Geraniin

Geraniin
Names
IUPAC name
(1R,7R,8S,26R,28S,29R,38R)-1,13,14,15,18,19,20,34,35,39,39-Undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.04,38.07,26.08,29.011,16.017,22.032,37]tetraconta-3,1 1,13,15,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate
Identifiers
60976-49-0
ChemSpider 10270376
Jmol-3D images Image
PubChem 3001497
Properties
C41H28O27
Molar mass 952.64 g/mol
Density 2.26 g/mL
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Geraniin is a dehydroellagitannin found in geraniums.[1] It is found for instance in Geranium thunbergii, which is one of the most popular folk medicines and also an official antidiarrheic drug in Japan.[2] It can also be found in the rind of Nephelium lappaceum (rambutan).[3]

It mediates apoptosis by cleavage of focal adhesion kinase through up-regulation of Fas ligand expression in human melanoma cells.[1]

It is formed with one hexahydroxydiphenic acid unit, one modified hexahydroxydiphenic acid unit (dehydrohexahydroxydiphenic acid or DHHDP) and one gallic acid unit linked to a glucose molecule. It is forming an equilibrium mixture of six-membered hemi-ketal and five-membered hemi-ketal forms.[4]

Chebulagic acid is formed from geraniin through a glutathione-mediated conversion.[5]


References

  1. 1.0 1.1 Lee, Jang-Chang; Tsai, Chih-Yen; Kao, Jung-Yie; Kao, Ming-Ching; Tsai, Shih-Chang; Chang, Chih-Shiang; Huang, Li-Jiau; Kuo, Sheng-Chu et al. (2008). "Geraniin-mediated apoptosis by cleavage of focal adhesion kinase through up-regulation of Fas ligand expression in human melanoma cells". Molecular Nutrition & Food Research 52 (6): 655–63. doi:10.1002/mnfr.200700381. PMID 18435487.
  2. Luger, P.; Weber, M.; Kashino, S.; Amakura, Y.; Yoshida, T.; Okuda, T.; Beurskens, G.; Dauter, Z. (1998). "Structure of the Tannin Geraniin Based on Conventional X-ray Data at 295 K and on Synchrotron Data at 293 and 120 K". Acta Crystallographica Section B Structural Science 54 (5): 687. doi:10.1107/S0108768198000081.
  3. Rapid isolation of geraniin from Nephelium lappaceum rind waste and its anti-hyperglycemic activity. Uma D. Palanisamy, Lai Teng Ling, Thamilvaani Manaharan, and David Appleton, Food Chemistry, 1 July 2011, Volume 127, Issue 1, Pages 21–27, doi:10.1016/j.foodchem.2010.12.070
  4. Herbal Drugs in Traditional Japanese Medicine, Tsutomu Hatano, doi:10.5772/53126
  5. Glutathione-mediated conversion of the ellagitannin geraniin into chebulagic acid. Tanaka T, Kouno I and Nonaka G.I, Chemical and pharmaceutical bulletin, 1996, volume 44, no 1, pages 34-40, INIST:3003361