液相層析電灑游離串聯質譜儀與電子鼻探討乳類製品暨食用油脂之鑑別與摻假

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研究生：	陳仁焜 Ren-Kun Chen
論文名稱：	液相層析電灑游離串聯質譜儀與電子鼻探討乳類製品暨食用油脂之鑑別與摻假 Classification and Adulteration Study of Milk Products and Edible Oil and Fat Using Liquid Chromatograph Electrospray Ionization Tandem Mass Spectrometer and Electronic Nose
指導教授：	凌永健 Yong-Chien Ling
口試委員:
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2004
畢業學年度：	92
語文別：	英文
論文頁數：	120頁
中文關鍵詞：	摻假、電灑游離串聯質譜、電子鼻、乳類製品、食用油脂、乳球蛋白、熱誘發醣化指標、三酸甘油酯
外文關鍵詞：	adulteration, electrospray ionization tandem mass spectrometer, electronic nose, milk product, edible oil and fat, lactoglobulin, thermally-induced glycation index, TGI, triglyceride
相關次數：	點閱：3 下載：0
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由於全球市場競爭日益激烈，而有越來越多國家加入世界關稅貿易組織(Word Trade Organization, WTO)，此舉已對部分國家的經濟產生嚴重衝擊，特別是食品及消費性產品的生產成本較高，同時人事成本亦逐漸攀升的國家。例如，為了謀取不當的利潤，某些製造商會以摻假的手法矇騙消費者。以牛乳為例，它是一種被廣泛消費的乳製品，在我國的生產成本卻相對偏高，約為世界主要乳品輸出地區(包含紐西蘭、澳大利亞、歐洲等地)的2~3倍，因此國人對於乳製品摻假的疑慮已有長達20年以上的歷史，其中以在鮮牛乳中摻雜低價乳粉與在羊乳中摻雜牛乳的情況最為常見。除了液態乳品之外，近年來在魚油產品中摻混植物油以求降低成本的傳聞亦漸有所聞。事實上，欲憑藉著食品的外觀或是簡易的可攜式設備去鑑別乳品與食用油脂的品質有極高的困難度，故有必要建立一套標準可靠的鑑別方法。為因應此類需求，本研究整合多種分析方法，能夠可靠的鑑別乳品與食用油脂的種類與測定該類樣品的摻假情形。
本論文利用電子鼻(electronic nose, EN)與電灑游離質譜(electrospray ionization mass spectrometer, ESI-MS)進行上述食品的鑑別與摻假測定。分析結果嘗試以樹狀群集分析(hierarchical cluster analysis, HCA)、主成分分析(principal components analysis, PCA)或因子分析(factor analysis, FA)等三種統計方式來簡化大量複雜的數據。根據分析結果顯示，電子鼻可以快速區分鮮乳與還原乳；而直接導入電灑游離質譜法(DI-ESI-MS)則可用來快速鑑別牛乳與羊乳，由此可見嗅覺指紋(smell-print)與三酸甘油酯分佈(triglyceride profile)具有取代傳統品評員(sensory panel)的潛力。
為了更進一步確認乳品摻假的情況，使用逆相液相層析/電灑游離質譜(RP-HPLC/ESI-MS)偵測乳品中的乳球蛋白(lactoglobulin)作為生物指標。實驗結果顯示，本研究所提出之方法在蛋白質分子量的定性上提供較佳之準確度與精密度，優於目前常用之尿素膠體電泳方法(urea SDS-PAGE)。本研究開發以RP-HPLC/ESI-MS分析乳清蛋白(whey protein)的方法能與現行之中國國家標準方法(CNS 14117)互補，使用內部標準化(internal normalization)的策略即能定量羊乳中添加牛乳的的比例。
更進一步藉由驗證樣品的層析圖與質譜圖，本方法亦可應用於鮮乳與還原乳的鑑別。根據計算所得的熱誘發醣化指標(thermally-induced glycation index, TGI)，還能夠以數值化的方式判定乳品的品質。研究結果顯示，TGI可成為一種乳品品質的指標，當鮮乳具有較低的TGI值時代表受熱誘發變性程度較小，反映出較佳的乳品品質。TGI值位於中位數的還原乳樣品(TGI-LGA=2.58)，在乳球蛋白分子(lactoglobulin)上共有5個位置發生乳糖修飾(lactose modification)的現象，此現象與使用RP-HPLC/ESI-MS/MS去探測牛乳中乳球蛋白的醣化位置的結果相符。
關於ESI-MS的應用還更進一步延伸到食用油脂樣品的判別與摻假鑑定。由於三酸甘油酯是食用油的主要成分，且不同的油脂樣品具有不同的三酸甘油酯組成比例與質譜指紋，因此具有成為指標化合物的潛力。合併使用三酸甘油酯指紋圖譜與HCA、PCA、FA等統計方法，不同種類的食用油脂可以被快速鑑別。更進一步使用電灑游離串連質譜(ESI-MS/MS)，可以探索三酸甘油酯的的細部化學結構與脂肪酸組成，此技術已可成功應用於市售魚油產品是否摻混植物油的鑑定。

Increasing competition in global market leads more countries to participate the “World Trade Organization” (WTO) program. This has serious impact on the economy of nations, of which the production cost of food and consumer product is increasing with higher labor cost. In an attempt to make dishonest profits, adulteration of diary products has been adopted by some manufacturers. Milk is one of the widely consumed dairy products. Its cost of production in Taiwan is estimated to be 2-3 times higher than that in major dairy products exporting countries like New Zealand, Australia, and Europe. Therefore, adulteration of milk and milk products has been suspected in Taiwan for the past two decades. Adulteration of fresh cow milk by inexpensive cow milk powder and goat milk by cow milk was noticed. Additionally, some fish oil products have been reported to be adulterated or vegetable oil products. It is difficult to characterize the quality of milk or oil by visualization or using simple portable instruments. Therefore, it is necessary to develop standard and reliable methods for the characterization of milk, oil and the detection of adulteration. In response to this demand, a variety of analytical methods were employed and integrated for reliable characterization and adulteration detection of milk and oil products.
Electronic nose (EN) and electrospray ionization mass spectrometer (ESI-MS) has been exploited for food characterization and adulteration detection of aforementioned food products. The results were processed using statistical tools like hierarchical cluster analysis (HCA), principal components analysis (PCA), and factor analysis (FA), to simplify their presentation. The EN demonstrates capability of rapid screening of fresh milk from reconstituted milk. Furthermore, direct infusion electrospray ionization mass spectrometer (DI-ESI-MS) is also employed for rapid classification of cow milk adulteration in goat milk. The smell-print and triglyceride (TG) profile thus obtained show the potential to replace traditional sensory panels.
To further support the developed method and confirm the adulteration, RP-HPLC/ESI-MS has been employed to detect lactoglobulins, the biomarkers. The results showed that mass spectrometry is superior to current urea sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) method in terms of accuracy and precision, enabling molecular mass identification of proteins. The analysis of whey protein by RP-HPLC/ESI-MS is complementary to currently used Chinese National Standard method (CNS 14117). It is capable of quantitatively determining the adulteration after internal normalization strategy. The method has been applied to differentiate authentic fresh milk and reconstituted milk by inspecting chromatograms and mass spectra. Additionally, calculation of thermally-induced glycation index (TGI) enables numerical representation and differentiation of milk sample quality. The TGI value is characteristic of milk quality, where lower TGI value represents better milk quality denoted as fresh milk. The results reveal that the reconstituted milk samples have median value of TGI (TGI-LGA=2.58) and possess five lactosylation sites on lactoglobulin. Moreover, RP-HPLC/ESI-MS/MS was used to probe the thermally-induced glycation sites on lactoglobulin of cow milk.
The applicability of ESI-MS is further extended for characterization and adulteration detection of edible oil and fat products. Different oil and fat samples have different triglyceride composition and mass spectral patterns. Taking this as an advantage and noting that triglycerides are major components of edible oil, the triglycerides are considered as marker molecules in classifying oil samples. The edible oil and fat can be rapidly characterized via combined use of TG profiles, HCA, PCA, and FA. Further, ESI-MS/MS has been used to investigate the fatty acid constituents and detailed structure of TGs. This strategy has been successfully used to distinguish adulterated fish oil which contained vegetable oil.

Contents
Abstract (Chinese)    I
Abstract    III
Acknowledgements    VI
Contents    VII
Chapter 1 Introduction    1
1 Motivation and goals    1
2 Instrumentation    3
2.1 Electronic nose    3
2.2 Electrospray ionization mass spectrometer    4
3 Statistical tools and analysis    5
3.1 Hierarchical cluster analysis (HCA)    5
3.2 Principal components analysis (PCA)    8
3.3 Factor analysis    9
References    11

Chapter 2     Classification of fresh cow milk, goat milk, and reconstituted milk using flavors and milk fat as target molecules by electronic nose and direct infusion ESI-MS  15
1 Introduction        15
2 Experimental        17
2.1 Sample preparation        17
2.2 Electronic nose        18
2.3 Electrospray ionization mass spectrometer    18
2.4 Urea SDS-PAGE        19
3 Results and discussion        20
3.1 Classification of fresh milk and adulterated milk samples        20
3.2 Evaluation of reconstituted milk concentration in fresh milk        21
3.3 Classification of cow milk and goat milk    24
3.4 Detection of casein by urea SDS-PAGE        28
4 Conclusions        29
References        29

Chapter 3 Investigation of adulterated goat milk by cow milk using high-performance liquid chromatography electrospray ionization mass spectrometry        32
1 Introduction        32
2 Experimental        34
2.1 Sample preparation        34
2.2 Liquid chromatography/mass spectrometry        34
3 Results and discussion        36
3.1 Sample pretreatment        36
3.2 Qualitative analysis by HPLC/ESI-MS        37
3.3 Selection of biological markers        41
3.4 Quantitative analysis of adulterated goat milk    43
3.5 Comparison to currently used CNS method        47
4 Conclusions        47
References        49


Chapter 4 Simple, rapid method for differentiating fresh cow milk from reconstituted and sterilized milk using HPLC/ESI-MS        52
1 Introduction        52
2 Experimental        55
2.1 Materials and sample preparation        55
2.2 Liquid chromatography/mass spectrometry        55
3 Results and discussion        56
3.1 Chromatographic analysis        56
3.2 Mass spectrometric analysis        57
3.3 Thermal-induced glycation index (TGI)        62
3.4 Characteristics of fresh, reconstituted and sterilized milk        64
3.5 Comparison of TGI-LGA and TGI-LGB        68
3.6 Quantitative analysis of adulterated fresh cow milk        69
3.7 Classification of milk based on milk treatment process    69
3.8 Comparison of currently available methods    71
4 Conclusions        72
References        73

Chapter 5 Probing the lactosylation sites of lactoglobulins in cow milk by HPLC/ESI-MS/MS        77
1 Introduction        77
2 Experimental        78
2.1 Separation of lactoglobulins using RP-HPLC    78
2.2 Digestion of lactoglobulins        79
2.3 Mass spectrometry for analysis of protein    79
2.4 Identification of protein        81
3 Results and discussion        81
3.1 Glycation process        81
3.2 Sequence coverage and protein identification    82
3.3 Probing lactosylation sites        84
3.4 Tandem mass spectrometry        87
3.5 Supplementary method for identification        87
4 Conclusions        89
References        90

Chapter 6 Characterization of edible oil and fat using triglycerides as biological markers by ESI-MS and ESI-MS/MS        93
1 Introduction        93
2 Experimental        95
2.1 Sample preparation        95
2.2 ESI-MS and ESI-MS/MS        95
2.3 Statistical analysis        96
3 Results and discussion        96
3.1 Mass spectral profiles of triglycerides        96
3.2 Calculation of equivalent carbon number        98
3.3 Statistical analysis of edible oil and fat samples        99
3.4 Biomarker selection approach    101
3.5 Identification of suspicious fish oil products    104
3.6 Tandem mass spectrometric analysis of triglycerides    107
4 Conclusions    108
References    109

Chapter 7 Comprehensive comments    112
1 Dual roles played by mass spectrometer    113
2 Total solution for milk identification    115
3 Differentiation of oil for diet assurance    117

Appendix    119
A1. Abbreviation    119
A2. Definition    120

                                

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Chapter 2
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Chapter 3
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4.Rodriguez, E.; Martin, R.; Garcia, T.; Gonzalez, I.; Morales, P.; Sanz, B.; Hernandez, P. E. "Detection of cows milk in ewes milk and cheese by a sandwich enzyme-linked-immunosorbent-assay (ELISA)." Journal of the Science of Food and Agriculture 1993, 61, 175-180.
5.Anguita, G.; Martin, R.; Garcia, T.; Morales, P.; Haza, A. I.; Gonzalez, I.; Sanz, B.; Hernandez, P. E. "Immunostick ELISA for detection of cow's milk in ewe's milk and cheese using a monoclonal antibody against bovine beta-casein." Journal of Food Protection 1996, 59, 436-437.
6.Iverson, J. L.; Sheppard, A. J. "Detection of Adulteration in Cow, Goat, and Sheep Cheeses Utilizing Gas-Liquid-Chromatographic Fatty-Acid Data." Journal of Dairy Science 1989, 72, 1707-1712.
7.Furtado, M. M. "Detection of cow milk in goat milk by polyacrylamide-gel electrophoresis." Journal of Dairy Science 1983, 66, 1822-1824.
8.Kim, H. H. Y.; Jimenezflores, R. "2-Dimensional analysis of skim milk-proteins using preparative isoelectric-focusing followed by polyacrylamide-gel electrophoresis." Journal of Food Biochemistry 1993, 16, 307-321.
9.Dejong, N.; Visser, S.; Olieman, C. "Determination of milk-proteins by capillary electrophoresis." Journal of Chromatography A 1993, 652, 207-213.
10.Bordin, G.; Raposo, F. C.; de la Calle, B.; Rodriguez, A. R. "Identification and quantification of major bovine milk proteins by liquid chromatography." Journal of Chromatography A 2001, 928, 63-76.
11.Bramanti, E.; Sortino, C.; Onor, M.; Beni, F.; Raspi, G. "Separation and determination of denatured alpha(s1)-, alpha(s2)-, beta- and kappa-caseins by hydrophobic interaction chromatography in cows', ewes' and goats' milk, milk mixtures and cheeses." Journal of Chromatography A 2003, 994, 59-74.
12.Marsilio, R.; Catinella, S.; Seraglia, R.; Traldi, P. "Matrix-assisted laser-desorption ionization mass-spectrometry for the rapid evaluation of thermal-damage in milk." Rapid Communications in Mass Spectrometry 1995, 9, 550-552.
13.Catinella, S.; Traldi, P.; Pinelli, C.; Dallaturca, E. "Matrix-assisted laser desorption ionization mass spectrometry: A valid analytical tool in the dairy industry." Rapid Communications in Mass Spectrometry 1996, 10, 1123-1127.
14.Catinella, S.; Traldi, P.; Pinelli, C.; Dallaturca, E.; Marsilio, R. "Matrix-assisted laser desorption/ionization mass spectrometry in milk science." Rapid Communications in Mass Spectrometry 1996, 10, 1629-1637.
15.Angeletti, R.; Gioacchini, A. M.; Seraglia, R.; Piro, R.; Traldi, P. "The potential of matrix-assisted laser desorption/ionization mass spectrometry in the quality control of water buffalo mozzarella cheese." Journal of Mass Spectrometry 1998, 33, 525-531.
16.Fanton, C.; Delogu, G.; Maccioni, E.; Podda, G.; Seraglia, R.; Traldi, P. "Matrix-assisted laser desorption/ionization mass spectrometry in the dairy industry 2. The protein fingerprint of ewe cheese and its application to detection of adulteration by bovine milk." Rapid Communications in Mass Spectrometry 1998, 12, 1569-1573.
17.Catinella, S.; Seraglia, R.; Marsilio, R. "Evaluation of protein profile of human milk by matrix-assisted laser desorption/ionization mass spectrometry." Rapid Communications in Mass Spectrometry 1999, 13, 1546-1549.
18.Siciliano, R.; Rega, B.; Amoresano, A.; Pucci, P. "Modern mass spectrometric methodologies in monitoring milk quality." Analytical Chemistry 2000, 72, 408-415.
19.Cozzolino, R.; Passalacqua, S.; Salemi, S.; Malvagna, P.; Spina, E.; Garozzo, D. "Identification of adulteration in milk by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry." Journal of Mass Spectrometry 2001, 36, 1031-1037.
20.Cozzolino, R.; Passalacqua, S.; Salemi, S.; Garozzo, D. "Identification of adulteration in water buffalo mozzarella and in ewe cheese by using whey proteins as biomarkers and matrix-assisted laser desorption/ionization mass spectrometry." Journal of Mass Spectrometry 2002, 37, 985-991.
21.Ho, Y. P.; Hsu, P. H. "Investigating the effects of protein patterns on microorganism identification by high-performance liquid chromatography-mass spectrometry and protein database searches." Journal of Chromatography A 2002, 976, 103-111.
22.Swiss-Prot "database at http://tw.expasy.org/."
23.PROWL "database at http://prowl.rockefeller.edu/PROWL/prowl.html."

Chapter 4
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2.Helrich, K., Ed. Official Methods of Analysis of the AOAC, 15th ed.; Association of Official Analytical Chemists, Inc.: Washington, D. C., 1990.
3.Walstra, P.; Geurts, T. J.; Noomen, A.; Jellema, A.; van Boekel, M. A. J. S. Dairy Technology; Marcel Dekker: New York, 1999, 459-460.
4.Hillier, R. M. "The quantitative measurement of whey proteins using polyacrylamide-gel electrophoresis." Journal of Dairy Research 1976, 43, 259-265.
5.Meyer, D. H.; Kunin, A. S.; Maddalena, J.; Meyer, W. L. "Ribionuclease activity and isozymes in raw and processed cows' milk and infant formulas." Journal of Dairy Science 1987, 70, 1797-1803.
6.Kislinger, T.; Humeny, A.; Peich, C. C.; Zhang, X. H.; Niwa, T.; Pischetsrieder, M.; Becker, C. M. "Relative quantification of N-epsilon-(carboxymethyl)lysine, imidazolone A, and the Amadori product in glycated lysozyme by MALDI-TOF mass spectrometry." Journal of Agricultural and Food Chemistry 2003, 51, 51-57.
7.Andrews, G. R. "Formation and occurrence of lactulose in heated milk." Journal of Dairy Research 1986, 53, 665-680.
8.Marconi, E.; Messia, M. C.; Amine, A.; Moscone, D.; Vernazza, F.; Stocchi, F.; Palleschi, G. "Heat-treated milk differentiation by a sensitive lactulose assay." Food Chemistry 2004, 84, 447-450.
9.Erbersdobler, H. F.; Dehn, B.; Nangpal, A.; Reuter, H. "Determination of furosine in heated milk as a measure of heat intensity during processing." Journal of Dairy Research 1987, 54, 147-151.
10.Corzo, N.; Delgado, T.; Troyano, E.; Olano, A. "Ratio of lactulose to furosine as indicator of quality of commercial milks." Journal of Food Protection 1994, 57, 737-739.
11.Cordella, C.; Moussa, I.; Martel, A. C.; Sbirrazzuoli, N.; Lizzani-Cuvelier, L. "Recent developments in food characterization and adulteration detection: Technique-oriented perspectives." Journal of Agricultural and Food Chemistry 2002, 50, 1751-1764.
12.Belloque, J.; Smith, G. M. "Thermal denaturation of beta-lactoglobulin. A H-1 NMR study." Journal of Agricultural and Food Chemistry 1998, 46, 1805-1813.
13.Aebersold, R.; Mann, M. "Mass spectrometry-based proteomics." Nature 2003, 422, 198-207.
14.Fanton, C.; Delogu, G.; Maccioni, E.; Podda, G.; Seraglia, R.; Traldi, P. "Matrix-assisted laser desorption/ionization mass spectrometry in the dairy industry 2. The protein fingerprint of ewe cheese and its application to detection of adulteration by bovine milk." Rapid Communications in Mass Spectrometry 1998, 12, 1569-1573.
15.Sabbadin, S.; Seraglia, R.; Allegri, G.; Bertazzo, A.; Traldi, P. "Matrix-assisted laser desorption/ionization mass spectrometry in evaluation of protein profiles of infant formulae." Rapid Communications in Mass Spectrometry 1999, 13, 1438-1443.
16.Catinella, S.; Seraglia, R.; Marsilio, R. "Evaluation of protein profile of human milk by matrix-assisted laser desorption/ionization mass spectrometry." Rapid Communications in Mass Spectrometry 1999, 13, 1546-1549.
17.Siciliano, R.; Rega, B.; Amoresano, A.; Pucci, P. "Modern mass spectrometric methodologies in monitoring milk quality." Analytical Chemistry 2000, 72, 408-415.
18.De Kok, P. M. T.; Rosing, E. A. E. In Thermally Generated Flavors; Parliment, T. H., Morello, M. J., McGorrin, R. J., Eds.; American Chemical Society: Washington, DC, 1994, pp 158-165.
19.Chen, R. K.; Chang, L. W.; Chung, Y. Y.; Lee, M. H.; Ling, Y. C. "Quantification of cow milk adulteration in goat milk using high-performance liquid chromatography with electrospray ionization mass spectrometry." Rapid Communications in Mass Spectrometry 2004, 18, 1167-1171.
20.Hearn, M. T. W. In HPLC of Biological Macromolecules, 2 ed.; Gooding, K. M., Regnier, F. E., Eds.; Marcel Dekker, Inc.: New York, 2002.
21.Hearn, M. T. W.; Quirino, J. P.; Whisstock, J.; Terabe, S. "Thermal unfolding of proteins studied by coupled reversed-phase HPLC-electrospray ionization mass spectrometry techniques based on isotope exchange effects." Analytical Chemistry 2002, 74, 1467-1475.
22.Chen, R. K.; Chang, L. W.; Chung, Y. Y.; Lee, M. H.; Ling, Y. C. "Quantification of Cow Milk Adulteration in Goat Milk Using High-Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometry." Rapid Commun. Mass Spectrom. 2004, (in press).
23.Cozzolino, R.; Passalacqua, S.; Salemi, S.; Malvagna, P.; Spina, E.; Garozzo, D. "Identification of adulteration in milk by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry." Journal of Mass Spectrometry 2001, 36, 1031-1037.
24.Pizzano, R.; Nicolai, M. A.; Siciliano, R.; Addeo, F. "Specific detection of the Amadori compounds in milk by using polyclonal antibodies raised against a lactosylated peptide." Journal of Agricultural and Food Chemistry 1998, 46, 5373-5379.
25.Del Castillo, M. D.; Corzo, N.; Olano, A. "Early stages of Maillard reaction in dehydrated orange juice." Journal of Agricultural and Food Chemistry 1999, 47, 4388-4390.
26.Sanz, M. L.; Del Castillo, M. D.; Corzo, N.; Olano, A. "Formation of Amadori compounds in dehydrated fruits." Journal of Agricultural and Food Chemistry 2001, 49, 5228-5231.
27.Sanz, M. L.; Del Castillo, M. D.; Corzo, N.; Olano, A. "2-Furoylmethyl amino acids and hydroxymethylfurfural as indicators of honey quality." Journal of Agricultural and Food Chemistry 2003, 51, 4278-4283.
28.Fox, P. F.; McSweeney, P. L. H. Dairy Chemistry and Biochemistry, 1st ed.; Blackie Academic & Professional: London, 1998, pp.347-348.
29.Walstra, P.; Geurts, T. J.; Noomen, A.; Jellema, A.; van Boekel, M. A. J. S. Dairy Technology; Marcel Dekker: New York, 1999, 208-209.

Chapter 5
1.Mottram, D. S. In Thermally Generated Flavors; Parliment, T. H., Morello, M. J., McGorrin, R. J., Eds.; American Chemical Society: Washington, DC, 1994, pp 104-126.
2.Humeny, A.; Kislinger, T.; Becker, C. M.; Pischetsrieder, M. "Qualitative determination of specific protein glycation products by matrix-assisted laser desorption/ionization mass spectrometry peptide mapping." Journal of Agricultural and Food Chemistry 2002, 50, 2153-2160.
3.French, S. J.; Harper, W. J. "Maillard reaction induced lactose attachment to bovine beta-lactoglobulin: Foam-and emulsion functionality." Milchwissenschaft-Milk Science International 2003, 58, 252-256.
4.Umetsu, H.; Van Chuyen, N. "Digestibility and peptide patterns of modified lysozyme after hydrolyzing by protease." Journal of Nutritional Science and Vitaminology 1998, 44, 291-300.
5.Naranjo, G. B.; Malec, L. S.; Vigo, M. S. "Reducing sugars effect on available lysine loss of casein by moderate heat treatment." Food Chemistry 1998, 62, 309-313.
6.Del Castillo, M. D.; Villamiel, M.; Olano, A.; Corzo, N. "Use of 2-furoylmethyl derivatives of GABA and arginine as indicators of the initial steps of Maillard reaction in orange juice." Journal of Agricultural and Food Chemistry 2000, 48, 4217-4220.
7.Elliott, A. J.; Dhakal, A.; Datta, N.; Deeth, H. C. "Heat-induced changes in UHT milks - Part 1." Australian Journal of Dairy Technology 2003, 58, 3-10.
8.Pizzano, R.; Nicolai, M. A.; Siciliano, R.; Addeo, F. "Specific detection of the Amadori compounds in milk by using polyclonal antibodies raised against a lactosylated peptide." Journal of Agricultural and Food Chemistry 1998, 46, 5373-5379.
9.Pallini, M.; Compagnone, D.; Di Stefano, S.; Marini, S.; Coletta, A.; Palleschi, G. "Immunodetection of lactosylated proteins as a useful tool to determine heat treatment in milk samples." Analyst 2001, 126, 66-70.
10.Galvani, M.; Hamdan, M.; Righetti, P. G. "Two-dimensional gel electrophoresis/matrix-assisted laser desorption/ionisation mass spectrometry of a milk powder." Rapid Communications in Mass Spectrometry 2000, 14, 1889-1897.
11.Fenaille, F.; Morgan, F.; Parisod, W.; Tabet, J. C.; Guy, P. A. "Solid-state glycation of beta-lactoglobulin monitored by electrospray ionisation mass spectrometry and gel electrophoresis techniques." Rapid Communications in Mass Spectrometry 2003, 17, 1483-1492.
12.Fenaille, F.; Morgan, F.; Parisod, V.; Tabet, J. C.; Guy, P. A. "Solid-state glycation of beta-lactoglobulin by lactose and galactose: localization of the modified amino acids using mass spectrometric techniques." Journal of Mass Spectrometry 2004, 39, 16-28.
13.Siciliano, R.; Rega, B.; Amoresano, A.; Pucci, P. "Modern mass spectrometric methodologies in monitoring milk quality." Analytical Chemistry 2000, 72, 408-415.
14.French, S. J.; Harper, W. J.; Kleinholz, N. M.; Jones, R. B.; Green-Church, K. B. "Maillard reaction induced lactose attachment to bovine beta-lactoglobulin: Electrospray ionization and matrix-assisted laser desorption/ionization examination." Journal of Agricultural and Food Chemistry 2002, 50, 820-823.
15.Kislinger, T.; Humeny, A.; Peich, C. C.; Zhang, X. H.; Niwa, T.; Pischetsrieder, M.; Becker, C. M. "Relative quantification of N-epsilon-(carboxymethyl)lysine, imidazolone A, and the Amadori product in glycated lysozyme by MALDI-TOF mass spectrometry." Journal of Agricultural and Food Chemistry 2003, 51, 51-57.
16.Fenaille, F.; Campos-Gimenez, E.; Guy, P. A.; Schmitt, C.; Morgan, F. "Monitoring of beta-lactoglobulin dry-state glycation using various analytical techniques." Analytical Biochemistry 2003, 320, 144-148.
17.Chen, R. K.; Chang, L. W.; Chung, Y. Y.; Lee, M. H.; Ling, Y. C. "Quantification of adulteration of goat milk by cow milk using high-performance liquid chromatography with electrospray ionization mass spectrometry." Rapid Communication in Mass Spectrometry 2004, 18, 1167-1171.
18.Dass, C. Principles and Practice of Biological Mass Spectrometry; John Wiley & Sons, Inc.: New York, 2001.
19.Yang, W. H.; Hattori, M.; Kawaguchi, T.; Takahashi, K. "Properties of starches conjugated with lysine and poly(lysine) by the Maillard reaction." Journal of Agricultural and Food Chemistry 1998, 46, 442-445.
20.Ajandouz, E. H.; Puigserver, A. "Nonenzymatic browning reaction of essential amino acids: Effect of pH on caramelization and Maillard reaction kinetics." Journal of Agricultural and Food Chemistry 1999, 47, 1786-1793.
21.Palzkill, T. Proteomics, 2nd ed.; Kluwer Academic Publishers: Norwell, 2002.
22.Griffiths, W. J. In Proteomics in Functional Genomics; Jolles, P., Jornvall, H., Eds.; Birkhauser Verlag: Basel, 2000, pp 69-79.

Chapter 6
1.Stryer, L. Biochemistry, 4th ed.; W. H. Freeman and Company: New York, 1995.
2.Nagy, K.; Jakab, A.; Fekete, J.; Vekey, K. "An HPLC-MS approach for analysis of very long chain fatty acids and other apolar compounds on octadecyl-silica phase using partly miscible solvents." Analytical Chemistry 2004, 76, 1935-1941.
3.Vauterin, L.; Yang, P.; Hoste, B.; Pot, B.; Swings, J.; Kersters, K. "Taxonomy of xanthomonads from cereals and grasses based on SDS-PAGE of proteins, fatty-acid analysis and DNA hybridization." Journal of General Microbiology 1992, 138, 1467-1477.
4.Basile, F.; Voorhees, K. J.; Hadfield, T. L. "Microorganism Gram type differentiation based on pyrolysis mass spectrometry of bacterial fatty acid methyl ester extracts." Applied and Environmental Microbiology 1995, 61, 1534-1539.
5.Barshick, S. A.; Wolf, D. A.; Vass, A. A. "Differentiation of microorganisms based on pyrolysis ion trap mass spectrometry using chemical ionization." Analytical Chemistry 1999, 71, 633-641.
6.Wolff, R. L.; Lavialle, O.; Pedrono, F.; Pasquier, E.; Destaillats, F.; Marpeau, A. M.; Angers, P.; Aitzetmuller, K. "Abietoid seed fatty acid compositions - A review of the genera Abies, Cedrus, Hesperopeuce, Keteleeria, Pseudolarix, and Tsuga and preliminary inferences on the taxonomy of Pinaceae." Lipids 2002, 37, 17-26.
7.Willis, W. M.; Marangoni, A. G. "Biotechnological strategies for the modification of food lipids." Biotechnology and Genetic Engineering Reviews, Vol 16 1999, 16, 141-175.
8.Fontecha, J.; Diaz, V.; Fraga, M. J.; Juarez, M. "Triglyceride analysis by gas chromatography in assessment of authenticity of goat milk fat." Journal of the American Oil Chemists Society 1998, 75, 1893-1896.
9.Povolo, H.; Bonfitto, E.; Contarini, G.; Toppino, P. M.; Daghetta, A. "Study on the performance of three different capillary gas chromatographic analyses in the evaluation of milk fat purity." Hrc-Journal of High Resolution Chromatography 1999, 22, 97-102.
10.Fontecha, J.; Rios, J. J.; Lozada, L.; Fraga, M. J.; Juarez, M. "Composition of goat's milk fat triglycerides analysed by silver ion adsorption-TLC and GC-MS." International Dairy Journal 2000, 10, 119-128.
11.Iverson, J. L.; Sheppard, A. J. "Detection of adulteration in cow, goat, and sheep cheeses utilizing gas-liquid-chromatographic fatty-acid data." Journal of Dairy Science 1989, 72, 1707-1712.
12.Ulberth, F. "Detection of milk-fat adulteration by linear discriminant analysis of fatty acid data." Journal of AOAC International 1994, 77, 1326-1334.
13.Gamazo-Vazquez, J.; Garcia-Falcon, M. S.; Simal-Gandara, J. "Control of contamination of olive oil by sunflower seed oil in bottling plants by GC-MS of fatty acid methyl esters." Food Control 2003, 14, 463-467.
14.Kim, S. J.; Woo, H. K.; Seo, M. Y.; Joh, Y. G. "Analysis of fatty acids in puffer fish liver oils by combined chromatographic procedures - Resolution of fatty acid methyl esters by Ag+-chromatography and their identification by GC-MS using 4,4-dimethyloxazoline derivatives." Food Science and Biotechnology 2003, 12, 326-336.
15.Fraga, M. J.; Fontecha, J.; Lozada, L.; Juarez, M. "Silver ion adsorption thin layer chromatography and capillary gas chromatography in the study of the composition of milk fat triglycerides." Journal of Agricultural and Food Chemistry 1998, 46, 1836-1843.
16.Goudjil, H.; Fontecha, J.; Fraga, M. J.; Juarez, M. "TAG composition of ewe's milk fat. Detection of foreign fats." Journal of the American Oil Chemists Society 2003, 80, 219-222.
17.Jakab, A.; Jablonkai, I.; Forgacs, E. "Quantification of the ratio of positional isomer dilinoleoyl-oleoyl glycerols in vegetable oils." Rapid Communications in Mass Spectrometry 2003, 17, 2295-2302.
18.Dorschel, C. A. "Characterization of the TAG of peanut oil by electrospray LC-MS-MS." Journal of the American Oil Chemists Society 2002, 79, 749-753.
19.Han, X. L.; Gross, R. W. "Quantitative analysis and molecular species fingerprinting of triacylglyceride molecular species directly from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry." Analytical Biochemistry 2001, 295, 88-100.
20.Mu, H. L.; Sillen, H.; Hoy, C. E. "Identification of diacylglycerols and triacylglycerols in a structured lipid sample by atmospheric pressure chemical ionization liquid chromatography/mass spectrometry." Journal of the American Oil Chemists Society 2000, 77, 1049-1059.
21.Jakab, A.; Nagy, K.; Heberger, K.; Vekey, K.; Forgacs, E. "Differentiation of vegetable oils by mass spectrometry combined with statistical analysis." Rapid Communications in Mass Spectrometry 2002, 16, 2291-2297.
22.Parcerisa, J.; Casals, I.; Boatella, J.; Codony, R.; Rafecas, M. "Analysis of olive and hazelnut oil mixtures by high-performance Liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry of triacylglycerols and gas-liquid chromatography of non-saponifiable compounds (tocopherols and sterols)." Journal of Chromatography A 2000, 881, 149-158.
23.Mottram, H. R.; Evershed, R. P. "Structure analysis of triacylglycerol positional isomers using atmospheric pressure chemical ionisation mass spectrometry." Tetrahedron Letters 1996, 37, 8593-8596.
24.Mottram, H. R.; Woodbury, S. E.; Evershed, R. P. "Identification of triacylglycerol positional isomers present in vegetable oils by high performance liquid chromatography atmospheric pressure chemical ionization mass spectrometry." Rapid Communications in Mass Spectrometry 1997, 11, 1240-1252.
25.Marzilli, L. A.; Fay, L. B.; Dionisi, F.; Vouros, P. "Structural characterization of triacylglycerols using electrospray ionization-MSn ion-trap MS." Journal of the American Oil Chemists Society 2003, 80, 195-202.

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