Tellimagrandin II

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
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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Infobox references

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]

Metabolism

It is formed by oxidation of pentagalloyl glucose in Tellima grandiflora by the enzyme pentagalloylglucose: O(2) oxidoreductase, a laccase-type phenol oxidase.[2]

It is further oxidized to casuarictin, a molecule formed via oxidative dehydrogenation of 2 other galloyl groups in Casuarina and Stachyurus species.[3]

Dimerization

It is laccase-catalyzed dimerized to cornusiin E in Tellima grandiflora.[4][5]

Uses

It has an extremely weak basic(essentially neutral) compound. The compound shows anti-herpesvirus properties.

References
  1. 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)
  2. Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves. Niemetz R and Gross GG, Phytochemistry, February 2003, volume 62, issue 3, pages 301-306, PMID 12620341
  3. Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. Okuda T., Yoshida T., Ashida M. and Yazaki K., Journal of the Chemical Society, 1983, no 8, pages 1765-1772, INIST:9467908
  4. Ellagitannin biosynthesis: laccase-catalyzed dimerization of tellimagrandin II to cornusiin E in Tellima grandiflora. Phytochemistry, December 2003, volume 64, issue 7, pages 1197-201, doi:10.1016/j.phytochem.2003.08.013
  5. Biosynthesis of the dimeric ellagitannin, cornusiin E, in Tellima grandiflora. Dedicated to the memory of Professor Jeffrey B. Harborne, Ruth Niemetz, Gerhard Schilling and Georg G Gross, Phytochemistry, Volume 64, Issue 1, September 2003, Pages 109–114, doi:10.1016/S0031-9422(03)00280-2
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