CUCURBITACIN I Chemical Properties

Melting point:

148-150°C

Boiling point:

698.3±55.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

≥22.45 mg/mL in DMSO; insoluble in EtOH; ≥51.2 mg/mL in H2O with ultrasonic

form 

solid

pka

8.51±0.70(Predicted)

color 

white to off-white

LogP

2.330 (est)

Safety Information

Hazard Codes 

Xi,T+

Risk Statements 

25-28

Safety Statements 

1-22-45-36/37-28

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

RTECS 

RC6200000

Toxicity

LD50 oral in mouse: 5mg/kg

CUCURBITACIN I Usage And Synthesis

Description

Cucurbitacin I is a naturally occurring tetracyclic triterpenoid compound with a variety of physiological effects, including induction of apoptosis and blockade of cell cycle progression in various cancer cells. It has also been shown to have anti-angiogenic activity. Cucurbitacin I inhibits the phosphorylation of vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1, which are key regulators of endothelial cell function and angiogenesis. Therefore, Cucurbitacin I is considered a potential angiogenesis inhibitor candidate for cancer therapy^[1].

Uses

Cucurbitacin I can be useful in the study of edible vitalmelon fruit extract and adipogenesis.

Definition

ChEBI: Cucurbitacin I is a cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22. It has a role as a plant metabolite and an antineoplastic agent. It is a cucurbitacin and a tertiary alpha-hydroxy ketone.

Biological Activity

Selective inhibitor of STAT3/JAK2 signaling. Inhibits the activation of STAT3 and JAK2 and displays no activity on Src, Akt, ERK and JNK. Suppresses phosphotyrosine levels of STAT3, inhibits STAT3 DNA binding and STAT3-mediated gene expression. Induces apoptosis in cell lines expressing constitutively active tyrosine-phosphorylated STAT3.

Biochem/physiol Actions

Cucurbitacin I (JSI-124) is a novel selective inhibitor of the janus kinase 2/signal transducer and activator of transcription 3 (JAK2/STAT3) signaling pathway with anti-proliferative and anti-tumor properties.

storage

Store at -20°C

References

[1] HYEON JIN KIM Jin K K. Antiangiogenic effects of cucurbitacin-I[J]. Archives of Pharmacal Research, 2014. DOI:10.1007/s12272-014-0386-5.
blaskovich ma, sun j, cantor a et al.  discovery of jsi-124 (cucurbitacin i), a selective janus kinase/signal transducer and activator of transcription 3 signaling pathway inhibitor with potent antitumor activity against human and murine cancer cells in mice.cancer res. 2003 mar 15;63(6):1270-9.yu h, lee h, herrmann a et al. revisiting stat3 signalling in cancer: new and unexpected biological functions.nat rev cancer. 2014 nov;14(11):736-46. doi: 10.1038/nrc3818.song j, liu h, li z et al.  cucurbitacin i inhibits cell migration and invasion and enhances chemosensitivity in colon cancer. oncol rep. 2015 apr;33(4):1867-71. qi j, xia g, huang cr et al.  jsi-124 (cucurbitacin i) inhibits tumor angiogenesis of human breast cancer through reduction of stat3 phosphorylation. am j chin med. 2015;43(2):337-47.kim hj, kim jk et al. antiangiogenic effects of cucurbitacin-i. arch pharm res. 2015 feb;38(2):290-8. yuan g, yan sf, xue h et al.  cucurbitacin i induces protective autophagy in glioblastoma in vitro and in vivo. j biol chem. 2014 apr 11;289(15):10607-19.

CUCURBITACIN I(2222-07-3)Related Product Information

• 2-Allylcyclohexanone
• 1,2-Cyclohexanedione
• Menthone
• 2-TERT-BUTYLPROPANE-1,3-DIOL
• CUCURBITACIN I
• 2,6,8-TRIMETHYL-4-NONANONE
• ADOXAL
• FITONE
• 2,6-Dimethyl-5-heptenal
• 2-Hydroxyhexanedial
• Cucurbitacin IIb
• Cucurbitacin C
• CUCURBITACIN D,CUCURBITACIN D WITH HPLC
• CUCURBITACIN IIA
• CUCURBITACIN D(SH)
• CUCURBITACIN E hplc,CUCURBITACIN E WITH HPLC,CUCURBITACIN E(SH),CUCURBITACIN E
• Cucurbitacin Ia,Cucurbitacin F-25-acetate
• Cucurbitacin F