Geraniin

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]

Geraniin

Chemical structure of 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
CAS Number	60976-49-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5328
ChEMBL	ChEMBL506069
ChemSpider	10270376
KEGG	C10230
PubChem CID	3001497
InChI InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2/t18-,23+,30-,32+,33-,39+,41+/m1/s1 Key: JQQBXPCJFAKSPG-SVYIMCMUSA-N
SMILES Oc1cc(cc(O)c1O)C(=O)O[C@@H]9O[C@@H]7COC(=O)c2cc(O)c(O)c(O)c2c3c(O)c(O)c(O)cc3C(=O)O[C@@H]8[C@H]9OC(=O)c4cc(O)c(O)c5O[C@@]6(O)C(=O)/C=C(\[C@@H](c45)C6(O)O)C(=O)O[C@H]78
Properties
Chemical formula	C41H28O27
Molar mass	952.64 g/mol
Density	2.26 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

Geraniin has also been shown to possess immunomodularity properties, as it inhibits tumor necrosis factor-alpha, and NF-κB in ovarian cancer cells. ^[4]

Geraniin was studied for its anticancer activity and shown to target apoptosis via inactivation of PI3K/Akt/mTOR signaling pathway involving NF-κB when treated against HT-29 human colorectal adenocarcinoma cells. ^[5]

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.^{[citation needed]}

Chebulagic acid is formed from geraniin through a glutathione-mediated conversion.^[6]