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{{short description|Chemical compound}}
{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 400994760
| verifiedrevid = 441141120
| Name = Grandinin
| Name = Grandinin
| ImageFile = Grandinin.PNG
| ImageFile = Grandinin.PNG
| ImageSize = 200px
| ImageName = Chemical structure of grandinin
| ImageName = Chemical structure of grandinin
| IUPACName =
| IUPACName =
| OtherNames = <!-- <br> -->
| OtherNames = <!-- <br> -->
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 115166-32-0
| CASNo = 115166-32-0
| CASNo_Ref =
| CASNoOther =
| CASOther =
| PubChem = 492392
| PubChem = 492392
| 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
| 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 =
| MeSHName =
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>46</sub>H<sub>34</sub>O<sub>30</sub>
| C=46 | H=34 | O=30
| MolarMass = 1066.74 g/mol
| ExactMass = 1066.11349 u
| Appearance =
| Appearance =
| Density =
| Density =
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}}
}}
}}
}}
'''Grandinin''' is an [[ellagitannin]]. It can be found in ''[[Melaleuca quinquenervia]]'' 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 (''[[Quercus alba]]'') and European red oak (''[[Quercus robur]]'').<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, [[red wine|red]]<ref>{{Cite journal
'''Grandinin''' is an [[ellagitannin]]. It can be found in ''[[Melaleuca quinquenervia]]'' leaves and in [[oak]]s.<ref>[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TG8-4117RPC-5&_user=10&_coverDate=09%2F01%2F2000&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=c2962d1d19188ce7ca9ab1fe9797bc92 Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. Pirjo Mämmelä, Heikki Savolainenb, Lasse Lindroosa, Juhani Kangasd and Terttu Vartiainen, Journal of Chromatography A, Volume 891, Issue 1, 1 September 2000, Pages 75-83]</ref> It shows antioxydant activity.<ref>[http://www3.interscience.wiley.com/journal/104552050/abstract?SRETRY=0 Polyphenols of Melaleuca quinquenervia leaves - pharmacological studies of grandinin. Moharram F. A., Marzouk M. S., El-Toumy S. A. A., Ahmed A. A. E. and Aboutabl E. A., Phytotherapy Research, Volume 17 Issue 7, Pages 767 - 773]</ref> It is a [[castalagin]] glycoside<ref>[http://cat.inist.fr/?aModele=afficheN&cpsidt=20325664 Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells. Fridrich D., Glabasnia A., Fritz J., Esselen M., Pahlke G., Hofmann T. and Marko D., Journal of agricultural and food chemistry, 2008, vol. 56, no9, pp. 3010-3015]</ref> by binding of the pentose [[lyxose]].<ref>[http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2597504/ Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose, Castalagin and Grandinin. Hofmann T., Glabasnia A., Schwarz B., Wisman K. N., Gangwer K. A. and Hagerman A. E., J Agric Food Chem., 2006 December 13, 54(25), pp. 9503–9509]</ref>
| last1 = García-Estévez | first1 = I.
| last2 = Escribano-Bailón | first2 = M. T.
| last3 = Rivas-Gonzalo | first3 = J. N. C.
| last4 = Alcalde-Eon | first4 = C.
| title = Development of a fractionation method for the detection and identification of oak ellagitannins in red wines
| doi = 10.1016/j.aca.2009.10.020
| journal = Analytica Chimica Acta
| volume = 660
| issue = 1–2
| pages = 171–176
| year = 2010
| pmid = 20103159
| bibcode = 2010AcAC..660..171G
| hdl = 10366/141103
| hdl-access = free
}}</ref> or [[white wine|white]],<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> [[wine ageing|aged]] in oak barrels.


It is a [[castalagin]] 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 [[lyxose]].<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 [[nonahydroxytriphenic acid]] moiety.
==Reference==

It suppresses the [[phosphorylation]] of the [[epidermal growth factor receptor]] in human [[colon carcinoma]] cells.<ref name=Fridrich/>

== See also ==
* [[Phenolic compounds in wine]]

== References ==
{{reflist}}
{{reflist}}



{{Ellagitannin}}
{{Ellagitannin}}
{{Growth factor receptor modulators}}


[[Category:Ellagitannins]]
[[Category:Ellagitannins]]
[[Category:Astringent flavors]]

[[Category:Receptor tyrosine kinase inhibitors]]
{{Natural-phenol-stub}}
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