Production of structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol from <i>Mortierella</i> single‐cell oil

Nagao, Toshihiro; Kawashima, A.; Sumida, Motoo; Watanabe, Yomi; Akimoto, Kengo; Fukami, Hironobu; Sugihara, Akio; Shimada, Yuji

doi:10.1007/s11746-003-0787-9

Cited by 12 publications

(6 citation statements)

References 21 publications

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“…The resulting AG-CLA was composed of 74.4 mol% TAG and 25.6 mol% DAG. When this preparation underwent acidolysis with C 8 FA using immobilized R. miehei lipase, TAG were converted efficiently to MLM-structured TAG, and DAG were converted to MMM and MLM because acyl migration, esterification of DAG with C 8 FA, and acidolysis of DAG and TAG with C 8 FA occurred simultaneously during the reaction (27,28). Hence, the AG-CLA preparation was used as a starting material without further purification.…”

Section: Resultsmentioning

confidence: 99%

Preparation of regioisomers of structured TAG consisting of one mole of CLA and two moles of caprylic acid

Kawashima

Nagao

Watanabe

et al. 2004

J Americ Oil Chem Soc

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TAG (MLM) with medium-chain FA (MCFA) at the 1,3-positions and long-chain FA (LCFA) at the 2-position, and TAG (LMM) with LCFA at the 1(3)-position and MCFA at 2,3(1)-positions are a pair of TAG regioisomers. Large-scale preparation of the two TAG regioisomers was attempted. A commercially available FFA mixture (FFA-CLA) containing 9-cis,11-trans (9c,11t)-and 10t,12c-CLA was selected as LCFA, and caprylic acid (C 8 FA) was selected as MCFA. The MLM isomer was synthesized by acidolysis of acylglycerols (AG) containing two CLA isomers with C 8 FA: A mixture of AG-CLA/C 8 FA (1:10, mol/mol) and 4 wt% immobilized Rhizomucor miehei lipase was agitated at 30°C for 72 h. The ratio of MLM to total AG was 51.1 wt%. Meanwhile, LMM isomer was synthesized by acidolysis of tricaprylin with FFA-CLA: A mixture of tricaprylin/FFA-CLA (1:2, mol/mol) and 4 wt% immobilized R. miehei lipase was agitated at 30°C for 24 h. The ratio of LMM to total AG was 51.8 wt%. MLM and LMM were purified from 1,968 and 813 g reaction mixtures by stepwise short-path distillation, respectively. Consequently, MLM was purified to 92.3% with 49.1% recovery, and LMM was purified to 93.2% with 52.3% recovery. Regiospecific analyses of MLM and LMM indicated that the 2-positions of MLM and LMM were 95.1 mol% LCFA and 98.3 mol% C 8 FA, respectively. The results showed that a process comprising lipase reaction and short-path distillation is effective for large-scale preparation of high-purity regiospecific TAG isomers.Much attention has been focused on the effect of position of FA in TAG on physiological activities. Two TAG regioisomers, which have the same FA composition and carry a functional FA at the 1(3)-and 2-position, are necessary in order to study this subject. The two regioisomers have been synthesized by transesterification of long-chain TAG (LLL) with medium-chain FA (MCFA) using a 1,3-position-specific lipase and by transesterification of medium-chain TAG (MMM) with long-chain FA (LCFA) (1-9). The products can reportedly be purified by HPLC (10,11). The process comprising lipase reaction and HPLC is effective for preparing high-purity TAG regioisomers, and the products have been used for examining the intestinal absorption of TAG (12). However, animal tests involving oral administration require larger amounts of TAG regioisomers, and the purification process by HPLC is not suitable for large-scale preparation. Xu and colleagues (7,8) carried out large-scale preparation of TAG regioisomers by short-path distillation, but the resulting preparations were mixtures of MMM, MLM, and MLL because the distillation removed only FFA. Negishi et al. (9) purified MLM from the reaction mixture, but the content of MLM was only 76%. For these reasons, a process for preparing larger amounts of pure TAG regioisomers (purity >90%) is strongly desired.TAG (MLM) with MCFA at the 1,3-positions and LCFA at the 2-position, and TAG (LMM) with LCFA at the 1(3)-position and MCFA at the 2,3(1)-positions, represent a pair of TAG regioisomers. To evaluate nutritional effects ...

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Section: Resultsmentioning

confidence: 99%

Preparation of regioisomers of structured TAG consisting of one mole of CLA and two moles of caprylic acid

Kawashima

Nagao

Watanabe

et al. 2004

J Americ Oil Chem Soc

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“…The simplest and most direct route for the synthesis of MLM type ST is the acidolysis between long-chain TAG and mediumchain FFAs catalyzed with a 1,3-specific lipase (Xu, 2003;Nagao et al, 2003;Shimada et al, 1999;Fomuso and Akoh, 2002;Xu et al, 1998;Torres and Hill, 2002;Camacho Páez et al, 2002). Lipases offer high catalytic efficiency, specificity and selectivity by incorporation of the required acyl group into a specific position of the native TAG.…”

Section: Introductionmentioning

confidence: 99%

Modeling of the kinetic for the acidolysis of different triacylglycerols and caprylic acid catalyzed by Lipozyme IM immobilized in packed bed reactor

Camacho¹,

Robles²,

Camacho³

et al. 2007

Chemical Engineering Science

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“…And it has potential pharmaceutical value and is a precursor of hormones, such as prostaglandins, leukotrienes and thromboxanes (Nagao et al . ). The supplement of ARA in dietary is helpful to the adults on improving the cognitive dysfunctions (Kotani et al .…”

Section: Introductionmentioning

confidence: 97%

“…Arachidonic acid (ARA; 20:4n-6) plays important roles in regulating lipid metabolism, biological processes and immune response . And it has potential pharmaceutical value and is a precursor of hormones, such as prostaglandins, leukotrienes and thromboxanes (Nagao et al 2003). The supplement of ARA in dietary is helpful to the adults on improving the cognitive dysfunctions (Kotani et al 2006).…”

Section: Introductionmentioning

confidence: 99%

Lipase Catalyzed Synthesis of ABA-Type Structured Lipid from Single Cell Oil and Tripalmitin

Liu

Dong

Wei

et al. 2016

Journal of Food Processing and Preservation

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Optimization of lipase‐catalyzed interesterification for the production of structured lipid, enriched with arachidonic acid (ARA) from tripalmitin and ARA single cell oil was carried out. Response surface methodology was applied to model and optimize the reaction system; factors of temperature, substrate molar ratio, reaction time and enzyme load were chosen for the optimization. The optimal conditions generated from the models were as follows: temperature of 50C, substrate molar ratio of 1 : 12, reaction time of 13.36 h, and enzyme load of 7.58 wt %. Under these conditions, the incorporation of ARA and acyl migration were 55.11 ± 0.15 and 15.85 ± 0.05%, respectively. It was found that 69.57% of ARA was mainly incorporated in the sn‐1, 3 positions and 62.31% of palmtic acid was located at the sn‐2 position of the TAG. Practical Applications This obtained structured lipid 1, 3‐arachidonoyl‐2‐palmitoyl‐glycerol could provide a fat source with high value‐added functional ARA at the sn‐1, 3 position and serve as a good source of palmitic acid at the sn‐2 position, which can improve the absorption of fat and reducing calcium loss of the human body. This synthesized APA‐type structured lipid enables a high similarity of human milk fat substitutes to human milk fat which can be potentially used as fat substitute in infant formula.

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Production of structured TAG rich in 1,3‐capryloyl‐2‐arachidonoyl glycerol from Mortierella single‐cell oil

Cited by 12 publications

References 21 publications

Preparation of regioisomers of structured TAG consisting of one mole of CLA and two moles of caprylic acid

Preparation of regioisomers of structured TAG consisting of one mole of CLA and two moles of caprylic acid

Modeling of the kinetic for the acidolysis of different triacylglycerols and caprylic acid catalyzed by Lipozyme IM immobilized in packed bed reactor

Lipase Catalyzed Synthesis of ABA-Type Structured Lipid from Single Cell Oil and Tripalmitin

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