Food Ellagitannins–Occurrence, Effects of Processing and Storage

REFERENCES

• Aherne , S. A. and O'Brien , N. M. 2002 . Dietary flavonols: Chemistry, food content, and metabolism . Nutrition , 18 : 75 – 81 .
   PubMed Web of Science ®Google Scholar
• Akiyama , H. , Fujii , K. , Yamasaki , O. , Oono , T. and Iwatsuki , K. 2001 . Antibacterial action of several tannins against Staphylococcus aureus . Journal of Antimicrobial Chemotherapy , 48 : 487 – 491 .
   PubMed Web of Science ®Google Scholar
• Amakura , Y. , Okada , M. , Tsuji , S. and Yasuhide , T. 2000 . High-performance liquid chromatographic determination with photodiode array detection of ellagic acid in fresh and processed fruits . Journal of Chromatography A , 896 : 87 – 93 .
   PubMed Web of Science ®Google Scholar
• Amakura , Y. , Umino , Y. , Tsuji , S. and Tonagai , Y. 2001 . Influence of jam processing on the radical scavenging activity and phenolic content in berries . Journal of Agricultural and Food Chemistry , 48 : 6292 – 6297 .
   Google Scholar
• Anttonen , M. J. and Karjalainen , R. O. 2005 . Environmental and genetic variation of phenolic compounds in red raspberry . Journal of Food Composition and Analysis , 18 : 759 – 769 .
   Web of Science ®Google Scholar
• Ariga , T. and Hamano , M. 1990 . Radical scavenging action and its mode in procyanidins B1 and B3 from azuki beans to peroxyl radicals . Agricultural and Biological Chemistry , 54 : 2499 – 2505 .
   Web of Science ®Google Scholar
• Aviram , M. , Rosenblat , M. , Gaitini , D. , Nitecki , S. , Hoffman , A. , Dornfeld , L. , Volkova , N. , Presser , D. , Attias , J. , Liker , H. and Hayek , T. 2004 . Pomegranate juice consumption for 3 years by patients with carotid artery stenosis reduces common carotid intima-media thickness, blood pressure and LDL oxidation . Clinical Nutrition , 23 : 423 – 433 .
   PubMed Web of Science ®Google Scholar
• Canas , S. , Leandro , M. C. , Spranger , M. I. and Belchior , A. P. 1999 . Low molecular weight organic compounds of chestnut wood (Castanea sativa L.) and corresponding aged brandies . Journal of Agricultural and Food Chemistry , 47 : 5023 – 5030 .
   Google Scholar
• Castonguay , A. , Gali , H. U. , Perchellet Gao , E. M. , Boukharta , X. M. M. , Jalbert , G. , Okuda , T. , Yoshida , T. , Hatano , T. and Perchellet , J. P. 1997 . Antitumorigenic and antipromoting activities of ellagic aicd, ellagitannins and oligomeric anthocyanin and procyanidin . International Journal of Oncology , 10 : 367 – 373 .
   PubMed Web of Science ®Google Scholar
• Chung , K. T. , Wong , T. Y. , Wei , C. , Huang , Y. W. and Lin , Y. 1998 . Tannins and human health: A review . Critical Reviews in Food Science and Nutrition , 38 ( 6 ) : 421 – 464 .
   PubMed Web of Science ®Google Scholar
• Clifford , M. N. and Scalbert , A. 2000 . Ellagitannins-nature, occurrence and dietary burden . Journal of The Science of Food and Agriculture , 80 : 1118 – 1125 .
   Web of Science ®Google Scholar
• Cordenunsi , B. R. , Genovese , M. I. , Oliveira do Nascimento , J. R. , Hassimotto , N. M. A. , José dos Santos , R. and Lajolo , F. M. 2005 . Effects of temperature on the chemical composition and antioxidant activity of three strawberry cultivars . Food Chemistry , 91 : 113 – 121 .
   Web of Science ®Google Scholar
• Daniel , E. M. , Krupnick , A. S. , Heur , Y. H. , Blinzler , J. A. , Nims , R. W. and Stoner , G. D. 1989 . Extraction, stability and, quantitation of ellagic acid in various fruits and nuts . Journal of Food Composition and Analysis , 2 : 338 – 349 .
   Google Scholar
• Da Porto , C. , Calligaris , S. , Celotti , E. and Nicoli , M. C. 2000 . Antiradical properties of commercial cognacs assessed by the DPPH test . Journal of Agricultural and Food Chemistry , 48 : 4241 – 4245 .
   PubMed Web of Science ®Google Scholar
• De Ancos , B. , González , E. M. and Cano , M. P. 2000 . Ellagic acid, vitamin C and total phenolic contents and radical scavenging capacity affected by freezing and frozen storage in raspberry fruit . Journal of Agricultural and Food Chemistry , 48 : 4565 – 4570 .
   PubMed Web of Science ®Google Scholar
• Deshpande , S. S. 2002 . Handbook of food toxicology , New York : Marcel Dekker Incorporated .
   Google Scholar
• Deshpande , S. S. , Cheryan , M. and Salunkhe , D. K. 1986 . Tannin analysis of food products . CRC Critical Reviews in Food Science and Nutrition , 24 ( 4 ) : 401 – 449 .
   Google Scholar
• Freudenberg , K. 1920 . Die Chemie der Naturlichen Garbstoffe , Berlin : Springer-Verlag .
   Google Scholar
• Fukuda , T. , Ito , H. and Yoshida , T. 2003 . Antioxidative polyphenols from walnuts (Juglans regia L.) . Phytochemistry , 63 : 795 – 801 .
   PubMed Web of Science ®Google Scholar
• Fukuda , T. , Ito , H. and Yoshida , T. 2004 . Effect of the walnut polyphenol fraction on oxidative stress in type 2 diabetes mice . BioFactors , 21 : 251 – 253 .
   PubMed Web of Science ®Google Scholar
• Fukumoto , L. R. and Mazza , G. 2000 . Assessing antioxidant and prooxidant activities of phenolic compounds . Journal of Agricultural and Food Chemistry , 48 : 3597 – 3604 .
   PubMed Web of Science ®Google Scholar
• Garrido , V. M. , Sims , C. A. , Marshall , M. R. and Bates , R. P. 1993 . Factors influencing ellagic acid precipitation in muscadine grape juice during storage . Journal of Food Science , 58 : 193 – 196 .
   Web of Science ®Google Scholar
• Gil , M. I. , Holcroft , D. M. and Kader , A. A. 1997 . Changes in strawberry anthocyanins and other polyphenols in response to carbon dioxide treatments . Journal of Agricultural and Food Chemistry , 45 : 1662 – 1667 .
   Web of Science ®Google Scholar
• Gil , M. I. , Tomás-Barberán , F. A. , Hess-Pierce , B. , Holcroft , D. M. and Kader , A. A. 2000 . Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing . Journal of Agricultural and Food Chemistry , 48 : 4581 – 4589 .
   PubMed Web of Science ®Google Scholar
• Gupta , R. K. , Al-Shafi , S. M. K. , Layden , K. and Haslam , E. 1982 . The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 2.1 esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (4C1) . Journal of The Chemical Society Perkin Transactions , 1 : 2525 – 2534 .
   Google Scholar
• Hagerman , A. E. , Riedl , K. M. , Jones , G. A. , Sovik , K. N. , Harzfeld , P. W. and Riechel , T. L. 1998 . High molecular weight plant polyphenolics (tannins) as biological antioxidants . Journal of Agricultural and Food Chemistry , 46 : 1887 – 1992 .
   PubMed Web of Science ®Google Scholar
• Haslam , E. 1989 . Plant Polyphenols, vegetable tannins revisited , Cambridge : Cambridge University Press .
   Google Scholar
• Hatano , T. , Kusuda , M. , Inada , K. , Ogawa , T. , Shiota , S. , Tsuchiya , T. and Yoshida , T. 2005 . Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus . Phytochemistry , 66 ( 17 ) : 2047 – 2055 .
   PubMed Web of Science ®Google Scholar
• Häkkinen , S. , Heinonen , M. , Kärenlampi , S. , Mykkänen , H. , Ruuskanen , J. and Törrönen , R. 1999 . Screening of selected flavanoids and phenolic acids in 19 berries . Food Research International , 32 : 345 – 353 .
   Web of Science ®Google Scholar
• Häkkinen , S. H. , Kärenlampi , S. O. , Mykkänen , H. M. , Heinonen , I. M. and Törrönen , A. R. 2000 . Ellagic acid content in berries: Influence of domestic processing and storage . European Food Research and Technology , 212 : 75 – 80 .
   Web of Science ®Google Scholar
• Helm , R. F. , Rnatunga , T. D. and Chandra , M. 1997 . Lignin hydrozable tannin interaction in wood . Journal of Agricultural and Food Chemistry , 45 : 3100 – 3106 .
   Web of Science ®Google Scholar
• Hollman , P. C. 2001 . Evidence for health benefits of plant phenols: Local or systemic effects . Journal of The Science of Food and Agriculture , 81 : 842 – 852 .
   Web of Science ®Google Scholar
• Juang , L. J. , Sheu , S. J. and Lin , T. A. 2004 . Determination of hydrolyzable tannins in the fruit of Terminalia chebula retz. By high-performance liquid chromatography and capillary electrophoresis . Journal of Seperation Science , 27 : 718 – 724 .
   PubMed Web of Science ®Google Scholar
• Khanbabaee , K. and van Ree , T. 2001 . Tannins: Classification and definition . Natural Product Reports , 18 : 641 – 649 .
   PubMed Web of Science ®Google Scholar
• Klumpers , J. , Scalbert , A. and Janin , G. 1994 . Ellagitannins in european oak wood: Polymerization during wood aging . Phytochemistry , 36 : 1249 – 1252 .
   Google Scholar
• Larrosa , M. , Tomás-Barberán , F. A. and Espin , J. C. 2006 . The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma caco-2 cells by using the mitochondrial pathway . Journal of Nutritional Biochemistry , 17 ( 9 ) : 611 – 625 .
   PubMed Web of Science ®Google Scholar
• Lee , J. H. and Talcott , S. T. 2002 . Ellagic acid and ellagitannins affect on sedimentation in muscadine juice and wine . Journal of Agricultural and Food Chemistry , 50 : 3971 – 3976 .
   PubMed Web of Science ®Google Scholar
• Lee , J. H. and Talcott , S. T. 2004 . Fruit maturity and juice extraction influences ellagic acid dervivatives and other antioxidant polyphenolics in muscadine grapes . Journal of Agricultural and Food Chemistry , 52 : 361 – 366 .
   PubMed Web of Science ®Google Scholar
• Lee , J. H. , Johnson , J. V. and Talcott , S. T. 2005 . Identification of ellagic acid conjugates and other polyphenolics in muscadine grapes by HPLC-ESI-MS . Journal of Agricultural and Food Chemistry , 53 : 6003 – 6010 .
   PubMed Web of Science ®Google Scholar
• Lei , Z. 2002 . Monomeric ellagitannins in oaks and sweetgum , Doctoral Dissertation Blacksburg, VA : Virginia Polytechnic Institute and State University .
   Google Scholar
• Lei , Z. , Jervis , J. and Helm , R. F. 2001 . Use of methanolysis for the determination of total ellagic and gallic acid contents of wood and food products . Journal of Agricultural and Food Chemistry , 49 : 1165 – 1168 .
   PubMed Web of Science ®Google Scholar
• Lin , C. C. , Hsu , Y. F. , Lin , T. C. and Hsu , H. Y. 2001 . Antioxidant and hepatoprotective effects of punicalagin and punicalin on acetaminophen-induced liver damage in rats . Phytotherapy Research , 15 : 206 – 212 .
   PubMed Web of Science ®Google Scholar
• Lin , T. Y. and Vine , R. P. 1990 . Identification and reduction of ellagic acid in muscadine grape juice . Journal of Food Science , 55 : 1607 – 1609 . 1613
   Google Scholar
• Maas , J. L. , Wang , S. Y. and Galletta , G. J. 1991 . Evaluation of strawberry cultivars for ellagic acid content . HortScience , 26 : 66 – 68 .
   Google Scholar
• Martino , V. , Morales , J. , Martinez-Irujo , J. J. , Font , M. , Monge , A. and Coussio , J. 2004 . Two ellagitannins from the leaves of Terminalia triflora with inhibitory activity on HIV-1 reverse transcriptase . Phytotherapy Research , 18 : 667 – 669 .
   PubMed Web of Science ®Google Scholar
• Masamune , A. , Satoh , M. , Kikuta , K. , Suzuki , N. , Satoh , K. and Shimosegawa , T. 2005 . Ellagic acid blocks activation of pancreatic stellate cells . Biochemical Pharmacology , 70 ( 6 ) : 869 – 878 .
   PubMed Web of Science ®Google Scholar
• Matta-Riihinen , K. R. , Kamal-Elin , A. and Torronen , A. R. 2004 . Identification and quantification of phenolic compounds in berries of Fragaria Rubus species (family rosaceae) . Journal of Agricultural and Food Chemistry , 52 : 6178 – 6187 .
   Google Scholar
• Matĕjĭček , D. , Mikeš , O. , Klejdus , B. , Štĕrbová , D. and Kubáň , V. 2005 . Changes in contents of phenolic compounds during maturing of barrique red wines . Food Chemistry , 90 : 791 – 800 .
   Web of Science ®Google Scholar
• Morton , J. 1987 . “ Longan ” . In Fruits of Warm Climates 259 – 262 . Miami, FL
   Google Scholar
• Mueller-Harvey , I. 2001 . Analysis of hydrolysable tannins . Animal Feed Science and Technology , 91 : 3 – 20 .
   Web of Science ®Google Scholar
• Mullen , W. , McGinn , J. , Lean , M. E. J. , MacLean , M. R. , Gardner , P. , Duthie , G. G. , Yokota , T. and Crozier , A. 2002a . Ellagitannins, flavonoids and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties . Journal of Agricultural and Food Chemistry , 50 : 5191 – 5196 .
   PubMed Web of Science ®Google Scholar
• Mullen , W. , Stewart , A. J. , Lean , M. E. J. , Gardner , P. , Duthie , G. G. and Crozier , A. 2002b . Effect of freezing and storage on the phenolics, ellagitannins, flavonoids and antioxidant capacity of red raspberries . Journal of Agricultural and Food Chemistry , 50 : 5197 – 5201 .
   PubMed Web of Science ®Google Scholar
• Mullen , W. , Yokota , T. , Lean , M. J. E. and Crozier , A. 2003 . Analysis of ellagitannins and conjugates of ellagic acid and quercetin in raspberry fruits by LC-MSn . Phytochemistry , 64 : 617 – 624 .
   PubMed Web of Science ®Google Scholar
• Narayanan , B. A. , Geoffroy , O. , Willingham , M. C. , Re , G. G. and Nixon , D. W. 1999 . p53/p21 (WAF1/CIP1) Expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells . Cancer Letters , 136 : 215 – 221 .
   PubMed Web of Science ®Google Scholar
• Niemetz , R. and Gross , G. G. 2005 . Enzymology of gallotannin and ellagitannin biosynthesis . Phytochemistry , 66 ( 17 ) : 2001 – 2011 .
   Google Scholar
• Nicoli , M. C. , Anese , M. and Parpinel , M. 1999 . Influence of processing on the antioxidant properties of fruit and vegetables . Trends in Food Science and Technology , 10 : 94 – 100 .
   Web of Science ®Google Scholar
• Nonaka , G. I. , Harada , M. and Nishioka , I. 1980 . Eugeniin, a new ellagitannin from cloves . Chemical and Pharmaceutical Bulletin , 28 : 685 – 687 .
   Google Scholar
• Nonaka , G. I. , Nishioka , I. , Nishizawa , M. , Yamagishi , T. , Kashiwada , Y. , Dutschman , G. E. , Bodner , A. J. , Kilkuskie , R. E. , Cheng , Y. and Lee , K. 1990 . Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells . Journal of Natural Products , 53 : 587 – 595 .
   PubMed Web of Science ®Google Scholar
• Nonaka , G. I. , Sakai , R. and Nishioka , I. 1984 . Hydrolysable tannins and proanthocyanidins from green tea . Phytochemistry , 23 ( 8 ) : 1753 – 1755 .
   Google Scholar
• Peng , S. , Scalbert , A. and Monties , B. 1991 . Insoluble ellagitannins in Castanea sativa Quercus petraea woods . Phytochemistry , 30 : 775 – 778 .
   Web of Science ®Google Scholar
• Perez-Vicente , A. , Serrano , P. , Abellán , P. and Garcia-Viguera , C. 2004 . Influence of packaging material on pomegranate juice colour and bioactive compounds, during storage . Journal of The Science of Food and Agriculture , 84 : 639 – 644 .
   Web of Science ®Google Scholar
• Reed , J. D. , Krueger , C. G. and Vestling , M. M. 2005 . MALDI-TOF mass spectrometry of oligomeric food polyphenols . Phytochemistry , 66 : 2248 – 2263 .
   PubMed Web of Science ®Google Scholar
• Rommel , A. and Wrolstad , R. E. 1993 . Ellagic acid content of red raspberry juice as influenced by cultivar, processing and environmental factors . Journal of Agricultural and Food Chemistry , 41 : 1951 – 1960 .
   Google Scholar
• Santos-Buelga , C. and Scalbert , A. 2000 . Proanthocyanidins and tannin-like compounds-nature, occurrence, dietary intake and effects on nutrition and health . Journal of The Science of Food and Agriculture , 80 : 1094 – 1117 .
   Web of Science ®Google Scholar
• Scalbert , A. , Monties , B. and Favre , J. M. 1988 . Polyphenols Quercus robur adult tree and in vitro grown calli and shoots . Phytochemistry , 27 : 3483 – 3488 .
   Web of Science ®Google Scholar
• Scalbert , A. , Monties , B. and Janin , G. 1989 . Tannins in wood: Comparison of different estimation methods . Journal of Agricultural and Food Chemistry , 37 : 1324 – 1329 .
   Web of Science ®Google Scholar
• Seeram , N. P. , Adams , L. S. , Henning , S. M. , Niu , Y. , Zhang , Y. , Nair , M. G. and Heber , D. 2005a . In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice . Journal of Nutritional Biochemistry , 16 : 360 – 367 .
   PubMed Web of Science ®Google Scholar
• Seeram , N. P. , Lee , R. , Hardy , M. and Heber , D. 2005b . Rapid large scale purification of ellagitannins from pomegranate husk, a by-product of the commercial juice industry . Seperation and Purification Technology , 41 : 49 – 55 .
   Web of Science ®Google Scholar
• Seeram , N. P. , Lee , R. , Scheuller , H. S. and Heber , D. 2006 . Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy . Food Chemistry , 97 : 1 – 11 .
   Web of Science ®Google Scholar
• Siriwoharn , T. and Wrolstad , E. R. 2004 . Polyphenolic composition of marion and evergreen blackberries . Journal of Food Science , 69 : 233 – 240 .
   Google Scholar
• Siriwoharn , T. , Wrolstad , E. R. and Durst , R. W. 2005 . Identification of ellagic acid in blacberry juice sediment . Journal of Food Science , 70 : 189 – 197 .
   Web of Science ®Google Scholar
• Soong , Y. Y. and Barlow , P. J. 2005 . 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 : 270 – 277 .
   PubMed Web of Science ®Google Scholar
• Tanaka , T. , Tachibana , H. , Nonaka , G. I. , Nishioka , I. , Hsu , F. L. , Kohda , H. and Tanaka , O. 1993 . Tannins and related compounds. CXXII. New dimeric, trimeric, and tetrameric ellagitannins, lambertianins A-D, from Rubus lambertianius seringue . Chemical and Pharmaceutical Bulletin , 41 : 1214 – 1220 .
   Google Scholar
• Vaillant , F. , Millan , A. , Dornier , M. , Decloux , M. and Reynes , M. 2001 . Stratetegy for economical optimisation of the clarification of pulpy fruit juices using crossflow microfiltration . Journal of Food Engineering , 48 : 83 – 90 .
   Web of Science ®Google Scholar
• Versari , A. , Biesenbruch , S. , Barbanti , D. , Farnell , P. J. and Galassi , S. 1997 . Effects of pectolytic enzymes on selected phenolic compounds in strawberry and raspberry juices . Food Research International , 30 : 811 – 817 .
   Web of Science ®Google Scholar
• Viriot , C. , Sclabert , A. , Herve du Penhoat , C. L. M. and Moutounet , M. 1994 . Ellagitannins in wood of sessile oak and sweet chestnut dimerization and hydrolysis during wood aging . Phytochemistry , 36 : 1253 – 1260 .
   Google Scholar
• Viriot , C. , Sclabert , A. , Lapierre , C. and Moutounet , M. 1993 . Ellagitannins and lignins in aging of spirits in oak barrels . Journal of Agricultural and Food Chemistry , 41 : 1872 – 1879 .
   Google Scholar
• Vivas , N. and Glories , Y. 1996 . Role of oak wood ellagitannins in the oxidation process of red wines during aging . American Journal of Enology and Viticulture , 47 : 103 – 107 .
   Web of Science ®Google Scholar
• Williner , M. R. , Pirovani , M. E. and Guemes , D. R. 2003 . Ellagic acid content in strawberries of different cultivars and ripening stages . Journal of The Science of Food and Agriculture , 83 : 842 – 845 .
   Google Scholar
• Yu , Y. M. , Chang , W. C. , Wu , C. H. and Chiang , S. Y. 2005 . Reduction of oxidative stress and apoptosis in hyperlipidemic rabbits by ellagic acid . Journal of Nutritional Biochemistry , 16 : 675 – 681 .
   PubMed Web of Science ®Google Scholar
• Zafrilla , P. , Ferreres , F. and Barberán-Tomás , F. A. 2001 . Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams . Journal of Agricultural and Food Chemistry , 49 : 3651 – 3655 .
   PubMed Web of Science ®Google Scholar