Food Lipids: Chemistry, Nutrition, and Biotechnology

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cation [100]. Similarly, the published literature contains an incorrect report that liquid canola shortening was contaminated with fatty acids found in animal fat [101]. To help identify peaks, a GC column can be interfaced to another instrument such as an infrared spectrometer or a mass spectrometer. Hyphenated techniques use on-line detection to confirm the identity of peaks in a chromatogram. Griffiths et al. [102] have reviewed interfaces between gas, supercritical fluid, and high performance liquid chromatography and Fourier transform spectrometery (GC-FTIR, SFC-FTIR, and HPLC-FTIR, respectively). Some of these hyphenated techniques were first used to elucidate the structure of unusual fatty acid isomers, including cyclic fatty acid monomers (CFAM) that often contain trans double bonds in the hydrocarbon chain and cis double bonds in five- or six-membered rings. The formation and the biological effects of these cyclic compounds have been reviewed [103]. A. GC-FTIR For many GC-FTIR instruments, the effluent from the GC column flows continuously through a light pipe (LP) gas cell [102]. LP instruments generally have detection limits of 10–50 ng for unknown complex mixtures of fatty acid methyl esters. Online infrared spectra of CFAM peaks eluting from a gas chromatogram were obtained with an LP GC-FTIR [104]. The results were used to show which of these CFAM contained cis and/or trans double bonds. Several minor peaks in this mixture could not be identified because of the limited sensitivity of the method. Bourne et al. [105] developed an improved GC-FTIR technique using a matrix isolation (MI) interface that increases the sensitivity of the GC-FTIR determination by an order of magnitude. GC–matrix isolation–FTIR is extremely useful for quantitating peak area, determining peak homogeneity, and obtaining structural information on a compound. Although the LP GC-FTIR technique can confirm the identity of intact molecules, its detection limits are higher than those of other GC detectors (e.g., flame ionization). Matrix isolation (MI) is a technique in which analytes and an inert gas (argon) are rapidly frozen at cryogenic temperatures (12 K) and are trapped as a solid matrix on the outer rim of a moving gold-plated disk. The IR spectra of these molecules are free from indications of intermolecular hydrogen bonding and other band broadening effects. These combined benefits yield greater sensitivity that equals, for many applications, that of gas chromatograpy–mass spectrometry (GC-MS) [106]. GC-MI-FTIR was used to quantitate low levels of saturated trans monoene [85], diene [107,108], triene, and conjugated diene fatty acids and their isomers [108] in hydrogenated vegetable and/or fish oils. Figure 7 shows the IR spectra (out-ofplane deformation absorption bands) for two trans-conjugated diene geometric isomers. The characteristic absorption bands shown were used for identification. The conjugated trans,trans diene isomer had an out-of-plane deformation absorption band at 990 cm �1 , whereas, the cis,trans isomer had absorption bands at 950 and 986 cm �1 . The absorption band for the corresponding methylene-interrupted trans diene and the trans monoene was at 971 cm �1 . There were also unique absorption bands for trans and cis diene isomers in the area of the spectrum typical of the carbon– hydrogen stretch vibrations (3035/3005 cm �1 and 3018 cm �1 , respectively) and in the area typical of the carbon–hydrogen out-of-plane deformation absorption bands (972 and 730 cm �1 , respectively). Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.
Figure 7 Expanded IR spectral range showing out-of-plane deformation bands for conjugated cis-trans (top spectrum) and trans-trans (bottom spectrum) 18:2 dienes. (From Ref. 108.) GC-MI-FTIR is also effective in determining the concentration of individual fatty acid methyl esters without having to consider the relative response of the gas chromatograph’s flame ionization detector (FID). It is possible to quantitate trans isomers even with partial GC peak overlap from cis isomers. Quantitation of trans diene isomers was based on measurement of the height of the observed C—H outof-plane deformation band at 971 cm �1 for trans groups and that of the CH 2 asymmetric stretching band at 2935 cm �1 for the 17:0 internal standard [107]. Calibration plots of absorbance versus nanograms injected were generated for the range of 2– 33 ng. Recovery (on cryogenic disk) was based on the determination of the internal standard. The amount of analyte present in injected aliquots was calculated from the observed absorbance values and the corresponding calibration plot. 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
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flow rate, decreasing the size of t
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sion be particularly small, it is u
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2. Electrostatic Interactions Elect
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profile of interdroplet pair potent
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Figure 12 Mechanisms of emulsion in
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[Eq. (9)], but at high droplet conc
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alteration in the system’s compos
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Food emulsions always contain dropl
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creaming and sedimentation in emuls
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Foams (E. Dickinson and G. Stainsby
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4 The Chemistry of Waxes and Sterol
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Shrinkage and flash point are two f
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lowing discussion on chemical analy
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violet chromophore. Application of
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Figure 1 Examples of naturally occu
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Scheme 1 Synthesis of mevalonic aci
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Scheme 3 Synthesis of farnesyl pyro
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Scheme 6 Biosynthesis of cholestero
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educe the risk of coronary heart di
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of cholesterol to bile acids (Schem
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Scheme 10 Metabolic alterations of
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sample preparation is usually emplo
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at levels of 1-100 �g per compone
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30. H. W. Chen, A. A. Kandutsch, an
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Biologically Significant Steroids (
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5 Extraction and Analysis of Lipids
Page 153 and 154: preparing nutritional labeling mate
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
Page 203: B. Gas Chromatography/IR Spectrosco
Page 207 and 208: CFAMs before converting them to the
Page 209 and 210: Figure 8 GC-EIMS chromatographic da
Page 211 and 212: flame ionization detection. The fat
Page 213 and 214: levels in excess of 50% of the tota
Page 215 and 216: 22. A. Huang and D. Firestone. Dete
Page 217 and 218: 59. E. G. Perkins and C. Smick. Oct
Page 219 and 220: 97. Association of Official Analyti
Page 221 and 222: 136. J. J. Myer and A. Kukis. Elect
Page 223 and 224: 7 Chemistry of Frying Oils KATHLEEN
Page 225 and 226: Table 1 Effects of Physical and Che
Page 227 and 228: Figure 3 Oxidation reactions in fry
Page 229 and 230: or intermittent frying, oil filtrat
Page 231 and 232: for the ultimate criteria to evalua
Page 233 and 234: triacylglycerol polymers, and triac
Page 235 and 236: 100 compounds identified in hydroge
Page 237 and 238: 5. J. Pokorny. Flavor chemistry of
Page 239 and 240: 50. Anonymous. Recommendations of t
Page 241 and 242: 8 Recovery, Refining, Converting, a
Page 243 and 244: Figure 1 Depiction of hard screw pr
Page 245 and 246: Figure 2 Depiction of prepress solv
Page 247 and 248: Seed containing more than the criti
Page 249 and 250: Figure 5 Steps in processing soybea
Page 251 and 252: specification of 50% protein is met
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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
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32. J. B. Ohlrogge and V. S. Eccles
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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.
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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
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(Fig. 9), foaming, color, viscosity
Page 497 and 498:
Yen and Duh [69] and Chen and Ho [7
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Figure 10 1 H Nuclear magnetic reso
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to Marquez-Ruiz et al. [93], who us
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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
Page 539 and 540:
Figure 2 Mechanism by which one phe
Page 541 and 542:
Figure 4 Formation of �-tocophero
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Figure 6 Formation of an epoxyquino
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gallate. The antioxidant mechanism
Page 547 and 548:
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
Page 557 and 558:
26. J. Kanner, J. B. German, and J.
Page 559 and 560:
68. J. Kanner, F. Sofer, S. Harel,
Page 561 and 562:
17 Fats and Oils in Human Health DA
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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
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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
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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
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production of commercially viable o
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acids synthesized de novo, primaril
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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
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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
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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
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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,
Page 675 and 676:
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
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the fat component and the other hal
Page 687 and 688:
shows that there is a negative corr
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C. Influence of Dietary Fat on Fatt
Page 691 and 692:
Figure 1 Signal transduction cascad
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mals indicate that high-fat feeding
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processes. Numerous studies provide
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monier (252) suggested that in cert
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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
Page 721 and 722:
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
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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
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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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