Chemistry: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 | |
PubChem CID
|
|
| |
| |
| 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). | |
| Infobox references | |
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]
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.[2]
- REDIRECT Template:Chemical reaction
It is further oxidized to casuarictin, a molecule formed via oxidative dehydrogenation of 2 other galloyl groups in Casuarina and Stachyurus species.[3]
- REDIRECT Template:Chemical reaction
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
- ↑ 1.0 1.1 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. http://jpet.aspetjournals.org/content/284/2/728.full.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
 |  |
