Tellimagrandin II is the first of the

ellagitannin image:Castalagin.svg, 130px, Castalagin is a representative ellagitannin, characterized by coupled gallic acid substituents The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative link ...

s formed from

1,2,3,4,6-pentagalloyl-glucose Pentagalloylglucose, or more specifically 1,2,3,4,6-penta-''O''-galloyl-β-D-glucose, is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins. Pentagalloylglucose can precipitate proteins, including human ...

. It can be found in '' Geum japonicum'' and ''

Syzygium aromaticum Cloves are the aromatic flower buds of a tree in the family Myrtaceae, ''Syzygium aromaticum'' (). They are native to the Maluku Islands, or Moluccas, in Indonesia, and are commonly used as a spice, flavoring, or fragrance in consumer products ...

'' (clove).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
Tellimagrandin II is an isomer of

punicafolin Punicafolin is an ellagitannin from the leaves of '' Punica granatum'' (pomegranate) and in '' Phyllanthus emblica''. Punicafolin is an isomer of tellimagrandin II and nupharin A, but the hexahydroxydiphenoyl group is not attached to the same h ...

nupharin A Nupharin A is an ellagitannin found in '' Nuphar japonica''.Tannins and Related Compounds. LXXV. : Isolation and Characterization of Novel Diastereoisomeric Ellagitannins, Nupharins A and B, and Their Homologues from Nuphar japonicum DC. Chemical & ...

, but the

hexahydroxydiphenoyl Hexahydroxydiphenic acid is an organic compound with the formula HO)3C6HCO2Hsub>2. It is the oxidatively coupled derivative of gallic acid It is a white solid, although samples are typically brown owing to oxidation. Occurrence left, 142px, ...

group is not attached to the same hydroxyl groups in the glucose molecule. The compound shows anti-

herpesvirus ''Orthoherpesviridae'', previously named and more widely known as ''Herpesviridae'', is a large family of DNA viruses that cause infections and certain diseases in animals, including humans. The members of this family are commonly known as herp ...

properties.

Metabolism

It is formed by oxidation of

pentagalloyl glucose Pentagalloylglucose, or more specifically 1,2,3,4,6-penta-''O''-galloyl-β-D-glucose, is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins. Pentagalloylglucose can precipitate proteins, including human ...

in '' Tellima grandiflora'' by the enzyme pentagalloylglucose: O(2) oxidoreductase, a

laccase Laccases () are multicopper oxidases found in plants, fungi, and bacteria. Laccases oxidize a variety of phenolic substrates, performing one-electron oxidations, leading to crosslinking. For example, laccases play a role in the formation of li ...

-type phenol oxidase. It is further oxidized to

casuarictin Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in ''Casuarina'' and ''Stachyurus'' species.Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, ...

, a molecule formed via oxidative

dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...

of 2 other

galloyl Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plant ...

groups in ''

Casuarina ''Casuarina'', also known as she-oak, Australian pine and native pine, is a genus of flowering plants in the family Casuarinaceae, and is native to Australia, the Indian subcontinent, Southeast Asia, islands of the western Pacific Ocean, and e ...

'' and ''

Stachyurus ''Stachyurus'' is the only genus in the flowering plant family Stachyuraceae, native to the Himalayas and eastern Asia. They are deciduous shrubs or small trees with pendent racemes of 4-petalled flowers which appear on the bare branches before t ...

'' species.

Dimerization

It is

-catalyzed dimerized to cornusiin E in '' Tellima grandiflora''.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,

Uses

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

References

Ellagitannins Polyphenols {{aromatic-stub