Lipase-Catalyzed Interesterification for the Synthesis of Medium-Long-Medium (MLM) Structured Lipids

Utama, Qabul Dinanta; Sitanggang, Azis Boing; Adawiyah, Dede Robiatul; Hariyadi, Purwiyatno

doi:10.17113/ftb.57.03.19.6025

Cited by 83 publications

(35 citation statements)

References 108 publications

(167 reference statements)

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“…They can be categorized as sn ‐1,3‐specific and nonspecific enzymes and are capable of catalyzing a variety of reactions including direct esterification, interesterification, acidolysis, and glycerolysis (Table ). Important technical and economic considerations when applying these types of reactions to produce various SLs can be found in numerous book chapters and review papers (Feltes et al., ; Ferreira & Tonetto, ; Phuah et al., ; Soumanou, Perignon, & Villeneuve, ; Utama et al., ). Depending on product requirement and substrate type, various kinds of SLs including trans ‐free plastic fats, CBEs, HMFSs, MLCTs, MAGs, and DAGs can be produced by adopting suitable methods.…”

Section: Synthesis Of Slsmentioning

confidence: 99%

“…Similarly, HMFSs particularly those enriched in PUFAs has been widely applied in emulsion‐based infant formula (Li, Sabir, Baeshen, & Akoh, ; Zou & Akoh, , ). MLM‐type SLs have been explored in various food‐related systems, such as cooking oil for sweet potato chips, energy bars, beverages, and edible films (Utama et al., ). MAGs/DAGs have been largely used as emulsifiers for a long time in many food products including baking products, margarines, and frozen desserts (Norn, ).…”

Section: Potential Food Applications Of Slsmentioning

confidence: 99%

“…Although there have been several reviews either on a particular type of SLs such as HMFSs (Şahin-Yeşilçubuk & Akoh, 2017;Wei, Jin, & Wang, 2019;Zou et al, 2016a), MAGs and/or DAGs (Feltes, De Oliveira, Block, & Ninow, 2013;Lee et al, 2019;Lo et al, 2008;Phuah et al, 2015), MLM-type SLs (Utama, Sitanggang, Adawiyah, & Hariyadi, 2019), and trans-free plastic fats (Berger & Idris, 2005;Pande & Akoh, 2013), or on an overview of several common SLs (Ferreira & Tonetto, 2017a;Kim & Akoh, 2015;Rohm, Schäper, & Zahn, 2018), very few of them have focused on processing-structure-function relationship of the corresponding SLs. An early review of Osborn and Akoh (2002) gave a concise introduction to several important physical and nutritional properties of SLs and their related applications.…”

Section: F I G U R E 1 Schematic Representation Of the Main Content Omentioning

confidence: 99%

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Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Guo

Cai

Xie

et al. 2020

Comp Rev Food Sci Food Safe

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Structured lipids (SLs) refer to a new type of functional lipids obtained by chemically, enzymatically, or genetically modifying the composition and/or distribution of fatty acids in the glycerol backbone. Due to the unique physicochemical characteristics and health benefits of SLs (for example, calorie reduction, immune function improvement, and reduction in serum triacylglycerols), there is increasing interest in the research and application of novel SLs in the food industry. The chemical structures and molecular architectures of SLs define mainly their physicochemical properties and nutritional values, which are also affected by the processing conditions. In this regard, this holistic review provides coverage of the latest developments and applications of SLs in terms of synthesis strategies, physicochemical properties, health aspects, and potential food applications. Enzymatic synthesis of SLs particularly with immobilized lipases is presented with a short introduction to the genetic engineering approach. Some physical features such as solid fat content, crystallization and melting behavior, rheology and interfacial properties, as well as oxidative stability are discussed as influenced by chemical structures and processing conditions. Health‐related considerations of SLs including their metabolic characteristics, biopolymer‐based lipid digestion modulation, and oleogelation of liquid oils are also explored. Finally, potential food applications of SLs are shortly introduced. Major challenges and future trends in the industrial production of SLs, physicochemical properties, and digestion behavior of SLs in complex food systems, as well as further exploration of SL‐based oleogels and their food application are also discussed.

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Section: Synthesis Of Slsmentioning

confidence: 99%

Section: Potential Food Applications Of Slsmentioning

confidence: 99%

Section: F I G U R E 1 Schematic Representation Of the Main Content Omentioning

confidence: 99%

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Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Guo

Cai

Xie

et al. 2020

Comp Rev Food Sci Food Safe

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“…Lipases find applications in many different industrial areas, such as energy, fine chemicals, food and polymer chemistry or as component of detergents [1][2][3][4][5][6][7][8]. This is because they do not require cofactors, are very stable in a variety of reaction media (including organic solvents [9][10][11] and new media [12][13][14][15][16][17][18][19]) and can recognize a great diversity of substrates (they are quite unspecific enzymes) and simultaneously exhibit a great regio-and enantio-selectivity and/or specificity [20][21][22][23][24], being able to catalyze a huge diversity of reactions, including promiscuous ones [25]. These features place lipases among the most used enzymes in biocatalysis [26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Multi-Combilipases: Co-Immobilizing Lipases with Very Different Stabilities Combining Immobilization via Interfacial Activation and Ion Exchange. The Reuse of the Most Stable Co-Immobilized Enzymes after Inactivation of the Least Stable Ones

et al. 2020

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The lipases A and B from Candida antarctica (CALA and CALB), Thermomyces lanuginosus (TLL) or Rhizomucor miehei (RML), and the commercial and artificial phospholipase Lecitase ultra (LEU) may be co-immobilized on octyl agarose beads. However, LEU and RML became almost fully inactivated under conditions where CALA, CALB and TLL retained full activity. This means that, to have a five components co-immobilized combi-lipase, we should discard 3 fully active and immobilized enzymes when the other two enzymes are inactivated. To solve this situation, CALA, CALB and TLL have been co-immobilized on octyl-vinyl sulfone agarose beads, coated with polyethylenimine (PEI) and the least stable enzymes, RML and LEU have been co-immobilized over these immobilized enzymes. The coating with PEI is even favorable for the activity of the immobilized enzymes. It was checked that RML and LEU could be released from the enzyme-PEI coated biocatalyst, although this also produced some release of the PEI. That way, a protocol was developed to co-immobilize the five enzymes, in a way that the most stable could be reused after the inactivation of the least stable ones. After RML and LEU inactivation, the combi-biocatalysts were incubated in 0.5 M of ammonium sulfate to release the inactivated enzymes, incubated again with PEI and a new RML and LEU batch could be immobilized, maintaining the activity of the three most stable enzymes for at least five cycles of incubation at pH 7.0 and 60 °C for 3 h, incubation on ammonium sulfate, incubation in PEI and co-immobilization of new enzymes. The effect of the order of co-immobilization of the different enzymes on the co-immobilized biocatalyst activity was also investigated using different substrates, finding that when the most active enzyme versus one substrate was immobilized first (nearer to the surface of the particle), the activity was higher than when this enzyme was co-immobilized last (nearer to the particle core).

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“…The enzymatic interesterification was preferably to synthesize MLM-SL due to its selectivity, less by-products, mild reaction conditions, and easy recovery of the biocatalysts. Herein, enzyme-based MLM-SL synthesis gains popularity in recent years (Utama et al, 2019) The continuous synthesis of MLM-SL was of importance especially at industrial scale.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of medium-long-medium structured lipid (MLM-SL) by lipase-catalyzed transesterification using palm olein and tricaprylin in packed-bed reactor (PBR)

Utama¹,

Sitanggang²,

Adawiyah³

et al. 2020

Preprint

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Lipase-catalyzed transesterification between refined bleached deodorized palm olein (RBDO) and tricaprylin to produce medium-long-medium structured lipid (MLM-SL) in a packed bed reactor has been investigated. A specific sn -1,3 commercial Lipozyme TL IM was used as biocatalyst. Within this study, the progress of transesterification was monitored especially for triacylglycerol (TAG) formation with equivalent carbon number (ECN) of 32, presumably 1,3-dicapryoyl-2-oleoyl- sn -glycerol (COC). Transesterification conditions investigated were residence times ( i.e ., 15, 30, and 60 min) and enzyme loadings (2 and 4.5 g). The highest yield of ECN 32 (13%) and transesterification degree (71%) were obtained at residence time of 15 mins for both enzyme loadings. Longer residence time seemed to facilitate lipid hydrolysis over transesterification. This was indicated by the number of peaks appearing in the high-performance liquid chromatography (HPLC) chromatograms and the reduction of of fat slip melting point (SMP). Additionally, at 4.5 enzyme loading the highest productivity was obtained for one-cycle reaction. Conclusively, this study has demonstrated the potential use of packed-bed reactor with immobilized Lipozyme TL IM for continuous synthesis of MLM-SLs especially TAG ECN32.

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Lipase-Catalyzed Interesterification for the Synthesis of Medium-Long-Medium (MLM) Structured Lipids

Cited by 83 publications

References 108 publications

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Multi-Combilipases: Co-Immobilizing Lipases with Very Different Stabilities Combining Immobilization via Interfacial Activation and Ion Exchange. The Reuse of the Most Stable Co-Immobilized Enzymes after Inactivation of the Least Stable Ones

The synthesis of medium-long-medium structured lipid (MLM-SL) by lipase-catalyzed transesterification using palm olein and tricaprylin in packed-bed reactor (PBR)

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