Tellimagrandin II

Tellimagrandin II
Chemical structure of 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
ChemSpider
KEGG
  • 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 checkY
    Key: JCGHAEBIBSEQAD-UUUCSUBKSA-N checkY
  • O=C(O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3-c3c(cc(O)c(O)c3O)C(=O)O[C@H]2[C@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H]1OC(=O)c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1
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).

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).

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.

Biosynthesis and metabolism

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

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

tellimagrandin II
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of casuarictin .
casuarictin

Dimerization

It is laccase-catalyzed dimerized to cornusiin E in Tellima grandiflora.

Uses

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

References

  1. 1 2 Kurokawa, Masahiko; Hozumi, Toyoharu; Basnet, Purusotam; Nakano, Michio; Kadota, Shigetoshi; Namba, Tuneo; Kawana, Takashi; Shiraki, Kimiyasu (1998). "Purification and Characterization of Eugeniin as an Anti-herpesvirus Compound from Geum japonicum and Syzygium aromaticum". JPET. 284: 728–735.
  2. ↑ Niemetz, R; Gross, GG (2003). "Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves". Phytochemistry. 62: 301–6. PMID 12620341.
  3. ↑ Okuda, Takuo; Yoshida, Takashi; Ashida, Mariko; Yazaki, Kazufumi (1983). "Tannis of Casuarina and Stachyurus species. Part 1. Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin". Journal of the Chemical Society, Perkin Transactions 1: 1765. doi:10.1039/P19830001765.
  4. ↑ Niemetz, Ruth (2003). "Ellagitannin biosynthesis: laccase-catalyzed dimerization of tellimagrandin II to cornusiin E in Tellima grandiflora". Phytochemistry. 64: 1197–201. doi:10.1016/j.phytochem.2003.08.013.
  5. ↑ Niemetz, R (2003). "Biosynthesis of the dimeric ellagitannin, cornusiin E, in Tellima grandiflora. Dedicated to the memory of Professor Jeffrey B. Harborne". Phytochemistry. 64: 109–114.