{{chembox | Watchedfields = | verifiedrevid = | Name = Casuarinin | ImageFile = Casuarinin.png | ImageName = Chemical structure of Casuarinin | IUPACName = | OtherNames = Stachyurin<!-- <br> --> |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 79786-01-9 | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1 = 81739-27-7 | ChemSpiderID = 138517 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = S45A8T6Q4C | InChI = 1S/C41H28O26/c42-11-1-7(2-12(43)23(11)47)37(58)64-16-6-63-38(59)8-3-13(44)24(48)27(51)17(8)18-9(4-14(45)25(49)28(18)52)39(60)65-34(16)36-35-32(56)22-21(41(62)66-35)20(30(54)33(57)31(22)55)19-10(40(61)67-36)5-15(46)26(50)29(19)53/h1-5,16,32,34-36,42-57H,6H2 | InChIKey = MMQXBTULXAEKQE-UHFFFAOYSA-N | MeSHName = | PubChem = 157395 | SMILES = C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C(C=C3C(=O)O1)O)O)O)O)O)O)C4C5C(C6=C(C(=C(C(=C6C(=O)O5)C7=C(C(=C(C=C7C(=O)O4)O)O)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O }} |Section2={{Chembox Properties | Formula = C<sub>41</sub>H<sub>28</sub>O<sub>26</sub> | MolarMass = 936.64 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }} '''Casuarinin''' is an ellagitannin. It is found in the pericarp of pomegranates (''Punica granatum''). It is also found in ''Casuarina'' and ''Stachyurus'' species<ref>{{cite journal |url=http://cat.inist.fr/?aModele=afficheN&cpsidt=9467908 |title=Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. |first=T. |last=Okuda |author2=T. Yoshida |author3=M. Ashida |author4=K. Yazaki |journal=Journal of the Chemical Society |year=1983 |number=8 |pages=1765–1772}}</ref> and in ''Alnus sieboldiana''.<ref>Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, {{INIST|19467830}} ([http://ci.nii.ac.jp/naid/110003627299 abstract])</ref>
It is an isomer of casuarictin. It is a highly active carbonic anhydrase inhibitor.<ref name=Satomi>{{Cite journal | last1 = Satomi | first1 = H. | last2 = Umemura | first2 = K. | last3 = Ueno | first3 = A. | last4 = Hatano | first4 = T. | last5 = Okuda | first5 = T. | last6 = Noro | first6 = T. | title = Carbonic anhydrase inhibitors from the pericarps of Punica granatum L | journal = Biological & Pharmaceutical Bulletin | volume = 16 | issue = 8 | pages = 787–790 | year = 1993 | pmid = 8220326 | doi=10.1248/bpb.16.787 | doi-access = free }}</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 castalin, vescalagin and vescalin forms.<ref>[http://www.users.muohio.edu/hagermae/tannin.pdf Tannins chemistry by Hagerman A. E.] {{Webarchive|url=https://web.archive.org/web/20130826003253/http://www.users.muohio.edu/hagermae/tannin.pdf |date=2013-08-26 }}</ref>{{Self-published inline|date=April 2010}}
== References == {{Reflist}}
{{Ellagitannin}}
Category:Ellagitannins Category:Pomegranate ellagitannins Category:Carbonic anhydrase inhibitors Category:Lactones Category:Heterocyclic compounds with 4 rings Category:Heterocyclic compounds with 3 rings Category:Oxygen heterocycles