Castalagin

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Castalagin
Chemical structure of castalagin
Identifiers
CAS number 24312-00-3 YesY
PubChem 3002104
ChEMBL CHEMBL607711 N
Jmol-3D images Image 1
Properties
Molecular formula C41H26O26
Molar mass 934.63 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood[1] and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides.[2]

Castalagin is the (33beta)-isomer of vescalagin.[3] During aging of alcohols in oak barrels, vescalagin can be extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions.[4] Vescalagin is one of the most abundant ellagitannins extracted from oak wood using white wine.[5]

Derivatives[edit]

The flavono-ellagitannin known as acutissimin A is created when the oak tannin vescalagin interacts with a flavonoid in wine.

Biosynthesis[edit]

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.[6]

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[7] and roburin D, and 33-carboxy-33-deoxyvescalagin.[8]

Glycosides[edit]

Grandinin is a castalagin glycoside[9] by binding of the pentose lyxose.[10]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ Tannins chemistry by Hagerman A. E.[self-published source?]
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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.