Castalagin

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Castalagin
Castalagin.svg
Castalagin 3d structure.png
Names
Other names
Vescalagin (treatment)
Identifiers
3D model (JSmol)
ChEMBL
PubChem CID
UNII
  • InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11?,31-,34?,35?,36?/m1/s1 [1]
    Key: UDYKDZHZAKSYCO-LSSWMSPRSA-N
  • C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
Properties
C41H26O26
Molar mass 934.63 g/mol
Appearanceoff-white amorphous powder [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood [3] and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides . [4]

Contents

Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic chain. [5] Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in oak barrels. [6] During aging of wines, these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions. [7] Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels. [5]

Sources

Castalagin was first isolated in Fagaceae family woody species : Quercus (oak) and Castanea (chestnut) by Walter Mayer and co-workers (1967). [8] In some chestnut species, such as Castanea sativa , heartwood could contain 63 mg of castalagin/ vescalagin per gram of dry wood. [9] In some wines, these two isomers represent about 40 to 70% of total ellagitannins. [10]

Castalagin was isolated in Myrciaria dubia , a polyphenol from the Amazonian fruit camu-camu. [11]

Biosynthesis

In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, vescalagin and vescalin forms. [12]

Castalagin thus forms from a pentagalloyl-glucose structure. Castalagin and vescalagin (1,2,3,5-nonahydroxytriphenoyl-4,6-hexahydroxydiphenoyl-glucoses) can be further polymerized in their corresponding dimers roburin A [13] and roburin D, and 33-carboxy-33-deoxyvescalagin. [14]

Derivatives

Castalagin and other related ellagitanins polymerizes or forms complexes with anthyocyanins and flavonoids. The flavono-ellagitannin known as acutissimin A is created when the oak tannin vescalagin interacts with catechin a flavan-3-ol found in wine. [15] Grandinin is a castalagin glycoside [16] which forms by binding to the pentose lyxose. [17] Chemical hydrolysis of Castalagin/ Vescalagin produces vescalene and vescalin which are potent topoisomerase II inhibitors. [18]

Related Research Articles

<span class="mw-page-title-main">Ellagic acid</span> Natural phenol antioxidant

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

<i>Tellima</i> Genus of flowering plants in the family Saxifragaceae

Tellima grandiflora, the bigflower tellima or fringecups, is a herbaceous perennial flowering plant in the family Saxifragaceae. It is the only species in the genus Tellima.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

A gallotannin is any of a class of molecules belonging to the hydrolysable tannins. Gallotannins are polymers formed when gallic acid, a polyphenol monomer, esterifies and binds with the hydroxyl group of a polyol carbohydrate such as glucose.

A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.

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.

<span class="mw-page-title-main">Grandinin</span> Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

<span class="mw-page-title-main">Tellimagrandin II</span> Chemical compound

Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum (clove).

<span class="mw-page-title-main">Roburin A</span> Chemical compound

Roburin A is a tannin found in oak wood or oak cork.

<span class="mw-page-title-main">Acutissimin A</span> Chemical compound

Acutissimin A is a flavono-ellagitannin, a type of tannin formed from the linking of a flavonoid with an ellagitannin.

<span class="mw-page-title-main">Condensed tannin</span> Polymers formed by the condensation of flavans.

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

<span class="mw-page-title-main">5-Deoxyinositol</span> Chemical compound

5-Deoxyinositol (quercitol) is a cyclitol. It can be found in wines aged in oak wood barrels. It can also be found in Quercus sp. (oaks) and in Gymnema sylvestre. It is different from quercetol, a synonym of quercetin.

<span class="mw-page-title-main">1,2,3,4,6-Pentagalloyl glucose</span> Chemical compound

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

<span class="mw-page-title-main">Pomegranate ellagitannin</span> Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of the pomegranate fruit.

<span class="mw-page-title-main">Casuarinin</span> Chemical compound

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana.

<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

<span class="mw-page-title-main">Sanguiin H-6</span> Chemical compound

Sanguiin H-6 is an ellagitannin.

<span class="mw-page-title-main">Nonahydroxytriphenic acid</span> Chemical compound

Nonahydroxytriphenic acid is a moiety found in some ellagitannins such as roburin A, B,C and D, castalagin or grandinin.

<span class="mw-page-title-main">Urolithin B</span> Chemical compound

Urolithin B (UB) is an urolithin, a type of phenolic compounds produced in the human gut after absorption of ellagitannins-containing food such as pomegranate, strawberries, red raspberries, walnuts or oak-aged red wine. Urolithin B is found in the urine in the form of urolithin B glucuronide.

References

  1. ↑ "Castalagin". PubChem. 2017-07-29.
  2. ↑ Yannai, Shmuel (2012-10-23). Dictionary of Food Compounds with CD-ROM, Second Edition. CRC Press. p. 861. ISBN   978-1-4200-8351-4.
  3. ↑ Zahri, S; Belloncle, C; Charrier, F; Pardon, P; Quideau, S; Charrier, B (2007). "UV light impact on ellagitannins and wood surface colour of European oak (Quercus petraea and Quercus robur)". Applied Surface Science. 253 (11): 4985–9. doi:10.1016/j.apsusc.2006.11.005.
  4. ↑ Shuaibu MN, Pandey K, Wuyep PA, et al. (November 2008). "Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro". Parasitology Research. 103 (6): 1333–8. doi:10.1007/s00436-008-1137-7. PMID   18690475. S2CID   37480828.
  5. 1 2 Vivas N, Laguerre M, Pianet de Boissel I, Vivas de Gaulejac N, Nonier MF (April 2004). "Conformational interpretation of vescalagin and castalagin physicochemical properties". Journal of Agricultural and Food Chemistry. 52 (7): 2073–8. doi:10.1021/jf030460m. PMID   15053554.
  6. ↑ Marinov, M. G.; Dimitrova, E. D.; Puech, J. -L. (1997). "Kinetics of ellagitannin extraction from oak wood using white wine". Journal of Wine Research. 8: 29–40. doi:10.1080/09571269708718095.
  7. ↑ Puech JL, Mertz C, Michon V, Le Guernevé C, Doco T, Hervé Du Penhoat C (May 1999). "Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives". Journal of Agricultural and Food Chemistry. 47 (5): 2060–6. doi:10.1021/jf9813586. PMID   10552496.
  8. ↑ Mayer, Walter; Gabler, Wilfried; Riester, Alfons; Korger, Helfried (1967). "Über die Gerbstoffe aus dem Holz der Edelkastanie und der Eiche, II. Die Isolierung von Castalagin, Vescalagin, Castalin und Vescalin". Justus Liebigs Annalen der Chemie (in German). 707 (1): 177–181. doi:10.1002/jlac.19677070125. ISSN   1099-0690.
  9. ↑ Viriot, Carole; Scalbert, Augustin; Hervé Du Penhoat, Catherine L.M.; Moutounet, Michel (1994-08-10). "Ellagitannins in woods of sessile oak and sweet chestnut dimerization and hydrolysis during wood ageing". Phytochemistry. 36 (5): 1253–1260. doi:10.1016/S0031-9422(00)89647-8. ISSN   0031-9422.
  10. ↑ Gadrat, Mathilde; Lavergne, Joel; Emo, Catherine; Teissedre, Pierre-Louis; Chira, Kleopatra (2021-02-10). "Ellagitannins quantification in oak wood and cognac eaux-de-vie: Sourced from the research article "Validation of a Mass Spectrometry Method to Identify and Quantify Ellagitannins in Oak Wood and Cognac during Aging in Oak Barrels." (Food Chem., 2020). Original language of the article: English". IVES Technical Reviews, Vine and Wine. doi: 10.20870/IVES-TR.2021.4610 . ISSN   2680-4905.
  11. ↑ "Cancer treatment: A berry from Brazil helps out". ScienceDaily. Retrieved 2024-02-07.
  12. ↑ Quideau, Stephane (2009-01-05). Chemistry And Biology Of Ellagitannins: An Underestimated Class Of Bioactive Plant Polyphenols. World Scientific. pp. 327–333. ISBN   978-981-4471-44-2.
  13. ↑ Herve Du Penhoat, Catherine L.M.; Michon, Veronique M.F.; Ohassan, Abdelhamid; Peng, Shuyun; Scalbert, Augustin; Gage, Douglas (1991). "Roburin A, A dimeric ellagitannin from heartwood of Quercus robur". Phytochemistry. 30: 329–32. doi:10.1016/0031-9422(91)84148-L.
  14. ↑ Glabasnia, Arne; Hofmann, Thomas (2007). "Identification and Sensory Evaluation of Dehydro- and Deoxy-ellagitannins Formed upon Toasting of Oak Wood (Quercus alba L.)". Journal of Agricultural and Food Chemistry. 55 (10): 4109–18. doi:10.1021/jf070151m. PMID   17444655.
  15. ↑ Gil, Luís; Pereira, Carlos; Branco, P.; Teixeira, Artur (2006-12-31). "Formation of acutissimin A in red wine through the contact with cork". OENO One. 40 (4): 217–222. doi: 10.20870/oeno-one.2006.40.4.862 . ISSN   2494-1271.
  16. ↑ Fridrich, Diana; Glabasnia, Arne; Fritz, Jessica; Esselen, Melanie; Pahlke, Gudrun; Hofmann, Thomas; Marko, Doris (2008). "Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells". Journal of Agricultural and Food Chemistry. 56 (9): 3010–15. doi:10.1021/jf073427z. PMID   18419129.
  17. ↑ Hofmann T, Glabasnia A, Schwarz B, Wisman KN, Gangwer KA, Hagerman AE (December 2006). "Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose, Castalagin and Grandinin". Journal of Agricultural and Food Chemistry. 54 (25): 9503–9. doi:10.1021/jf062272c. PMC   2597504 . PMID   17147439.
  18. ↑ Quideau, Stéphane; Jourdes, Michael; Lefeuvre, Dorothée; Montaudon, Danièle; Saucier, Cédric; Glories, Yves; Pardon, Patrick; Pourquier, Philippe (2005-11-04). "The Chemistry of Wine PolyphenolicC-Glycosidic Ellagitannins Targeting Human Topoisomerase II". Chemistry - A European Journal. 11 (22): 6503–6513. doi:10.1002/chem.200500428. ISSN   0947-6539. PMID   16110520.
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