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C8499

Sigma-Aldrich

Cucurbitacin B hydrate

≥97% (HPLC)

Synonym(e):

(2β,9β,10α,16α,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-Norlanosta-5,23-diene-3,11,22-trione

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About This Item

Empirische Formel (Hill-System):
C32H46O8 · xH2O
CAS-Nummer:
Molekulargewicht:
558.70 (anhydrous basis)
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥97% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 10 mg/mL, clear

Lagertemp.

2-8°C

SMILES String

CC1(C)C([C@@H](O)C[C@]2([H])C1=CC[C@]([C@@](C[C@@H](O)[C@]3([H])[C@@](C)(O)C(/C=C/C(C)(C)OC(C)=O)=O)(C)[C@]3(C)C4)([H])[C@@]2(C)C4=O)=O

InChI

1S/C32H46O8/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/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1

InChIKey

IXQKXEUSCPEQRD-DKRGWESNSA-N

Anwendung

Cucurbitacin B hydrate has been used:
  • as a signal transducer and activator of transcription 3 (stat3) inhibitor to determine its effect on the expression of human lysosomal acid lipase (hLAL) in myeloid-derived suppressor cells (MDSCs).
  • as an ecdysone receptor (EcR) antagonist injection to lower the levels of 20-hydoxyecdysone (20E) signaling in butterflies.
  • to determine its effect on the cell viability of pancreatic cancer cell lines.

Biochem./physiol. Wirkung

Cucurbitacin B also exhibits anti-cancer activity by inhibiting telomerase and c-Myc in breast cancer. It also exhibits anti- artherosclerotic activity. Cucurbitacin B also possesses anti-inflammatory and anti-microbial activity.
Cucurbitacin B is a triterpenoid constituent of Cucurbitaceae plant species. Cucurbitacin B inhibits proliferation in a wide variety of tumor cell lines (IC50 15-30 nM) by inducing apoptosis and inducing cell cycle arrest at G2/M phase. Although the mechanism of action is unclear, Cucurbitacin B inhibits STAT 3 phosphorylation and expression levels and has been shown to block JAK2 activity. Curcubitacin B also inhibits the transcriptional activity of HIF1a and Nf-KB. Curcubitacin B is structurally similar to the JAK inhibitor Curcubitacin I.

Leistungsmerkmale und Vorteile

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the JAKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Piktogramme

Skull and crossbones

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Acute Tox. 2 Oral

Lagerklassenschlüssel

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Sumana Dakeng et al.
Journal of cellular biochemistry, 113(1), 49-60 (2011-08-26)
The cucurbitacins are tetracyclic triterpenes found in plants of the family Cucurbitaceae. Cucurbitacins have been shown to have anti-cancer and anti-inflamatory activities. We investigated the anti-cancer activity of cucurbitacin B extracted from Thai medicinal plant Trichosanthes cucumerina Linn. Cell viability
Ping Lu et al.
Cancer biotherapy & radiopharmaceuticals, 27(8), 495-503 (2012-07-04)
The aberrant activation of the JAK2/STAT3 signaling in immature myeloid dendritic cells (DCs) is associated with immune tolerance and poor antitumor immunity. The objective of this study was to test the hypothesis that Cucurbitacin B (CuB), a selective inhibitor of
Cytotoxic Effect of Bitter Melon (Momordica charantia L.) Ethanol Extract and Its Fractions on Pancreatic Cancer Cells in vitro
Richmond, et al.
Exploratory research and hypothesis in medicine, 2, 139-139 (2017)
Moltira Promkan et al.
PloS one, 8(2), e55732-e55732 (2013-02-09)
Cucurbitacin B (CuB) is one of the potential agents for long term anticancer chemoprevention. Cumulative evidences has shown that cucurbitacin B provides potent cellular biological activities such as hepatoprotective, anti-inflammatory and antimicrobial effects, but the precise mechanism of this agent
Meixia Zhang et al.
Pancreas, 39(6), 923-929 (2010-02-26)
Pancreatic cancer is a serious disease worldwide for its high mortality. Gemcitabine has become the frontline option for the treatment of this disease since its approval. However, resistance to the drug has been on the rise in recent years. Searching

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