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Grandinin

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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 1066.74 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

References

  1. ^ a b 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
  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. doi:10.1016/j.aca.2009.10.020. 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. 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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