A triterpenoid with diverse biological activities
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Cucurbitacin IIa

Item No. 37371

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2β,3α,9β,10α,16α)-25-(acetyloxy)-2,3,16,20-tetrahydroxy-9-methyl-19-norlanost-5-ene-11,22-dione
CAS Number
58546-34-2
Synonyms
  • Dihydrocucurbitacin Q1
  • Hemslecin A
Molecular Formula
C32H50O8
Formula Weight
562.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
SMILES
C[C@]12[C@@]([C@]([C@@](C(CCC(C)(C)OC(C)=O)=O)(C)O)([H])[C@@H](C1)O)(CC([C@@]3([C@@]2([H])CC=C4[C@@]3([H])C[C@@H]([C@H](C4(C)C)O)O)C)=O)C
InChi Code
InChI=1S/C32H50O8/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/h10,19-22,25-26,34-35,38-39H,11-16H2,1-9H3/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
InChi Key
LKYNAQSYQLFTCM-GYXNDICUSA-N
Origin
Plant/Hemsleya amabilis Diels
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Cucurbitacin IIa is a triterpenoid that has been found in H. amabilis and has diverse biological activities. 1,2,3 It decreases the proliferation of (IC50 = 370 nM), and induces cell cycle arrest at the G2/M phase and apoptosis in, HT-29 colorectal adenocarcinoma cells when used at a concentration of 1 µM.1 Cucurbitacin IIa (2.5 µM) induces cell cycle arrest at the G0/G1 phase in LPS-stimulated, but not unstimulated, RAW 264.7 macrophages.2 In vivo, cucurbitacin IIa (5 mg/kg) decreases immobility time in the forced swim test and the tail suspension test in a mouse model of intermittent unpredictable stress.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, W., Yang, H., Li, Y., et al. Identification of 16,25- O-diacetyl-cucurbitane F and 25- O-acetyl-23,24-dihydrocucurbitacin F as novel anti-cancer chemicals. R. Soc. Open Sci. 5(8), 180723 (2018).

    2. He, J., Wang, Y., Xu, L.H., et al. Cucurbitacin IIa induces caspase-3-dependent apoptosis and enhances autophagy in lipopolysaccharide-stimulated RAW 264.7 macrophages. Int. Immunopharmacol. 16(1), 27-34 (2013).

    3. Zhou, S.M., Guan, S.Y., Yang, L., et al. Cucurbitacin IIa exerts antidepressant-like effects on mice exposed to chronic unpredictable mild stress. Neuroreport 28(5), 259-267 (2017).