Cucurbitacin E
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Cucurbitacin E is a biochemical compound from the family of cucurbitacins. These are found in plants which are member of the family Cucurbitaceae, most of them coming from traditional Chinese medicinal plants, but also in other plants such as pumpkins and gourds. Cucurbitacin E is a highly oxidated
steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...
consisting of a tetracyclic triterpene. Specific modifications in this molecule under certain conditions can form other types of cucurbitacins such as cucurbitacin I, J, K and L. , it is being investigated for its potential biological effects. Cucurbitacin E has been found to increase activity of anti-cancer drugs in certain types of cancers. It selectively increases
chemosensitivity A chemosensitivity assay is a laboratory test that measures the number of tumor cells that are killed by chemotherapy. The test is done after the tumor cells are removed from the body. A chemosensitivity assay may help in choosing the best drug o ...
of nutrient receptors, on or inside cancer cells, to anti-cancer drug molecules, thereby decreasing binding of the nutrients to cancer cells, and decreasing their growth, leading to selective cell death of cancer cells.


Research


Anti-inflammatory

Cucurbitacin E anti-inflammatory activities are proved in vivo and in vitro. It is useful in the treatment of inflammation because of the inhibition of cyclooxygenase and reactive nitrogen species (RNS) but not reactive oxygen species (ROS).
Macrophage Macrophages (abbreviated as M φ, MΦ or MP) ( el, large eaters, from Greek ''μακρός'' (') = large, ''φαγεῖν'' (') = to eat) are a type of white blood cell of the immune system that engulfs and digests pathogens, such as cancer cel ...
s are responsible for the production of various cytokines, RNS and ROS, growth factors and chemokines as a response to activation signal such as chemical mediators, cytokines and lipopolysaccharide. Although these molecules have an important role, they can also have damaging effects, like some RNS. Cucurbitacin possesses dose-dependent anti-inflammatory activity related to its inhibition of
nitric oxide Nitric oxide (nitrogen oxide or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes denoted by a dot in its che ...
(an RNS) production in macrophages without affecting the viability of these cells. As cucurbitacin E doesn't affect normal human liver cells, it may have therapeutic potential and effective treatment for a variety of inflammation mediated diseases.


Antioxidant

Cucurbitacin E glycoside has demonstrated
antioxidant Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricant ...
and free-radical scavenging properties. Its antioxidant and free-radical scavenging properties were measured by the ability of cucurbitacin glycoside combination (CGC), a combination of cucurbitacin B and E glycosides, to reduce
ABTS In biochemistry, ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) is a chemical compound used to observe the reaction kinetics of specific enzymes. A common use for it is in the enzyme-linked immunosorbent assay (ELISA) to detect the ...
cation to its original form and also the capacity to inhibit MDA formation originated in the oxidation of linoleic acid. Using electron paramagnetic resonance, it was confirmed that CGC had antioxidant properties because of its capacity for scavenging free radicals, such as: superoxide anion (O2-), hydroxyl radical (OH-) and singlet oxygen. Not all natural antioxidants have strong free-radical scavenging properties against multiple free-radicals. CGC is being investigated as a treatment for human diseases that are linked to oxidative or free-radical damage such as atherosclerosis, cancer, Alzheimer's disease and diabetes.


Cytostatic

Cucurbitacin E is an inhibitor during the S to M phase in the cell mitosis. It causes a reduction of cell multiplication.


Cytotoxicity

This triterpene can inhibit the
phosphorylation In chemistry, phosphorylation is the attachment of a phosphate group to a molecule or an ion. This process and its inverse, dephosphorylation, are common in biology and could be driven by natural selection. Text was copied from this source, wh ...
of the cofilin protein, a family of actin-binding proteins that disassembles actin filaments. Cucurbitacin E shows cytotoxicity to: * The colon cancer cell line HCT-116 * The lung cancer cell line NCI-H460 * The breast cancer cell lines MCF-7 and
ZR-75-1 ZR-75-1 is a human breast cancer cell line An immortalised cell line is a population of cells from a multicellular organism which would normally not proliferate indefinitely but, due to mutation, have evaded normal cellular senescence and ins ...
* The central nervous system tumor cell line SF-268 * The oral epidermoid carcinoma cell line KB * The cervical cancer cell line HeLa * The fibrosarcoma cell line HT1080 * The acute leukemia cell lines U937 and HL-60 * The prostate cancer cell lines PC, LNCaP and DU145 * The pancreatic cancer cell line
Panc-1 PANC-1 is a human pancreatic cancer cell line isolated from a pancreatic carcinoma of Ductal cells, ductal cell origin. PANC-1 was derived from the tissue of a 56-year-old male. The cells can metastasis, metastasize but have poor differentiation a ...
* The ovarian cancer cell line S-2 * The bladder cancer cell line T24 * The hepatic carcinoma cell lines BEL-7402 and
HepG2 Hep G2 (or HepG2) is a human liver cancer cell line. Hep G2 is an immortal cell line which was derived in 1975 from the liver tissue of a 15-year-old Caucasian male from Argentina with a well-differentiated hepatocellular carcinoma. T ...


Anti-angiogenesis

Cucurbitacin can also inhibit VEGFR2-mediated Jak-STAT3 and MAPK signaling pathways. Anti-angiogenesis property of cucurbitacin E was demonstrated in vitro but also in vivo in a chick embryo chorioallantoic membrane and in a mouse corneal angiogenesis model.


Anti-invasion and anti-metastasis

In vitro, cucurbitacin E inhibits the adhesion of cancer cells in type I collagen.


Hepatoprotecive effect

In vitro, cucurbitacin E protects hepatocytes from CCl4 (
carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...
), by reducing GPT, GOT, ALP, TP and TBIL serums.


Insecticide

Curcurbitacin E has insecticidal effects against the aphid ''
Aphis craccivora ''Aphis craccivora'', variously known as the cowpea aphid, groundnut aphid or black legume aphid, is a true bug in the family ''Aphididae''. Originally of probable Palearctic origin, it is now an invasive species of cosmopolitan distribution. ...
''.Torkey, H.M., Abou-Yousef, H.M., Abdel Azeiz, A.Z. and Hoda, E.A. Farid. Insecticidal Effect of Cucurbitacin E Glycoside Isolated from Citrullus colocynthis Against Aphis craccivora. Australian Journal of Basic and Applied Sciences 2009; 3(4): 4060-4066


See also

* Angiogenesis * Hepatocyte * Glycoside * JAK-STAT signaling pathway


References


External links

* http://www.chemicalbook.com/ChemicalProductProperty_EN_CB3372306.htm * https://web.archive.org/web/20120426084358/http://home.ncifcrf.gov/mtdp/Catalog/compounds/106399.html * http://www.chemblink.com/products/18444-66-1.htm


Further reading

* * * {{cite journal , url=http://www.romj.org/2012-0203 , last1=Navolokin, first1=NA , last2=Polukonova, first2=NV , last3=Maslyakova, first3=GN , last4=Bucharskaya, first4=AB , last5=Durnova, first5=NA , title=Effect of extracts of Gratiola officinalis and Zea mays on the tumor and the morphology of the internal organs of rats with transplanted liver cancer , journal=Russian Open Medical Journal , year=2012 , volume=1 , issue=2, page=0203, doi=10.15275/rusomj.2012.0203, doi-access=free Steroids