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]
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]
^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.
Bibcode:
2007ApSS..253.4985Z.
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.
PMID18690475.
S2CID37480828.
^
abVivas 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.
PMID15053554.
^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.
^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.
PMID10552496.
^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.
Bibcode:
1991PChem..30..329H.
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.
PMID17444655.