Preparation of Novel Structured Lipids
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1 JOURNAL OF OLEO SCIENCE Copyright 2005 by Japan Oil Chemists Society JOS Setsuko HARA, Ayato KANDA and Yoichiro TOTANI Faculty of Engineering, Seikei University 3-1 Kichijoji-kitamachi 3, Musashino-shi, Tokyo , JAPAN Edited by K. Miyashita, Hokkaido Univ., and accepted April 18, 2005 (received for review March 7, 2005) Abstract: Structured lipids with n-6/n-3 polyunsaturated fatty acids PUFA or medium chain fatty acids MC at optimal ratios were prepared by lipase catalyzed transacylation of tuna orbital oil consisting of about 40 n-3 PUFA such as eicosapentaenoic acid EPA and docosahexaenoic acid DHA with purified linoleic acid or MC, such as caprylic, capric, and lauric acids, at 60. 1, 3- Specific immobilized lipases of Lipozyme TL-IM and Lipozyme RM- IM originated from Thermomyces lanuginosus and Rhizomucor miehei were used in the preparation, respectively. By controlling enzyme amount from IUN for Lipozyme TL-IM and 1-12 BAUN for Lipozyme RM-IM with reaction time from 4 to 24h, structured lipids at n-6/n-3 ratios from 1.3 till 6.9 were easily prepared by the reaction of tuna orbital oil with highly purified linoleic acid. MC was introduced into tuna orbital oil at various MC/n-3 PUFA ratios such as for caprylic, for capric, and for lauric acids, respectively during transacylation for 32 h. Lipozyme RM-IM was clearly shown a better enzyme for the present transacylation, compared to Lipozyme TL-IM in consideration of the above ratio values and triglycerides recovery. Key words: transacylation, Lipozyme TL-IM, Lipozyme RM-IM, n-3 PUFA, n-6 PUFA, MC Correspondence to: Setsuko HARA, Faculty of Engineering, Seikei University, 3-1 Kichijoji-kitamachi 3, Musashino-shi, Tokyo , JAPAN shara@ch.seikei.ac.jp Journal of Oleo Science ISSN print / ISSN online 473
2 S. Hara, A. Kanda and Y. Totani b Riozopus delemar Candida rugosa Fig Fig. 1 Preparation of Structured Lipids. 474
3 Table Thermomyces lanuginosus 75 Rhizomucor miehei m Table Table 1 Fatty Acid Composition of Substrates. Tuna Oil Linoleic Acid Caprylic Acid Capric Acid Lauric Acid Caprylic Acid 99.5 Capric Acid 99.3 Lauric Acid 99.1 Linoleic Acid (n-6 PUFA) EPA + DHA (n-3 PUFA) 39.4 Others
4 S. Hara, A. Kanda and Y. Totani Fig Fig Table Table Table Fig. 2 Procedure of Transacylation. Fig. 3 Effects of Enzyme Amounts on PUFA-TG Preparation Catalyzed by Lipozyme TL-IM or Lipozyme RM-IM. 476
5 Table 2 Comparison of n-6/n-3 Ratio of PUFA-TG Prepared. Lipozyme TL-IM Lipozyme RM-IM Effect of Enzyme Amounts Enzyme Amounts (Unit) 20 IUN 40 IUN 60 IUN 80 IUN 1 BAUN 4 BAUN 8 BAUN 12 BAUN Reaction Time (h) 8 8 PUFA Content (%) n-6/n-3 Ratio Enzyme Amounts 80 IUN 8 BAUN Effect of Reaction Time Reaction Time (h) 4 h 8 h 16 h 24 h 4 h 8 h 16 h 24 h PUFA Content (%) n-6/n-3 Ratio IUN: Interesterification Unit, BAUN: Batch Acidolysis Unit Fig. 4 6 Fig Fig Fig Fig. 4 Fatty Acid Composition of n-3 PUFA-C8-TG Prepared Fig Fig. 5 Fatty Acid Composition of n-3pufa-c10-tg Prepared. 477
6 S. Hara, A. Kanda and Y. Totani References Fig. 6 Fig. 7 Fatty Acid Composition of n-3 PUFA-C12-TG Prepared. Time Course of Transacylation Ratio in Structured Lipids Prepared with Various Fatty Acids K. FUJIMOTO, Structured Lipids, J. Jpn Oil Chem. Soc., Vol. 48, (1999). 2. I. IKEDA, Structured Lipids: Application for Food and Medical Use., Bioscience Industry, Vol. 59, (2001). 3. H. MU and C.E. HOY, Intestinal Absorption of Specific Structured Triacylglycerlos, J. Lipid Res., Vol. 42, (2001). 4. D.C. RUPPIN and W.R.J. MIDDLETON, Clinical Use of Medium Chain Triglycerides, Drugs, Vol. 49, (1980). 5. T. AOYAMA, Nutritional Studies on Structured Lipids-Their Adsoption and Metabolic Effects- J. Jpn Oil Chem. Soc., Vol. 47, (1999). 6. O. NOGUCHI, H. SHIMADA, F. KUBOTA, H. TSUJI and T. AOYAMA, Nutritional Effects of Randomly Interesterified and Physically Mixed Oils Containing Medium-chain Fatty Acids on Rats, J. Oleo Sci., Vol. 51, (2002). 7. I. IKEDA, Y. TOMARI, M. SUGANO, S. WATANABE and J. NAGATA, Lymphatic Absorption of Structured Glycerolipids Containing Medium Chain Fatty Acids and Linoleic Acid, and Their Effect on Cholesterol Absoption in Rats, Lipids, Vol. 26, (1991). 8. Y. SHIMADA, T. SUGIHARA, K. MARUYAMA, T. NAGAO, S. NAKAYAMA, H. NAKANO and Y. TOMINAGA, Production of Structured Lipid Containing Docosahexaenoic and Caprylic Acids Using Immobilized Rhizopus delemer Lipase, J. Ferment. Bioeng., Vol. 81, (1996). 9. Y. SHIMADA, T. NAGAO, Y. HAMASAKI, K. AKIMOTO, A. SUGIHARA, S. FUJIKAWA, S. KOMEMUSHI and Y. TOMI- NAGA, Enzymatic Synthesis of Structred Lipid Containing Arachidonic and Palmitic Acids, J. Am. Oil Chem. Soc., Vol. 77, (2000). 10. M. HOSOKAWA, K. TAKAHASHI, N. MIYAZAKI, K. OKA- MURA and M. HATANO, Application of Water Mimics on Preparation of Eicosapentaenoic and Docosahexaenoic Acids Containing Glycerolipids, J. Am. Oil Chem. Soc., Vol. 72, (1995). 11. K. TANE, S. HARA and Y. TOTANI, Preparation of Polyunsaturated Oil by Repeated Transesterification with Lipase, J. Jpn Oil Chem. Soc., Vol. 46, (1997). 12. X. XU, Engineering of Enzymatic Reactions and Reactors for- Lipid Modification and Synthesis, Eur. J. Lipid Sci. Technol., Vol. 105, (2003). 13. A. ROCHA-URIBE, E. HERNANDEZ, Solvent-Free Enzymatic 478
7 Synthesis of Structured Lipids Containing CLA from Coconut Oil and Tricaprylin, J. Am. Oil Chem. Soc., Vol. 81, (2004). 14. G.N. JHAM, F.F.F. TELES and L.G. CAMPOS, Use of Aqueous HCl/MeOH as Esterification Reagent for Analysis of Fatty Acids Derived from Soybean Lipids, J. Am. Oil Chem. Soc., Vol. 59, (1982). 15. Standard Methods for the Analysis of Fats, Oils and Related Materials (Japan Oil Chem. Soc., ed.), Tentative Method , Peroxide Value (Potentiometric Method), (2003). 479
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