Optimization of omega-3 enriched-diacylglycerol production by enzymatic esterification using a response surface methodology

Qi, Jin-Feng; Wang, Xiangyu; Zhang, Hua; Lee, Jeung Hee

doi:10.1007/s10068-014-0154-9

Cited by 6 publications

(5 citation statements)

References 27 publications

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“…After cooling, BF 3 -methanol (2 mL) was added, and methylated at 85 °C for 10 min. The FA composition was analyzed using a gas chromatography (GC-2010 Plus, Shimadzu Corp., Kyoto, Japan) equipped with a flame ionization detector, and an SP TM -2560 capillary column (100 m × 0.25 mm × 0.2 μm film thickness, Supelco Inc., Bellefonte, PA, USA) [ 39 ]. The oven temperature was held at 100 °C for 5 min, increased to 240 °C at 4 °C/min, and maintained for 40 min.…”

Section: Methodsmentioning

confidence: 99%

Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties

Chang

Lee

2021

Molecules

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Tripalmitin-(PPP, 81.2%), 1,3-dipalmitoyl-2-oleoylglycerol-(POP, 64.4%), 1,2-dipalmitoyl-3-oleoylglycerol-(PPO, 86.5%), and 1,3-dioleoyl-2-palmitoylglycerol-(OPO, 50.2%)-rich lipids with different regiospecific positions of palmitic acid (P) were synthesized via acetone fractionation and lipase-catalyzed acidolysis, and their physicochemical and hydrolytic characteristics were compared. Triacylglycerols (TAGs) with higher content of P, wherein P was at the sn-1 (or 3) position, had higher melting points, crystallization temperatures, and packing densities of fat crystals compared to those with a lower content of P, and with P at the sn-2 position. The in vitro digestion degree calculated as released fatty acid (FA) (%) at 30, 60, and 120 min was in the following order: OPO-rich > PPO-rich > POP-rich lipids. At 120 min, in vitro digestion of the OPO-rich lipid released 92.6% of fatty acids, resulting in the highest digestibility, while 89.7% and 87.2% of fatty acids were released from the OPO-rich and PPO-rich lipids, respectively. Over the digestion period, the TAG and monoacylglycerol (MAG) contents decreased, while the diacylglycerol (DAG) content initially increased and then decreased, and the 1,2-DAG content exceeded the 1,3-DAG content. Therefore, the content and stereospecific position of P attached to a specific TAG affected the physicochemical and in vitro digestion characteristics of the lipids.

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Section: Methodsmentioning

confidence: 99%

Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties

Chang

Lee

2021

Molecules

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“…The upper layer was collected, passed through an anhydrous sodium sulfate column to remove water, concentrated using a rotary evaporator, and dried completely with nitrogen. To analyze the acylglycerol composition, a high‐performance liquid chromatography (HPLC) system (Younglin Acme, Anyang, Korea) equipped with a Hypersil BDS CPS column (5 μm, 250 mm × 4.6 mm, Bellefonte, PA, USA) and an evaporative light scattering detector (SEDEX MODEL 75, Sedere, Alfortville, France) was used . Gradient elution was carried out using hexane–acetic acid (100:0.4, v / v ) as solvent A and t ‐butyl ether–acetic acid (100:0.4) as solvent B with the following gradient: hold A for 5 min, decrease the ratio of A and B to 20:80 ( v / v ) over 10 min and hold for 2 min, and then increase the ratio of A and B to 100:0 over 5 min and hold for 5 min.…”

Section: Methodsmentioning

confidence: 99%

“…The DAG‐rich algae oil (25 mg) or lipid extracted from the emulsions was saponified and methylated, and its fatty acid composition was analyzed by gas chromatography (GC) (Agilent 6890, Avondale, PA, USA) equipped with a flame ionization detector and an SP™‐2560 column (biscyanopropyl polysiloxane, 100 m × 0.25 nm × 0.2 μm film thickness, Supelco Co., St Louis, MO, USA) …”

Section: Methodsmentioning

confidence: 99%

Emulsification and oxidation stabilities of DAG‐rich algae oil‐in‐water emulsions prepared with the selected emulsifiers

Chang

Lee

2019

J Sci Food Agric

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BACKGROUND: Diacylglycerol (DAG) reduces body weight, suppresses body fat accumulation, and lowers the blood lipid concentration, and docosahexaenoic acid (DHA) can reduce the risk of occurrence of coronary artery diseases. RESULTS: DAG-rich algae oil with a high DHA content (55.9%) was synthesized via the lipase-catalyzed glycerolysis of algae oil, which consisted of triacylglycerol (43.9 mol%), DAG (40.9 mol%), and monoacylglycerol (15.2 mol%). The DAG-rich algae oil-in-water emulsions were prepared using three emulsifiers [whey protein concentrate (WPC), Tween80, and Tween80 + Span80]. The WPC-emulsion formed a thicker serum layer (6.67% at day 51) and larger oil droplets (d 32 , 0.37 m at day 28) than the Tween80-and Tween80 + Span80-emulsions (3.33-4.17%; 0.26 m), and an upper cream layer with excess oil droplets was observed in only the WPC-emulsion, indicating that WPC-emulsion possesses the lowest emulsification stability. The hydroperoxide value and reduction rate of the DHA content were higher in the WPC-emulsions than in the Tween80-and Tween80 + Span80-emulsions during storage, which suggested that the WPC-emulsion had the lowest oxidation stability. CONCLUSION: The DAG-rich algae oil-in-water emulsion prepared with suitable emulsifiers, such as non-ionic emulsifiers, would have excellent emulsification and oxidative stabilities and provides a health benefit for special purposes in the food processing industry. Industry and Tween80 + Span80-emulsions were maintained during storage, but the d 32 of the WPC-emulsion increased over the storage period and was 0.37 μm on day 28, which was significantly larger than that of the Tween80-and Tween80 + Span80-emulsions J Sci Food Agric 2020; 100: 287-294

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“…The acylglycerol composition in SDO and SSBO were determined by HPLC‐ELSD and 1 H NMR analyses (Hazakis and others ; Qi and others ).…”

Section: Methodsmentioning

confidence: 99%

Relative Oxidative Stability of Diacylglycerol and Triacylglycerol Oils

Wang

Shin

et al. 2015

Journal of Food Science

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To compare the oxidative stability between diacylglycerol (DAG) oil and conventional triacylglycerol (TAG) oil (that is, soybean oil), the prepared stripped diacylglycerol oil (SDO) and soybean oil (SSBO) were stored at 60 °C in the dark for 144 h. During storage peroxide values (POVs), contents of aldehydes, unsaturated fatty acids were measured to evaluate the oxidative stabilities of the 2 oils. The results showed the content of C18:2, C18:3, and total unsaturated fatty acid decreased faster in DAG oil than in soybean oil, whereas the decreased rate of C18:1 was similar in 2 oils. Also, both rate constants (K1 and K2) obtained from POV (K1 ) and total aldehydes (K2 ) indicated that DAG oil (K1 = 3.22 mmol/mol FA h(-1) , K2 = 0.023 h(-1)) was oxidized more rapidly than soybean oil (K1 = 2.56 mmol/mol FA h(-1) , K2 = 0.021 h(-1)), which was mainly due to the difference of acylglycerol composition of the 2 oils along with higher C18:3 (9.6%) in SDO than SSBO (5.7%). It is concluded that DAG was more easily oxidized than soybean oil at 60 °C in the dark for 144 h.

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Optimization of omega-3 enriched-diacylglycerol production by enzymatic esterification using a response surface methodology

Cited by 6 publications

References 27 publications

Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties

Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties

Emulsification and oxidation stabilities of DAG‐rich algae oil‐in‐water emulsions prepared with the selected emulsifiers

Relative Oxidative Stability of Diacylglycerol and Triacylglycerol Oils

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