Geraniin
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Geraniin is a dehydro
ellagitannin image:Castalagin.svg, 130px, Castalagin is a representative ellagitannin, characterized by coupled gallic acid substituents The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative link ...
found in
geranium ''Geranium'' is a genus of 422 species of annual, biennial, and perennial plants that are commonly known as geraniums or cranesbills. They are found throughout the temperate regions of the world and the mountains of the tropics, with the gre ...
s. 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. It can also be found in the rind of ''
Nephelium lappaceum Rambutan ( ; ; ''Nephelium lappaceum'') is a medium-sized tropical tree in the family Sapindaceae. The name also refers to the edible fruit produced by this tree. The rambutan is native to Southeast Asia. It is closely related to several other ed ...
'' (rambutan). It mediates
apoptosis Apoptosis (from ) is a form of programmed cell death that occurs in multicellular organisms and in some eukaryotic, single-celled microorganisms such as yeast. Biochemistry, Biochemical events lead to characteristic cell changes (Morphology (biol ...
by cleavage of
focal adhesion kinase PTK2 protein tyrosine kinase 2 (PTK2), also known as focal adhesion kinase (FAK), is a protein that, in humans, is encoded by the ''PTK2'' gene. PTK2 is a focal adhesion-associated protein kinase involved in cellular adhesion (how cells stick to ...
through up-regulation of
Fas ligand Fas ligand (FasL, also known as CD95L or Apo-1L) is a type-II transmembrane protein in the tumor necrosis factor (TNF) superfamily. It binds to the Fas receptor (CD95) to induce apoptosis, and also activates non-apoptotic pathways such as NF-κB ...
expression in human
melanoma Melanoma is the most dangerous type of skin cancer; it develops from the melanin-producing cells known as melanocytes. It typically occurs in the skin, but may rarely occur in the mouth, intestines, or eye (uveal melanoma). In very rare case ...
cells. Geraniin has also been shown to possess immunomodularity properties, as it inhibits
tumor necrosis factor-alpha Tumor necrosis factor (TNF), formerly known as TNF-α, is a chemical messenger produced by the immune system that induces inflammation. TNF is produced primarily by activated macrophages, and induces inflammation by binding to its receptors o ...
, and
NF-κB Nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) is a family of transcription factor protein complexes that controls transcription (genetics), transcription of DNA, cytokine production and cell survival. NF-κB is found i ...
in ovarian cancer cells. 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. It is formed with one
hexahydroxydiphenic acid Hexahydroxydiphenic acid is an organic compound with the formula HO)3C6HCO2Hsub>2. It is the oxidatively coupled derivative of gallic acid It is a white solid, although samples are typically brown owing to oxidation. Occurrence left, 142px, ...
unit, one modified hexahydroxydiphenic acid unit (
dehydrohexahydroxydiphenic acid Dehydrohexahydroxydiphenic acid is a group found in dehydroellagitannins. It is formed from hexahydroxydiphenic acid (HHDP) through oxidation of the plant hydrolysable tannins.Correlation of oxidative transformations of hydrolyzable tannins and pla ...
or DHHDP) and one
gallic acid Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plant ...
unit linked to a
glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...
molecule. It is forming an equilibrium mixture of six-membered hemi-ketal and five-membered hemi-ketal forms.
Chebulagic acid Chebulagic acid is a benzopyran tannin and an antioxidant that has many potential uses in medicine. It has been found to be immunosuppressive, hepatoprotective, and a potent alpha-glucosidase inhibitor, a human gut enzyme useful in diabetic studi ...
is formed from geraniin through a
glutathione Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources ...
-mediated conversion.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,


References

{{ellagitannin Dibenzofurans Ellagitannins