.
22. Soumanou MM, Bornscheuer UT, Schmid U, Schmid RD. 1999. Crucial role of support and water activity on the lipase-catalyzed synthesis of structured triglycerides. Biocatal Biotransformation 16:443-459. (Pubitemid 29094927)
23. Sugano M, Ikeda I, Wakamatsu K, Oka T. 1994. Infl uence of Korean pine ( Pinus koraiensis )-seed oil containing cis -5, cis -9, cis -12-octadecatrienoic acid on polyunsaturated fatty acid metabolism, eicosanoid production and blood pressure of rats. Br J Nutr 72:775-783. (Pubitemid 24362453)
24. Takagi T, Itabashi Y. 1982. cis -5-Olefi nic unusual fatty acids in seed lipids of gymnospermae and their distribution in triacylglycerols. Lipids 17:716-723.
25. Wang A, Loo R, Chen Z, Dennis EA. 1997. Regiospecifi city and catalytic triad of lysophospholipase I. J Biol Chem 272:22030-22036. (Pubitemid 27382827)
26. Watanabe Y, Shimada Y, Sugihara A, Tominaga Y. 1999. Stepwise ethanolysis of tuna oil using immobilized Candida Antarctica lipase. J Biosci Bioeng 88:622-626. (Pubitemid 30046430)
27. Watanabe Y, Nagao T, Shimada Y. 2009. Control of the regiospecifi city of Candida antarctica lipase by polarity. N Biotechnol 26:23-28.
28. Wolff RL, Bayard CC. 1995. Fatty acid composition of some pine seed oils. J Am Oil Chem Soc 72:1043-1046.
29. Wolff RL, Christie WW, Coakley D. 1997a. Bishomopinolenic (7,11,14-20:3) acid in pinaceae seed oils. J Am Oil Chem Soc 74:1583-1586. (Pubitemid 127638971)
30. Wolff RL, Dareville E, Martin JC. 1997b. Positional distribution of à 5-olefi nic acids in triacylglycerols from conifer seed oils: general and specifi c enrichment in the sn- 3 position. J Am Oil Chem Soc 74:515-523. (Pubitemid 127553529)
31. Wolff RL, Comps B, Deluc LG, Marpeau AM. 1998. 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 75:45-50. (Pubitemid 128553433)
32. Wolff RL, Christie WW, Pedrono F, Marpeau AM, Tsevegsuren N, Aitzetmuller K, Gunstone FD. 1999. Delta5-olefi nic acids in the seed lipids from four Ephedra species and their distribution between the alpha and beta positions of triacylglycerols. Characteristics common to coniferophytes and cycadophytes. Lipids 34:855-864. (Pubitemid 29439836)
33. Wolff RL, Lavialle O, Pedrono F, Pasquier E, Deluc LG, Marpeau AM, Aitzetmuller K. 2001. Fatty acid composition of Pinaceae as taxonomic markers. Lipids 36: 439-451. (Pubitemid 32550044)