punicalin
{{chembox
| verifiedrevid =
| Name = Punicalin
| ImageFile = Punicalin.svg
| ImageName = Chemical structure of punicalin
| IUPACName =
| OtherNames = 4,6-(S,S)-Gallagyl-D-glucose
|Section1={{Chembox Identifiers
| CASNo = 65995-64-4
| CASNo_Ref = [http://www.chemicalbook.com/ChemicalProductProperty_EN_CB71379252.htm]
| CASNoOther =
| PubChem = 5388496
| ChemSpiderID = 28428695
| SMILES = c1c2c(c(c(c1O)O)O)-c3c4c5c6c(c(c(c(c6oc4=O)O)O)-c7c(cc(c(c7O)O)O)C(=O)O[C@@H]8[C@@H](COC2=O)OC([C@@H]([C@H]8O)O)O)c(=O)oc5c(c3O)O
| InChI = 1/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1
| InChIKey = IQHIEHIKNWLKFB-OBOTWMKHBV
| StdInChI = 1S/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1
| StdInChIKey = IQHIEHIKNWLKFB-OBOTWMKHSA-N
| MeSHName =
}}
|Section2={{Chembox Properties
| Formula = C34H22O22
| MolarMass = 782.52 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
}}
Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate){{Cite journal | last1 = Zhang | first1 = Y. | last2 = Wang | first2 = D. | last3 = Lee | first3 = R. P. | last4 = Henning | first4 = S. M. | last5 = Heber | first5 = D. | title = Absence of Pomegranate Ellagitannins in the Majority of Commercial Pomegranate Extracts: Implications for Standardization and Quality Control | doi = 10.1021/jf9010017 | journal = Journal of Agricultural and Food Chemistry | volume = 57 | issue = 16 | pages = 7395–7400 | year = 2009 | pmid = 20349921}} or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis.{{Cite journal
| last1 = Lin | first1 = C. C.
| last2 = Hsu | first2 = Y. F.
| last3 = Lin | first3 = T. C.
| last4 = Hsu | first4 = F. L.
| last5 = Hsu | first5 = H. Y.
| title = Antioxidant and hepatoprotective activity of punicalagin and punicalin on carbon tetrachloride-induced liver damage in rats
| journal = The Journal of Pharmacy and Pharmacology
| volume = 50
| issue = 7
| pages = 789–794
| year = 1998
| pmid = 9720629 | doi=10.1111/j.2042-7158.1998.tb07141.x
| s2cid = 8639399
| doi-access = free
}}{{Cite journal | journal = The American Journal of Chinese Medicine | volume = 27 | issue = 3 & 4 | pages = 371–376 | doi = 10.1142/S0192415X99000422 | year = 1999 | pmid = 10592846| last1 = Lin | first1 = Chun-Ching | last2 = Hsu | first2 = YF | last3 = Lin | first3 = TC | title = Effects of punicalagin and punicalin on carrageenan-induced inflammation in rats }} It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.
It is a highly active carbonic anhydrase inhibitor.{{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
}}
Chemistry
The molecule contains a gallagic acid component linked to a glucose.