Ellagitannins

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Punicalagin , an ellagitannin from the pomegranate
Casuarictin, an ellagitannin from Casuarina stricta

Ellagitannins (also ellagitannins ) are a group of polyphenols and tannins from plants . The constituent ellagic acid was named by Henri Braconnot based on gallic acid , which occurs frequently in plant galls, by reversing the word bile .

properties

Ellagitannins are formed by the oxidative linkage of gallic acids in 1,2,3,4,6-pentagallylglucose . The gallic acids form CC bonds with one another, in contrast to the gallotannins , in which the bond between the gallic acids is depsidic . Another contrast to gallotannins are the macrocycles in ellagitannins, which contain hexahydroxydiphenyl groups , gallyl groups, or sanguisorbyl groups.

Biodegradation of the ellagitannins

The ellagitannins are biosynthesized via 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose by a laccase- like phenol oxidase to tellimagrandin II , followed by further oxidation by another phenol oxidase to cornusiin E ( a dimeric ellagitannin). Ellagitannins are broken down into urolithines by the human intestinal flora .

Examples

More than 1000 ellagitannins have been described. Examples of ellagitannins are Castalagin , Castalin , Casuarictin , Casuarinin , Castanopsinine A to H, Excoecarianin , Grandinin , Pterocarinine A and B, Rhoipteleanine A to G, Roburin A , Tellimagrandin II , Terflavin B , punicalagin , Punicalin , Punigluconin , Alnusiin , Alnusnin A , Alnusnin B , Cercidinin A , Cercidinin B , Chebulagic Acid , Chebulinic Acid , Corilagin , Geraniine , Isoterchebine , Nobotanine B, C, E, G, H, I, J, and K, Roxbin B , Sanguiine H-2, H-3 and H-6, Stachyurin , Terchebin , vascalagin and vescalin . They are mainly used in dicotyledonous angiosperms before, as in Myrtales , which include the pomegranate counts.

analysis

Ellagitannins can be separated by chromatography . For analysis, the ester bonds are hydrolyzed with trifluoroacetic acid in aqueous methanol . The ester bonds can also be cleaved by ellagitannin acyl hydrolase (synonym ellagitannase ). The hexahydroxydiphenylic acid released in this way forms the lactone ellagic acid and the released sanguisorbic acid the dilactone sanguisorbic acid dilactone , while gallic acid is retained.

use

Ellagitannins have anti-inflammatory effects and are being studied for neuroprotection , the prevention of infectious diseases , cancer , inflammatory bowel diseases and cardiovascular diseases .

The ellagitannins Castalagin and vascalagin from the English oak (Ellagitanninmassenanteil 4.84%) and the Traubeneiche (Ellagitanninmassenanteil 3.44%) diffuse in the production of wine in the barrel extension from the wood of the barrel in the wine and belong to the phenols in the wine . The ellagitannins inhibit malolactic fermentation in wine . With the oxidation of the ellagitannins, the astringency decreases.

literature

  • KS Feldman, MR Iyer, Y. Liu: Ellagitannin chemistry. Studies on the stability and reactivity of 2,4-HHDP-containing glucopyranose systems. In: The Journal of organic chemistry. Volume 68, Number 19, September 2003, pp. 7433-7438, doi : 10.1021 / jo034495x , PMID 12968897 .

Individual evidence

  1. ^ R. Niemetz, GG Gross: Enzymology of gallotannin and ellagitannin biosynthesis. In: Phytochemistry. Volume 66, Number 17, September 2005, pp. 2001-2011, doi : 10.1016 / j.phytochem.2005.01.009 , PMID 16153405 .
  2. ^ CD Davis, JA Milner: Gastrointestinal microflora, food components and colon cancer prevention. In: The Journal of nutritional biochemistry. Volume 20, number 10, October 2009, pp. 743-752, doi : 10.1016 / j.jnutbio.2009.06.001 , PMID 19716282 , PMC 2743755 (free full text).
  3. ^ C. Garcia-Muñoz, F. Vaillant: Metabolic fate of ellagitannins: implications for health, and research perspectives for innovative functional foods. In: Critical reviews in food science and nutrition. Volume 54, number 12, 2014, pp. 1584–1598, doi : 10.1080 / 10408398.2011.644643 , PMID 24580560 .
  4. ↑ a b c d e f g h i j k l m n o p q r s t u v w x H. Yamada, S. Wakamori, T. Hirokane, K. Ikeuchi, S. Matsumoto: Structural Revisions in Natural Ellagitannins . In: Molecules. Volume 23, number 8, July 2018, p., Doi : 10.3390 / molecules23081901 , PMID 30061530 , PMC 6222896 (free full text).
  5. ↑ M. Ageta, G.-I. Nonaka, I. Nishioka: Tannins and related compounds. LXVII: Isolation and characterization of castanopsinins AH, novel ellagitannins containing a triterpenoid glycoside core, from castanopsis cuspidata var. Sieboldii NAKAI . In: Chemical and pharmaceutical bulletin, Tokyo (Japan) , JAACC, Volume 36, Number 5, 1988, pp. 1646-1663.
  6. ↑ Lin Jer-huei, T. Tanaka, G.-I. Nonaka, I. Nishioka, Chen Ih-sheng: Tannins and related compounds: XCVIII, Structures of three new dimeric ellagitannins, excoecarianin and excoecarinins A and B, isolated from the leaves of Excoecaria kawakamii Hayata . In: Chemical and pharmaceutical bulletin , JAACC, Volume 38, Number 8, 1990, pp. 2162-2171.
  7. ↑ G. Nonaka, K. Ishimaru, R. Azuma, M. Ishimatsu, I. Nishioka: Tannins and related compounds. LXXXV: Structures of novel C-glycosidic ellagitannins, grandinin and pterocarinins A and B . In: Chemical and pharmaceutical bulletin , JAACC, Volume 37, Number 8, 1989, pp. 2071-2077.
  8. ↑ T. Tanaka, Z.-H. Jiang, I. Kouno: Structures and biogenesis of rhoipteleanins, ellagitannins formed by stereospecific intermolecular CC oxidative coupling, isolated from Rhoiptelea chiliantha . In: Chemical and pharmaceutical bulletin , JAACC, Volume 45, Number 12, 1997, pp. 1915-1921.
  9. ↑ Takashi Yoshida, Yoshiaki Amakura, Morio Yoshimura: Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales. In: International Journal of Molecular Sciences. 11, 2010, p. 79, doi : 10.3390 / ijms11010079 .
  10. ↑ AM Gómez-Caravaca, V. Verardo, M. Toselli, A. Segura-Carretero, A. Fernández-Gutiérrez, MF Caboni: Determination of the major phenolic compounds in pomegranate juices by HPLC-DAD-ESI-MS. In: Journal of agricultural and food chemistry. Volume 61, Number 22, June 2013, pp. 5328-5337, doi : 10.1021 / jf400684n , PMID 23656584 .
  11. ↑ a b P. Aguilar-Zarate, JE Wong-Paz, JJ Buenrostro-Figueroa, JA Ascacio, JC Contreras-Esquivel, CN Aguilar: Ellagitannins: Bioavailability, Purification and Biotechnological Degradation. In: Mini reviews in medicinal chemistry. Volume 18, Number 15, 2018, pp. 1244–1252, doi : 10.2174 / 1389557517666170208144742 , PMID 28183264 .
  12. ↑ T. Yoshida, Ts. Hatano, H. Ito, T. Okuda, S. Quideau: Structural diversity and antimicrobial activities of ellagitannins. In: Chemistry and Biology of Ellagitannins , World Scientific Publishing, 2009, pp. 55-93.
  13. ^ S. Tejada, WN Setzer, M. Daglia, SF Nabavi, A. Sureda, N. Braidy, O. Gortzi, SM Nabavi: Neuroprotective Effects of Ellagitannins: A Brief Review. In: Current drug targets. Volume 18, number 13, 2017, pp. 1518-1528, doi : 10.2174 / 1389450117666161005112002 , PMID 27719661 .
  14. ^ A b L. Lipińska, E. Klewicka, M. Sójka: The structure, occurrence and biological activity of ellagitannins: a general review. In: Acta scientiarum polonorum. Technologia alimentaria. Volume 13, Number 3, 2014 Jul-Sep, pp. 289-299, PMID 24887944 .
  15. ^ A b A. K. Kiss, JP Piwowarski: Ellagitannins, Gallotannins and their Metabolites- The Contribution to the Anti-Inflammatory Effect of Food Products and Medicinal Plants. In: Current medicinal chemistry. Volume 25, number 37, 2018, pp. 4946-4967, doi : 10.2174 / 0929867323666160919111559 , PMID 27655073 .
  16. ^ A b Jean-Louis Puech, Andrei Prida, Jean-Claude Boulet, Bacchus in Bourgogne: Second Interdisciplinary and International Wine Conference - 3rd - 4th - 5th November 2005. Effet de l'espèce et de la forêt ou "terroir" sur la teneur en ellagitanins du bois de chêne à merrain dans une forêt mixedte (Quercus robur L., Quercus petraea Liebl). P. 49.
  17. ↑ Augustin Scalbert, Catherine Lapierre: Ellagitanins et lignines du cœur de chêne: Structure et évolution au cours du bois du vieillissement . In: Revue des Œnologues , 1994, Volume 71, pp. 9-12.
  18. ^ A b Nicolas Vivas, Marie Francoise Nonier, Nathalie Vivas de Gaulejac: Caractérisation et rôle des ellagitanins du bois de chêne dans l'élevage des vins rouges: Interaction avec les bactéries. In: Bulletin de l'OIV , Office international de la vigne et du vin, 2006, Volume 79, Numbers 901-903, pp. 141-161.