Jump to content

Cucurbitacin E

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by The chemistds (talk | contribs) at 14:54, 17 February 2016 (added CSID and InChI(Key)s). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Cucurbitacin E
Skeletal structure of Cucuribitacin E
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.463 Edit this at Wikidata
UNII
  • InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
    Key: NDYMQXYDSVBNLL-MUYMLXPFSA-N
  • InChI=1/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
    Key: NDYMQXYDSVBNLL-MUYMLXPFBV
  • CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)C)O)O
Properties
C32H44O8
Molar mass 556.76 g/mol
Density 1.249 g/cm3
Melting point 228 to 232 °C; 442 to 449 °F; 501 to 505 K
Boiling point 712.47 °C; 1,314.45 °F; 985.62 K
Hazards
Flash point 497.45 °C (927.41 °F; 770.60 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 consisting of a tetracyclic triterpene. Specific changes on this molecule under certain conditions can generate other types of Cucurbitacins such as Cucurbitacin I, J, K and L.

Nowadays it is being highly investigated because it has been discovered that this molecule has a wide range of biological properties that could help treating many diseases.


Cucumbers belong to the family Cucurbitaceae
Watermelons are a rich source of Cucurbitacin E

Properties

  • Anti-inflammatory.
  • Inhibition of the tumor growth through inhibiting tumor angiogenesis.
  • It has also been proved that Cucurbitacin E is an activator of T-lymphocytes and its effect increases when it is associated with PHA molecule.
  • Antioxidant properties.
  • Cytotoxic effect.
  • Cytostatic effect.
  • Hepatoprotecive effect
  • Insecticide effect [1]

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 but not reactive oxygen species.

Macrophages 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's clue role is that it has a dose-dependent anti-inflammatory activity related with the inhibition of nitric oxide (an RNS) production in macrophages without affecting the viability of these cells.

As cucurbitacin E doesn't affect normal human liver cells, it could have therapeutic potencial and effective treatment for a variety of inflammation mediated diseases.[2]

Antioxidant properties

Cucurbitacin E glycoside was demonstrated as antioxidant and free-radical scavenger. 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 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 their capacity to make a scavenging effect on different free radicals: superoxide anion (O2-), hydroxyl radical (OH-) and singlet oxygen. That's relevant because not all the natural antioxidants that have been studied have strong scavenging activity against different radicals.[3]

Therefore, a strong potential could exist for CGC in treating human diseases that are linked to oxidative or free-radical damage such as atherosclerosis, cancer, Alzheimer's disease and diabetes.[4]

Cytostatic

Cucurbitacin E is an important inhibitor during the S to M phase in the cell mitosis. It causes a reduction of cell multiplication. This antiproliferation effect is caused by the cytoskeleton actin disruption induced by Cucurbitacin E.[5]

Cytotoxicity

This triterpene can inhibit the phosphorylation of the cofilin protein, a family of actin-binding proteins that disassembles actin filaments.[6][7]

Therefore, Cucurbitacin E can induce to tumoral-cell apoptosis and can also reduce cancer metastasis. It is tested that Cucurbitacin E shows cytotoxicity to:[8]

  • 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
  • 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
  • The ovarian cancer cell line S-2
  • The bladder cancer cell line T24
  • The hepatic carcinoma cell lines BEL-7402 and HepG2

Anti-angiogenesis

Cucurbitacin can also inhibit VEGFR2-mediated Jak-STAT3[8] 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

Cucurbitacin E inhibits the adhesion of cancer cells in type I collagen .[8]

Hepatoprotecive effect

Cucurbitacin-E protects hepatocytes from CCl4 (carbon tetrachloride), by reducing GPT, GOT, ALP, TP and TBIL serums.[8]

See also

References

  1. ^ 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
  2. ^ Abdelwahab, S. I.; Hassan, L. E. A.; Sirat, H. M.; Yagi, S. M. A.; Koko, W. S.; Mohan, S.; Taha, M. M. E.; Ahmad, S.; Chuen, C. S.; Narrima, P.; Rais, M. M.; Hadi, A. H. A. (2011). "Anti-inflammatory activities of cucurbitacin E isolated from Citrullus lanatus var. Citroides: Role of reactive nitrogen species and cyclooxygenase enzyme inhibition". Fitoterapia. 82 (8): 1190–1197. doi:10.1016/j.fitote.2011.08.002. PMID 21871542.
  3. ^ Tannin-Spitz, T.; Bergman, M.; Grossman, S. (2007). "Cucurbitacin glucosides: Antioxidant and free-radical scavenging activities". Biochemical and Biophysical Research Communications. 364 (1): 181–186. doi:10.1016/j.bbrc.2007.09.075. PMID 17942079.
  4. ^ Clancy, D.; Birdsall, J. (2012). "Flies, worms and the Free Radical Theory of ageing". Ageing Research Reviews. 12 (1): 404–12. doi:10.1016/j.arr.2012.03.011. PMID 22504404.
  5. ^ Zia-Ul-Haq, M; Kausar, A; Shahid, SA; Qayum, M; Ahmad, S; Khan, I (2012). "Phytopharmacological profile of Gratiola officinalis Linn.: A review" (PDF). Journal of Medicinal Plants Research. 6 (16): 3087–3092. doi:10.5897/jmpr12.172.
  6. ^ Drubin, D. G.; Lappalainen, P. (1997). "Cofilin promotes rapid actin filament turnover in vivo". Nature. 388 (6637): 78–82. doi:10.1038/40418. PMID 9214506.
  7. ^ Nakashima, S.; Matsuda, H.; Kurume, A.; Oda, Y.; Nakamura, S.; Yamashita, M.; Yoshikawa, M. (2010). "Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells". Bioorganic & Medicinal Chemistry Letters. 20 (9): 2994–2997. doi:10.1016/j.bmcl.2010.02.062. PMID 20347305.
  8. ^ a b c d Chen, X.; Bao, J.; Guo, J.; Ding, Q.; Lu, J.; Huang, M.; Wang, Y. (2012). "Biological activities and potential molecular targets of cucurbitacins". Anti-Cancer Drugs. 23 (8): 777–787. doi:10.1097/CAD.0b013e3283541384. PMID 22561419.

Further reading

Retrieved from "https://en.wikipedia.org/w/index.php?title=Cucurbitacin_E&oldid=705443972"