Tellimagrandin II

Tellimagrandin II
Chemical structure of tellimagrandin II
Names
Systematic IUPAC name
(11aR,13S,14R,15S,15aR)-2,3,4,5,6,7-Hexahydroxy-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-13,14,15-triyl tris(2,3,4-trihydroxybenzoate)
Other names
Tellimagrandin II
Eugeniin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
  • InChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41+/m1/s1
  • C1C2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C(C=C7C(=O)O1)O)O)O)O)O)O
Properties
C41H30O26
Molar mass 938.66 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum (clove).[1]

Tellimagrandin II is an isomer of punicafolin or nupharin A, but the hexahydroxydiphenoyl group is not attached to the same hydroxyl groups in the glucose molecule.

The compound shows anti-herpesvirus properties.[1]

  1. ^ a b Purification and Characterization of Eugeniin as an Anti-herpesvirus Compound from Geum japonicum and Syzygium aromaticum. Masahiko Kurokawa, Toyoharu Hozumi, Purusotam Basnet, Michio Nakano, Shigetoshi Kadota, Tuneo Namba, Takashi Kawana and Kimiyasu Shiraki, JPET, February 1, 1998 vol. 284 no. 2, pages 728-735 (article)