VITAMINS IN FOODS Analysis, Bioavailability, and Stability GEORGE F M BALL Boca Raton London New York A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc Published in 2006 by CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2006 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group No claim to original U.S Government works Printed in the United States of America on acid-free paper 10 International Standard Book Number-10: 1-57444-804-8 (Hardcover) International Standard Book Number-13: 978-1-57444-804-7 (Hardcover) Library of Congress Card Number 2005049926 This book contains information obtained from authentic and highly regarded sources Reprinted material is quoted with permission, and sources are indicated A wide variety of references are listed Reasonable efforts have been made to publish reliable data and information, but 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are used only for identification and explanation without intent to infringe Library of Congress Cataloging-in-Publication Data Ball, G.F.M Vitamins in foods : analysis, bioavailability, and stability / by George F.M Ball p cm (Food science and technology ; 156) Includes bibliographical references and index ISBN 1-57444-804-8 (alk paper) Food Vitamin content I Title II Food science and technology (Taylor & Francis) ; 156 TX553.V5B358 2005 613.2'85 dc22 2005049926 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com Taylor & Francis Group is the Academic Division of Informa plc and the CRC Press Web site at http://www.crcpress.com Dedication This work is dedicated to my wife and dearest friend, Kazuko (Kako) About the Author George Ball has accumulated many years of commercial and research laboratory experience in pharmaceutical analysis, clinical analysis, biochemical analysis, and food analysis He has contributed to original research publications relating to biochemistry (platelet function) and endocrinology (control of ovulation) and is the author of several books and book chapters on vitamins He received the B.Sc honors degree in agricultural sciences from the University of Nottingham, UK in 1975 Preface Optimal vitamin status is a prerequisite for good health, and governmentapproved food fortification strategies are deemed necessary to ensure adequate intake of certain vitamins Knowledge about vitamin bioavailability from food is essential for the estimation of dietary requirements Equally important is knowledge of a vitamin’s stability toward postharvest handling of food, processing, storage, and preparation for consumption To acquire this knowledge, one must learn about vitamin chemistry and how the vitamin is absorbed and metabolized Successful research into vitamin bioavailability and stability is entirely dependent on the development and validation of suitable analytical methods Vitamin bioavailability from food is subject to many variables imposed by food constituents and the preparation of food Great progress has been made over the past decade, largely attributable to innovative analytical methodology, but there are many inconsistencies and the continuation of a multipronged research effort from independent laboratories must be encouraged to achieve solid and vital data I would like to acknowledge the expertise and diligence of Lynn Saliba at the British Library George F M Ball Contents Part I Properties of Vitamins Chapter Nutritional Aspects of Vitamins 1.1 Definition and Classification of Vitamins 1.2 Nutritional Vitamin Deficiency 1.3 Vitamin Requirements 1.4 Vitamin Enhancement of Foods 1.5 Stability of Vitamins 1.5.1 Water Activity and Lipid Oxidation 1.5.2 First-Order Kinetics 1.5.3 Effects of Food Processing on Vitamin Retention 1.5.3.1 Dehydration 1.5.3.2 Blanching 1.5.3.3 Canning 1.5.3.4 Pasteurization and Ultra-High-Temperature Processing 1.5.3.5 Microwave Heating 1.5.3.6 Hydrothermal Processes (Flaking, Puffing, and Extrusion) 1.5.3.7 Freezing 1.5.3.8 Irradiation 1.5.3.9 High Hydrostatic Pressure Treatment 1.5.3.10 Curing and Smoking 1.5.4 Milling 1.5.5 Effects of Food Storage on Vitamin Retention 1.5.6 Effects of Domestic Cooking on Vitamin Retention References Intestinal Absorption and Bioavailability of Vitamins: Introduction 2.1 General Principles of Solute Translocation 2.2 Intestinal Absorption 2.2.1 The Villus 2.2.2 The Luminal Environment 2.2.3 Adaptive Regulation of Intestinal Nutrient Transport 4 6 9 10 11 11 12 13 14 14 15 16 17 17 17 18 Chapter 23 24 24 25 25 Vitamins in Foods: Analysis, Bioavailability, and Stability 773 36 Ollilainen, V., Mattila, P., Varo, P., Koivistoinen, P., and Huttunen, J., The HPLC determination of total riboflavin in foods, J Micronutr Anal., 8, 199, 1990 37 Fernando, S.M and Murphy, P.A., HPLC determination of thiamin and riboflavin in soybeans and tofu, J Agric Food Chem., 38, 163, 1990 38 Lumley, I.D and Wiggins, R.A., Determination of riboflavin and flavin mononucleotide in foodstuffs using high-performance liquid chromatography and a column-enrichment technique, Analyst, 106, 1103, 1981 39 Johnsson, H and Branzell, C., High performance liquid chromatographic determination of riboflavin in food — a comparison with a microbiological method, Int J Vitam Nutr Res., 57, 53, 1987 40 Barna, E´., Comparison of data obtained by HPLC and microbiological determination of riboflavin in ready-to-eat foods, Acta Aliment., 21, 3, 1992 41 LaCroix, D.E., Wolf, W.R., and Vanderslice, J.T., Determination of niacin in infant formula and wheat flour by anion-exchange liquid chromatography with solid-phase extraction cleanup, J AOAC Int., 82, 128, 1999 42 Lahe´ly, S., Bergaentzle´, M., and Hasselmann, C., Fluorimetric determination of niacin in foods by high-performance liquid chromatography with postcolumn derivatization, Food Chem., 65, 129, 1999 43 Rose-Sallin, C., Blake, C.J., Genoud, D., and Tagliaferri, E.G., Comparison of microbiological and HPLC — fluorescence detection methods for determination of niacin in fortified food products, Food Chem., 73, 473, 2001 44 Bogna˚r, A and Ollilainen, V., Influence of extraction on the determination of vitamin B6 in food by HPLC, Z Lebensm Unters Forsch A, 204, 327, 1997 45 Reitzer-Bergaentzle´, M., Marchioni, E., and Hasselmann, C., HPLC determination of vitamin B6 in foods after pre-column derivatization of free and phosphorylated vitamers into pyridoxal, Food Chem., 48, 321, 1993 46 Woollard, D.C., Indyk, H.E., and Christiansen, S.K., The analysis of pantothenic acid in milk and infant formulas by HPLC, Food Chem., 69, 201, 2000 47 Lahe´ly, S., Ndaw, S., Arella, F., and Hasselmann, C., Determination of biotin in foods by high-performance liquid chromatography with post-column derivatization and fluorimetric detection, Food Chem., 65, 253, 1999 48 Doherty, R.F and Beecher, G.R., A method for the analysis of natural and synthetic folate in foods, J Agric Food Chem., 51, 354, 2003 49 Ndaw, S., Bergaentzle´, M., Aoude´-Werner, D., Lahe´ly, S., and Hasselmann, C., Determination of folates in foods by high-performance liquid chromatography with fluorescence detection after precolumn conversion to 5-methyltetrahydrofolates, J Chromatogr A, 928, 77, 2001 50 Goăkmen, V., Kahraman, N., Demir, N., and Acar, J., Enzymatically validated liquid chromatographic method for the determination of ascorbic and dehydroascorbic acids in fruit and vegetables, J Chromatogr A, 881, 309, 2000 51 Furusawa, N., Rapid high-performance liquid chromatographic identification/quantification of total vitamin C in fruit drinks, Food Control, 12, 27, 2001 52 Brause, A.R., Woollard, D.C., and Indyk, H.E., Determination of total vitamin C in fruit juices and related products by liquid chromatography, J AOAC Int., 86, 367, 2003 774 Summarized Appraisal of Analytical Techniques 53 Lesellier, E., Gurdale, K., and Tchapla, A., Separation of cis/trans isomers of b-carotene by supercritical fluid chromatography, J Chromatogr A, 844, 307, 1999 54 Yarita, T., Nomura, A., Abe, K., and Takeshita, Y., Supercritical fluid chromatographic determination of tocopherols on an ODS-silica gel column, J Chromatogr A, 679, 329, 1994 55 Iban˜ez, E., Palacios, J., and Reglero, G., Analysis of tocopherols by on-line coupling supercritical fluid extraction – supercritical fluid chromatography, J Microcolumn Sep., 11, 605, 1999 56 Vidal-Valverde, C and Diaz-Polla´n, C., Optimization analysis by capillary electrophoresis of thiamine in meat: comparison with high performance liquid chromatography, Eur Food Res Technol., 209, 355, 1999 57 Vidal-Valverde, C and Diaz-Polla´n, C., Comparison of capillary electrophoresis and high performance liquid chromatographic thiamin determination in milk, Milchwissenschaft, 55, 307, 2000 58 Cataldi, T.R.I., Nardiello, D., De Benedetto, G.E., and Bufo, S.A., Optimizing separation conditions for riboflavin, flavin mononucleotide and flavin adenine dinucleotide in capillary zone electrophoresis with laser-induced fluorescence detection, J Chromatogr A, 968, 229, 2002 59 Ward, C.M and Trenerry, V.C., The determination of niacin in cereals, meat and selected foods by capillary electrophoresis and high performance liquid chromatography, Food Chem., 60, 667, 1997 60 Ward, C.M., Trenerry, V.C., and Pant, I., The application of capillary electrophoresis to the determination of total niacin in concentrated yeast spreads, Food Chem., 58, 185, 1997 61 Windahl, K.L., Trenerry, V.C., and Ward, C.M., The determination of niacin in selected foods by capillary electrophoresis and high performance liquid chromatography: acid extraction, Food Chem., 65, 263, 1998 62 Thompson, C.O and Trenerry, V.C., A rapid method for the determination of total L-ascorbic acid in fruits and vegetables by micellar electrokinetic capillary chromatography, Food Chem., 53, 43, 1995 63 Cancalon, P.F., Routine analysis of ascorbic acid in citrus juice using capillary electrophoresis, J AOAC Int., 84, 987, 2001 64 Choi, O.-K and Jo, J.-S., Determination of L-ascorbic acid in foods by capillary zone electrophoresis, J Chromatogr A, 781, 435, 1997 65 Greenway, G.M and Ongomo, P., Determination of L-ascorbic acid in fruit and vegetable juices by flow injection with immobilised ascorbic oxidase, Analyst, 115, 1297, 1990 66 Daily, S., Armfield, S.J., Haggett, B.G.D., and Downs, M.E.A., Automated enzyme packed-bed system for the determination of vitamin C in foodstuffs, Analyst, 116, 569, 1991 67 Alcock, S.C., Finglas, P.M., and Morgan, M.R.A., An enzyme-linked immunosorbent assay for pyridoxamine and its comparison with alternative analytical procedures, Food Agric Immunol., 2, 197, 1990 68 Finglas, P.M., Faulks, R.M., Morris, H.C., Scott, K.J., and Morgan, M.R.A., The development of an enzyme-linked immunosorbent assay (ELISA) for the analysis of pantothenic acid and analogues Part II — Determination of pantothenic acid in foods, J Micronutr Anal., 4, 47, 1988 Vitamins in Foods: Analysis, Bioavailability, and Stability 775 69 Finglas, P.M., Faulks, R.M., and Morgan, M.R.A., The analysis of biotin in liver using a protein-binding assay, J Micronutr Anal., 2, 247, 1986 70 Finglas, P.M., Faulks, R.M., and Morgan, M.R.A., The development and characterization of a protein-binding assay for the determination of folate — potential use in food analysis, J Micronutr., Anal., 4, 295, 1988 71 Phillips, D.R and Wright, A.J.A., Studies on the response of Lactobacillus casei to different monoglutamates, Br J Nutr., 47, 183, 1982 72 Finglas, P.M., Kwiatkowska, C., Faulks, R.M., and Morgan, M.R.A., Comparison of a non-isotopic, microtitration plate folate-binding protein assay and a microbiological method for the determination of folate in raw and cooked vegetables, J Micronutr Anal., 4, 309, 1988 73 Bell, J.G., Microbiological assay of vitamins of the B group in foodstuffs, Lab Pract., 23, 235, 1974 74 Finglas, P.M., Faure, U., and Southgate, D.A.T., First BCR-intercomparison on the determination of folates in food, Food Chem., 46, 199, 1993 75 Alcock, S.C., Finglas, P.M., and Morgan, M.R.A., Production and purification of an R-protein-enzyme conjugate for use in a microtitration plate proteinbinding assay for vitamin B12 in fortified food, Food Chem., 45, 199, 1992 76 Indyk, H.E., Evans, E.A., Bostroăm Caselunghe, M.C., Persson, B.J., Finglas, P.M., Woollard, D.C., and Filonzi, E.L., Determination of biotin and folate in infant formula and milk by optical biosensor-based immunoassay, J AOAC Int., 83, 1141, 2000 77 Indyk, H.E., Persson, B.J., Bostroăm Caselunghe, M.C., Moberg, A., Filonzi, E.L., and Woollard, D.C., Determination of vitamin B12 in milk products and selected foods by optical biosensor protein-binding assay: method comparison, J AOAC Int., 85, 72, 2002 78 Gregory, J.F., III and Kirk, J.R., Comparison of chemical and biological methods for determination of thiamin in foods, J Agric Food Chem., 26, 338, 1978 79 Chia, C.P., Addison, R., and McCormick, D.B., Absorption, metabolism, and excretion of 8a-(amino acid) riboflavins in the rat, J Nutr., 108, 373, 1978 80 Carter, E.G.A and Carpenter, KJ., The available niacin values of foods for rats and their relation to analytical values, J Nutr., 112, 2091, 1982 81 Gregory, J.F., III and Litherland, S.A., Efficacy of the rat bioassay for the determination of biologically available vitamin B-6, J Nutr., 116, 87, 1986 82 Ekanayake, A and Nelson, P.E., An in vitro method for estimating biologically available vitamin B6 in processed foods, Br J Nutr., 55, 235, 1986 83 Gregory, J.F., III and Ink, S.L., Identification and quantification of pyridoxineb-glucoside as a major form of vitamin B6 in plant-derived foods, J Agric Food Chem., 35, 76, 1987 84 Addo, C and Augustin, J., Changes in the vitamin B6 content in potatoes during storage, J Food Sci., 53, 749, 1988 85 Sampson, D.A., Eoff, L.A., Yan, X.L., and Lorenz, K., Analysis of free and glycosylated vitamin B6 in wheat by high-performance liquid chromatography, Cereal Chem., 72, 217, 1995 86 Gregory, J.F., III, Case study: folate bioavailability, J Nutr., 131, 1376S, 2001 87 Tamura, T., Determination of food folate, J Nutr Biochem., 9, 285, 1998 Index Absorption, intestinal, 24–31 Acyl carrier protein, 212 Adenosylcobalamin, 276, 277, 278 Adequate Intake, 4– Alcohol, effects on vitamin status flavins, 173 folate, 264 thiamin, 159– 160 vitamin B6, 201 vitamin B12, 284 vitamin C, 305 vitamin D, 116 Analysis approach, 312– 313 method evaluation, 314– 320 error, 314– 316 quality assurance, 316 validation, 316– 320 sample preparation, 313– 314 Antibody, 735, 741 Antigen, 735, 736 Antigenic determinant, 736 Antiserum, 735, 736 AOAC methods of analysis flavins, 341, 375– 376, 382 folate, 341 niacin, 341, 373– 374, 382 pantothenic acid, 341 thiamin, 375 vitamin A, 105, 465, 759 vitamin B6, 341 vitamin B12, 341 vitamin C, 369– 372, 377– 378, 383 vitamin D, 503, 504, 760 vitamin E, 760 vitamin K, 546, 760 Apocarotenoids, 41, 43, 64– 65 Aquocobalamin, 277, 278 Ascorbic acid, see Vitamin C Ascorbigen, 293 Ascorbyl palmitate, 290 –291, 292 Avidin, 226 Bile salts, 27, 32 Bioassays, 311 – 312 Bioavailability concepts, 32 – 33 methods for determining, 33 – 36 Biocytin, 222, 227 Biomolecular interaction analysis, see Biosensor-based assays Biosensor-based assays, 750 – 751 applications biotin, 750 – 751, 767 folate, 750 – 751, 767 vitamin B12, 751, 767 principle, 749 – 750 Biotin absorption (intestinal), 226 –228 analysis biosensor-based immunoassay, 750 – 751, 775 enzyme-labeled protein binding assay, 747 extraction techniques, 328 – 329 HPLC, 646 – 647, 648, 763 microbiological assay, 360, 758 radiolabeled protein-binding assay, 741 bioavailability, 228, 769 biochemical functions, 221 dietary sources, 223, 224 solubility, 222 stability in aqueous solution, 222 in foods, 223 – 225 structure, 221 – 222 synthesis by gut flora, 226, 227 777 778 Caco-2 cells, 76 Caffeic acid, 157–158 Capillary electrophoresis, 394– 409 applications flavins, 399, 401, 406, 765 niacin, 402– 403, 406– 408, 765 thiamin, 399, 400– 401, 764–765 vitamin C, 403– 405, 408–409, 765 operation, 397– 399 principle, 394– 397, 764 Capillary zone electrophoresis, see Capillary electrophoresis b-Carotene, see also Carotenoids bioavailability, 67– 88 dietary fiber, effect of, 86– 87 energy, effect of, 85 fat, effect of, 81– 86 food matrix, effect of, 78– 80 methods for assessing, 68– 77 protein, effect of, 80– 81 sterols, effect of, 87– 88 bioaccessibility, 68, 74– 76 bioefficacy, 68 provitamin A activity of cis isomers, 43 metabolism, 63– 66 solubility, 43 spectrum, visible, 469, 471– 472 structure, 42– 43 supplementation, 88– 91 Carotenoids, see also b-Carotene absorption (intestinal), 62– 63, 68, 76 –77 analysis extraction techniques, 422, 427, 432 HPLC, 61, 469– 488, 759– 760 dietary sources, 47–48, 49–50 nomenclature, 44 plasma levels, 67 provitamin A activity, 44 stability in nonaqueous solution, 45 in foods, 57– 60 structures, 41– 43, 44 Certified reference materials, 317 Index Chlorogenic acid, 157 – 158 Cholecalciferol (vitamin D3), see Vitamin D Chromoplasts, 78 Chylomicrons, 27 – 28 Clean-up (analytical), 435 – 439 adsorption chromatography, 436 – 437 solid-phase extraction, 437 – 438 sterols, precipitation of, 436 Coenzyme B12, see Adenosylcobalamin Conjugase, 245 – 246, 329 – 330 Continuous-flow analysis, 380 – 384 applications, flavins, 382 niacin, 382 thiamin, 381 –382 vitamin A, 381 vitamin C, 383 – 384 vitamin E, 381 Corilagin, 157 Cyanocobalamin, 276 – 278, see also Vitamin B12 Dehydroascorbic acid, 291 – 292, 302, see also Vitamin C 7-Dehydrocholesterol, 107 Dehydroretinol, 41 Dietary fiber components, 30, 31 effects on nutrient absorption, 30, 33 Dihydrophylloquinone, 142, 145 1,25-Dihydroxyvitamin D, 107, 115 ELISA, see Enzyme-linked immunosorbent assay Enzyme-labeled protein binding assay applications biotin, 747 folate, 747 – 748, 766 vitamin B12, 748 – 749 principle, 747 Enzyme-linked immunosorbent assay applications pantothenic acid, 740 vitamin B6, 741 principle, 738 – 740 Vitamins in Foods: Analysis, Bioavailability, and Stability Ergocalciferol (vitamin D2), see Vitamin D Ergosterol, 107, 110 Erythorbic acid, see D -Isoascorbic acid Estimated Average Requirement, Extraction (analytical), 419– 435 alcoholysis, 424 alkaline hydrolysis (saponification), 419– 421 enzymatic hydrolysis, 424– 425 matrix solid-phase dispersion, 429 solvent extraction, 425– 426 supercritical fluid extraction, 430 – 435 specific procedures biotin, 328– 329 carotenoids, 422, 427, 432 flavins, 322– 323 folate, 329– 331 niacin, 323– 326 pantothenic acid, 328 thiamin, 321– 322 vitamin A, 421– 422, 426 vitamin B6, 326– 328 vitamin B12, 331– 332 vitamin C, 332– 333 vitamin D, 422– 423, 427 vitamin E, 423– 424, 428, 432 – 435 vitamin K, 428– 429, 431– 432 FAD (flavin adenine dinucleotide), see Vitamin B2 Fat absorption (intestinal), 27– 28 digestion, 27– 28 transport, 28 Fiber, see Dietary fiber Flavin adenine dinucleotide, see Vitamin B2 Flavin mononucleotide, see Vitamin B2 Flow-injection analysis, see Continuous-flow analysis FMN (flavin mononucleotide), see Vitamin B2 Folacin, see Folate 779 Folate absorption (intestinal), 246 –250 analysis biosensor-based immunoassay, 750 – 751, 775 cleanup procedures, 648 – 650 enzyme-labeled protein binding assay, 747 – 748, 765 extraction techniques, 329 – 331 HPLC, 647, 649 – 677, 719, 763 microbiological assay, 360 – 361, 758 radiolabeled protein-binding assay, 741 – 747 bioavailability, 252 –264, 769 – 770 dietary fiber, effect of, 262 – 263 soluble food components, effect of, 260 – 262 in milk, 258 – 260 methods for assessing, 252 – 256 biochemical functions, 231 deconjugation, 245 – 246 deficiency syndromes, 231 dietary sources, 236 – 237 enterohepatic circulation, 251 – 252 fluorescence, 650, 652 fortification, 236 – 237 homeostasis, 251 – 252 metabolism, 251 solubility, 234 stability in aqueous solution, 234 – 236 in foods, 238 – 244 structures, 232 – 233 synthesis by gut flora, 250 toxicity, 231 –232 transport in plasma, 251 UV absorbance, 651 – 652 Folic acid, see Folate Food cooking, 17 –18 processing, blanching, 10 – 11 canning, 11 curing, 16 – 17 dehydration, – 10 extrusion, 13 –14 Index 780 Food processing (Continued ) flaking, 13– 14 freezing, 14 hydrostatic pressure treatment, 15 –16 irradiation, 14– 15 microwave heating, 12– 13 milling, 17 pasteurization, 11 –12 puffing, 13– 14 smoking, 17 ultrahigh-temperature processing, 11 – 12 reference materials, 316– 318 storage, 17 Gas chromatography, 385– 390 applications, niacin, 388 pantothenic acid, 389– 390 thiamin, 388 vitamin B6, 388– 399 vitamin E, 387 columns, 385– 386 derivatization, 386– 387 detectors, 386 principle, 385 quantification, 387 Glucose, absorption (intestinal), 28– 30 Hapten, 736 Haptocorrin, 282 High-performance liquid chromatography applications, biotin, 646– 647, 648, 763 carotenoids, 469–488, 759–760 fat-soluble vitamins (multiple), 546 – 567 folate, 647, 649– 677, 763 niacin, 612– 623, 717, 726, 762 pantothenic acid, 638– 645, 763 thiamin, 592– 597, 706– 719, 761 vitamin A, 457– 469, 551– 560, 759 vitamin B2, 598– 612, 762– 763 vitamin B6, 624– 638, 715 – 719, 762 vitamin B12, 676 – 677, 678, 719 vitamin C, 677, 680 – 706, 763 – 764 vitamin D, 489 – 505, 556, 559, 560, 760 vitamin E, 505 – 527, 551 – 560, 760 vitamin K, 527 – 546, 560, 760 water-soluble vitamins (multiple), 703 – 720, 761 chromatographic modes adsorption, 444 – 447 ion exchange, 585 – 587 ion exclusion, 587 – 588 ion pair (interaction), 589 – 591 ion suppression, 588 – 589 polar bonded-phase, 447 – 448 reversed-phase, 448 – 452 columns, 442 – 444 derivatization, 591 – 592 detection, 453 – 457 absorbance, 454 – 455 electrochemical, 456 – 457 fluorescence, 455 – 456 mass spectrometry, 457 efficiency, 442 principle, 439 – 440 resolution, 441 retention factor, 440 separation factor, 440 – 441 two-dimensional, 452 – 453 Hydroxocobalamin, 278, 279, 281 25-Hydroxyvitamin D absorption (intestinal), 114, 115 amount in foods, 110 – 111 analysis by HPLC, 504 –505 Immunogen, 735 – 736 Intrinsic factor, 282 D -Isoascorbic acid, 290 Km (Michaelis constant), 23 – 24 Kinetics, – Leucine, 187 Lumichrome, 167 Lumiflavin, 167 Lycopene, 41 – 42 Mass spectrometry, 36 Matrix solid-phase dispersion, 429 Vitamins in Foods: Analysis, Bioavailability, and Stability Megaloblastic anemia, 275, 231 Membrane structure, 23 transport, 23–24 Menaquinones, see Vitamin K Methylcobalamin, 276, 277, 278 5-Methyl-5,6-dihydrofolate, salvage of, 249 – 250 Micellar electrokinetic capillary chromatography, see Capillary electrophoresis Micelle, 27 Michaelis constant, see Km Microbiological methods AOAC methods, 341 applications biotin, 360, 752 flavins, 352– 354 folate, 360– 361, 758 niacin, 354– 356 pantothenic acid, 359– 360 thiamin, 351– 352 vitamin B6, 356– 358, 757– 758 vitamin B12, 361– 362 metabolic CO2 measurement, 341 – 342 microtiter plate assays, 350– 351 organisms, 340 principle, 339– 341 tube assays, 342– 350 Milk, vitamin A, 51– 56 Mixed micelle, see Micelle Monoclonal antibody, 736 NAD (nicotinamide adenine dinucleotide) absorption (intestinal), 183 biochemical functions, 177 stability, 179, 181 structures, 178– 179 Niacin absorption (intestinal), 183 analysis capillary electrophoresis, 402– 403, 406 – 408, 765 colorimetric method, 373– 374 continuous-flow analysis, 382 enzymatic method, 378– 379 781 extraction techniques, 323 – 326 gas chromatography, 388 HPLC, 612 – 623, 714, 719, 762 microbiological assay, 354 – 356 bioavailability, 183 –187, 768 dietary sources, 179 – 181 equivalency, 182 solubility, 179 stability in aqueous solution, 179 in foods, 181 – 182 structures, 178 synthesis by gut flora, 183 toxicity, 177 UV absorbance, 612 Niacinamide, see Niacin Niacinogen, 184 Niacytin, 184 Nicotinamide, see Niacin Nicotinamide adenine dinucleotide, see NAD Nicotinic acid, see Niacin Nicotinoyl glucose, 184 Osteoclasts, 107 Osteomalacia, 108 Pantothenic acid absorption (intestinal), 216 –217 analysis extraction techniques, 328 ELISA, 740 gas chromatography, 389 – 390 HPLC, 639 – 646, 763 microbiological assay, 359 – 360 radioimmunoassay, 737 – 738 bioavailability, 217 –218, 769 biochemical functions, 211 dietary sources, 213, 214 solubility, 213 stability in aqueous solution, 213 in foods, 213 – 215 structures, 211 – 212 synthesis by gut flora, 217 toxicity, 211 Pernicious anemia, 275 Phylloquinone, see Vitamin K 782 Polyclonal antibody, 736 Protein-binding assay; see Enzyme-labeled protein binding assay; Radio-labeled protein binding assay Previtamin D, 107, 109, 110 Provitamin A carotenoids, see Carotenoids Pyridoxal and pyridoxal phosphate, see Vitamin B6 Pyridoxamine and pyridoxamine phosphate, see Vitamin B6 Pyridoxine (pyridoxol) and pyridoxine phosphate, see Vitamin B6 Pyridoxine glucoside, 190 –191, 193, 199, 202– 205 1-Pyridoxyllysine, 196– 197, 327 Index Scurvy, 289 Segmented-flow analysis, see Continuous-flow analysis Smoking (tobacco), effects on vitamin status vitamin B12, 285 vitamin D, 116 Solid-phase extraction, 437 – 438 Stable isotopes, 35, 71 – 73, 253 – 255 Standard reference materials, 317 – 318 Sulfitocobalamin, 276, 279 Supercritical fluid chromatography, 390 – 394 applications, 394 columns, 393 – 394 instrumentation, 391 – 393 principle, 390 – 391 Supercritical fluid extraction, 430 – 435 Quercetin, 157– 158 Radioassay, see Radio-labeled protein binding assay Radioimmunoassay application to pantothenic acid, 737 – 738 principle, 737 Radio-labeled protein binding assay applications biotin, 743 folate, 743– 744 vitamin B12, 745– 747 principle, 741– 743 Radiometric microbiological assay, 341 – 342 Recommended Dietary Allowances, Red palm oil, 91 Retinaldehyde, biopotency, 41 Retinoic acid, physiological function, 39 Retinol, see Vitamin A Retinol activity equivalent, 60– 61 Retinol equivalent, 60 Retinyl acetate, 41 Retinyl palmitate, 41 Riboflavin, see Vitamin B2 Rickets, 108 Sample preparation, 313– 314 Saponification, 419– 421 Tannin (tannic acid), 158 – 159 Thiamin (vitamin B1) absorption (intestinal), 154 –155 analysis capillary electrophoresis, 399, 400 – 401, 764 – 765 continuous-flow analysis, 381 – 382 extraction techniques, 321 – 322 fluorometric method, 375 gas chromatography, 388 HPLC, 592 – 597, 707 – 719, 761 microbiological assay, 351 – 352 bioavailability, 155 –160, 767 – 768 antithiamin factors, effect of, 156 – 159 dietary fiber, effect of, 160 deficiency syndromes, 149 dietary sources, 151 – 152 fluorescence, of thiochrome, 592, 593 international unit, 154 solubility, 150 stability in aqueous solution, 150 – 151 in foods, 152 – 154 structures, 149 – 150 supplementation forms, 150 synthesis by gut flora, 154 toxicity, 149 UV absorbance, 592, 593 Vitamins in Foods: Analysis, Bioavailability, and Stability Thiaminases, 156 Thiamin diphosphate, 149 –150 Thiamin disulphide, 150, 158 – 159 Thiamin pyrophosphate, see Thiamin diphosphate Thiochrome, 150– 151 Tight junction, 23 Tocochromanols, see Vitamin E Tocopherols, see Vitamin E a-Tocopheryl acetate Tocotrienol, 120, see also Vitamin E Transthyretin, 67 Trigonelline, 180 Tryptophan, 179– 180, 182, 187 Ultra Rice, 56– 57 Unstirred layer, 25 Utilization (metabolic), 32 Villus, 24 – 25 Vitamer, Vitamin, see also Individual entries deficiency (nutritional), definition, essentiality, fortification of foods, requirements, – stability, factors affecting, Vitamin A absorption (intestinal), 62– 63, 68 activity of cis isomers, 40– 41 analysis extraction techniques, 421– 422, 426 HPLC, 457– 469, 551– 560, 759 quantification, 463– 465 dietary sources, 45–47 equivalency, 60 fluorescence, 463, 464 liver uptake, 66 metabolism, 67 physiological functions, 39 solubility, 43 stability in nonaqueous solution, 45 in foods, 48, 51– 57 storage, in liver, 66 783 structures, 40 supplementation forms, 41 tissue uptake, 67 toxicity, 39 transport in plasma, 66 – 67 utilization (metabolic), 66 UV absorbance, 457, 463 Vitamin B1, see Thiamin Vitamin B2 absorption (intestinal), 171 –173 analysis capillary electrophoresis, 399, 401, 406, 765 continuous-flow analysis, 382 extraction techniques, 322 – 323 fluorometric method, 375 – 376 HPLC, 598 – 612, 707 – 719, 761 – 762 microbiological assay, 352 – 354 bioavailability, 173, 768 biochemical functions, 165 dietary sources, 168 – 169 fluorescence, 598 – 600 solubility, 167 stability in aqueous solution, 167 – 168 in foods, 169 – 170 structures, 165 – 166 synthesis by gut flora, 172 –173 toxicity, 165 UV-visible absorption, 598 Vitamin B6 absorption (intestinal), 198 –199 activity, 198 analysis ELISA, 741 extraction techniques, 326 – 328 fluorometric method, 376 – 377 gas chromatography, 388 – 389 HPLC, 624 – 639, 714 – 719, 762 microbiological assay, 356 – 358, 757 – 758 bioavailability, 199 –205, 769 biochemical functions, 189 deficiency syndromes, 189 dietary sources, 193 – 194 equivalency, 198 fluorescence, 625 – 626 784 Vitamin B6 (Continued ) glycosylated forms, 190– 191, 193, 199, 202– 205 solubility, 191 stability in aqueous solution, 192– 193 in foods, 194– 197 structures, 190– 192 supplemental form, 190 synthesis by gut flora, 198 toxicity, 189 UV absorption, 625 Vitamin B12 absorption (intestinal), 281– 284 analysis biosensor-based protein-binding assay, 751, 775 enzyme-labeled protein binding assay, 748– 749 extraction techniques, 331– 332 HPLC, 677– 678, 679, 719 microbiological assay, 361– 362 radio-labeled protein binding assay, 741– 747 bioavailability, 283– 285, 769 conservation, 283 deficiency disease, 275 dietary sources, 278– 279 entereohepatic circulation, 283 solubility, 277– 278 stability in aqueous solution, 278 in foods, 279– 281 storage in liver, 283 structures, 276– 277 synthesis by gut flora, 281 Vitamin C absorption (intestinal), 300– 303 analysis capillary electrophoresis, 403– 405, 408 – 409, 764 colorimetric method, 374– 375 continuous-flow analysis, 383 – 384 enzymatic method, 379 extraction techniques, 332– 333 fluorometric method, 377–378 HPLC, 678, 680– 706, 763– 764 Index spectrophotometric method, 372 – 373 titrimetric method, 369 – 372 bioavailability, 303 –304, 769 biochemical functions, 289 dietary sources, 292 – 294 fluorescence, of quinoxaline derivative, 377, 681 redox potential, 292 solubility, 291 – 292 stability in aqueous solution, 292 in foods, 294 – 299 structures, 290 toxicity, 289 UV absorbance, 489, 499 Vitamin D absorption (intestinal), 114 – 115 analysis cleanup procedures, 499 – 500 extraction techniques, 422 – 423, 427 HPLC, 489 – 505, 556, 559, 560, 760 quantification, 489, 499 solid-phase extraction, 438 – 439 bioavailability, 115 – 116 biogenesis, 107 biopotency, 108 deficiency diseases, 108 dietary sources, 110 – 112 international unit, 113 isomerization, 109 –110, 111 metabolism, 107, 115 physiological functions, 107 –108 solubility, 108 stability in nonaqueous solution, 109 – 110 in foods, 112 – 113 structures, 109 toxicity, 108, 115 UV absorbance, 489, 499 Vitamin D sulfate, 111 Vitamin E absorption (intestinal), 129, 130 analysis extraction techniques, 423 – 424, 432 – 435 gas chromatography, 387 Vitamins in Foods: Analysis, Bioavailability, and Stability HPLC, 505– 527, 551– 560, 760 quantification, 510 antioxidant activity, in vitro, 122– 123 bioavailability, 130– 132 dietary fiber, effect of, 131– 132 polyunsaturated fats, effect of, 131 sterols, effects of, 132 biochemical functions, 119 biopotency, 121– 122 dietary sources, 123– 126 equivalency, 128 fluorescence, 507– 509, 523 nomenclature, 120, 121 requirement, 132 solubility, 122 stability in nonaqueous solution, 122 in foods, 126– 128 storage, in tissues, 130 structures, 120 supplementation forms, 126 synthesis (chemical) 120– 121 transport in plasma lipoproteins, 129 – 130 UV absorbance, 506– 507, 522 785 Vitamin K absorption (intestinal), 143 –145 analysis extraction techniques, 428 – 429, 431 – 432 HPLC, 527 – 546, 560, 760 bioavailability, 145 biochemical functions, 137 dietary sources, 139 – 141 fluorescence of reduction products, 540 hydrogenation, 142 solubility, 139 stability in nonaqueous solution, 139 in foods, 141 – 142 structures, 138 synthesis by gut flora, 143 –145 transport in plasma lipoproteins, 143 UV absorbance, 528, 540 Water activity, – Xanthophylls, 41