General Description
Cream-colored needles (from pyridine) or yellow powder. Odorless.
Reactivity Profile
ELLAGIC ACID(476-66-4) reacts as a weak acid. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated. Heat is also generated by the acid-base reaction between phenols and bases. May be sulfonated exothermically very readily (for example, by concentrated sulfuric acid at room temperature). May be nitrated very rapidly, even by dilute nitric acid.
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available; however, ELLAGIC ACID is probably combustible.
Chemical Properties
cream to light yellow crystalline solid
Application
Ellagic acid is used in medicine and cosmetics, as an antioxidant, and has anti-cancer and anti-viral effects.
Ellagic acid, a common plant polyphenol, is an inhibitor of glutathione S-transferase with Exhibits antitumor activity. It can be used for the determination of factor XIIa in plasma. Contact activation can occur in blood coagulation. It is also used as selective, ATP-competitive inhibitor of casein kinase 2 and a Topo I and II, FGR, GSK, and PKA inhibitor.
Uses
Ellagic Acid is a phenol antioxidant found naturally in various fruits and vegetables. Ellagic Acid was shown to exhibit high levels of antiproliferative and antioxidant properties in studies, which s
uggests its potential health benefits following ellagic acid consumption.
Uses
hemostatic, antineoplastic, antimutagenic
Definition
ChEBI: An organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables,
ncluding raspberries, strawberries, cranberries, and pomegranates.
Preparation
Ellagic acid is mainly extracted from plants, and it is present in several fruits such as cranberries, strawberries, raspberries, and pomegranates. Usually, the raw materials are degreasing and then extracted with an alkaline aqueous solution or extracted with ethanol. Then, after removing water-soluble proteins and gliadins, the sugar ligands can be decomposed by enzymes to obtain purer ellagic acid.
Biological Activity
Selective, ATP-competitive inhibitor of casein kinase 2 (CK2) (IC 50 values are 40, 2900, 3500, 4300 and 9400 nM for CK2, Lyn, PKA, Syk? and FGR respectively). Exhibits antioxidant, antitumor and anticarcinogenic activity and also inhibits glutathione S-transferase.
Biochem/physiol Actions
Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase. Used for the assay of factor XIIa in plasma. Contact activation in blood coagulation.
Mechanism of action
The molecular mechanism of Ellagic acid is mainly reflected in inhibiting the proliferation of tumor cells through VEGFR-2 signaling pathway, Notch signaling pathway, PKC signaling pathway and COX-2 signaling pathway. PI3K/Akt signaling pathway, JNK (cJun) signaling pathway, mitochondrial pathway, Bcl-2 / Bax signaling pathway, TGF-β/Smad3 signaling pathway induced apoptosis of tumor cells and blocked EMT process and MMP SDF1α/CXCR4 signaling pathway inhibits the metastasis and invasion of tumor cells, induces autophagy and affects tumor metabolic reprogramming to produce anti-tumor effects[1].
Anticancer Research
Ellagic acid is a naturally occurring phenolic constituent present in natural productsand nuts, most elevated amounts of which are found in raspberries (Daniel et al.1990). EA is considered as a potent anticarcinogenic and antimutagenic compound.EA shows anti-angiogenic property by repressing PDGF-R movement and phosphorylationof its substrate. It can intrude with endothelial cell-associated VEGR-2phosphorylation bringing about the restraint of the downstream signaling activatedby this receptor and in the hindrance of two key events fundamental in angiogenesis,i.e., EC movement and morphogenic separation into capillary-like structure. In parallel,EA indicated robust inhibitory activity against perivascular cells through itsrestraint of PDGF-R action and signaling prompting hindrance of VSMC relocation(Labrecque et al. 2005).
It is a phenolic compound extracted from pomegranate. It is an antiproliferative andantioxidant compound (Murakami et al. 1996). It induces apoptosis in cancer cellsof the prostate and breast and prevents the process of metastasis in different cancers(Singh et al. 2016b).
Source
Fruits including strawberries, berries, pomegranate, and nuts and seeds are rich in edible Ellagitannins (ETs), within which raspberries and cloudberries are the most abundant sources. In general, fruits of the genus Rubus are the most studied for their content in ETs and ellagic acid (EA). Among them, raspberries of different species, such as R. idaeus, R. occidentalis, and R. ursinusxidaeus, have been investigated showing an ETs/EA content ranging from 16 to 17.92 mg/g. In addition, other kinds of fruits native to tropical countries have been found to contain significant amounts of ETs and EA.[2]
Purification Methods
This antioxidant crystallises from pyridine. It forms a dark green solution in aqueous N NaOH. The tetraactetate dilactone crystallises from Ac2O, with m 340o. [Beilstein 19 H 261, 19 III/IV 3164, 19/7 V 108.]
References
[1] Lu, G., Wang, X., Cheng, M., Wang, S., Ma, K. (2023). The multifaceted mechanisms of ellagic acid in the treatment of tumors: State-of-the-art. Biomedicine & Pharmacotherapy, 165, Article 115132.
https://doi.org/10.1016/j.biopha.2023.115132[2] Mantzourani, C., Kakouri, E., Palikaras, K., Tarantilis, P., Kokotou, M. G. (2024). Urolithins and Their Precursors Ellagic Acid and Ellagitannins: Natural Sources, Extraction and Methods for Their Determination. Separations, 41 6.
https://doi.org/10.3390/separations11060174
