Production of structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol from Mortierella single‐cell oil
Two oils containing a large amount of 2‐arachidonoyl‐TAG were selected to produce structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol (CAC). An oil (TGA58F oil) was prepared by fermentation of Mortierella alpina, in which the 2‐arachidonyoyl‐TAG content was 67 mol%. Another oil (TGA55E oil)...
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Published in | Journal of the American Oil Chemists' Society Vol. 80; no. 9; pp. 867 - 872 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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Berlin/Heidelberg
Springer-Verlag
01.09.2003
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Abstract | Two oils containing a large amount of 2‐arachidonoyl‐TAG were selected to produce structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol (CAC). An oil (TGA58F oil) was prepared by fermentation of Mortierella alpina, in which the 2‐arachidonyoyl‐TAG content was 67 mol%. Another oil (TGA55E oil) was prepared by selective hydrolysis of a commercially available oil (TGA40 oil) with Candida rugosa lipase. The 2‐arachidonoyl‐TAG content in the latter was 68 mol%. Acidolysis of the two oils with caprylic acid (CA) using immobilized Rhizopus oryzae lipase showed that TGA55E oil was more suitable than TGA58F oil for the production of structured TAG containing a higher concentration of CAC. Hence, a continuous‐flow acidolysis of TGA55E oil was performed using a column (18×125 mm) packed with 10 g immobilized R. oryzae lipase. When a mixture of TGA55E oil/CA (1∶2, w/w) was fed at 35°C into the fixed‐bed reactor at a flow rate of 4.0 mL (3.6 g)/h, the degree of acidolysis initially reached 53%, and still achieved 48% even after continuous operation for 90 d. The reaction mixture that flowed from the reactor contained small amounts of partial acylglycerols and tricaprylin in addition to FFA. Molecular distillation was used for purification of the structured TAG, and removed not only FFA but also part of the partial acylglycerols and tricaprylin, resulting in an increase in the CAC content in acylglycerols from 44.0 to 45.8 mol%. These results showed that a process composed of selective hydrolysis, acidolysis, and molecular distillation is effective for the production of CAC‐rich structured TAG. |
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AbstractList | Abstract
Two oils containing a large amount of 2‐arachidonoyl‐TAG were selected to produce structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol (CAC). An oil (TGA58F oil) was prepared by fermentation of
Mortierella alpina
, in which the 2‐arachidonyoyl‐TAG content was 67 mol%. Another oil (TGA55E oil) was prepared by selective hydrolysis of a commercially available oil (TGA40 oil) with
Candida rugosa
lipase. The 2‐arachidonoyl‐TAG content in the latter was 68 mol%. Acidolysis of the two oils with caprylic acid (CA) using immobilized
Rhizopus oryzae
lipase showed that TGA55E oil was more suitable than TGA58F oil for the production of structured TAG containing a higher concentration of CAC. Hence, a continuous‐flow acidolysis of TGA55E oil was performed using a column (18×125 mm) packed with 10 g immobilized
R. oryzae
lipase. When a mixture of TGA55E oil/CA (1∶2, w/w) was fed at 35°C into the fixed‐bed reactor at a flow rate of 4.0 mL (3.6 g)/h, the degree of acidolysis initially reached 53%, and still achieved 48% even after continuous operation for 90 d. The reaction mixture that flowed from the reactor contained small amounts of partial acylglycerols and tricaprylin in addition to FFA. Molecular distillation was used for purification of the structured TAG, and removed not only FFA but also part of the partial acylglycerols and tricaprylin, resulting in an increase in the CAC content in acylglycerols from 44.0 to 45.8 mol%. These results showed that a process composed of selective hydrolysis, acidolysis, and molecular distillation is effective for the production of CAC‐rich structured TAG. Two oils containing a large amount of 2‐arachidonoyl‐TAG were selected to produce structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol (CAC). An oil (TGA58F oil) was prepared by fermentation of Mortierella alpina, in which the 2‐arachidonyoyl‐TAG content was 67 mol%. Another oil (TGA55E oil) was prepared by selective hydrolysis of a commercially available oil (TGA40 oil) with Candida rugosa lipase. The 2‐arachidonoyl‐TAG content in the latter was 68 mol%. Acidolysis of the two oils with caprylic acid (CA) using immobilized Rhizopus oryzae lipase showed that TGA55E oil was more suitable than TGA58F oil for the production of structured TAG containing a higher concentration of CAC. Hence, a continuous‐flow acidolysis of TGA55E oil was performed using a column (18×125 mm) packed with 10 g immobilized R. oryzae lipase. When a mixture of TGA55E oil/CA (1∶2, w/w) was fed at 35°C into the fixed‐bed reactor at a flow rate of 4.0 mL (3.6 g)/h, the degree of acidolysis initially reached 53%, and still achieved 48% even after continuous operation for 90 d. The reaction mixture that flowed from the reactor contained small amounts of partial acylglycerols and tricaprylin in addition to FFA. Molecular distillation was used for purification of the structured TAG, and removed not only FFA but also part of the partial acylglycerols and tricaprylin, resulting in an increase in the CAC content in acylglycerols from 44.0 to 45.8 mol%. These results showed that a process composed of selective hydrolysis, acidolysis, and molecular distillation is effective for the production of CAC‐rich structured TAG. Two oils containing a large amount of 2-arachidonoyl-TAG were selected to produce structured TAG rich in 1,3-capryloyl-2-arachidonoyl glycerol (CAC). An oil (TGA58F oil) was prepared by fermentation of Mortierella alpina, in which the 2-arachidonyoyl-TAG content was 67 mol%. Another oil (TGA55E oil) was prepared by selective hydrolysis of a commercially available oil (TGA40 oil) with Candida rugosa lipase. The 2-arachidonoyl-TAG content in the latter was 68 mol%. Acidolysis of the two oils with caprylic acid (CA) using immobilized Rhizopus oryzae lipase showed that TGA55E oil was more suitable than TGA58F oil for the production of structured TAG containing a higher concentration of CAC. Hence, a continuous-flow acidolysis of TGA55E oil was performed using a column (18X125 mm) packed with 10 g immobilized R. oryzae lipase. When a mixture of TGA55E oil/CA (1∶ 2, w/w) was fed at 35°C into the fixed-bed reactor at a flow rate of 4.0 mL (3.6 g)/h, the degree of acidolysis initially reached 53%, and still achieved 48% even after continuous operation for 90 d. The reaction mixture that flowed from the reactor contained small amounts of partial acylglycerols and tricaprylin in addition to FFA. Molecular distillation was used for purification of the structured TAG, and removed not only FFA but also part of the partial acylglycerols and tricaprylin, resulting in an increase in the CAC content in acylglycerols from 44.0 to 45.8 mol%. These results showed that a process composed of selective hydrolysis, acidolysis, and molecular distillation is effective for the production of CAC-rich structured TAG. |
Author | Watanabe, Yomi Sumida, Motoo Akimoto, Kengo Kawashima, Akiko Sugihara, Akio Nagao, Toshihiro Fukami, Harukazu Shimada, Yuji |
Author_xml | – sequence: 1 givenname: Toshihiro surname: Nagao fullname: Nagao, Toshihiro organization: Osaka Municipal Technical Research Institute – sequence: 2 givenname: Akiko surname: Kawashima fullname: Kawashima, Akiko organization: Sonoda Women's University – sequence: 3 givenname: Motoo surname: Sumida fullname: Sumida, Motoo organization: Suntory Ltd – sequence: 4 givenname: Yomi surname: Watanabe fullname: Watanabe, Yomi organization: Osaka Municipal Technical Research Institute – sequence: 5 givenname: Kengo surname: Akimoto fullname: Akimoto, Kengo organization: Suntory Ltd – sequence: 6 givenname: Harukazu surname: Fukami fullname: Fukami, Harukazu organization: Suntory Ltd – sequence: 7 givenname: Akio surname: Sugihara fullname: Sugihara, Akio organization: Tokushima Bunri University – sequence: 8 givenname: Yuji surname: Shimada fullname: Shimada, Yuji email: shimaday@omtri.city.osaka.jp organization: Osaka Municipal Technical Research Institute |
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CitedBy_id | crossref_primary_10_1016_j_bej_2012_06_004 crossref_primary_10_3390_catal10111277 crossref_primary_10_1016_j_neulet_2008_11_039 crossref_primary_10_1111_jfpp_12843 crossref_primary_10_3390_life12020187 crossref_primary_10_1016_j_ces_2007_03_011 crossref_primary_10_3136_fstr_12_247 |
Cites_doi | 10.1007/BF02537201 10.1007/BF02535779 10.1093/ajcn/61.1.56 10.1016/S0753-3322(02)00254-8 10.1016/S0140-6736(94)90692-0 10.1007/s11746-001-0313-0 10.1201/9781439832103.ch3 10.1007/BF02546206 10.1073/pnas.90.3.1073 10.1016/S0922-338X(97)80136-5 10.1007/BF00252518 10.1016/B978-0-12-024921-3.50008-3 10.1002/3527606033.ch9 10.1093/oxfordjournals.jbchem.a123061 10.1002/3527606033.ch8 10.1172/JCI13210 |
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Keywords | Structured lipid Mortierella alpina Phycomycetes Triacylglycerol lipase fixed-bed bioreactor Lipids Esterases Arachidonic acid Octanoic acid structured TAG Mortierella Fungi caprylic acid Triacylglycerol Biotransformation Thallophyta Distillation Enzyme Fixed bed reactor Fatty acids Carboxylic ester hydrolases Bioreactor Rhizopus oryzae lipase Hydrolases single-cell oil Immobilized enzyme |
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References | 1994; 344 1987; 22 1990; 107 1995; 61 1995; 72 1995; 71 1997; 83 1989; 31 1993; 28 1991; 26 2000 2002; 56 2000; 11 2000; 77 2002; 79 1998 1999; 76 1993; 90 2001; 107 2001; 78 1985; 21 Shimada Y. (e_1_2_1_12_1) 2000 Irimescu R. (e_1_2_1_23_1) 2000; 77 Minno G.D. (e_1_2_1_3_1) 1987; 22 Shimada Y. (e_1_2_1_22_1) 1995; 71 Shimada Y. (e_1_2_1_21_1) 1995; 72 e_1_2_1_7_1 e_1_2_1_8_1 e_1_2_1_5_1 e_1_2_1_6_1 Shimada Y. (e_1_2_1_20_1) 1999; 76 e_1_2_1_4_1 e_1_2_1_13_1 Kawashima A. (e_1_2_1_24_1) 2002; 79 e_1_2_1_10_1 e_1_2_1_2_1 Xu X. (e_1_2_1_11_1) 2000; 11 e_1_2_1_16_1 e_1_2_1_17_1 e_1_2_1_14_1 e_1_2_1_15_1 e_1_2_1_9_1 e_1_2_1_18_1 e_1_2_1_19_1 |
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Biochem. – volume: 22 start-page: 63 year: 1987 end-page: 82 article-title: Lipids in Platelet Function: Platelet and Vascular Prostaglandins in Thromboembolic Disease publication-title: Ibid. – volume: 344 start-page: 1319 year: 1994 end-page: 1322 article-title: Neurological Differences Between 9‐Year‐Old Children Fed Breast‐Milk as Babies publication-title: Lancet – volume: 26 start-page: 369 year: 1991 end-page: 373 article-title: Lymphatic Absorption of Structured Glycerolipids Containing Medium‐Chain Fatty Acids and Linoleic Acid, and Their Effect on Cholesterol Absorption in Rats publication-title: Lipids – volume: 107 start-page: 1339 year: 2001 end-page: 1345 article-title: Arachidonic Acid as a Bioactive Molecule publication-title: J. Clin. Invest. – volume: 61 start-page: 56 year: 1995 end-page: 61 article-title: Intestinal Absorption and Lymphatic Transport of Eicosapentaenoic (EPA), Docosahexaenoic (DHA), and Decanoic Acids: Dependence on Intramolecular Triacylglycerol Structure publication-title: Am. J. Clin. Nutr. – volume: 78 start-page: 611 year: 2001 end-page: 616 article-title: Enzymatic Synthesis of High‐Purity Structured Lipids with Caprylic Acid at 1,3‐Positions and Polyunsaturated Fatty Acid at 2‐Position publication-title: J. Am. Oil Chem. Soc. – volume: 79 start-page: 871 year: 2002 end-page: 877 article-title: Production of Structured TAG Rich in 1,3‐Dicapryloyl‐2‐γ‐linolenoyl Glycerol from Borage Oil publication-title: Ibid. – volume: 11 start-page: 1121 year: 2000 end-page: 1131 article-title: Enzymatic Production of Structured Lipids: Process Reactions and Acyl Migration publication-title: inform – start-page: 148 end-page: 169 article-title: Lipase‐Catalyzed Synthesis of Structured Triacylglycerols Containing Polyunsaturated Fatty Acids: Monitoring the Reaction and Increasing the Yield – volume: 72 start-page: 1577 year: 1995 end-page: 1581 article-title: Selective Hydrolysis of Polyunsaturated Fatty Acid‐Containing Oil with Geotrichum candidum Lipase publication-title: Ibid. – volume: 71 start-page: 951 year: 1995 end-page: 954 article-title: Enrichment of Polyunsaturated Fatty Acids with Geotrichum candidum Lipase publication-title: Ibid. – start-page: 46 year: 1998 end-page: 72 article-title: Synthesis of Positional Isomers of Structured Lipids with Lipases as Biocatalysts – volume: 90 start-page: 1073 year: 1993 end-page: 1077 article-title: Arachidonic Acid Status Correlates with First Year Growth in Preterm Infants publication-title: Proc. Natl. Acad. Sci. USA – volume: 72 start-page: 1323 year: 1995 end-page: 1327 article-title: Enrichment of Arachidonic Acid: Selective Hydrolysis of a Single‐Cell Oil from Mortierella with Candida cylindracea Lipase publication-title: J. Am. Oil Chem. Soc. – volume: 21 start-page: 47 year: 1985 end-page: 77 article-title: Leucotrienes: Biosynthesis, Metabolism, and Analysis – volume: 31 start-page: 11 year: 1989 end-page: 16 article-title: Production of Arachidonic Acid by Mortierella Fungi publication-title: Appl. Microbiol. Biotechnol. – volume: 56 start-page: 380 year: 2002 end-page: 387 article-title: Dietary Polyunsaturated Fatty Acids and Colorectal Neoplasia publication-title: Biomed. Pharmacother. – start-page: 128 year: 2000 end-page: 147 article-title: Production of Functional Lipids Containing Polyunsaturated Fatty Acids with Lipase – ident: e_1_2_1_9_1 doi: 10.1007/BF02537201 – volume: 71 start-page: 951 year: 1995 ident: e_1_2_1_22_1 article-title: Enrichment of Polyunsaturated Fatty Acids with Geotrichum candidum Lipase publication-title: Ibid. contributor: fullname: Shimada Y. – ident: e_1_2_1_17_1 doi: 10.1007/BF02535779 – volume: 77 start-page: 501 year: 2000 ident: e_1_2_1_23_1 article-title: Enzymatic Synthesis of 1,3‐Dicapryloyl‐2‐eicosapentaenoyl Glycerol publication-title: Ibid. contributor: fullname: Irimescu R. – ident: e_1_2_1_8_1 doi: 10.1093/ajcn/61.1.56 – ident: e_1_2_1_5_1 doi: 10.1016/S0753-3322(02)00254-8 – ident: e_1_2_1_7_1 doi: 10.1016/S0140-6736(94)90692-0 – ident: e_1_2_1_19_1 doi: 10.1007/s11746-001-0313-0 – volume: 72 start-page: 1577 year: 1995 ident: e_1_2_1_21_1 article-title: Selective Hydrolysis of Polyunsaturated Fatty Acid‐Containing Oil with Geotrichum candidum Lipase publication-title: Ibid. contributor: fullname: Shimada Y. – ident: e_1_2_1_10_1 doi: 10.1201/9781439832103.ch3 – ident: e_1_2_1_16_1 doi: 10.1007/BF02546206 – volume: 79 start-page: 871 year: 2002 ident: e_1_2_1_24_1 article-title: Production of Structured TAG Rich in 1,3‐Dicapryloyl‐2‐γ‐linolenoyl Glycerol from Borage Oil publication-title: Ibid. contributor: fullname: Kawashima A. – ident: e_1_2_1_6_1 doi: 10.1073/pnas.90.3.1073 – volume: 22 start-page: 63 year: 1987 ident: e_1_2_1_3_1 article-title: Lipids in Platelet Function: Platelet and Vascular Prostaglandins in Thromboembolic Disease publication-title: Ibid. contributor: fullname: Minno G.D. – ident: e_1_2_1_14_1 doi: 10.1016/S0922-338X(97)80136-5 – volume: 76 start-page: 189 year: 1999 ident: e_1_2_1_20_1 article-title: Continuous Production of Structured Lipid Containing y‐Linolenic and Caprylic Acids by Immobilized Rhizopus dele‐mar Lipase publication-title: Ibid. contributor: fullname: Shimada Y. – ident: e_1_2_1_15_1 doi: 10.1007/BF00252518 – volume: 11 start-page: 1121 year: 2000 ident: e_1_2_1_11_1 article-title: Enzymatic Production of Structured Lipids: Process Reactions and Acyl Migration publication-title: inform contributor: fullname: Xu X. – ident: e_1_2_1_2_1 doi: 10.1016/B978-0-12-024921-3.50008-3 – ident: e_1_2_1_13_1 doi: 10.1002/3527606033.ch9 – ident: e_1_2_1_18_1 doi: 10.1093/oxfordjournals.jbchem.a123061 – start-page: 128 volume-title: Enzymes in Lipid Modification year: 2000 ident: e_1_2_1_12_1 doi: 10.1002/3527606033.ch8 contributor: fullname: Shimada Y. – ident: e_1_2_1_4_1 doi: 10.1172/JCI13210 |
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Snippet | Two oils containing a large amount of 2‐arachidonoyl‐TAG were selected to produce structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol (CAC). An oil... Abstract Two oils containing a large amount of 2‐arachidonoyl‐TAG were selected to produce structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol (CAC).... Two oils containing a large amount of 2-arachidonoyl-TAG were selected to produce structured TAG rich in 1,3-capryloyl-2-arachidonoyl glycerol (CAC). An oil... |
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SubjectTerms | Arachidonic acid Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Candida rugosa caprylic acid distillation fixed‐bed bioreactor Fundamental and applied biological sciences. Psychology immobilized enzyme Methods. Procedures. Technologies Mortierella Mortierella alpina Rhizopus oryzae Rhizopus oryzae lipase single‐cell oil structured TAG |
Title | Production of structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol from Mortierella single‐cell oil |
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