Castalagin
| Castalagin | ||
|---|---|---|
 | ||
| Other names Vescalagin (treatment) | ||
| Identifiers | ||
| CAS number | 24312-00-3  | |
| PubChem | 3002104 | |
| ChEMBL | CHEMBL607711  | |
| Jmol-3D images | Image 1 | |
| ||
| Properties | ||
| Molecular formula | C41H26O26 | |
| Molar mass | 934.63 g/mol | |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| 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]
In 2003, scientists at Institut Européen de Chimie et Biologie in Pessac, France found that when the oak tannin vescalagin interacts with a phenol in wine a flavono-ellagitannin known as acutissimin A is created. In separate studies this polyphenol has been shown to be 250 times more effective than the pharmaceutical drug Etoposide in stopping the growth of cancerous tumors.[6][7][8]
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.[9]
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[10] and roburin D, and 33-carboxy-33-deoxyvescalagin.[11]
Glycosides
Grandinin is a castalagin glycoside[12] by binding of the pentose lyxose.[13]
References
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Quideau S, Jourdes M, Saucier C, Glories Y, Pardon P, Baudry C (December 2003). "DNA topoisomerase inhibitor acutissimin a and other flavano-ellagitannins in red wine". Angewandte Chemie 42 (48): 6012–4. doi:10.1002/anie.200352089. PMID 14679557.
- ↑ Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH (August 1992). "Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents". Journal of Natural Products 55 (8): 1033–43. doi:10.1021/np50086a002. PMID 1431932.
- ↑ Quideau, StéPhane; Jourdes, Michael; Saucier, Cédric; Glories, Yves; Pardon, Patrick; Baudry, Christian (2003). "DNA Topoisomerase Inhibitor Acutissimin A and Other Flavano-Ellagitannins in Red Wine". Angewandte Chemie 115 (48): 6194–6. doi:10.1002/ange.200352089. "While it would be quite inappropriate to infer from the presence of acutissimin A in red wine that this beverage possesses antitumor properties, our work shows for the first time that wine contains polyphenolic molecules displaying both ellagitannin and flavanoid structural features."
- ↑ Tannins chemistry by Hagerman A. E.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
| |||||||||||||||||||||||||||