Structured Lipids-Novel Fats with Medical, Nutraceutical, and Food Applications.

Generally, structured lipids (SLs) are triacylglycerols (TAGs) that have been modified to change the fatty acid composition and/or their positional distribution in glycerol backbone by chemically and/or enzymatically catalyzed reactions and/or genetic engineering. More specifically, SLs are modified TAGs with improved nutritional or functional properties. SLs provide an effective means for producing tailor-made lipids with desired physical characteristics, chemical properties, and/or nutritional benefits. The production, commercialization outlook, medical, and food applications of SLs are reviewed here. Physical property measurements for SL in food systems and future research needs for increased industrial acceptance are also included in this review.

[1]  J. King,et al.  Oilseed volatile analysis by supercritical fluid and thermal desorption methods , 1994 .

[2]  H. Sliwka,et al.  Synthesis of structured lipids and etherlipids with antioxidants: combination of a selena fatty acid and a selena fatty alcohol with a carotenoic acid in glyceride molecules. , 2000, Chemistry and physics of lipids.

[3]  J. Curfs,et al.  With medium-chain triglycerides, higher and faster oxygen radical production by stimulated polymorphonuclear leukocytes occurs. , 2000, JPEN. Journal of parenteral and enteral nutrition.

[4]  E. Brown,et al.  Enzymatic interesterification of triolein with tripalmitin in canola lecithin-hexane reverse micelles , 1993 .

[5]  V. Hubbard,et al.  Linoleic Acid Absorption from Lipid Supplements in Patients with Cystic Fibrosis with Pancreatic Insufficiency and in Control Subjects , 1985, Journal of pediatric gastroenterology and nutrition.

[6]  Markus Lipp,et al.  Review of cocoa butter and alternative fats for use in chocolate-Part A. Compositional data , 1998 .

[7]  S. Lelcuk,et al.  Structured triacylglycerol emulsion, containing both medium- and long-chain fatty acids, in long-term home parenteral nutrition: a double-blind randomized cross-over study. , 2000, Nutrition.

[8]  A. Marangoni,et al.  Lipid modification strategies in the production of nutritionally functional fats and oils. , 1998, Critical reviews in food science and nutrition.

[9]  C. Høy,et al.  Effects of different medium-chain fatty acids on intestinal absorption of structured triacylglycerols , 2000, Lipids.

[10]  C. Akoh,et al.  Modification of menhaden oil by enzymatic acidolysis to produce structured lipids: Optimization by response surface design in a packed bed reactor , 2000 .

[11]  J. deMan.  Consistency of fats: A review , 1983 .

[12]  G. Blackburn,et al.  Alternative lipid sources for enteral and parenteral nutrition: long- and medium-chain triglycerides, structured triglycerides, and fish oils. , 1991, Journal of the American Dietetic Association.

[13]  C. Akoh,et al.  Structured lipids: Synthesis and applications , 1998 .

[14]  C. Akoh,et al.  Enzymatically Modified Beef Tallow as a Substitute for Cocoa Butter , 2002 .

[15]  M. Denke,et al.  Comparison of the effects of medium-chain triacylglycerols, palm oil, and high oleic acid sunflower oil on plasma triacylglycerol fatty acids and lipid and lipoprotein concentrations in humans. , 1997, The American journal of clinical nutrition.

[16]  Casimir C. Akoh,et al.  Four-factor response surface optimization of the enzymatic modification of triolein to structured lipids , 1995 .

[17]  S. Innis,et al.  Development of visual acuity in relation to plasma and erythrocyte omega-6 and omega-3 fatty acids in healthy term gestation infants. , 1994, The American journal of clinical nutrition.

[18]  T. Voelker,et al.  Genetic engineering of a quantitative trait: metabolic and genetic parameters influencing the accumulation of laurate in rapeseed , 1996 .

[19]  K. Lundholm,et al.  Structured triglycerides to postoperative patients: a safety and tolerance study. , 1993, JPEN. Journal of parenteral and enteral nutrition.

[20]  K. Warner,et al.  Frying quality and oxidative stability of high-oleic corn oils , 1997 .

[21]  K. Shahani.  CHAPTER 8 – Lipases and Esterases , 1975 .

[22]  W. Fehr,et al.  A fap5 allele for elevated palmitate in soybean. , 2000 .

[23]  A. Marangoni,et al.  Assessment of lipase- and chemically catalyzed lipid modification strategies for the production of structured lipids , 1999 .

[24]  C. Akoh,et al.  Characterization and oxidative stability of enzymatically produced fish and canola oil-based structured lipids , 2001 .

[25]  P. Mortensen,et al.  Essential fatty acid deficiency in patients receiving home parenteral nutrition. , 1998, The American journal of clinical nutrition.

[26]  T. Babineau,et al.  Effect of a fish oil structured lipid-based diet on prostaglandin release from mononuclear cells in cancer patients after surgery. , 1997, JPEN. Journal of parenteral and enteral nutrition.

[27]  K. Dehesh,et al.  Production of high levels of 8:0 and 10:0 fatty acids in transgenic canola by overexpression of Ch FatB2, a thioesterase cDNA from Cuphea hookeriana. , 1996, The Plant journal : for cell and molecular biology.

[28]  J. Kennedy.  Structured lipids : fats of the future , 1991 .

[29]  T. Koyano,et al.  Fat polymorphism and crystal seeding effects on fat bloom stability of dark chocolate , 1990 .

[30]  C. Akoh,et al.  Enzymatic synthesis of position-specific low-calorie structured lipids , 1997 .

[31]  P. Boulétreau,et al.  Medium- and long-chain triacylglycerols in postoperative patients: structured lipids versus a physical mixture. , 1999, Nutrition.

[32]  D. Firestone,et al.  Official methods and recommended practices of the American Oil Chemists' Society , 1990 .

[33]  T. Yamane,et al.  Enhancement of both reaction yield and rate of synthesis of structured triacylglycerol containing eicosapentaenoic acid under vacuum with water activity control , 1999, Lipids.

[34]  T. Foglia,et al.  Lipase-catalyzed synthesis of structured low-calorie triacylglycerols , 1999 .

[35]  H. Ghazali,et al.  Effect of enzymatic transesterification on the melting points of palm stearin-sunflower oil mixtures , 1998 .

[36]  W. Neff,et al.  Low-linolenic acid soybean oil—Alternatives to frying oils , 1994 .

[37]  D. Seidner,et al.  Lymphatic absorption of enterally fed structured triacylglycerol vs physical mix in a canine model. , 1994, The American journal of clinical nutrition.

[38]  Jinap Selamat,et al.  Effect of storage temperature on texture, polymorphic structure, bloom formation and sensory attributes of filled dark chocolate , 2001 .

[39]  Y. Yeh,et al.  Stearic acid modifies very low density lipoprotein lipid composition and particle size differently from shorter-chain saturated fatty acids in cultured rat hepatocytes , 1997, Lipids.

[40]  S. H. Feairheller,et al.  Enzymatic interesterification of tallow-sunflower oil mixtures , 1993 .

[41]  Gary R. List,et al.  Preparation and properties of zeroTrans soybean oil margarines , 1995 .

[42]  C. Akoh,et al.  Effects of a structured lipid, Captex, and a protein-based fat replacer, Simplesse, on energy metabolism, body weight, and serum lipids in lean and obese Zucker rats , 1998 .

[43]  R. A. Forse,et al.  The new dietary fats in health and disease. , 1997, Journal of the American Dietetic Association.

[44]  M. Ollivon,et al.  Dynamic Crystallization of Dark Chocolate as Affected by Temperature and Lipid Additives , 1998 .

[45]  X. Xu,et al.  Synthesis of structured triacylglycerols by lipase-catalyzed acidolysis in a packed bed bioreactor. , 2000, Journal of agricultural and food chemistry.

[46]  P. Mortensen,et al.  Essential fatty acid deficiency in patients with severe fat malabsorption. , 1997, The American journal of clinical nutrition.

[47]  S. Narine,et al.  Relating structure of fat crystal networks to mechanical properties: a review , 1999 .

[48]  C. Akoh,et al.  Food Lipids: Chemistry, Nutrition, and Biotechnology , 1998 .

[49]  E. Lien,et al.  Corandomization of fats improves absorption in rats. , 1993, The Journal of nutrition.

[50]  G. Blackburn,et al.  Enhanced skeletal muscle and liver protein synthesis with structured lipid in enterally fed burned rats. , 1988, Metabolism: clinical and experimental.

[51]  R. Bellantone,et al.  Structured versus long-chain triglycerides: a safety, tolerance, and efficacy randomized study in colorectal surgical patients. , 1999, JPEN. Journal of parenteral and enteral nutrition.

[52]  T. L. Mounts,et al.  Frying stability of soybean and canola oils with modified fatty acid compositions , 1993 .

[53]  P. Broun,et al.  Genetic engineering of plant lipids. , 1999, Annual review of nutrition.

[54]  C. Akoh,et al.  EFFECTS OF STRUCTURED LIPID CONTAINING OMEGA‐3 AND MEDIUM CHAIN FATTY ACIDS ON SERUM LIPIDS AND IMMUNOLOGICAL VARIABLES IN MICE , 1999 .

[55]  J. Adler-Nissen,et al.  Pilot batch production of specific-structured lipids by lipase-catalyzed interesterification: Preliminary study on incorporation and acyl migration , 1998 .

[56]  G. Talbot.  Fat eutectics and crystallisation , 1995 .

[57]  L. Johnson.  Recovery, Refining, Converting, and Stabilizing Edible Fats and Oils , 2002 .

[58]  J. Adler-Nissen,et al.  Production of specific-structured lipids by enzymatic interesterification in a pilot continuous enzyme bed reactor , 1998 .

[59]  E. Decker.  The role of stereospecific saturated fatty acid positions on lipid nutrition. , 2009, Nutrition reviews.

[60]  C. Akoh,et al.  Enzymatic modification of high-laurate canola to produce margarine fat. , 2001, Journal of agricultural and food chemistry.

[61]  R. Timms.  Physical properties of oils and mixtures of oils , 1985 .

[62]  T. Babineau,et al.  Early enteral feeding in postsurgical cancer patients. Fish oil structured lipid-based polymeric formula versus a standard polymeric formula. , 1996, Annals of surgery.

[63]  J. Adler-Nissen,et al.  Production of specific-structured lipids by enzymatic interesterification: Elucidation of Acyl migration by response surface design , 1998 .

[64]  J. Nordenström,et al.  Metabolic effects of infusion of a structured-triglyceride emulsion in healthy subjects. , 1995, Nutrition.

[65]  T. Kaimal,et al.  Synthesis and estimation of calorific value of a structured lipid-potential reduced calorie fat , 1999, Lipids.

[66]  S. Kubow.  Lipid oxidation products in food and atherogenesis. , 2009, Nutrition reviews.

[67]  C. Akoh,et al.  Nutritional effects of enzymatically modified soybean oil with caprylic acid versus physical mixture analogue in obese Zucker rats , 2000 .

[68]  D. Rousseau,et al.  Restructing butterfat through blending and chemical interesterification. 1. Melting behavior and triacylglycerol modifications , 1996 .

[69]  R. Hartel,et al.  Effect of milk fat fractions on fat bloom in dark chocolate , 1994 .

[70]  C. Akoh,et al.  Enzymatic transesterification of triolein and stearic acid and solid fat content of their products , 1998 .

[71]  D. Rousseau,et al.  The effects of interesterification on physical and sensory attributes of butterfat and butterfat–canola oil spreads , 1998 .

[72]  D. Rousseau,et al.  Tailoring the Textural Attributes of Butter Fat/Canola Oil Blends via Rhizopus arrhizus Lipase-Catalyzed Interesterification. 2. Modifications of Physical Properties , 1998 .

[73]  M. Corredig,et al.  A comparative study of mayonnaise and italian dressing prepared with lipase-catalyzed transesterified olive oil and caprylic acid , 2001 .

[74]  M. Dobarganes,et al.  Thermal stability and frying performance of genetically modified sunflower seed (Helianthus annuus L.) oils , 1993 .

[75]  T. Tang,et al.  Chemical composition and physical properties of soft (tub) margarines sold in Malaysia , 1996 .