Food Lipids: Chemistry, Nutrition, and Biotechnology

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Table 1 General Classification of Lipids Simple lipids: Compounds with two types of structural moieties Glyceryl esters: esters of glycerol and fatty acids (e.g., triacylglycerols, partial acylglycerols) Cholesteryl esters: esters of cholesterol and fatty acids Waxes: true waxes are esters of long chain alcohols and fatty acids; esters of vitamins A and D are also included Ceramides: amides of fatty acids with long chain di- or trihydroxy bases containing 12–22 carbon atoms in the aliphatic chain (e.g., sphingosine) Complex lipids: Compounds with more than two types of structural moieties Phospholipids: glycerol estesr of fatty acids, phosphoric acid, and other groups containing nitrogen Phosphatidic acid: diacylglycerol esterified to phosphoric acid Phosphatidylcholine: phosphatidic acid linked to choline, lecithin Phosphatidylethanolamine Phosphatidylserine Phosphatidylinositol Phosphatidyl acylglycerol: more than one glycerol molecule is esterified to phosphoric acid (e.g., cardiolipin, diphosphatidyl acylglycerol) Glycoglycerolipids: 1,2-diacylglycerol joined by a glycosidic linkage through position sn-3 to a carbohydrate moiety [e.g., monogalactosyl diacylglycerol, digalactosyl monoacylglycerol, sulfoquinovosyl diacylglycerol (monoglycosyl diacylglycerol at position 6 of the disaccharide moiety is linked by carbon–sulfur bond to a sulfonic acid)] Gangliosides: glycolipids that are structurally similar to ceramide polyhexoside and also contain 1–3 sialic acid residues, most contain an amino sugar in addition to the other sugars Sphingolipids: derivatives of ceramides Sphingomyelin: ceramide phosphorylcholine Cerebroside: ceramide monohexoside (i.e., ceramide linked to a single sugar moiety at the terminal hydroxyl group of the base) Ceramide dihexoside: linked to a disaccharide Ceramide polyhexoside: linked to a tri- or oligosaccharide Cerebroside sulfate: ceramide monohexoside esterified to a sulfate group Derived lipids: Compounds that occur as such or released from simple or complex lipids due to hydrolysis (e.g., fatty acids; fatty alcohols; fat-soluble vitamins A, D, E, and K; hydrocarbons; sterols) Source: Adapted from Ref. [3–5]. Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.
preparing nutritional labeling material, as well as for promoting and understanding the effects of fats and oils on food functionality. At the same time, knowledge about the structural characteristics of lipids may allow development of tailor-made products designed for a particular function or application. II. EXTRACTION OF LIPIDS FROM FOODS AND BIOLOGICAL MATERIALS Lipids in nature are associated with other molecules via (a) van der Waals interaction, e.g., interaction of several lipid molecules with proteins; (b) electrostatic and hydrogen bonding, mainly between lipids and proteins; and (c) covalent bonding among lipids, carbohydrates, and proteins. Therefore, to separate and isolate lipids from a complex cellular matrix, different chemical and physical treatments must be administered. Water insolubility is the general property used for the separation of lipids from other cellular components. Complete extraction may require longer extraction time or a series or combination of solvents so that lipids can be solubilized from the matrix. The existing procedures of lipid extraction from animal or plant tissues usually include several steps: (a) pretreatment of the sample, which includes drying, size reduction, or hydrolysis; (b) homogenization of the tissue in the presence of a solvent; (c) separation of liquid (organic and aqueous) and solid phases; (d) removal of nonlipid contaminants; and (e) removal of solvent and drying of the extract. Standard methods for lipid extraction have been established by the Association of Official Analytical Chemists (AOAC) International for different types of materials/tissues. However, when it comes to practical situations, each case might require modification of the method. A. Sample Preparation As with any form of chemical analysis, proper sampling and storage of the samples are essential for obtaining valid results. According to Pomeranz and Meloan [5], an ideal sample should be identical in all of its intrinsic properties to the bulk of the material from which it is taken. In practice, a sample is satisfactory if its properties under investigation correspond to those of the bulk material within the limits set by the nature of the test. Sample preparation for lipid analysis depends on the type of food and the nature of its lipids. Effective analysis calls for a knowledge of the structure, chemistry, and occurrence of principal lipid classes and their constituents. Therefore, it is not possible to devise a single standard method for extraction of all kinds of lipids in different foods. Extraction of lipids should be performed as soon as possible after the removal of tissues from the living organism so as to minimize any subsequent changes. Immediate extraction is not always possible; however, the samples usually are stored at very low temperatures in sealed containers, under an inert (nitrogen) atmosphere or on dry ice. Yet the freezing process itself may permanently damage the tissues as a result of osmotic shock, which alters the original environment of the tissue lipids and brings them into contact with enzymes from which they are normally protected. Thawing the sample taken from frozen storage before extraction may enhance this deterioration. Therefore, tissue samples should be homogenized and extracted with Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.
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TM Food Lipids Chemistry, Nutrition
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FOOD SCIENCE AND TECHNOLOGY A Serie
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37. Omega-3 Fatty Acids in Health a
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90. Dairy Technology: Principles of
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Preface to the Second Edition Reade
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Preface to the First Edition There
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Contents Preface to the Second Edit
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20. Dietary Fats and Coronary Heart
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J. Bruce German Department of Food
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1 Nomenclature and Classification o
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described as 2-methyl-3-phytyl-1,4-
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Table 3 A Summary of Sequence Prior
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Table 5 Systematic, Common, and Sho
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saturation of EFA occurs (primarily
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Figure 5 Prostaglandin metabolites
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Figure 7 Prostanoic acid and prosta
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Figure 9 Eicosenoid isomers in part
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Figure 10 Nomenclature of cyclic fa
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Figure 13 Hydroxy fatty acid struct
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Figure 15 Furanoid fatty acid struc
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Table 7 Short Abbreviations for Som
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Figure 20 Steroid nomenclature. rep
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Figure 22 Cholesterol oxidation pro
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E. Phosphoglycerides (Phospholipids
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Figure 26 Glyceroglycolipid structu
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Figure 28 Structures of some vitami
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Page 55 and 56:
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6. IUPAC. Nomenclature of Organic C
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2 Chemistry and Function of Phospho
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variant [1]. Phosphonolipids are ma
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nonelectrolytes, however, the perme
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pensations in that enthalpy lost by
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Table 3 Membrane Deterioration in A
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erols to generate semisolid or plas
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The interaction of phospholipids wi
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fatty acid occurs when Fe 3� at t
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4. M. C. Blok, L. L. M. van Deenen,
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47. N. Markova, E. Sparr, L. Wadso,
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87. R. J. Hsieh. Contribution of li
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3 Lipid-Based Emulsions and Emulsif
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may be composed of surface-active c
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2. Cloud Point When a surfactant so
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HLB=7� � (hydrophilic group num
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sion is known as the phase inversio
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strongly with each other rather tha
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� = � (1 � 2.5�) (3) 0 wher
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Figure 8 Biopolymer molecules or ag
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divide homogenization into two cate
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2� �P 1 = (4) r where � is th
Page 101 and 102: flow rate, decreasing the size of t
Page 103 and 104: sion be particularly small, it is u
Page 105 and 106: 2. Electrostatic Interactions Elect
Page 107 and 108: profile of interdroplet pair potent
Page 109 and 110: Figure 12 Mechanisms of emulsion in
Page 111 and 112: [Eq. (9)], but at high droplet conc
Page 113 and 114: alteration in the system’s compos
Page 115 and 116: Food emulsions always contain dropl
Page 117 and 118: creaming and sedimentation in emuls
Page 119 and 120: Foams (E. Dickinson and G. Stainsby
Page 121 and 122: 4 The Chemistry of Waxes and Sterol
Page 123 and 124: Shrinkage and flash point are two f
Page 125 and 126: lowing discussion on chemical analy
Page 127 and 128: violet chromophore. Application of
Page 129 and 130: Figure 1 Examples of naturally occu
Page 131 and 132: Scheme 1 Synthesis of mevalonic aci
Page 133 and 134: Scheme 3 Synthesis of farnesyl pyro
Page 135 and 136: Scheme 6 Biosynthesis of cholestero
Page 137 and 138: educe the risk of coronary heart di
Page 139 and 140: of cholesterol to bile acids (Schem
Page 141 and 142: Scheme 10 Metabolic alterations of
Page 143 and 144: sample preparation is usually emplo
Page 145 and 146: at levels of 1-100 �g per compone
Page 147 and 148: 30. H. W. Chen, A. A. Kandutsch, an
Page 149 and 150: Biologically Significant Steroids (
Page 151: 5 Extraction and Analysis of Lipids
Page 155 and 156: polar solvents, such as alkanols, f
Page 157 and 158: a ternary system consisting of chlo
Page 159 and 160: lipids from meat or hydrolytic prod
Page 161 and 162: perature under vacuum. Acid hydroly
Page 163 and 164: IV. ANALYSIS OF LIPID EXTRACTS Lipi
Page 165 and 166: ments, etc.) primarily involves chr
Page 167 and 168: 2. Gas Chromatography The GC (or GL
Page 169 and 170: 4. Supercritical Fluid Chromatograp
Page 171 and 172: Table 3 Solvent Systems that Could
Page 173 and 174: sibility of determining all compone
Page 175 and 176: the isolated trans band is another
Page 177 and 178: ionized molecule has the highest m/
Page 179 and 180: 3. W. R. Bloor. Outline of a classi
Page 181 and 182: 45. Association of Official Analyti
Page 183 and 184: 90. M. N. Vaghela and A. Kilara. A
Page 185 and 186: 132. C. G. Walton, W. M. N. Ratnaya
Page 187 and 188: 6 Methods for trans Fatty Acid Anal
Page 189 and 190: where A = abc (1) 1 A = absorbance
Page 191 and 192: methyl elaidate weight equivalents
Page 193 and 194: method was modified by inclusion of
Page 195 and 196: may be packed or bound to a column,
Page 197 and 198: Figure 4 The C-18 region of the gas
Page 199 and 200: Table 2 Response Factors of Unsatur
Page 201 and 202: Figure 5 Separation of the phenacyl
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B. Gas Chromatography/IR Spectrosco
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Figure 7 Expanded IR spectral range
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CFAMs before converting them to the
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Figure 8 GC-EIMS chromatographic da
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flame ionization detection. The fat
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levels in excess of 50% of the tota
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22. A. Huang and D. Firestone. Dete
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59. E. G. Perkins and C. Smick. Oct
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97. Association of Official Analyti
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136. J. J. Myer and A. Kukis. Elect
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7 Chemistry of Frying Oils KATHLEEN
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Table 1 Effects of Physical and Che
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Figure 3 Oxidation reactions in fry
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or intermittent frying, oil filtrat
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for the ultimate criteria to evalua
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triacylglycerol polymers, and triac
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100 compounds identified in hydroge
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5. J. Pokorny. Flavor chemistry of
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50. Anonymous. Recommendations of t
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8 Recovery, Refining, Converting, a
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Figure 1 Depiction of hard screw pr
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Figure 2 Depiction of prepress solv
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Seed containing more than the criti
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Figure 5 Steps in processing soybea
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specification of 50% protein is met
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tent of prepress cake is 15-18%, an
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in successive passes through the be
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Figure 10 Additional commonly used
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that follow the DT. Drying at norma
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B. Extraction of Oil-Bearing Fruits
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1. Wet Rendering Wet rendering is t
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Figure 15 Process flow sheet for de
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Table 2 Properties of Some Crude an
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Figure 16 Process flow sheet for al
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Figure 17 Process flow sheet for va
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for problematic high wax contents (
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Figure 19 Oil processing facilities
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Figure 20 Depiction of physical ref
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4-7�C, and then to tanks with slo
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Figure 21 Hydrogenation reaction me
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ond, which may form in its original
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Figure 24 Plasticization of margari
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Figure 25 Equipment used in expande
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selectivity, others claim success i
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48. E. J. Campbell. Sunflower oil.
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9 Crystallization and Polymorphism
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Generally, it is accepted that both
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Figure 2 A point lattice. (Adapted
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structure.... The term ‘fat’ us
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Figure 6 Schematic representation o
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Figure 8 Polymorphic transitions of
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where A = B = C and all are saturat
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LMF was found to facilitate the tra
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Table 3 Nomenclature and Melting Po
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Other mixed-fat systems have been s
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Figure 12 Proposed intermediate str
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17. K. Larsson. The crystal structu
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59. G. G. Jewell. Vegetable fats. I
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10 Chemical Interesterification of
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however, since monoacylglycerols an
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D. The ‘‘Real’’ Catalyst Th
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Figure 3 Proposed reaction mechanis
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Figure 5 Kinetics of interesterific
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Table 1 Theoretical Triacylglycerol
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Cast et al. [55] demonstrated the r
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Solid: Liquid: SSS, 33.3% OOO, 8.3%
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Figure 11 Changes in the fatty acid
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fication and blending on butterfat-
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influence of interesterification on
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B. Margarines In the manufacture of
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Figure 16 Proportion of soild fat o
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Tautorus and McCurdy [102] demonstr
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ACKNOWLEDGMENTS The authors acknowl
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54. A. Kuksis, M. J. McCarthy, and
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101. S. Zalewski and A. M. Gaddis.
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11 Lipid Oxidation of Edible Oil DA
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Figure 1 Molecular orbital of tripl
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Figure 3 Singlet oxygen formation b
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tween substrate and triplet oxygen
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Figure 8 Conjugated and nonconjugat
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Figure 11 Conjugated hydroperoxide
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etween the oxygen and the oxygen of
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cadienal, trans,trans-2,4-decadiena
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Figure 14 Mechanism for the formati
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Copyright 2002 by Marcel Dekker, In
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Figure 18 Formation and reactions o
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Figure 19 Effect of 0, 0.25, 0.5, a
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Figure 21 Singlet oxygen quenching
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10. E. N. Frankel. Chemistry of aut
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52. A. L. Callison. Singlet oxygen
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12 Lipid Oxidation of Muscle Foods
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A. Initiation The direct reaction o
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undles), and endomysia (sheaths of
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sosomes, etc. A comparison of the l
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dative stability, comparisons betwe
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5. Hydrolysis of Lipids and Associa
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of iron from the heme pocket by coo
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Membrane systems that reduce iron c
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phases of storage [51,187,188]. In
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4. Glutathione While the traditiona
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G. Mathematical Modeling The pathwa
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with this chemical, treated salmon
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multicomponent alternatives [304,30
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and its extent was related to inten
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esponded similarly to vacuum packag
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31. M. L. Greaser, R. G. Cassens, W
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72. J. S. Elmore, D. S. Mottram, M.
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112. J. Kanner, H. Mendel, and P. B
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154. M. B. Korycka-Dahl and T. Rich
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193. P. Akhtar, J. I. Gray, T. H. C
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230. B. Bjerkeng and G. Johnsen. Fr
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271. C.-J. Huang, and M.-L. Fwu. De
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313. M. G. Mast and J. H. MacNeil.
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353. H. A. Ghanbari, W. B. Wheeler,
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13 Fatty Acid Oxidation in Plant Ti
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1. Fatty Acid Activation Prior to d
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L.) leaf peroxisomes exhibits highe
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Figure 2 The glyoxylate cycle in gl
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C. �-Oxidation of Specific Fatty
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cotyledons and partially purified.
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Catabolism of heptanoyl CoA as well
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Figure 6 Peroxisome catabolism of m
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onstrated that �-oxidations requi
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that the member of the enzyme famil
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Plant oxylipin pathway, also named
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Figure 9 Proposed scheme for lipoxy
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oleic acid. These results suggest t
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of the seed pod reversed senescnece
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Figure 11 ‘‘Heterolytic’’-t
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Since 1971, when this physiologic r
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Table 1 Physiological Effects of Ja
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erides, although PUFAs in both form
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9-hydroperoxides and did not attack
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aerial parts of plants, constitutes
Page 471 and 472:
32. J. B. Ohlrogge and V. S. Eccles
Page 473 and 474:
74. L. J. Morris. The mechanism of
Page 475 and 476:
115. B. A. Vick. Oxygenated fatty a
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153. T. K. Peterman and J. N. Siedo
Page 479 and 480:
193. B. A. Stelmach, A. Müller, P.
Page 481 and 482:
230. M. Hamberg, C. A. Herman, and
Page 483 and 484:
14 Methods for Measuring Oxidative
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ated fatty acids during oxidation (
Page 487 and 488:
Several other chemical methods have
Page 489 and 490:
Figure 3 Relationship between perox
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distillate. In case of the distilla
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and ketones. This ion is formed fro
Page 495 and 496:
(Fig. 9), foaming, color, viscosity
Page 497 and 498:
Yen and Duh [69] and Chen and Ho [7
Page 499 and 500:
Figure 10 1 H Nuclear magnetic reso
Page 501 and 502:
to Marquez-Ruiz et al. [93], who us
Page 503 and 504:
35. F. Shahidi, J. Yun, L.J. Rubin,
Page 505 and 506:
77. H. Saito and K. Nakamura. Appli
Page 507 and 508:
15 Antioxidants DAVID W. REISCHE Th
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Hydroperoxide degradation leads to
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e cyclical, with regeneration of th
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A. Synthetic Antioxidants Synthetic
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Propyl gallate (PG) 212.20 White cr
Page 517 and 518:
4. 6-Ethoxy-1,2-dihydro-2,2,4-trime
Page 519 and 520:
Figure 3 Structures of tocopherols
Page 521 and 522:
Figure 4 Structures of ascorbic aci
Page 523 and 524:
4. Enzymatic Antioxidants Glucose o
Page 525 and 526:
would be imprudent to discount any
Page 527 and 528:
droxycoumarin (scopoletin), and hyd
Page 529 and 530:
Figure 7 Structures of sesame antio
Page 531 and 532:
8. G. Minotti. Sources and role of
Page 533 and 534:
50. K. Shimada, H. Muta, Y. Nakamur
Page 535 and 536:
16 Antioxidant Mechanisms ERIC A. D
Page 537 and 538:
For instance, the hydrogen of the h
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Figure 2 Mechanism by which one phe
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Figure 4 Formation of �-tocophero
Page 543 and 544:
Figure 6 Formation of an epoxyquino
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gallate. The antioxidant mechanism
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Figure 8 Products formed from the o
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in food systems, transition metals
Page 551 and 552:
An intersystem energy transfer occu
Page 553 and 554:
V. ALTERATIONS IN LIPID OXIDATION B
Page 555 and 556:
VII. ANTIOXIDANT INTERACTIONS Biolo
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26. J. Kanner, J. B. German, and J.
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68. J. Kanner, F. Sofer, S. Harel,
Page 561 and 562:
17 Fats and Oils in Human Health DA
Page 563 and 564:
Table 1 Classification of LDL Parti
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stearic) had been incorporated by i
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studies contains equal amounts (40-
Page 569 and 570:
Table 5 Influence of 25% Caloric Re
Page 571 and 572:
26. L. D. Cowan, D. L. O’Connell,
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fatty acid margarine on serum lipid
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nutrition examination survey. I. Ep
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18 Unsaturated Fatty Acids STEVEN M
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Figure 1 A generalized scheme for h
Page 581 and 582:
Plant fatty acids provide a seminal
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plants [27]. However, the requireme
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The reciprocal response of the �6
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fatty acids and a dynamic system fo
Page 589 and 590:
production of commercially viable o
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acids synthesized de novo, primaril
Page 593 and 594:
Figure 4 The cis and trans configur
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VI. SYNTHESIS AND ABUNDANCE OF PUFA
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of eicosanoids. It is present in al
Page 599 and 600:
usual NMIFA structures with potenti
Page 601 and 602:
10. S. P. Baykousheva, D. L. Luthri
Page 603 and 604:
47. M. J. T. Alaniz, I. N. T. d. Go
Page 605 and 606:
86. R. J. Henderson and D. R. Toche
Page 607 and 608:
19 Dietary Fats, Eicosanoids, and t
Page 609 and 610:
synthesize EPA from linolenic acid
Page 611 and 612:
Figure 2 Immune responses as a func
Page 613 and 614:
done predominantly in rodent specie
Page 615 and 616:
guinea pigs showed increased immune
Page 617 and 618:
of energy from fat. Feeding the low
Page 619 and 620:
14. P. Purasiri, A. Murray, S. Rich
Page 621 and 622:
20 Dietary Fats and Coronary Heart
Page 623 and 624:
(HDLs). Each class has its own char
Page 625 and 626:
70% of the total amount of choleste
Page 627 and 628:
McGandy and coworkers [8] have care
Page 629 and 630:
Figure 4 Effects of myristic and pa
Page 631 and 632:
3. Polyunsaturated Fatty Acids Poly
Page 633 and 634:
Figure 8 Effects of a mixture of sa
Page 635 and 636:
chemoattractant protein-1 (MCP-1),
Page 637 and 638:
Figure 11 In vitro LDL oxidation. F
Page 639 and 640:
Table 4 Fatty Acid Composition of a
Page 641 and 642:
Figure 12 Processes involved in thr
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as compared with a diet rich in but
Page 645 and 646:
from cardiovascular disease [73,74]
Page 647 and 648:
Figure 16 Schematic representation
Page 649 and 650:
aggregation tendency induced by som
Page 651 and 652:
35. D. R. Janero. Malondialdehyde a
Page 653 and 654:
68. B. J. Burrl, R. M. Dougherty, D
Page 655 and 656:
21 Conjugated Linoleic Acids: Nutri
Page 657 and 658:
method that works optimally in all
Page 659 and 660:
adipose tissue contained two major
Page 661 and 662:
providing rats with 0.5% and 1% CLA
Page 663 and 664:
with the control group. Interesting
Page 665 and 666:
feeding. These findings suggest tha
Page 667 and 668:
In contrast to the antioxidative pr
Page 669 and 670:
esponsible, at least in part, for t
Page 671 and 672:
Yamasaki et al. studied CLA and ant
Page 673 and 674:
17. J. K. G. Kramer, P. W. Parodi,
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55. C. Ip, S. F. Chin, J. A. Scimec
Page 677 and 678:
90. J. S. Munday, K. G. Thompson, a
Page 679 and 680:
126. J. Singh, R. Hamid, and B. S.
Page 681 and 682:
22 Dietary Fats and Obesity DOROTHY
Page 683 and 684:
For example, some have reported tha
Page 685 and 686:
the fat component and the other hal
Page 687 and 688:
shows that there is a negative corr
Page 689 and 690:
C. Influence of Dietary Fat on Fatt
Page 691 and 692:
Figure 1 Signal transduction cascad
Page 693 and 694:
mals indicate that high-fat feeding
Page 695 and 696:
processes. Numerous studies provide
Page 697 and 698:
monier (252) suggested that in cert
Page 699 and 700:
4. National Task Force on Obesity.
Page 701 and 702:
46. F. Lucas, K. Ackroff, and A. Sc
Page 703 and 704:
90. D. Mela. Sensory preference for
Page 705 and 706:
133. D. R. Romsos and G. A. Leveill
Page 707 and 708:
169. T. Ide, H. Kobayashi, L. Ashak
Page 709 and 710:
207. A. B. Awad and E. A. Zepp. Alt
Page 711 and 712:
246. Y. B. Kim, R. Nakajima, T. Mat
Page 713 and 714:
23 Lipid-Based Synthetic Fat Substi
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operations, and in theory, can repl
Page 717 and 718:
Table 3 Types of Lipid-Based Fat Su
Page 719 and 720:
Figure 1 Structure of sucrose polye
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Figure 3 Synthetic scheme for olest
Page 723 and 724:
Figure 5 Structure of sorbitol poly
Page 725 and 726:
Figure 8 Structure of raffinose pol
Page 727 and 728:
Figure 11 Structure of methyl galac
Page 729 and 730:
Table 4 Some Properties of Sucrose
Page 731 and 732:
Figure 15 Structure of trialkoxytri
Page 733 and 734:
Figure 19 Structure of polysiloxane
Page 735 and 736:
inversely related to the degree of
Page 737 and 738:
Table 8 Some Nutritional Uses of No
Page 739 and 740:
genetic assay in Chinese hamster ov
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IX. PERSPECTIVES With the approval
Page 743 and 744:
30. L. Osipow, F. D. Snell, D. Marr
Page 745 and 746:
72. K. W. Miller and P. H. Long. A
Page 747 and 748:
24 Food Applications of Lipids FRAN
Page 749 and 750:
Table 3 Typical Fatty Acid Composit
Page 751 and 752:
are significant differences in oil
Page 753 and 754:
Table 6 Production and Disappearanc
Page 755 and 756:
and margarine should be pronounced
Page 757 and 758:
Table 8 Approximate Fatty Acid Comp
Page 759 and 760:
egions of the world. In addition to
Page 761 and 762:
50-55% fat. Production figures for
Page 763 and 764:
utter with up to 5% of another fat
Page 765 and 766:
market with high overrun and good s
Page 767 and 768:
11. D. Hettinga. Butter. In: Bailey
Page 769 and 770:
25 Lipid Biotechnology KUMAR D. MUK
Page 771 and 772:
Table 1 Lipid Content and Levels of
Page 773 and 774:
as 80% lipids of which about 90% ar
Page 775 and 776:
Table 6 Wax Esters Formed by Acinet
Page 777 and 778:
Some other biosurfactants include e
Page 779 and 780:
Figure 6 Microbial production of hy
Page 781 and 782:
Figure 9 Microbial production of ke
Page 783 and 784:
Figure 12 Microbial production of k
Page 785 and 786:
Table 8 Specificity of Triacylglyce
Page 787 and 788:
Figure 16 Lipase-catalyzed transest
Page 789 and 790:
Figure 20 Preparation of structured
Page 791 and 792:
Figure 24 Preparation of monoacylgl
Page 793 and 794:
Fatty acid esters of polyols are us
Page 795 and 796:
Figure 29 Specificity constants in
Page 797 and 798:
Figure 31 Preparation of concentrat
Page 799 and 800:
Figure 35 Enrichment of very long c
Page 801 and 802:
B. Phospholipases Figure 38 shows t
Page 803 and 804:
Lysophosphatidic acid has been prep
Page 805 and 806:
Figure 41 Transesterification of ph
Page 807 and 808:
Figure 46 Enzymatic production of h
Page 809 and 810:
Figure 50 Hydration of linoleic aci
Page 811 and 812:
Figure 51 Principle of enzymatic de
Page 813 and 814:
13. E. Molina Grima, J. A. Sánchez
Page 815 and 816:
53. M. Powalla, S. Lang, and V. Wra
Page 817 and 818:
96. R. Schuch and K. D. Mukherjee.
Page 819 and 820:
138. K. D. Mukherjee and I. Kiewitt
Page 821 and 822:
179. U. T. Bornscheuer, H. Stamatis
Page 823 and 824:
222. H. Stamatis, V. Sereti, and F.
Page 825 and 826:
265. S. R. Moore and G. P. McNeill.
Page 827 and 828:
303. C. Virto, I. Svensson, and P.
Page 829 and 830:
343. E. Blee and F. Schuber. Regio-
Page 831 and 832:
26 Microbial Lipases JOHN D. WEETE
Page 833 and 834:
ation. Fungal lipases typically exi
Page 835 and 836:
of buffer A containing 1 M ammonium
Page 837 and 838:
without shaking for 30 minutes, whe
Page 839 and 840:
the C domain of the protein through
Page 841 and 842:
Figure 2 (Continued) Figure 3 Schem
Page 843 and 844:
on the substrate and presence or ab
Page 845 and 846:
Table 3 Selectivities of Multiple E
Page 847 and 848:
lanuginosa, C. antarctica B, Rhizop
Page 849 and 850:
10. C. T. Hou and T. M. Johnston. S
Page 851 and 852:
53. C. C. Akoh. Enzymatic synthesis
Page 853 and 854:
94. D. M. Lawson, A. M. Brzozowski,
Page 855 and 856:
135. B. K. Yang and J. P. Chen. Gel
Page 857 and 858:
27 Enzymatic Interesterification WE
Page 859 and 860:
esterification of butterfat at 40
Page 861 and 862:
also found to decrease the crystall
Page 863 and 864:
T c than animal fats. The T c for v
Page 865 and 866:
in the oxyanion hole is the amino a
Page 867 and 868:
of the interface as a measure of su
Page 869 and 870:
Figure 11 Catalytic mechanism for l
Page 871 and 872:
Figure 13 Triacylglycerol products
Page 873 and 874:
imization of interesterification, a
Page 875 and 876:
supports include high losses of act
Page 877 and 878:
is a thin layer located directly ne
Page 879 and 880:
volume per year. The volumetric act
Page 881 and 882:
and removal of reactants and produc
Page 883 and 884:
vinyl chloride. In a membrane such
Page 885 and 886:
of the enzyme. Animal and plant lip
Page 887 and 888:
esters as surface active agents dur
Page 889 and 890:
14. P. Kalo, H. Huotari, and M. Ant
Page 891 and 892:
57. F. Pabai, S. Kermasha, and A. M
Page 893 and 894:
94. J. Kurashige. Enzymatic convers
Page 895 and 896:
28 Structured Lipids CASIMIR C. AKO
Page 897 and 898:
Figure 2 Structure of a physical mi
Page 899 and 900:
2. Medium Chain Fatty Acids and Tri
Page 901 and 902:
Figure 4 Pathway for eicosanoid bio
Page 903 and 904:
leukotrienes (hydroxy fatty acids a
Page 905 and 906:
Figure 7 Structure of Benefat (bran
Page 907 and 908:
cause of the huge capital investmen
Page 909 and 910:
Figure 8 Reaction scheme showing ac
Page 911 and 912:
alters the native conformation of t
Page 913 and 914:
Table 6 Advantages of Enzymatic App
Page 915 and 916:
Figure 13 Stereochemical configurat
Page 917 and 918:
IV. NUTRITIONAL AND MEDICAL APPLICA
Page 919 and 920:
Table 9 Factors That Affect Outlook
Page 921 and 922:
27. G. O. Burr and M. D. Burr. A ne
Page 923 and 924:
69. M. Reslow, P. Aldercreutz, and
Page 925 and 926:
113. C. J. Gollaher, E. S. Swenson,
Page 927 and 928:
29 Biosynthesis of Fatty Acids and
Page 929 and 930:
olive (Olea europea), and avocado (
Page 931 and 932:
Table 2 (Continued) Fatty acid a Sp
Page 933 and 934:
2. Basic Features The functional un
Page 935 and 936:
Hydroxy-Acyl ACP dehydrase (Crotony
Page 937 and 938:
Figure 1 Steps of fatty acid biosyn
Page 939 and 940:
The three KAS isoforms are assigned
Page 941 and 942:
chain length acyl-ACP residues, and
Page 943 and 944:
10-carbon and 14- to 16-carbon acyl
Page 945 and 946:
In developing castor seed, BC and A
Page 947 and 948:
(viz., seed, fruit) genes, and this
Page 949 and 950:
Figure 4 Fatty acid modification re
Page 951 and 952:
12-MO, the cDNA for the enzyme has
Page 953 and 954:
Table 5 Enzyme Activities Involved
Page 955 and 956:
of reactivity is also supported by
Page 957 and 958:
tems, PTAP is a likely candidate fo
Page 959 and 960:
ifying 18:1 �9 and deacylating 18
Page 961 and 962:
oils (rich in 18:3 �6,9,12), and
Page 963 and 964:
eticulum subpopulations also finds
Page 965 and 966:
CPT (DAG ↔ PC) Extensive involvem
Page 967 and 968:
available (cf. Sec. V.C.4 and Ref.
Page 969 and 970:
erol backbone of triacylglycerols c
Page 971 and 972:
14. E. Heinz. Biosynthesis of polyu
Page 973 and 974:
56. R. C. Clough, A. L. Matthis, S.
Page 975 and 976:
91. R. J. Heath and C. O. Rock. Eno
Page 977 and 978:
124. R. Schuch, F. M. Brück, M. Br
Page 979 and 980:
Kader and P. Mazliak, eds.). Kluwer
Page 981 and 982:
197. Y. Cao, K. Oo, and A. H. C. Hu
Page 983 and 984:
241. M. C. Dobarganes, G. Márquez-
Page 985 and 986:
30 Genetic Engineering of Crops Tha
Page 987 and 988:
existing genes in the host plant ge
Page 989 and 990:
It becomes the plant breeder’s jo
Page 991 and 992:
previously mentioned low-linolenic
Page 993 and 994:
develop and apply methods, evaluate
Page 995 and 996:
enzyme with high activity for placi
Page 997 and 998:
activity in the oil palm mesocarp s
Page 999 and 1000:
Figure 4 Commercial applications of
Page 1001 and 1002:
and mildness. Because the perennial
Page 1003 and 1004:
In the context of developing increa
Page 1005 and 1006:
occurs esterified at the sn-2 posit
Page 1007 and 1008:
as high as coconut or palm kernel o
Page 1009 and 1010:
systems. Key to assessing the oppor
Page 1011 and 1012:
property encouraged us to look for
Page 1013 and 1014:
mercial lauric fats based on both P
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Food Lipids: Chemistry, Nutrition, and Biotechnology

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