Ellagitannin
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The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.[1]
Ellagitannins contain various numbers of hexahydroxydiphenoyl units, as well as galloyl units and/or sanguisorboyl units bounded to sugar moiety. In order to determine the quantity of every individual unit, the hydrolysis of the extracts with trifluoroacetic acid in methanol/water system is performed. Hexahydroxydiphenic acid, created after hydrolysis, spontaneously lactonized to ellagic acid, and sanguisorbic acid to sanguisorbic acid dilactone, while gallic acid remains intact.[2]
Ellagitannins generally form macrocycles, whereas gallotannins do not.
Contents
1 Examples
2 Metabolism
2.1 Degradation
3 Natural occurrences
4 See also
5 References
6 Further reading
7 External links
Examples
- Castalagin
- Castalin
- Casuarictin
- Grandinin
- Roburin A
- Tellimagrandin II
- Terflavin B
- Vescalagin
Pomegranate ellagitannins, many compounds
- Punicalagin
- Punicalin
Metabolism
Degradation
Urolithins, such as urolithin A, are microflora human metabolites of dietary ellagic acid derivatives.[3]
Natural occurrences
Ellagitannins are reported in dicotyledoneous angiospermes, and notably in species in the order Myrtales, such as the pomegranate.[4][5]
See also
Urolithin - Urolithin A
- Polyphenols
- List of antioxidants in food
References
^ MALDI-TOF Mass Spectrometric Analysis of Hydrolysable Tannins
^ Structural diversity and antimicrobial activities of ellagitannins. T. Yoshida, Ts. Hatano, H. Ito, T. Okuda, S. Quideau (Ed.), Chemistry and Biology of Ellagitannins, World Scientific Publishing, Singapore (2009), pages 55–93
^ Davis CD, Milner JA. Gastrointestinal microflora, food components and colon cancer prevention. J Nutr Biochem. 2009 Oct;20(10):743-52. doi: 10.1016/j.jnutbio.2009.06.001. .mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
PMID 19716282
^ Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales. Takashi Yoshida *, Yoshiaki Amakura and Morio Yoshimura, Int. J. Mol. Sci., 2010, 11, pages 79-106, doi:10.3390/ijms11010079
^ Gómez-Caravaca, A. M.; Verardo, V; Toselli, M; Segura-Carretero, A; Fernández-Gutiérrez, A; Caboni, M. F. (2013). "Determination of the major phenolic compounds in pomegranate juices by HPLC−DAD−ESI-MS". Journal of Agricultural and Food Chemistry. 61 (22): 5328–37. doi:10.1021/jf400684n. PMID 23656584.
Further reading
- Quideau, Stéphane (editor). Chemistry and Biology of Ellagitannins: An Underestimated Class of Bioactive Plant Polyphenols, 2009, World Scientific Publishing. Table of Contents. Preface. Chapter 1.
External links
Tannin Chemistry (Tannin Handbook, Copyright 1998, 2002, 2011, Ann E. Hagerman)
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