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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>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, {{doi|10.1002/ptr.1214}}</ref> and in oaks species like the North American white oak (''[[Quercus alba]]'') and European red oak (''[[Quercus robur]]'').<ref>{{Cite doi|10.1016/S0021-9673(00)00624-5}}</ref> It shows antioxydant activity.<ref name=Moharram/> It is a [[castalagin]] glycoside<ref name=Fridrich>{{cite doi|10.1021/jf073427z}}, {{INIST|20325664}}</ref> by binding of the pentose [[lyxose]].<ref name=Hofmann>{{Cite doi|10.1021/jf062272c}}</ref> It is an astringent compound.<ref name=Hofmann/> It is also found in wine, [[red wine|red]]<ref>{{Cite PMID|20103159}}</ref> or [[white wine|white]],<ref>{{Cite doi|10.1080/09571269708718095}}</ref> [[wine ageing|aged]] in oak barrels.
'''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
| 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.


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



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


[[Category:Ellagitannins]]
[[Category:Ellagitannins]]
[[Category:Astringent flavors]]
[[Category:Astringent flavors]]
[[Category:Receptor tyrosine kinase inhibitors]]
[[Category:Receptor tyrosine kinase inhibitors]]
[[Category:Phenolic compounds in wine]]
[[Category:Phenolic compounds found in Quercus]]

{{Natural-phenol-stub}}

Latest revision as of 14:04, 3 September 2024

Grandinin
Chemical structure of grandinin
Identifiers
3D model (JSmol)
  • 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
Properties
C46H34O30
Molar mass 1066.748 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves[1] and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).[2] It shows antioxydant activity.[1] It is an astringent compound.[3] It is also found in wine, red[4] or white,[5] aged in oak barrels.

It is a castalagin glycoside[6] by binding of the pentose lyxose.[3] It contains a nonahydroxytriphenic acid moiety.

It suppresses the phosphorylation of the epidermal growth factor receptor in human colon carcinoma cells.[6]

See also

[edit]

References

[edit]
  1. ^ a b Moharram, F. A.; Marzouk, M. S.; El-Toumy, S. A. A.; Ahmed, A. A. E.; Aboutabl, E. A. (2003). "Polyphenols of Melaleuca quinquenervia leaves – pharmacological studies of grandinin". Phytotherapy Research. 17 (7): 767–773. doi:10.1002/ptr.1214. PMID 12916075.
  2. ^ Mämmelä, P.; Savolainen, H.; Lindroos, L.; Kangas, J.; Vartiainen, T. (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A. 891 (1): 75–83. doi:10.1016/S0021-9673(00)00624-5. PMID 10999626.
  3. ^ a b Hofmann, T.; Glabasnia, A.; Schwarz, B.; Wisman, K. N.; Gangwer, K. A.; Hagerman, A. E. (2006). "Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-d-glucopyranose, Castalagin, and Grandinin". Journal of Agricultural and Food Chemistry. 54 (25): 9503–9509. doi:10.1021/jf062272c. PMC 2597504. PMID 17147439.
  4. ^ García-Estévez, I.; Escribano-Bailón, M. T.; Rivas-Gonzalo, J. N. C.; Alcalde-Eon, C. (2010). "Development of a fractionation method for the detection and identification of oak ellagitannins in red wines". Analytica Chimica Acta. 660 (1–2): 171–176. Bibcode:2010AcAC..660..171G. doi:10.1016/j.aca.2009.10.020. hdl:10366/141103. PMID 20103159.
  5. ^ Marinov, M. G.; Dimitrova, E. D.; Puech, J. -L. (1997). "Kinetics of ellagitannin extraction from oak wood using white wine". Journal of Wine Research. 8: 29–40. doi:10.1080/09571269708718095.
  6. ^ a b Fridrich, D.; Glabasnia, A.; Fritz, J.; Esselen, M.; Pahlke, G.; Hofmann, T.; Marko, D. (2008). "Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells". Journal of Agricultural and Food Chemistry. 56 (9): 3010–3015. doi:10.1021/jf073427z. PMID 18419129., INIST 20325664


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