Castalagin: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400995150

| ImageFile = Castalagin.svg

| ImageName = Chemical structure of castalagin

| ImageSize = 250px

| IUPACName =

| OtherNames = Vescalagin (treatment)

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID =

| 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<ref>{{cite web| title=Castalagin| date=2017-07-29| website=PubChem| url=https://pubchem.ncbi.nlm.nih.gov/compound/3002104}}</ref>

| InChIKey = UDYKDZHZAKSYCO-LSSWMSPRSA-N

| CASNo = 24312-00-3

| 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

| Formula = C₄₁H₂₆O₂₆

| 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>

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

| MainHazards=

| FlashPt=

| AutoignitionPt =

'''Castalagin''' is an [[ellagitannin]], a type of hydrolyzable tannin, found in [[oak]] and [[chestnut]] 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 ''[[Terminalia leiocarpa]]'' and ''[[Terminalia avicennoides]]''.<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 [[diastereomer]] 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}}</ref> Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in [[Oak (wine)|oak barrels]].<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 [[Aging of wine|aging of wines]], 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}}</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 ==

Castalagin was first isolated in [[Fagaceae]] family woody species : [[Oak|''Quercus'']] (oak) and ''[[Chestnut|Castanea]]'' (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 ''[[Castanea sativa]]'', 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 [[Wine|wines]], 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 ''[[Myrciaria dubia]]'' , 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>

== 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.<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[[galloyl]]-glucose structure. Castalagin and vescalagin (1,2,3,5-[[nonahydroxytriphenoyl]]-4,6-[[hexahydroxydiphenoyl]]-glucoses) can be further polymerized in their corresponding [[Dimer (chemistry)|dimer]]s [[roburin A]]<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|bibcode=1991PChem..30..329H }}</ref> and [[roburin D]], 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}}</ref>

== Derivatives ==

Castalagin and other related ellagitanins polymerizes or forms complexes with [[Anthocyanins (wine)|anthyocyanins]] and [[Flavonoid|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. <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> [[Grandinin]] 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}}</ref> which forms by binding to the pentose [[lyxose]].<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}}</ref> Chemical hydrolysis of Castalagin/ Vescalagin produces vescalene and vescalin which are potent [[Type II topoisomerase|topoisomerase II]] 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>

== References ==

{{Reflist}}

{{Ellagitannin}}

[[Category:Ellagitannins]]

[[Category:Wood extracts]]