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Cucurbitacin E

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Cucurbitacin E
Skeletal structure of Cucuribitacin E
Names
IUPAC name
(23E)-2,16α,20-Trihydroxy-3,11,22-trioxo-19-nor-9β,10α-lanosta-1,5,23-dien-25-yl acetate
Systematic IUPAC name
(3E,6R)-6-[(1R,2R,3aS,3bS,9aR,9bR,11aR)-2,8-Dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-2,3,3a,3b,4,6,7,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2-methyl-5-oxohept-3-en-2-yl acetate
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 556.696 g·mol−1
Density 1.249 g/cm3
Melting point 228 to 232 °C; 442 to 449 °F; 501 to 505 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.

It is being investigated for its potential biological effects.

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

Research

Anti-inflammatory

Cucurbitacin E anti-inflammatory activities are proved in vivo and in vitro.[citation needed] 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).[citation needed]

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.[citation needed] Although these molecules have an important role, they can also have damaging effects, like some RNS.[citation needed] Cucurbitacin possesses dose-dependent anti-inflammatory activity related to its inhibition of nitric oxide (an RNS) production in macrophages without affecting the viability of these cells.[citation needed]

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.[1]

Antioxidant

Cucurbitacin E glycoside has demonstrated antioxidant 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 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.[2]

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.[3]

Cytostatic

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

Cytotoxicity

This triterpene can inhibit the phosphorylation of the cofilin protein, a family of actin-binding proteins that disassembles actin filaments.[4][5]

Cucurbitacin E shows cytotoxicity to:[6]

  • 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[dubious – discuss]
  • 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[6] 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.[citation needed]

Anti-invasion and anti-metastasis

In vitro, cucurbitacin E inhibits the adhesion of cancer cells in type I collagen.[6]

Hepatoprotecive effect

In vitro, cucurbitacin E protects hepatocytes from CCl4 (carbon tetrachloride), by reducing GPT, GOT, ALP, TP and TBIL serums.[6]

Insecticide

Curcurbitacin E has insecticidal effects against the aphid Aphis craccivora.[7]

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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. S2CID 23139852.
  4. ^ Drubin, D. G.; Lappalainen, P. (1997). "Cofilin promotes rapid actin filament turnover in vivo". Nature. 388 (6637): 78–82. Bibcode:1997Natur.388R..78L. doi:10.1038/40418. PMID 9214506. S2CID 205027806.
  5. ^ 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.
  6. ^ 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. S2CID 30016950.
  7. ^ 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

Further reading

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