2222-07-3

Basic information

• Product Name: CUCURBITACIN I
• Synonyms: 1,2-dehydroelatericina;19-nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione,9-methyl-2,16,20,2;5-tetrahydroxy-;cucurbitacine(i);ELATERICIN B;ELATERIN B;CUCURBITACIN I;JSI-124
• CAS NO: 2222-07-3
• Molecular Formula: C₃₀H₄₂O₇
• Molecular Weight: 514.65
• EINECS: 218-736-8
• Product Categories: Tri-Terpenoids;Herb extract;API;Inhibitor
• Mol File: 2222-07-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 148-150°C
• Boiling Point: 716.9 °C at 760 mmHg
• Flash Point: 401.3 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 1.5E-22mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: −20°C
• Solubility: ≥22.45 mg/mL in DMSO; insoluble in EtOH; ≥51.2 mg/mL in H2O with ultrasonic
• PKA: 8.51±0.70(Predicted)
• CAS DataBase Reference: CUCURBITACIN I(CAS DataBase Reference)
• NIST Chemistry Reference: CUCURBITACIN I(2222-07-3)
• EPA Substance Registry System: CUCURBITACIN I(2222-07-3)

Safety Data

• Hazard Codes: Xi,T+
• Statements: 25-28
• Safety Statements: 1-22-45-36/37-28
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: RC6200000
• Hazardous Substances Data: 2222-07-3(Hazardous Substances Data)

Usage

Description

CUCURBITACIN I is a type of cucurbitacin, which is a group of tetracyclic triterpenoid compounds found in the Cucurbitaceae family of plants. It is characterized by the presence of hydroxy groups at positions 2, 16, 20, and 25, and oxo groups at positions 1, 11, and 22. CUCURBITACIN I exhibits various biological activities and has potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
CUCURBITACIN I is used as a pharmaceutical agent for its anti-inflammatory, antipyretic, and analgesic properties. It has been found to inhibit the production of pro-inflammatory cytokines and modulate immune responses, making it a potential candidate for the treatment of inflammatory diseases.
Used in Cancer Therapy:
CUCURBITACIN I is used as an anticancer agent due to its ability to induce apoptosis, arrest cell cycle progression, and inhibit angiogenesis in various cancer cell lines. It has shown potential against a range of cancers, including breast, lung, and prostate cancer, by targeting multiple signaling pathways and molecular targets involved in cancer development and progression.
Used in Drug Delivery Systems:
To enhance the bioavailability, solubility, and therapeutic efficacy of CUCURBITACIN I, various drug delivery systems have been developed. These systems, such as nanoparticles, liposomes, and hydrogels, aim to improve the stability, targeted delivery, and controlled release of CUCURBITACIN I, thereby enhancing its pharmacological effects and reducing side effects.
Used in Cosmetic Industry:
CUCURBITACIN I is used as an active ingredient in cosmetic products for its anti-aging and skin-whitening properties. It has been reported to inhibit the activity of tyrosinase, a key enzyme involved in melanin synthesis, thus reducing skin pigmentation and promoting a lighter skin tone.
Used in Agricultural Industry:
CUCURBITACIN I is used as a natural pesticide and insect repellent in agriculture. It has been found to possess insecticidal and repellent properties against various pests, such as aphids, whiteflies, and mosquitoes, making it a potential alternative to synthetic chemical pesticides.

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.

references

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.

InChI:InChI=1/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+

Upstream product

• 16307-33-8 cucurbitacin I 2-O-β-D-glucopyranoside 
• 18444-66-1 cucurbitacin E 
• 3877-86-9 cucurbitacin D 

Relevant articles and documents

Cucurbitacin derivatives and preparation method thereof

The invention discloses multiple new derivatives of cucurbitacin-B and cucurbitacin-E and salts of the new derivatives, and also discloses a preparation method of the new derivatives. As the new derivatives and the salts thereof have the same basic structures as cucurbitacin-B and cucurbitacin-E respectively, the nature of the new derivatives and the salts thereof is basically the same as that ofcucurbitacin-B and cucurbitacin-E, and the new derivatives and the salts thereof have good anti-cancer, anti-virus, anti-inflammation and liver protection effects with low toxic and side effects.

Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells

Cucurbitane-type triterpenes, cucurbitacins B and E, were reported to exhibit cytotoxic effects in several cell lines mediated by JAK/STAT3 signaling. However, neither compound inhibited phosphorylation of STAT3 in human leukemia (U937) cells at low concentrations. We therefore synthesized a biotin-linked cucurbitacin E to isolate target proteins based on affinity for the molecule. As a result, cofilin, which regulates the depolymerization of actin, was isolated and suggested to be a target. Cucurbitacins E and I inhibited the phosphorylation of cofilin in a concentration-dependent manner, and their effective concentrations having the same range as the concentrations at which they had cytotoxic effects in U937 cells. In addition, the fibrous-/globular-actin ratio was decreased after treatment with cucurbitacin E in HT1080 cells. These findings suggested that the inhibition of cofilin's phosphorylation increased the severing activity of cofilin, and then the depolymerization of actin was enhanced after treatment with cucurbitacin E at lower concentrations.