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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
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
  • 58970-75-5 Y=
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:4916 N
ChEMBL
  • ChEMBL450745 N
  • 442679
  • 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).
N verify (what is YN ?)

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 edit

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 edit

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

Uses edit

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

References edit

  1. ^ a b 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

tellimagrandin, first, ellagitannins, formed, from, pentagalloyl, glucose, found, geum, japonicum, syzygium, aromaticum, clove, names, systematic, iupac, name, 11ar, 15ar, hexahydroxy, dioxo, octahydrodibenzo, pyrano, dioxacycloundecine, triyl, tris, trihydrox. 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 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 IIEugeniin Identifiers CAS Number 58970 75 5 Y 3D model JSmol Interactive image ChEBI CHEBI 4916 N ChEMBL ChEMBL450745 N 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 N verify what is Y N 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 Contents 1 Metabolism 1 1 Dimerization 1 2 Uses 2 ReferencesMetabolism editIt 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 edit It is laccase catalyzed dimerized to cornusiin E in Tellima grandiflora 4 5 Uses edit It has an extremely weak basic essentially neutral compound The compound shows anti herpesvirus properties References edit a b 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 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Tellimagrandin II amp oldid 1153689236, wikipedia, wiki, book, books, library,

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