Tellimagrandin II

Tellimagrandin II
Names
	Other names Tellimagrandin II; Eugeniin
Identifiers
CAS Number	58970-75-5 =;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4916 ;
ChEMBL	ChEMBL450745 ;
PubChem CID	442679;
	InChI 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;
	SMILES 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
Chemical formula	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 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]

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]

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gollark: It actually detects Discord URLs and replaces them with URLs to osmarksCDN™, as well as embedding authorship data in them steganographically.

References

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)
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
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
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
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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[Kurokawa-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