:Castalagin
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400995150
| ImageFile = Castalagin.svg
| ImageName = Chemical structure of castalagin
| ImageSize = 250px
| IUPACName =
| OtherNames = Vescalagin (treatment)
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 23340135
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| 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{{cite web| title=Castalagin| date=2017-07-29| website=PubChem| url=https://pubchem.ncbi.nlm.nih.gov/compound/3002104}}
| InChIKey = UDYKDZHZAKSYCO-LSSWMSPRSA-N
| CASNo = 24312-00-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BZ58QSX2MQ
| CASNo_Comment =
| 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
| Formula = C41H26O26
| MolarMass = 934.63 g/mol
| Appearance = off-white amorphous powder {{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}}
| Density=
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|Section3={{Chembox Hazards
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Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood{{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 }} and in the stem barks of Terminalia leiocarpa and Terminalia avicennoides.{{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}}
Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic chain.{{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 }} Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in oak barrels.{{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}} During aging of wines, these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions.{{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 }} Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels.
Sources
Castalagin was first isolated in Fagaceae family woody species : Quercus (oak) and Castanea (chestnut) by Walter Mayer and co-workers (1967). {{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|url-access=subscription}} In some chestnut species, such as Castanea sativa, heartwood could contain 63 mg of castalagin/ vescalagin per gram of dry wood. {{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 |url-access=subscription}} In some wines, these two isomers represent about 40 to 70% of total ellagitannins. {{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}}
Castalagin was isolated in Myrciaria dubia , a polyphenol from the Amazonian fruit camu-camu.{{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}}
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 castalin, vescalagin and vescalin forms.{{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}}
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{{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 }} and roburin D, and 33-carboxy-33-deoxyvescalagin.{{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 }}
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. {{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|url-access=subscription}} Grandinin is a castalagin glycoside {{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 }} which forms by binding to the pentose lyxose.{{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 }} Chemical hydrolysis of Castalagin/ Vescalagin produces vescalene and vescalin which are potent topoisomerase II inhibitors. {{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|url-access=subscription}}