Structure, occurrence and biological activity of ellagitannins: A general review

Acta Scientiarum Polonorum, Technologia Alimentaria

Volumn 13, Issue 3, 2014, Pages 289-299

  Lipińska, Lidia ^a   Klewicka, Elzbieta ^a   Sójka, Michał ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Biological activity; Ellagitannins; Hydrolysable tannins

Indexed keywords

BACTERIA; BIOCHEMISTRY; BLOOD VESSELS; CELL CULTURE; ELLAGIC ACID; FLAVONOIDS; FRUITS; GLUCOSE; HYDROLYSIS; METABOLISM; MICROORGANISMS; PHYSIOLOGY; TANNINS; VIRUSES;

ANTI-MICROBIAL ACTIVITY; ANTITUMOR PROPERTY; CANCER CELL LINES; ELLAGITANNINS; GASTROINTESTINAL TRACT; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; PHYSICAL AND CHEMICAL PROPERTIES; RESISTANT STRAINS;

BIOACTIVITY;

ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; ELLAGIC ACID; POLYPHENOL; TANNIN;

CHEMISTRY; FRUIT; GASTROINTESTINAL TRACT; HUMAN; METABOLISM; NUT;

ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; ELLAGIC ACID; FRUIT; GASTROINTESTINAL TRACT; HUMANS; HYDROLYZABLE TANNINS; NUTS; POLYPHENOLS;

EID: 84901848129     PISSN: 16440730     EISSN: 18989594     Source Type: Journal    
DOI: 10.17306/J.AFS.2014.3.7     Document Type: Article

References (75)

1. Aaby K., Wrolstad R.E., Ekeberg D., Skrede G., 2007. Polyphenol composition and antioxidant activity in strawberry purees, impact of achen e level and storage. J. Agric. Food Chem. 55, 13, 5156-5166.
2. Aqil F., Gupta A., Munagala R., Jeyabalan J., Kausar H., Sharma R.J., Gupta R.C., 2012. Antioxidant and antiproliferative activities of anthocyanin/ellagitannin-enriched extracts from Syzygium cumini L. (Jamun, the Indian Blackberry). Nutr. Cancer 64, 428-438.
3. Anderson K.J., Teuber S.S., Gobeille A., Cremin P., Waterhouse A.L., Steinberg F.M., 2001. Walnut polyphenolics inhibit in vitro human plasma and LDL oxidation. J. Nutr. 131, 11, 2837-2842.
4. Ascacio-Valdés J., Burboa E., Aguilera-Carbo A.F., Aparicio M., Pérez-Schmidt R., Rodríguez R., Aguilar C.N., 2013. Antifungal ellagitannin isolated from Euphorbia antisyphilitica Zucc. Asian Pac. J. Trop. Biomed. 3, 1, 41-46.
5. Beretta G., Rossoni G., Santagati N.A., Facino R.M., 2009. Anti-ischemic activity and endothelium-dependent vasorelaxant effect of hydrolysable tannins from the leaves of Rhus coriaria (Sumac) in isolated rabbit heart and thoracic aorta. Planta Med. 5, 14, 1482-1488.
6. Blomhoff R., Carlsen M.H., Andersen L.F., Jacobs D.R., 2006. Health benefits of nuts: potential role of antioxidants. Br. J. Nutr. 96, 1, 52-60.
7. Carlton P.S., Kresty L.A., Siglin J.C., Morse M.A., Lu J., Morgan C., Stoner G.D., 2001. Inhibition of N-nitrosomethylbenzylamine-induced tumorigenesis in the rat esophagus by dietary freeze-dried strawberries. Carcinogenesis 22, 3, 441-446.
8. Cerdá B., Espin J.C., Parra S., Martínez P., Tomás-Barberán F.A., 2004. The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. Eur. J. Nutr. 43, 4, 205-220.
9. Cerdá B., Soto C., Albaladejo M.D., Martinez P., Sanchez--Gasco F., Tomás-Barberán F., Espin J.C., 2006. Pomegranate juice supplementation in chronic obstructive pulmonary disease: a 5-week randomized, doubleblind, placebo-controlled trial. Eur. J. Clin. Nutr. 60, 2, 245-253.
10. Chemistry and biology of ellagitannins: an underestimated class of bioactive plant polyphenols. 2009. Ed. S. Quideau. World Scientific Singapore.
11. Clifford M.N., Scalbert A., 2000. Ellagitannins-nature, occurrence and dietary burden. J. Sci. Food Agric. 80, 7, 1118-1125.
12. Crescente M., Jessen G., Momi S., Höltje H.D., Gresele P., Cerletti C., de Gaetano G., 2009. Interactions of gallic acid, resveratrol, quercetin and aspirin at the platelet cyclooxygenase-1 level. Functional and modelling studies. J. Thromb. Haemost. 102, 2, 336-346.
13. De Lange D.W., Verhoef S., Gorter G., Kraaijenhagen R.J., Van De Wiel A., Akkerman J.W.N., 2007. Polyphenolic grape extract inhibits platelet activation through PECAM-1: An explanation for the French paradox. Alcoholism:Clin. Exp. Res. 31, 8, 1308-1314.
14. Erdman J.W., Balentine D., Arab L., Beecher G., Dwyer J.T., Folts J., Burrowes J., 2007. Flavonoids and heart health: Proceedings of the ILSI North America flavonoids worksh. May 31-June 1, 2005. Washington D.C. J. Nutr. 137, 3, 718-737.
15. Espin J.C., Larrosa M., García-Conesa M.T., Tomás-Barberán F., 2013. Biological significance of urolithins, the gut microbial ellagic acid-derived metabolites: The evidence so far. Evid.-Based Compl. Alternat. Med. 2013, ID 270418
16. Funatogawa K., Hayashi S., Shimomura H., Yoshida T., Hatano T., Ito H., Hirai Y., 2004. Antibacterial activity of hydrolyzable tannins derived from medicinal plants against Helicobacter pylori. Microbiol. Immunol. 48, 4, 251-261.
17. Gil M.I., Tomás-Barberán F.A., Hess-Pierce B., Holcroft D.M., Kader A.A., 2000. Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing. J. Agric. Food Chem. 48, 10, 4581-4589.
18. Glabasnia A., Hofmann T., 2006. Sensory-directed identifi-cation 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. J. Agric. Food Chem. 54, 9, 3380-3390.
19. Goncalves B., Borges O., Costa H.S., Bennett R., Santos M., Silva A.P., 2010. Metabolite composition of chestnut (Castanea sativa Mill.) upon cooking: Proximate analysis, fibre, organic acids and phenolics. Food Chem. 122, 1, 154-160.
20. González-Sarrías A., Giménez-Bastida J.A., Núñez-Sánchez M.Á., Larrosa M., García-Conesa M.T., Tomás-Barberán F.A., Espín J.C., 2013 a. Phase-II metabolism limits the antiproliferative activity of urolithins in human colon cancer cells. Eur. J. Nutr. 29, 1-12.
21. González-Sarrías A., Miguel V., Merino G., Lucas R., Morales J.C., Tomás-Barberán F., Espín J.C., 2013 b. The gut microbiota ellagic acid-derived metabolite Urolithin A and its sulfate conjugate are substrates for the drug efflux transporter breast cancer resistance protein (ABCG2/BCRP). J. Agric. Food Chem. 61, 18, 4352-4359.
22. Grajek W., 2007. Przeciwutleniacze w żywności. Aspekty zdrowotne, technologiczne, molekularne i analityczne [Antioxidants in food. Health, technology, molecular and analytical aspects]. WN-T Warszawa.
23. Grundhöfer P., Niemetz R., Schilling G., Gross G.G., 2001. Biosynthesis and subcellular distribution of hydrolyzable tannins. Phytochemistry 57, 6, 915-927.
24. Grywalska E., Markowicz J., Grabarczyk P., Pasiarski M., Roliński J., 2013. Epstein-Barr virus-associated lymphoproliferative disorders. Post. Hig. Med. Dośw. 67, 481-490.
25. Hannum S.M., 2004. Potential impact of strawberries on human health: a review of the science. Crit. Rev. Food Sci. Nutr. 44, 1, 1-17.
26. Haslam E., 2009. Preface. In: Chemistry and biology of ellagitannins: an underestimated class of bioactive plant polyphenols. Ed. S. Quideau. World Scientific Singapore.
27. Hatano T., Kusuda M., Inada K., Ogawa T.O., Shiota S., Tsuchiya T., Yoshida T., 2005. Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus. Phytochemistry 66, 17, 2047-2055.
28. Hatano T., Tsugawa M., Kusuda M., Taniguchi S., Yoshida T., Shiota S., Tsuchiya T., 2008. Enhancement of antibacterial effects of epigallocatechin gallate, using ascorbic acid. Phytochemistry 69, 18, 3111-3116.
29. Heber D., 2008. Multitargeted therapy of cancer by ellagitannins. Cancer Lett. 269, 2, 262-268.
30. Hukkanen A., Kostamo K., Kärenlampi S., Kokko H., 2008. Impact of agrochemicals on Peronospora sparsa and phenolic profiles in three Rubus arcticus cultivars. J. Agric. Food Chem. 56, 3, 1008-1016.
31. Jeon K.S., Na H.J., Kim Y.M., Kwon H.J., 2005. Antiangiogenic activity of 4-O-methylgallic acid from Canavalia gladiata, a dietary legume. Biochem. Biophys. Res. Commun. 330, 4, 1268-1274.
32. Kaneto H., Katakami N., Matsuhisa M., Matsuoka T.A., 2010. Role of reactive oxygen species in the progression of type 2 diabetes and atherosclerosis. Mediators Inflamm. 2010, DOI 10.1155/2010/453892.
33. Kaplan M., Hayek T., Raz A., Coleman R., Dornfeld L., Vaya J., Aviram M., 2001. Pomegranate juice supplementation to atherosclerotic mice reduces macrophage lipid peroxidation, cellular cholesterol accumulation and development of atherosclerosis. J. Nutr. 131, 8, 2082-2089.
34. Khateeb J., Gantman A., Kreitenberg A.J., Aviram M., Fuhrman B., 2010. Paraoxonase 1 (PON1) expression in hepatocytes is upregulated by pomegranate polyphenols:a role for PPAR-γ pathway. Atherosclerosis 208, 1, 119-125.
35. Kim S.K., Kim H., Kim S.A., Park H.K., Kim W., 2013. Anti-inflammatory and anti-superbacterial activity of polyphenols isolated from black raspberry. Korean J. Phys. Pharm. 17, 1, 73-79.
36. Klimczak E., Król B., 2010. Oznaczanie zawartości różnych form kwasu elagowego w ubocznych produktach przerobu truskawek [Macro-and microelements in determination of different forms of ellagic acid in by-products from strawberry processing]. Żywn. Nauka Techn. Jakość 17, 4, 81-94 [in Polish].
37. Kołodziej H., Kayser O., Latté K.P., Kiderlen A.F., 2000. Enhancement of antimicrobial activity of tannins and related compounds by immune modulatory effects. Plant Polyphen. 2, 575-594.
38. Koponen J.M., Happonen A.M. Mattila P.H., Törrönen A.R., 2007. Contents of anthocyanins and ellagitannins in selected foods consumed in Finland. J. Agric. Food Chem. 55, 4, 1612-1619.
39. Kresty L.A., Morse M.A., Morgan C., Carlton P.S., Lu J., Gupta A., Stoner G.D., 2001. Chemoprevention of esophageal tumorigenesis by dietary administration of lyophilized black raspberries. Cancer Res. 61, 16, 6112-6119.
40. Larrosa M., Tomás-Barberán F.A., Espín 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. J. Nutr. Biochem. 17, 9, 611-625.
41. Larrosa M., García-Conesa M.T., Espín J.C., Tomás-Barberán F.A., 2010. Ellagitannins, ellagic acid and vascular health. Mol. Aspects Med. 31, 6, 513-539.
42. Lee J.H., Talcott S.T., 2002. Ellagic acid and ellagitannins affect on sedimentation in muscadine juice and wine. J. Agric. Food Chem. 50, 14, 3971-3976.
43. Lee S.J., Lee H.K., 2005. Sanguiin H-6 blocks endothelial cell growth through inhibition of VEGF binding to VEGF receptor. Arch. Pharm. Res. 28, 11, 1270-1274.
44. Lee G., Na H.J., Namkoong S., Jeong Kwon H., Han S., Ha K.S., Kim Y.M., 2006. 4-O-methylgallic acid downregulates endothelial adhesion molecule expression by inhibiting NF-κB-DNA-binding activity. Eur. J. Pharmacol. 551, 1, 143-151.
45. Malik N.S., Perez J.L., Lombardini L., Cornacchia R., Cisneros-Zevallos L., Braford J., 2009. Phenolic compounds and fatty acid composition of organic and conventional grown pecan kernels. J. Sci. Food Agric. 89, 13, 2207-2213.
46. Matthay M.A., Ware L.B., Zimmerman G.A., 2012. The acute respiratory distress syndrome. J. Clin. Invest. 122, 8, 2731-2740.
47. Mattiello T., Trifirò E., Jotti G.S., Pulcinelli F.M., 2009. Effects of pomegranate juice and extract polyphenols on platelet function. J. Med. Food 12, 2, 334-339.
48. Na H.J., Lee G., Oh H.Y., Jeon K.S., Kwon H.J., Ha K.S., Kim Y.M., 2006. 4-O-Methylgallic acid suppresses inflammation-associated gene expression by inhibition of redox-based NF-κB activation. Int. Immunopharm. 6, 10, 1597-1608.
49. Ngoumfo R.M., Ngounou G.E., Tchamadeu C.V., Qadir M.I., Mbazoa C.D., Begum A., Choudhary M.I., 2008. Inhibitory effect of macabarterin, a polyoxygenated ellagitannin from Macaranga barteri, on human neutrophil respiratory burst activity. J. Nat. Prod. 71, 11, 1906-1910.
50. Oak M.H., Bedoui J.E., Madeira S.F., Chalupsky K., Schini-Kerth V.B., 2006. Delphinidin and cyanidin inhibit PDGFAB-induced VEGF release in vascular smooth muscle cells by preventing activation of p38 MAPK and JNK. Br. J. Pharmacol. 149, 3, 283-290.
51. Okuda T., Yoshida T., Hatano T., Ito H., 2009. Ellagitannins renewed the concept of tannins. Chemistry and biology of ellagitannins. In: Chemistry and biology of ellagitannins:an underestimated class of bioactive plant polyphenols. Ed. S. Quideau. World Scientific Singapore, 1-54.
52. Rogerio P.A., 2013. Anti-inflammatory effects of ellagic acid on acute lung injury induced by acid in mice. Mediators Inflamm. 2013. DOI 10.1155/2013/164202.
53. Sakagami H., Jiang Y., Kusama K., Atsumi T., Ueha T., Toguchi M., Yoshida T., 2000. Cytotoxic activity of hydrolyzable tannins against human oral tumor cell lines-a possible mechanism. Phytomedicine 7, 1, 39-47.
54. Salminen J. P., Ossipov V., Haukioja E., Pihlaja K., 2001. Seasonal variation in the content of hydrolysable tannins in leaves of Betula pubescens. Phytochemistry 57, 1, 15-22.
55. Sangiovanni E., Vrhovsek U., Rossoni G., Colombo E., Brunelli C., Brembati L., Dell'Agli M., 2013. Ellagitannins from Rubus berries for the control of gastric inflammation: in vitro and in vivo studies. PloS ONE 8, 8, e71762.
56. Scalbert A., Manach C., Morand C., Rémésy C., Jiménez L., 2005. Dietary polyphenols and the prevention of diseases. Crit. Rev. Food Sci. Nutr. 45, 4, 287-306.
57. Seeram N.P., Lee R., Heber D., 2004. Bioavailability of ellagic acid in human plasma after consumption of ellagitannins from pomegranate (Punica granatum L.) juice. Clin. Chim. Acta 348, 1, 63-68.
58. Seeram N.P., Lee R., Scheuller H.S., Heber D., 2006. Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy. Food Chem. 97, 1, 1-11.
59. Shiota S., Shimizu M., Sugiyama J.I., Morita Y., Mizushima T., Tsuchiya T., 2004. Mechanisms of action of corilagin and tellimagrandin I that remarkably potentiate the activity of beta-lactams against methicillin-resistant Staphylococcus aureus. Microbiol. Immunol. 48, 1, 67.
60. Silva Pinto M., Lajolo F.M., Genovese M.I., 2008. Bioactive compounds and quantification of total ellagic acid in strawberries (Fragaria × ananassa Duch.). Food Chem. 107, 4, 1629-1635.
61. Stoner G.D., Kresty L.A., Carlton P.S., Siglin J.C., Morse M.A., 1999. Isothiocyanates and freeze-dried strawberries as inhibitors of esophageal cancer. Toxicol. Sci. 52, 95-100.
62. Taguri T., Tanaka T., Kouno I., 2006. Antibacterial spectrum of plant polyphenols and extracts depending upon hydroxyphenyl structure. Biol. Pharm. Bull. 29, 11, 2226-2235.
63. Teng C.M., Kang Y.F., Chang Y.L., Ko F.N., Yang S.C., Hsu F.L., 1997. ADP-mimicking platelet aggregation caused by rugosin E, an ellagitannin isolated from Rosa rugosa Thunb. Thromb. Haemost. 77, 3, 555-561.
64. Tomas-Barberan F.A., Espín J.C., García-Conesa M.T., 2009. Bioavailability and metabolism of ellagic acid and ellagitannins. In: Chemistry and biology of ellagitannins:an underestimated class of bioactive plant polyphenols. Ed. S. Quideau. World Scientific Singapore 293-297.
65. Tomas-Barberan F.A., Seeram N.P., Espin J.C., 2006. Bioavailability of pomegranate polyphenols. In: Ancient roots to modern medicine. Eds N.P. Seeram, R.N. Schulman, D. Heber. CRC Boca Raton, USA, 3, 45-60.
66. Törrönen R., 2009. Sources and health Effects of dietary ellagitannins. In: Chemistry and biology of ellagitannins:an underestimated class of bioactive plant polyphenols. Ed. S. Quideau. World Scientific Singapore, 298-319.
67. Umar A., Boisseau M., Segur M.C., Begaud B., Moore N., 2003. Effect of age of Armagnac extract and duration of treatment on antithrombotic effects in a rat thrombosis model. Thromb. Res. 111, 3, 185-189.
68. Villarreal-Lozoya J.E., Lombardini L., Cisneros-Zevallos L., 2007. Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis Wangenh. K. Koch cultivars. Food Chem. 102, 4, 1241-1249.
69. Wang L.S., Hecht S., Carmella S., Seguin C., Rocha C., Yu N., Stoner G., 2010. Berry ellagitannins may not be sufficient for prevention of tumors in the rodent esophagus. J. Agric. Food Chem. 58, 7, 3992-3995.
70. Wang Y., Ma J., Chow S.C., Li C.H., Xiao Z., Feng R., Chen Y., 2014. A potential antitumor ellagitannin, davidiin, inhibited hepatocellular tumor growth by targeting EZH2. Tumour Biol. 35, 205-212.
71. Whitley A.C., Stoner G.D., Darby M.V., Walle T., 2003. Intestinal epithelial cell accumulation of the cancer preventive polyphenol ellagic acid-extensive binding to protein and DNA. Biochem. Pharmacol. 66, 6, 907-915.
72. Xiang L., Xing D., Lei F., Wang W., Xu L., Nie L., Du L., 2008. Effects of season, variety, and processing method on ellagic acid content in pomegranate leaves. Tsinghua Sci. Techn. 13, 4, 460-465.
73. Yamaguchi M.U., Garcia F.P., Cortez D.A.G., Ueda-Nakamura T., Dias Filho B.P., Nakamura C.V., 2011. Antifungal effects of ellagitannin isolated from leaves of Ocotea odorifera (Lauraceae). Anton. Leeuw. 99, 3, 507-514.
74. Yoshida T., Hatano T., Ito H., Okuda T., 2009. Structural diversity and antimicrobial activities of ellagitannins. In: Chemistry and biology of ellagitannins: an underestimated class of bioactive plant polyphenols. Ed. S. Quideau. World Scientific Singapore, 55-93.
75. Zafrilla P., Ferreres F., Tomás-Barberán F.A., 2001. Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams. J. Agric. Food Chem. 49, 8, 3651-3655.