Hydrolyzable tannin analysis in food

Food Chemistry

Volumn 135, Issue 3, 2012, Pages 1708-1717

  Arapitsas, Panagiotis ^a  

^a RESEARCH AND INNOVATION CENTRE   (Italy)

Author keywords

Analytical chemistry; Ellagitannins; Food; Gallotannins; Tannins

Indexed keywords

ANALYTICAL CHEMICALS; CHRONIC DISEASE; ELLAGITANNINS; FOOD ANALYSIS; FOOD QUALITY AND SAFETIES; FOOD SCIENCE; GALLOTANNINS; HYDROLYZABLE TANNINS; OPTIMISATIONS; PLANT POLYPHENOLS; TANNINS;

FOOD PRODUCTS; HEALTH RISKS;

CHEMICAL ANALYSIS;

1,2,3,6 TETRAGALLOYL GLUCOSE; 1,2,4,6 TETRAGALLOYL GLUCOSE; CASTALAGIN; CASTALAGIN DERIVATIVE; CASUARININ; CORILAGIN; DIGALLOYL GLUCOSE; ELLAGIC ACID; ELLAGITANNIN; ETHYLVESCALAGIN; GALLIC ACID; GALLIC ACID METHYL ESTER; GLANSREGININ; GLANSRIN; GRANATIN A; GRANATIN B; GRANDININ; HYPERIN; LAGERSTANNIN B; LAMBERTIANIN C; NOBOTANIN; POTENTILIN; PTEROCARININ A; PUNICALAGIN B; PUNICALIN A; PUNICALIN B; ROBUNIN; SANGUIIN H6; TANNIN; UNCLASSIFIED DRUG; VESCALAGIN;

ANTIBACTERIAL ACTIVITY; ANTIDIABETIC ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; BIOCHEMISTRY; BIOSYNTHESIS; BLACKBERRY; BRASSICALES; CANCER RISK; CARDIOVASCULAR RISK; CLASSIFICATION; ESTERIFICATION; EXTRACTION; FOOD ANALYSIS; FOOD PROCESSING; FOOD QUALITY; FOOD STORAGE; GRAPE; HAMAMELIS; ISOLATION PROCEDURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MYRTALES; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN ANALYSIS; REVIEW; ROSID; SAPINDALES; STRAWBERRY; VITACEAE; WHISKEY;

CHEMISTRY TECHNIQUES, ANALYTICAL; FOOD ANALYSIS; HUMANS; HYDROLYZABLE TANNINS; POLYPHENOLS;

EID: 84865703215     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.05.096     Document Type: Review

References (92)

1. K. Aaby, D. Ekeberg, and G. Skrede Characterization of phenolic compounds in strawberry (Fragaria × ananassa) fruits by different hplc detectors and contribution of individual compounds to total antioxidant capacity Journal of Agricultural and Food Chemistry 55 11 2007 4395 4406 (Pubitemid 46932635)
2. K. Aaby, R.E. Wrolstad, D. Ekeberg, and G. Skrede Polyphenol composition and antioxidant activity in strawberry purees; impact of achene level and storage Journal of Agricultural and Food Chemistry 55 13 2007 5156 5166 (Pubitemid 47056071)
3. F. Afag, M. Saleem, C.G. Krueger, J.D. Reed, and H. Mukhtar Anthocyanin- and Hydrolyzable Tannin-rich Pomegranate fruit extract modulates MAPK and NF-kB pathways and inhibits skin tumorigenesis in CD-1 Mice International Journal of Cancer 113 2005 423 433 (Pubitemid 40038710)
4. n Journal of Agricultural and Food Chemistry 58 8 2010 4681 4692
5. P. Arapitsas, S. Menichetti, F.F. Vincieri, and A. Romani Hydrolyzable Tannins with the Hexahydroxydiphenoyl Unit and the m-Depsidic Link: HPLC-DAD-MS identification and model synthesis Journal of Agricultural and Food Chemistry 55 1 2007 48 55 (Pubitemid 46059120)
6. J. Beekwilder, H. Jonker, P. Meesters, R.D. Hall, I.M. van der Meer, and C.H. de Vos Antioxidants in raspberry: on-line analysis links antioxidant activity to a diversity of individual metabolites Journal of Agricultural and Food Chemistry 53 9 2005 3313 3320 (Pubitemid 40758160)
7. G. Borges, W. Mullen, and A. Crozier Comparison of the polyphenolic composition and antioxidant activity of European commercial fruit juices Food & Function 1 1 2010 73
8. B. Buendía, M.I. Gil, J.A. Tudela, A.L. Gady, J.J. Medina, and C. Soria HPLC-MS Analysis of Proanthocyanidin Oligomers and Other Phenolics in 15 Strawberry Cultivars† Journal of Agricultural and Food Chemistry 58 7 2010 3916 3926
9. P. Buzzini, P. Arapitsas, M. Goretti, E. Branda, B. Turchetti, and P. Pinelli Antimicrobial and antiviral activity of hydrolysable tannins Mini Reviews in Medicinal Chemistry 8 12 2008 1179 1187
10. Y. Cai, Q. Luo, M. Sun, and H. Corke Antioxidant activity and phenolic compounds of 112 traditional Chinese medicinal plants associated with anticancer Life Sciences 74 17 2004 2157 2184 (Pubitemid 38210440)
11. Y. Cai, Mei. Sun, Jie. Xing, Q. Luo, and H. Corke Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants Life Sciences 78 25 2006 2872 2888
12. M. Çam, and Y. HIsIl Pressurised water extraction of polyphenols from pomegranate peels Food Chemistry 123 3 2010 878 885
13. G. Cao, E. Sofic, and R.L. Prior Antioxidant and Prooxidant Behavior of Flavonoids: Structure-Activity Relationships Free Radical Biology and Medicine 22 5 1997 749 760 (Pubitemid 27058337)
14. N.H. Darton II. On the estimation of tannic acid in tanning materials, etc. Journal of the American Chemical Society 4 1 1882 4 6
15. N.H. Darton XI. On the comparative value of the several methods of the determing of tannic acid Journal of the American Chemical Society 4 5 1882 49 56
16. C. Engels, M.G. Ganzle, and A. Schieber Fractionation of Gallotannins from Mango (Mangifera indica L.) Kernels by High-Speed Counter-Current Chromatography and Determination of Their Antibacterial Activity Journal of Agricultural and Food Chemistry 58 2 2010 775 780
17. C. Engels, M. Knodler, Y. Zhao, R. Carle, M.G. Ganzle, and A. Schieber Antimicrobial Activity of Gallotannins Isolated from Mango (Mangifera indica L.) Kernels Journal of Agricultural and Food Chemistry 57 17 2009 7712 7718
18. L. Falcão, and M.E.M. Araújo Tannins characterisation in new and historic vegetable tanned leathers fibres by spot tests Journal of Cultural Heritage 12 2 2011 149 156
19. A. Fernandes, A. Sousa, N. Mateus, M. Cabral, and V. de Freitas Analysis of phenolic compounds in cork from Quercus suber L. by HPLC-DAD/ESI-MS Food Chemistry 125 4 2011 1398 1405
20. E. Fischer Synthesis of depsides, lichen-substances and tannins Journal of the American Chemical Society 36 6 1914 1170 1201
21. U.A. Fischer, R. Carle, and D.R. Kammerer Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD-ESI/MSn Food Chemistry 127 2 2011 807 821
22. P. Franceschi, U. Vrhovsek, and G. Guella Ion mobility mass spectrometric investigation of ellagitannins and their non-covalent aggregates Rapid Communications in Mass Spectrometry 25 7 2011 827 833
23. M. Fujieda, T. Tanaka, Y. Suwa, S. Koshimizu, and I. Kouno Isolation and structure of whiskey polyphenols produced by oxidation of oak wood Ellagitannins Journal of Agricultural and Food Chemistry 56 16 2008 7305 7310
24. R. Furuuchi, T. Yokoyama, Y. Watanabe, and M. Hirayama Identification and quantification of short oligomeric proanthocyanidins and other polyphenols in boysenberry seeds and juice Journal of Agricultural and Food Chemistry 59 8 2011 3738 3746
25. I. García-Estévez, M.T. Escribano-Bailón, J.C. Rivas-Gonzalo, and C. Alcalde-Eon Development of a fractionation method for the detection and identification of oak ellagitannins in red wines Analytica Chimica Acta 660 1-2 2010 171 176
26. M. Gasperotti, D. Masuero, U. Vrhovsek, G. Guella, and F. Mattivi Profiling and Accurate Quantification of Rubus Ellagitannins and Ellagic Acid Conjugates Using Direct UPLC-Q-TOF HDMS and HPLC-DAD Analysis Journal of Agricultural and Food Chemistry 58 8 2010 4602 4616
27. F. Gironi, and V. Piemonte Temperature and solvent effects on polyphenol extraction process from chestnut tree wood Chemical Engineering Research and Design 89 7 2011 857 862
28. A. Glabasnia, and T. Hofmann Sensory-Directed Identification of Taste-Active Ellagitannins in American (Quercus alba L.) and European Oak Wood (Quercus robur L.) and Quantitative Analysis in Bourbon Whiskey and Oak-Matured Red Wines Journal of Agricultural and Food Chemistry 54 9 2006 3380 3390 (Pubitemid 43798210)
29. M.J. González, J.L. Torres, and I. Medina Impact of thermal processing on the activity of gallotannins and condensed tannins from Hamamelis virginiana used as functional ingredients in seafood Journal of Agricultural and Food Chemistry 58 7 2010 4274 4283
30. G.G. Gross From lignins to tannins: Forty years of enzyme studies on the biosynthesis of phenolic compounds Phytochemistry 69 18 2008 3018 3031
31. T.J. Hager, L.R. Howard, and R.L. Prior Processing and storage effects on the Ellagitannin composition of processed blackberry products Journal of Agricultural and Food Chemistry 58 22 2010 11749 11754
32. R.A. Halberstein Medicinal plants: Historical and cross-cultural usage patterns Annals of Epidemiology 15 9 2005 686 699 (Pubitemid 41266973)
33. B. Halliwell Dietary polyphenols: Good, bad, or indifferent for your health? Cardiovascular Research 73 2 2007 341 347 (Pubitemid 44937697)
34. J.B. Harborne, and C.A. Williams Advances in flavonoid research since 1992 Phytochemistry 55 6 2000 481 504
35. P.W. Hartzfeld, R. Forkner, M.D. Hunter, and A.E. Hagerman Determination of Hydrolyzable tannins (Gallotannins and Ellagitannins) after reaction with potassium iodate Journal of Agricultural and Food Chemistry 50 7 2002 1785 1790 (Pubitemid 34259968)
36. E. Haslam Plant Polyphenols: Vegetable tannins revisited 2nd ed. 1989 Cambridge University Press Cambridge University Press
37. E. Haslam Natural polyphenols (Vegetable Tannins) as drugs: Possible modes of action Journal of Natural Products 59 2 1996 205 215 (Pubitemid 27079849)
38. E. Haslam Vegetable tannins - Lessons of a phytochemical lifetime Phytochemistry 68 22-24 2007 2713 2721 (Pubitemid 350180951)
39. T. Hatano, T. Yoshida, and T. Okuda Chromatography of tannins: III. Multiple peaks in high-performance liquid chromatography of some hydrolyzable tannins Journal of Chromatography A 435 1988 285 295
40. B.H. Havsteen The biochemistry and medical significance of the flavonoids Pharmacology & Therapeutics 96 2-3 2002 67 202 (Pubitemid 35356564)
41. Q. He, B. Shi, K. Yao, Y. Luo, and Z. & Ma Synthesis of gallotannins Carbohydrate Research 335 4 2001 245 250 (Pubitemid 32938162)
42. Z. He, W. Xia, and J. Chen Isolation and structure elucidation of phenolic compounds in Chinese olive (Canarium album L.) fruit European Food Research and Technology 226 5 2007 1191 1196
43. H. Ito, A. Iguchi, and T. Hatano Identification of Urinary and Intestinal Bacterial Metabolites of Ellagitannin Geraniin in Rats Journal of Agricultural and Food Chemistry 56 2 2008 393 400 (Pubitemid 351212563)
44. Jourdes, M., Poysegu, L., Quideau, S., Mattivi, F., Truchado, P., & Tomas-Barberan, F.A. (2011) Handbook of Analysis of Active Compounds in Functional Foods Chapter 20. CRC Press.
45. A. Kanaujia, R. Duggar, S.T. Pannakal, S.S. Yadav, C.K. Katiyar, and V. Bansal Insulinomimetic activity of two new gallotannins from the fruits of Capparis moonii Bioorganic & Medicinal Chemistry 18 11 2010 3940 3945
46. Y. Kim, A.J. Lounds-Singleton, and S.T. Talcott Antioxidant phytochemical and quality changes associated with hot water immersion treatment of mangoes (Mangifera indica L.) Food Chemistry 115 3 2009 989 993
47. M.M. Kool, D.J. Comeskey, J.M. Cooney, and T.K. McGhie Structural identification of the main ellagitannins of a boysenberry (Rubus loganbaccus × baileyanus Britt.) extract by LC-ESI-MS/MS, MALDI-TOF-MS and NMR spectroscopy Food Chemistry 119 4 2010 1535 1543
48. J.M. Koponen, A.M. Happonen, P.H. Mattila, and A.R. Törrönen Contents of Anthocyanins and Ellagitannins in Selected Foods Consumed in Finland Journal of Agricultural and Food Chemistry 55 4 2007 1612 1619
49. + ions Toxicology in Vitro 21 1 2007 146 156 (Pubitemid 44855521)
50. J. Landete Ellagitannins, ellagic acid and their derived metabolites: A review about source, metabolism, functions and health Food Research International 44 5 2011 1150 1160
51. M. Larrosa, M.T. García-Conesa, J.C. Espín, and F.A. Tomás-Barberán Ellagitannins, ellagic acid and vascular health Molecular Aspects of Medicine 31 6 2010 513 539
52. D.W. Lau, A.J. King, and A.L. Waterhouse An assay to estimate tannins added to postmortem turkey meat Journal of Agricultural and Food Chemistry 51 23 2003 6640 6644
53. L. Le Marchand Cancer preventive effects of flavonoids - A review Biomedecine & Pharmacotherapy 56 6 2002 296 301 (Pubitemid 35245313)
54. K.R. Määttä, A. Kamal-Eldin, and A.R. Törrönen High-performance liquid chromatography (hplc) analysis of phenolic compounds in berries with diode array and electrospray ionization mass spectrometric (ms) detection: ribes species Journal of Agricultural and Food Chemistry 51 23 2003 6736 6744
55. K.R. Määttä-Riihinen, A. Kamal-Eldin, and A.R. Törrönen Identification and Quantification of Phenolic Compounds in Berries of Fragaria and Rubus Species (Family Rosaceae) Journal of Agricultural and Food Chemistry 52 20 2004 6178 6187
56. S. Madrigal-Carballo, G. Rodriguez, C. Krueger, M. Dreher, and J. Reed Pomegranate (Punica granatum) supplements: Authenticity, antioxidant and polyphenol composition Journal of Functional Foods 1 3 2009 324 329
57. M. Markom, M. Hasan, W.R.W. Daud, H. Singh, and J.M. Jahim Extraction of hydrolysable tannins from Phyllanthus niruri Linn. Effects of solvents and extraction methods Separation and Purification Technology 52 3 2007 487 496 (Pubitemid 44822583)
58. K.J. Meyers, T.J. Swiecki, and A.E. Mitchell Understanding the native californian diet: identification of condensed and hydrolyzable tannins in tanoak acorns (Lithocarpus densiflorus) Journal of Agricultural and Food Chemistry 54 20 2006 7686 7691 (Pubitemid 44645790)
59. J. Michel, M. Jourdes, M.A. Silva, T. Giordanengo, N. Mourey, and P. Teissedre Impact of concentration of Ellagitannins in oak wood on their levels and organoleptic influence in red wine Journal of Agricultural and Food Chemistry 59 10 2011 5677 5683
60. I. Mueller-Harvey Analysis of hydrolysable tannins Animal Feed Science and Technology 91 1-2 2001 3 20 (Pubitemid 32515976)
61. W. Mullen, A.J. Stewart, M.E.J. Lean, P. Gardner, G.G. Duthie, and A. Crozier Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries Journal of Agricultural and Food Chemistry 50 18 2002 5197 5201 (Pubitemid 34925112)
62. W. Mullen, T. Yokota, M.E. Lean, and A. Crozier Analysis of ellagitannins and conjugates of ellagic acid and quercetin in raspberry fruits by LC-MSn Phytochemistry 64 2 2003 617 624 (Pubitemid 37168986)
63. T. Okuda, and H. Ito Tannins of constant structure in medicinal and food plants - hydrolyzable tannins and polyphenols related to tannins Molecules 16 3 2011 2191 2217
64. T. Okuda, T. Yoshida, and T. Hatano Ellagitannins as active constituents of medicinal plants Planta Medica 55 2 1989 117 122 (Pubitemid 19095275)
65. T. Okuda, T. Yoshida, and T. Hatano New methods of analyzing tannins Journal of Natural Products 52 1 1989 1 31 (Pubitemid 19084190)
66. R.W. Owen, R. Haubner, W.E. Hull, G. Erben, B. Spiegelhalder, and H. Bartsch Isolation and structure elucidation of the major individual polyphenols in carob fibre Food and Chemical Toxicology 41 12 2003 1727 1738 (Pubitemid 37249340)
67. n Journal of Agricultural and Food Chemistry 52 2004 3784 3791
68. B. Pfundstein, S.K. El Desouky, W.E. Hull, R. Haubner, G. Erben, and R.W. & Owen Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities Phytochemistry 71 10 2010 1132 1148
69. S. Quideau, and K.S. Feldman Ellagitannin Chemistry Chemical Reviews 96 1 1996 475 504
70. N. Rangkadilok, L. Worasuttayangkurn, R.N. Bennett, and J. Satayavivad Identification and Quantification of Polyphenolic Compounds in Longan (Euphoria longana Lam.) Fruit Journal of Agricultural and Food Chemistry 53 5 2005 1387 1392 (Pubitemid 40322124)
71. H.M. Rau ON the estimation of tannins, with critical notes on the methods of hammer and loewenthal Journal of the American Chemical Society 9 4 1887 52 75
72. J.D. Reed, C.G. Krueger, and M.M. Vestling MALDI-TOF mass spectrometry of oligomeric food polyphenols Phytochemistry 66 18 2005 2248 2263 (Pubitemid 41254099)
73. A. Romani, R. Coinu, S. Carta, P. Pinelli, C. Galardi, and F.F. Vincieri Evaluation of antioxidant effect of different extracts of Myrtus communis L Free Radical Research 38 1 2004 97 103 (Pubitemid 38128520)
74. Romani, A., Pinelli, P., Vignolini, P., Arapitsas, P., Nieddu, G., & Chessa, E. (2006). Analisi di composti polifenolici in frutti e foglie in diverse selezioni varietali di Myrtus Communis L'. Procceding of VI congresso Nazionale di Chimica degli alimenti. Alba, Italy, 7-10 November 2006. pp. 177-181.
75. A. Romani, S. Menichetti, P. Arapitsas, C. Nativi, B. Turchetti, and P. Buzzini O-Methylglucogalloyl esters: synthesis and evaluation of their antimycotic activity Bioorganic & Medicinal Chemistry Letters 15 18 2005 4000 4003 (Pubitemid 41132650)
76. A. Russell The Natural Tannins Chemical Reviews 17 2 1935 155 186
77. J. Salminen, M. Karonen, and J. Sinkkonen Chemical Ecology of Tannins: Recent Developments in Tannin Chemistry Reveal New Structures and Structure-Activity Patterns Chemistry - A European Journal 17 10 2011 2806 2816
78. A.K. Sandhu, and L. Gu Antioxidant capacity, phenolic content, and profiling of phenolic compounds in the seeds, skin, and pulp of vitis rotundifolia (muscadine grapes) as determined by HPLC-DAD-ESI-MSn Journal of Agricultural and Food Chemistry 58 8 2010 4681 4692
79. C. Saucier, M. Jourdes, Y. Glories, and S. Quideau Extraction, detection, and quantification of flavano-ellagitannins and ethylvescalagin in a bordeaux red wine aged in oak barrels Journal of Agricultural and Food Chemistry 54 19 2006 7349 7354 (Pubitemid 44554962)
80. N.P. Seeram, R. Lee, H.S. Scheuller, and D. Heber Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy Food Chemistry 97 1 2006 1 11 (Pubitemid 41773934)
81. M.J. Simirgiotis, and G. Schmeda-Hirschmann Determination of phenolic composition and antioxidant activity in fruits, rhizomes and leaves of the white strawberry (Fragaria chiloensis spp. chiloensis form chiloensis) using HPLC-DAD-ESI-MS and free radical quenching techniques Journal of Food Composition and Analysis 23 2010 545 553
82. Y.Y. Soong, and P.J. Barlow Isolation and structure elucidation of phenolic compounds from longan (Dimocarpus longan Lour.) seed by high-performance liquid chromatography-electrospray ionization mass spectrometry Journal of Chromatography A 1085 2 2005 270 277 (Pubitemid 40994931)
83. K.A. Steinmetz, and J.D. Potter Vegetables, fruit, and cancer II. Mechanisms Cancer Causes and Control 2 6 1991 427 442
84. K.A. Steinmetz, and J.D. Potter Vegetables, Fruit, and Cancer Prevention: A Review Journal of the American Dietetic Association 96 10 1996 1027 1039 (Pubitemid 27382158)
85. The Merk Index, 2001 The Merk Index (2001). (13th ed.) (pp. 1615-1616). Whitehouse Station, NJ: Merk & Co., Inc.
86. F. Tian, B. Li, B. Ji, G. Zhang, and Y. Luo Identification and structure-activity relationship of gallotannins separated from Galla chinensis LWT - Food Science and Technology 42 7 2009 1289 1295
87. R. Tzulker, I. Glazer, I. Bar-Ilan, D. Holland, M. Aviram, and R. Amir Antioxidant activity, polyphenol content, and related compounds in different fruit juices and homogenates prepared from 29 different pomegranate accessions Journal of Agricultural and Food Chemistry 55 23 2007 9559 9570 (Pubitemid 350205310)
88. U. Vrhovsek, A. Palchetti, F. Reniero, C. Guillou, D. Masuero, and F. Mattivi Concentration and mean degree of polymerization of rubus ellagitannins valuated by optimized acid methanolysis Journal of Agricultural and Food Chemistry 54 12 2006 4469 4475 (Pubitemid 44013355)
89. J.A. Wilson The natural organic tannins (Nierenstein, M.) Journal of Chemical Education 11 12 1934 670
90. T. Yoshida, Y. Amakura, and M. Yoshimura Structural features and biological properties of ellagitannins in some plant families of the order myrtales International Journal of Molecular Sciences 11 1 2010 79 106
91. Y. Zhang, D. Wang, R. Lee, S.M. Henning, and D. Heber Absence of pomegranate ellagitannins in the majority of commercial pomegranate extracts: implications for standardization and quality control Journal of Agricultural and Food Chemistry 57 16 2009 7395 7400
92. Zhao, X., Sun, H., Hou, A., Zhao, Q., Wei, T., & Xin, W. (2005). Antioxidant properties of two gallotannins isolated from the leaves of Pistacia weinmannifolia. Biochimica et Biophysica Acta (BBA) - General Subjects, 1725 (1), 103-110. (Pubitemid 41169181)