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{{chembox {{chembox
| Verifiedfields = changed
⚫ | ImageFile = Castalagin.PNG
| Watchedfields = changed
⚫ | ImageName = Chemical structure of castalagin
| verifiedrevid = 400995150
⚫ | ImageSize = 200px
⚫ | ImageFile = Castalagin.svg
⚫ | IUPACName =
⚫ | ImageName = Chemical structure of castalagin
⚫ | OtherNames = Vescalagin (treatment)
⚫ | ImageSize = 250px
⚫ | IUPACName =
⚫ | OtherNames = Vescalagin (treatment)
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID =
| ChemSpiderID1 = 23340135
| InChI =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| InChIKey =
| CASNo = 24312-00-3 | ChEMBL = 607711
| 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<ref>{{cite web| title=Castalagin| date=2017-07-29| website=PubChem| url=https://pubchem.ncbi.nlm.nih.gov/compound/3002104}}</ref>
⚫ | CASNo_Comment = <!-- 10-14-0, 36001-47-5 -->
| InChIKey = UDYKDZHZAKSYCO-LSSWMSPRSA-N
⚫ | PubChem = 3002104
| CASNo = 24312-00-3
⚫ | SMILES = 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
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BZ58QSX2MQ
⚫ | CASNo_Comment = <!-- 10-14-0, 36001-47-5 -->
⚫ | PubChem = 3002104
⚫ | SMILES = 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
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>41</sub>H<sub>26</sub>O<sub>26</sub> | Formula = C<sub>41</sub>H<sub>26</sub>O<sub>26</sub>
| MolarMass = 934.63 g/mol | MolarMass = 934.63 g/mol
| Appearance = off-white amorphous powder <ref>{{Cite book|last=Yannai|first=Shmuel|url=https://books.google.com/books?id=_pHQQQkl8FMC&pg=PA861|title=Dictionary of Food Compounds with CD-ROM, Second Edition|date=2012-10-23|publisher=CRC Press|isbn=978-1-4200-8351-4|pages=861|language=en}}</ref>
| ExactMass = 934.071231
| Density=
| Appearance =
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Castalagin''' is a ] (hydrolyzable tannin) found in ] and ] wood<ref>{{cite journal |doi=10.1016/j.apsusc.2006.11.005 |title=UV light impact on ellagitannins and wood surface colour of European oak (Quercus petraea and Quercus robur) |year=2007 |last1=Zahri |first1=S |last2=Belloncle |first2=C |last3=Charrier |first3=F |last4=Pardon |first4=P |last5=Quideau |first5=S |last6=Charrier |first6=B |journal=Applied Surface Science |volume=253 |pages=4985–9}}</ref> and in the stem barks of '']'' and '']''.<ref>{{cite journal |author=Shuaibu MN, Pandey K, Wuyep PA, ''et al.'' |title=Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro |journal=Parasitology Research |volume=103 |issue=6 |pages=1333–8 |year=2008 |month=November |pmid=18690475 |doi=10.1007/s00436-008-1137-7}}</ref> '''Castalagin''' is an ], a type of hydrolyzable tannin, found in ] and ] wood<ref>{{cite journal |doi=10.1016/j.apsusc.2006.11.005 |title=UV light impact on ellagitannins and wood surface colour of European oak (Quercus petraea and Quercus robur) |year=2007 |last1=Zahri |first1=S |last2=Belloncle |first2=C |last3=Charrier |first3=F |last4=Pardon |first4=P |last5=Quideau |first5=S |last6=Charrier |first6=B |journal=Applied Surface Science |volume=253 |pages=4985–9 |issue=11|bibcode=2007ApSS..253.4985Z }}</ref> and in the stem barks of '']'' and '']''.<ref>{{cite journal |vauthors=Shuaibu MN, Pandey K, Wuyep PA |title=Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro |journal=Parasitology Research |volume=103 |issue=6 |pages=1333–8 |date=November 2008 |pmid=18690475 |doi=10.1007/s00436-008-1137-7|s2cid=37480828 |display-authors=etal}}</ref>


Castalagin is the (33beta)-isomer of vescalagin.<ref>{{cite journal |author=Vivas N, Laguerre M, Pianet de Boissel I, Vivas de Gaulejac N, Nonier MF |title=Conformational interpretation of vescalagin and castalagin physicochemical properties |journal=Journal of Agricultural and Food Chemistry |volume=52 |issue=7 |pages=2073–8 |year=2004 |month=April |pmid=15053554 |doi=10.1021/jf030460m}}</ref> During aging of alcohols in ], vescalagin can be extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions.<ref>{{cite journal |author=Puech JL, Mertz C, Michon V, Le Guernevé C, Doco T, Hervé Du Penhoat C |title=Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives |journal=Journal of Agricultural and Food Chemistry |volume=47 |issue=5 |pages=2060–6 |year=1999 |month=May |pmid=10552496 |doi=10.1021/jf9813586}}</ref> Vescalagin is one of the most abundant ellagitannins extracted from oak wood using white wine.<ref>{{cite journal |doi=10.1080/09571269708718095 |title=Kinetics of ellagitannin extraction from oak wood using white wine |year=1997 |last1=Marinov |first1=M. G. |last2=Dimitrova |first2=E. D. |last3=Puech |first3=J. -L. |journal=Journal of Wine Research |volume=8 |pages=29–40}}</ref> Castalagin is the ] of '''vescalagin''' in C-1 of the glycosidic chain.<ref name=":0">{{cite journal |vauthors=Vivas N, Laguerre M, Pianet de Boissel I, Vivas de Gaulejac N, Nonier MF |title=Conformational interpretation of vescalagin and castalagin physicochemical properties |journal=Journal of Agricultural and Food Chemistry |volume=52 |issue=7 |pages=2073–8 |date=April 2004 |pmid=15053554 |doi=10.1021/jf030460m|bibcode=2004JAFC...52.2073V }}</ref> Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in ].<ref>{{cite journal|last1=Marinov|first1=M. G.|last2=Dimitrova|first2=E. D.|last3=Puech|first3=J. -L.|year=1997|title=Kinetics of ellagitannin extraction from oak wood using white wine|journal=Journal of Wine Research|volume=8|pages=29–40|doi=10.1080/09571269708718095}}</ref> During ], these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions.<ref>{{cite journal |vauthors=Puech JL, Mertz C, Michon V, Le Guernevé C, Doco T, Hervé Du Penhoat C |title=Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives |journal=Journal of Agricultural and Food Chemistry |volume=47 |issue=5 |pages=2060–6 |date=May 1999 |pmid=10552496 |doi=10.1021/jf9813586|bibcode=1999JAFC...47.2060P }}</ref> Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels. <ref name=":0" />


== Sources ==
In 2003, scientists at Institut Européen de Chimie et Biologie in ] found that when the oak tannin vescalagin interacts with a phenol in wine known as ] is created. In separate studies this polyphenol has been shown to be 250 times more effective then the pharmaceutical drug ] in stopping the growth of ] ].<ref>{{cite journal |author=Quideau S, Jourdes M, Saucier C, Glories Y, Pardon P, Baudry C |title=DNA topoisomerase inhibitor acutissimin a and other flavano-ellagitannins in red wine |journal=Angewandte Chemie |volume=42 |issue=48 |pages=6012–4 |year=2003 |month=December |pmid=14679557 |doi=10.1002/anie.200352089}}</ref><ref>{{cite journal |author=Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH |title=Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents |journal=Journal of Natural Products |volume=55 |issue=8 |pages=1033–43 |year=1992 |month=August |pmid=1431932 |doi=10.1021/np50086a002}}</ref><ref>{{cite journal |doi=10.1002/ange.200352089 |quote=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. |title=DNA Topoisomerase Inhibitor Acutissimin A and Other Flavano-Ellagitannins in Red Wine |year=2003 |last1=Quideau |first1=StéPhane |last2=Jourdes |first2=Michael |last3=Saucier |first3=Cédric |last4=Glories |first4=Yves |last5=Pardon |first5=Patrick |last6=Baudry |first6=Christian |journal=Angewandte Chemie |volume=115 |pages=6194–6}}</ref>
Castalagin was first isolated in ] family woody species : ] (oak) and '']'' (chestnut) by Walter Mayer and co-workers (1967). <ref>{{Cite journal|last1=Mayer|first1=Walter|last2=Gabler|first2=Wilfried|last3=Riester|first3=Alfons|last4=Korger|first4=Helfried|date=1967|title=Über die Gerbstoffe aus dem Holz der Edelkastanie und der Eiche, II. Die Isolierung von Castalagin, Vescalagin, Castalin und Vescalin|url=https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/jlac.19677070125|journal=Justus Liebigs Annalen der Chemie|language=de|volume=707|issue=1|pages=177–181|doi=10.1002/jlac.19677070125|issn=1099-0690}}</ref> In some chestnut species, such as '']'', heartwood could contain 63 mg of castalagin/ vescalagin per gram of dry wood. <ref>{{Cite journal|date=1994-08-10|title=Ellagitannins in woods of sessile oak and sweet chestnut dimerization and hydrolysis during wood ageing|url=https://www.sciencedirect.com/science/article/abs/pii/S0031942200896478|journal=Phytochemistry|language=en|volume=36|issue=5|pages=1253–1260|doi=10.1016/S0031-9422(00)89647-8|issn=0031-9422|last1=Viriot|first1=Carole|last2=Scalbert|first2=Augustin|last3=Hervé Du Penhoat|first3=Catherine L.M.|last4=Moutounet|first4=Michel|bibcode=1994PChem..36.1253V }}</ref> In some ], these two isomers represent about 40 to 70% of total ellagitannins. <ref>{{Cite journal|last1=Gadrat|first1=Mathilde|last2=Lavergne|first2=Joel|last3=Emo|first3=Catherine|last4=Teissedre|first4=Pierre-Louis|last5=Chira|first5=Kleopatra|date=2021-02-10|title=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.|url=https://ives-technicalreviews.eu/article/view/4610|journal=IVES Technical Reviews, Vine and Wine|language=en|doi=10.20870/IVES-TR.2021.4610|issn=2680-4905|doi-access=free}}</ref>


Castalagin was isolated in '']'' , a polyphenol from the Amazonian fruit camu-camu.<ref>{{Cite web |title=Cancer treatment: A berry from Brazil helps out |url=https://www.sciencedaily.com/releases/2022/02/220202111801.htm |access-date=2024-02-07 |website=ScienceDaily |language=en}}</ref>
==Chemistry==
⚫ In some plants including oak and chestnut, the ellagitannins are formed from ] and further elaborated via oxidative dehydrogenation (] and ] formations). After conversion of ] to ], the pyranose ring of the ] opens and the family of compounds including ], ], castalagin, and ], ], vescalagin and ] forms.<ref>{{Self-published inline|date=April 2010}}</ref>


== Biosynthesis ==
⚫ Castalagin thus forms from a penta]-glucose structure. castalagin and vescalagin (1,2,3,5-nonahydroxytriphenoyl-4,6-hexahydroxydiphenoyl-glucoses) can be further polymerized in their corresponding ]s ]<ref>{{cite journal |doi=10.1016/0031-9422(91)84148-L |title=Roburin A, A dimeric ellagitannin from heartwood of Quercus robur |year=1991 |last1=Herve Du Penhoat |first1=Catherine L.M. |last2=Michon |first2=Veronique M.F. |last3=Ohassan |first3=Abdelhamid |last4=Peng |first4=Shuyun |last5=Scalbert |first5=Augustin |last6=Gage |first6=Douglas |journal=Phytochemistry |volume=30 |pages=329–32}}</ref> and ], and ].<ref>{{cite journal |doi=10.1021/jf070151m |title=Identification and Sensory Evaluation of Dehydro- and Deoxy-ellagitannins Formed upon Toasting of Oak Wood (Quercus alba L.) |year=2007 |last1=Glabasnia |first1=Arne |last2=Hofmann |first2=Thomas |journal=Journal of Agricultural and Food Chemistry |volume=55 |pages=4109–18 |pmid=17444655 |issue=10}}</ref>
⚫ In some plants including oak and chestnut, the ellagitannins are formed from ] and further elaborated via oxidative dehydrogenation (] and ] formations). After conversion of ] to ], the pyranose ring of the ] opens and the family of compounds including ], ], castalagin, and ], vescalagin and ] forms.<ref>{{Cite book|last=Quideau|first=Stephane|url=https://books.google.com/books?id=-z_ICgAAQBAJ|title=Chemistry And Biology Of Ellagitannins: An Underestimated Class Of Bioactive Plant Polyphenols|date=2009-01-05|publisher=World Scientific|isbn=978-981-4471-44-2|pages=327–333|language=en}}</ref>


⚫ Castalagin thus forms from a penta]-glucose structure. Castalagin and vescalagin (1,2,3,5-]-4,6-]-glucoses) can be further polymerized in their corresponding ]s ]<ref>{{cite journal |doi=10.1016/0031-9422(91)84148-L |title=Roburin A, A dimeric ellagitannin from heartwood of Quercus robur |year=1991 |last1=Herve Du Penhoat |first1=Catherine L.M. |last2=Michon |first2=Veronique M.F. |last3=Ohassan |first3=Abdelhamid |last4=Peng |first4=Shuyun |last5=Scalbert |first5=Augustin |last6=Gage |first6=Douglas |journal=Phytochemistry |volume=30 |issue=1 |pages=329–32|bibcode=1991PChem..30..329H }}</ref> and ], and 33-carboxy-33-deoxyvescalagin.<ref>{{cite journal |doi=10.1021/jf070151m |title=Identification and Sensory Evaluation of Dehydro- and Deoxy-ellagitannins Formed upon Toasting of Oak Wood (Quercus alba L.) |year=2007 |last1=Glabasnia |first1=Arne |last2=Hofmann |first2=Thomas |journal=Journal of Agricultural and Food Chemistry |volume=55 |pages=4109–18 |pmid=17444655 |issue=10|bibcode=2007JAFC...55.4109G }}</ref>
==Glycosides==
] is a castalagin glycoside<ref>{{cite journal |doi=10.1021/jf073427z |title=Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells |pmid=18419129 |year=2008 |last1=Fridrich |first1=Diana |last2=Glabasnia |first2=Arne |last3=Fritz |first3=Jessica |last4=Esselen |first4=Melanie |last5=Pahlke |first5=Gudrun |last6=Hofmann |first6=Thomas |last7=Marko |first7=Doris |journal=Journal of Agricultural and Food Chemistry |volume=56 |issue=9 |pages=3010–15}}</ref> by binding of the pentose ].<ref>{{cite journal |author=Hofmann T, Glabasnia A, Schwarz B, Wisman KN, Gangwer KA, Hagerman AE |title=Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose, castalagin, and grandinin |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=25 |pages=9503–9 |year=2006 |month=December |pmid=17147439 |pmc=2597504 |doi=10.1021/jf062272c}}</ref>


==References== == Derivatives ==
Castalagin and other related ellagitanins polymerizes or forms complexes with ] and ]. The flavono-ellagitannin known as ] is created when the oak tannin vescalagin interacts with ] a ] found in wine. <ref>{{Cite journal|last1=Gil|first1=Luís|last2=Pereira|first2=Carlos|last3=Branco|first3=P.|last4=Teixeira|first4=Artur|date=2006-12-31|title=Formation of acutissimin A in red wine through the contact with cork|url=https://oeno-one.eu/article/view/862|journal=OENO One|language=en|volume=40|issue=4|pages=217–222|doi=10.20870/oeno-one.2006.40.4.862|issn=2494-1271|doi-access=free}}</ref> ] is a castalagin glycoside <ref>{{cite journal|last1=Fridrich|first1=Diana|last2=Glabasnia|first2=Arne|last3=Fritz|first3=Jessica|last4=Esselen|first4=Melanie|last5=Pahlke|first5=Gudrun|last6=Hofmann|first6=Thomas|last7=Marko|first7=Doris|year=2008|title=Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells|journal=Journal of Agricultural and Food Chemistry|volume=56|issue=9|pages=3010–15|doi=10.1021/jf073427z|pmid=18419129|bibcode=2008JAFC...56.3010F }}</ref> which forms by binding to the pentose ].<ref>{{cite journal|vauthors=Hofmann T, Glabasnia A, Schwarz B, Wisman KN, Gangwer KA, Hagerman AE|date=December 2006|title=Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose, Castalagin and Grandinin|journal=Journal of Agricultural and Food Chemistry|volume=54|issue=25|pages=9503–9|doi=10.1021/jf062272c|pmc=2597504|pmid=17147439|bibcode=2006JAFC...54.9503H }}</ref> Chemical hydrolysis of Castalagin/ Vescalagin produces vescalene and vescalin which are potent ] inhibitors. <ref>{{Cite journal|last1=Quideau|first1=Stéphane|last2=Jourdes|first2=Michael|last3=Lefeuvre|first3=Dorothée|last4=Montaudon|first4=Danièle|last5=Saucier|first5=Cédric|last6=Glories|first6=Yves|last7=Pardon|first7=Patrick|last8=Pourquier|first8=Philippe|date=2005-11-04|title=The Chemistry of Wine PolyphenolicC-Glycosidic Ellagitannins Targeting Human Topoisomerase II|url=https://onlinelibrary.wiley.com/doi/10.1002/chem.200500428|journal=Chemistry - A European Journal|language=en|volume=11|issue=22|pages=6503–6513|doi=10.1002/chem.200500428|pmid=16110520|issn=0947-6539}}</ref>
⚫ {{Reflist}}


== References ==
{{Hydrolysable tannin}}
⚫ {{Reflist}}


{{Ellagitannin}}
]
⚫ ]


⚫ ]
{{polyphenol-stub}}
]
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