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{{chembox |
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| verifiedrevid = 400996132 |
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| Name = Tellimagrandin II |
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| Name = Tellimagrandin II |
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| ImageFile = Tellimagrandin II.PNG |
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| ImageFile = Tellimagrandin II.svg |
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| ImageSize = 200px |
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| ImageName = Chemical structure of tellimagrandin II |
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| ImageName = Chemical structure of tellimagrandin II |
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| SystematicName = (11a''R'',13''S'',14''R'',15''S'',15a''R'')-2,3,4,5,6,7-Hexahydroxy-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzopyranodioxacycloundecine-13,14,15-triyl tris(2,3,4-trihydroxybenzoate) |
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| IUPACName = |
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| OtherNames = Tellimagrandin II<br>Eugeniin |
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| OtherNames = Tellimagrandin II<br>Eugeniin |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 58970-75-5 |
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| CASNo = 58970-75-5 |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|??}}= |
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| CASOther = |
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| CASNoOther = |
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| PubChem = 442679 |
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| PubChem = 442679 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 4916 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 450745 |
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| 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 |
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| 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 |
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| 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 |
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| InChI = |
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| MeSHName = |
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| MeSHName = |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>41</sub>H<sub>30</sub>O<sub>26</sub> |
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| Formula = C<sub>41</sub>H<sub>30</sub>O<sub>26</sub> |
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| MolarMass = 938.66 g/mol |
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| MolarMass = 938.66 g/mol |
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| ExactMass = 938.102531 u |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = <!-- °C --> |
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| BoilingPt = <!-- °C --> |
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'''Tellimagrandin II''' is the first of the ]s formed from ]. It can be found in '']'' and '']'' (clove)<ref></ref>. The compound shows anti-] properties. |
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'''Tellimagrandin II''' is the first of the ]s formed from ]. It can be found in '']'' and '']'' (clove).<ref name=Kurokawa>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 ()</ref> |
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Tellimagrandin II is an isomer of ] or ], but the ] group is not attached to the same hydroxyl groups in the glucose molecule. |
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It is ]-catalyzed dimerized to ] in '']''<ref></ref>. ] can be formed from it via oxidative ] of 2 other ] groups in '']'' and '']'' species<ref></ref>. |
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The compound shows anti-] properties.<ref name=Kurokawa/> |
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==References== |
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== Metabolism == |
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It is formed by oxidation of ] in '']'' by the enzyme ], a ]-type phenol oxidase.<ref>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}}</ref> |
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It is further oxidized to ], a molecule formed via oxidative ] of 2 other ] groups in '']'' and '']'' species.<ref>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}}</ref> |
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=== Dimerization === |
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It is ]-catalyzed dimerized to ] in '']''.<ref>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}}</ref><ref>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}}</ref> |
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=== Uses === |
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It has an extremely weak basic(essentially neutral) compound. The compound shows anti-herpesvirus properties. |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Ellagitannin}} |
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{{Hydrolysable tannin}} |
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] |
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] |
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] |
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] |
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{{polyphenol-stub}} |
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{{aromatic-stub}} |