| Revision as of 08:44, 24 July 2011 editNono64 (talk | contribs)Autopatrolled, Pending changes reviewers, Rollbackers96,246 editsm Ellagitannin← Previous edit |
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{{short description|Chemical compound}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 400994760 |
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| verifiedrevid = 441141120 |
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| Name = Grandinin |
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| Name = Grandinin |
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| ImageFile = Grandinin.PNG |
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| ImageFile = Grandinin.PNG |
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| ImageSize = 200px |
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| ImageName = Chemical structure of grandinin |
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| ImageName = Chemical structure of grandinin |
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| IUPACName = |
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| IUPACName = |
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| OtherNames = <!-- <br> --> |
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| OtherNames = <!-- <br> --> |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 115166-32-0 |
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| CASNo = 115166-32-0 |
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| CASNo_Ref = |
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| CASNoOther = |
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| CASOther = |
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| PubChem = 492392 |
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| PubChem = 492392 |
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| SMILES = C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)C8(C(C(C(O8)CO)O)O)O)OC(=O)C9=CC(=C(C(=C9C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O |
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| SMILES = C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)C8(C(C(C(O8)CO)O)O)O)OC(=O)C9=CC(=C(C(=C9C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O |
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| MeSHName = |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>46</sub>H<sub>34</sub>O<sub>30</sub> |
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| C=46 | H=34 | O=30 |
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| MolarMass = 1066.74 g/mol |
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| ExactMass = 1066.11349 u |
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| Appearance = |
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'''Grandinin''' is an ]. It can be found in '']'' leaves<ref name=Moharram>{{cite journal | doi = 10.1002/ptr.1214 | title = Polyphenols of ''Melaleuca quinquenervia'' leaves – pharmacological studies of grandinin | date = 2003 | last1 = Moharram | first1 = F. A. | last2 = Marzouk | first2 = M. S. | last3 = El-Toumy | first3 = S. A. A. | last4 = Ahmed | first4 = A. A. E. | last5 = Aboutabl | first5 = E. A. | journal = Phytotherapy Research | volume = 17 | issue = 7 | pages = 767–773 | pmid = 12916075 }}</ref> and in oaks species like the North American white oak ('']'') and European red oak ('']'').<ref>{{Cite journal | last1 = Mämmelä | first1 = P. | last2 = Savolainen | first2 = H. | last3 = Lindroos | first3 = L. | last4 = Kangas | first4 = J. | last5 = Vartiainen | first5 = T. | title = Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry | doi = 10.1016/S0021-9673(00)00624-5 | journal = Journal of Chromatography A | volume = 891 | issue = 1 | pages = 75–83 | year = 2000 | pmid = 10999626}}</ref> It shows antioxydant activity.<ref name=Moharram/> It is an astringent compound.<ref name=Hofmann/> It is also found in wine, ]<ref>{{Cite journal |
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'''Grandinin''' is an ]. It can be found in '']'' leaves and in ]s.<ref></ref> It shows antioxydant activity.<ref></ref> It is a ] glycoside<ref></ref> by binding of the pentose ].<ref></ref> |
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| last1 = García-Estévez | first1 = I. |
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| last2 = Escribano-Bailón | first2 = M. T. |
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| last3 = Rivas-Gonzalo | first3 = J. N. C. |
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| last4 = Alcalde-Eon | first4 = C. |
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| title = Development of a fractionation method for the detection and identification of oak ellagitannins in red wines |
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| doi = 10.1016/j.aca.2009.10.020 |
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| journal = Analytica Chimica Acta |
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| volume = 660 |
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| issue = 1–2 |
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| pages = 171–176 |
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| year = 2010 |
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| pmid = 20103159 |
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| bibcode = 2010AcAC..660..171G |
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| hdl = 10366/141103 |
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| hdl-access = free |
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}}</ref> or ],<ref>{{Cite journal | last1 = Marinov | first1 = M. G. | last2 = Dimitrova | first2 = E. D. | last3 = Puech | first3 = J. -L. | title = Kinetics of ellagitannin extraction from oak wood using white wine | doi = 10.1080/09571269708718095 | journal = Journal of Wine Research | volume = 8 | pages = 29–40 | year = 1997 }}</ref> ] in oak barrels. |
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It is a ] glycoside<ref name=Fridrich>{{Cite journal | last1 = Fridrich | first1 = D. | last2 = Glabasnia | first2 = A. | last3 = Fritz | first3 = J. | last4 = Esselen | first4 = M. | last5 = Pahlke | first5 = G. | last6 = Hofmann | first6 = T. | last7 = Marko | first7 = D. | doi = 10.1021/jf073427z | title = Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells | journal = Journal of Agricultural and Food Chemistry | volume = 56 | issue = 9 | pages = 3010–3015 | year = 2008 | pmid = 18419129}}, {{INIST|20325664}}</ref> by binding of the pentose ].<ref name=Hofmann>{{Cite journal | last1 = Hofmann | first1 = T. | last2 = Glabasnia | first2 = A. | last3 = Schwarz | first3 = B. | last4 = Wisman | first4 = K. N. | last5 = Gangwer | first5 = K. A. | last6 = Hagerman | first6 = A. E. | doi = 10.1021/jf062272c | title = Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-d-glucopyranose, Castalagin, and Grandinin | journal = Journal of Agricultural and Food Chemistry | volume = 54 | issue = 25 | pages = 9503–9509 | year = 2006 | pmid = 17147439| pmc =2597504 }}</ref> It contains a ] moiety. |
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==Reference== |
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It suppresses the ] of the ] in human ] cells.<ref name=Fridrich/> |
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== See also == |
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* ] |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Ellagitannin}} |
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{{Ellagitannin}} |
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{{Growth factor receptor modulators}} |
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] |
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] |
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] |
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] |
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{{Natural-phenol-stub}} |
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