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| Targets |
Cucurbitacin Q1 shares mechanisms common to the cucurbitacin family, primarily targeting the JAK2/STAT3 signaling pathway and the actin cytoskeleton. Based on studies of structurally related cucurbitacin IIA (dihydrocucurbitacin Q1), the compound suppresses cancer cell expansion by disrupting the actin cytoskeleton and directing cells to undergo PARP-mediated apoptosis through inhibition of survivin downstream of JAK2/STAT3 activation . This mechanism positions cucurbitacin Q1 as a promising anticancer agent that acts through both cytoskeletal disruption and apoptosis induction pathways. The selective targeting of cancer cells over normal cells has been suggested by cytotoxicity studies showing lower toxicity to normal bronchial epithelial cells .
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| ln Vitro |
Cucurbitacin Q1 exhibits exceptionally potent in vitro cytotoxic activity against a broad panel of human cancer cell lines. In a 2024 study evaluating cucurbitacins from Aquilaria sinensis stem bark, cucurbitacin Q1 demonstrated the most potent inhibitory activity among all isolated compounds against seven cancer cell lines, with IC50 values ranging from 0.017 μM to 7.68 μM . Notably, it showed low toxicity toward normal human bronchial epithelial BEAS-2B cells (IC50 > 40 μM), indicating favorable selectivity . Additional cytotoxicity data from ChEMBL database reports GI50 values of 110.0 nM (MCF7 breast cancer), 65.0 nM (H460 lung cancer), and 87.0 nM (SF268 CNS cancer), as well as an IC50 of 540.0 nM against HT-29 colon cancer cells in a 3-day SRB assay .
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| ln Vivo |
However, related cucurbitacin compounds (such as cucurbitacin B and IIA) have demonstrated in vivo antitumor and anti-inflammatory activities in animal models. A 1973 study first isolated and characterized cucurbitacin Q1 from Cucumis prophetarum, and subsequent research has focused primarily on its in vitro characterization and natural product isolation . Direct in vivo studies are required to confirm the pharmacological effects of cucurbitacin Q1 in living systems.
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| Enzyme Assay |
For related cucurbitacin compounds, target engagement studies typically employ techniques such as Western blot analysis to assess phosphorylation levels of JAK2 and STAT3 proteins in treated cell lysates. The JAK2/STAT3 pathway has been identified as a key target for cucurbitacin IIA, a reduced derivative of cucurbitacin Q1 . For direct binding confirmation, methods such as cellular thermal shift assay (CETSA) or surface plasmon resonance (SPR) can be employed. The absence of detailed binding assay protocols in the literature suggests that such studies have not yet been extensively reported for this specific compound.
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| Cell Assay |
The cytotoxic activity of cucurbitacin Q1 has been evaluated using standard in vitro cell viability assays. Based on the methodology described in the 2024 Aquilaria sinensis study, the typical protocol involves: (1) Culturing human cancer cell lines (e.g., HGC-27 gastric cancer, A549 lung cancer, HL-60 leukemia, MDA-MB-231 breast cancer, SW480 colon cancer) in appropriate media such as RPMI-1640 or DMEM supplemented with 10% fetal bovine serum; (2) Seeding cells in 96-well plates at densities suitable for each cell line; (3) Treating cells with cucurbitacin Q1 at various concentrations (typically ranging from 0.001 to 100 μM) for 48-72 hours; (4) Assessing cell viability using the MTT or SRB colorimetric assay; (5) Measuring absorbance using a microplate reader and calculating IC50 values by regression analysis . The compound is soluble in DMSO at 65 mg/mL (115.92 mM) for stock solution preparation .
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| Animal Protocol |
For related cucurbitacin compounds, standard in vivo protocols typically involve administration via intraperitoneal injection or oral gavage in rodent models (e.g., mice or rats). For low water solubility compounds like cucurbitacin Q1 (predicted LogS = -4.46, low aqueous solubility), recommended formulation strategies may include DMSO:PEG300:Tween 80:Saline (10:40:5:45) for injection or suspension in 0.5% CMC-Na for oral administration . Doses are typically determined based on preliminary toxicity studies and pharmacokinetic profiles of related compounds.
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| ADME/Pharmacokinetics |
Based on its physicochemical properties, the compound has a molecular weight of 560.72, a predicted logP of 2.5 (moderately lipophilic), a topological polar surface area (TPSA) of 141.0 Ų, with 4 hydrogen bond donors and 8 hydrogen bond acceptors . The molecular complexity is high (1170), which may present challenges for oral absorption . Predicted LogS is -4.46, indicating low water solubility (approximately 0.0035 mg/mL) . The compound contains 10 defined stereocenters and 1 defined bond stereocenter . For in vivo formulation, solubility enhancers such as DMSO, PEG300, Tween 80, or cyclodextrins are recommended. The compound is soluble in DMSO at 65 mg/mL for stock solution preparation .
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| Toxicity/Toxicokinetics |
Regarding carcinogenicity, it is not listed by NTP, IARC Monographs, OSHA, or ACGIH . It should be emphasized that this compound is strictly for research use only and is not approved for human therapeutic use . The compound has been shown to exhibit low toxicity toward normal human bronchial epithelial BEAS-2B cells (IC50 > 40 μM), which contrasts with its potent activity against cancer cells (IC50 as low as 0.017 μM), suggesting favorable selectivity for cancer cells over normal cells . According to computational predictions from NCBS, the compound shows a Brenk violation (True), which may indicate potential toxicity concerns related to structural alerts or reactive functional groups .
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| References | |
| Additional Infomation |
- Natural Source and Isolation: Cucurbitacin Q1 was isolated from the fresh fruits of Cucumis prophetarum Jusl. AP. L. ssp. Dissectus (Naud.) Jeffery (CPJ) and from the stems and leaves of Cucumis prophetarum L. (CPL) [1].
- Co-occurrence with Derivatives: The compound was isolated as a mixture (in a 3:2 ratio) with its dihydro derivative, dihydrocucurbitacin Q1. This marked the first report of dihydrocucurbitacin Q1 in nature [1]. - Physicochemical Properties: It was obtained as a mixture of white crystals (from MeOH) with a melting point of 234-236°C. Its IR spectrum showed absorption bands at 3400 (OH), 1740, 1240 (acetate), 1690 (CO in six-membered ring), and 1635 cm⁻¹ (trans olefinic absorption conjugated with CO). The LC-MS analysis showed a molecular ion peak at m/z 578 [M⁺ + 18], corresponding to the molecular formula C₃₂H₄₈O₈ [1]. - TLC Identification: On TLC (Silica Gel G, toluene-ethyl acetate 6:4), compound 6 (the mixture of cucurbitacin Q1 and dihydrocucurbitacin Q1) showed an Rf value of 0.06. When sprayed with vanillin/phosphoric acid reagent, it appeared as a reddish-pink spot in visible light and a brick-red spot under long-range UV [1]. - Structural Features: The absence of a carbonyl in ring A was indicated by the presence of an extra oxygenated carbon. The H-3 proton was observed at δ 3.51 as a doublet, suggesting a diol system in ring A. The extra low-intensity carbon signals at δ 32.84 and 35.81 were assigned to saturated C-23 and C-24, respectively, from the dihydro derivative [1]. Reports indicate that both Elaeocarpus decipiens and Crataegus pinnatifida contain cucurbitacin Q1, and relevant data is available for reference. |
| Molecular Formula |
C32H48O8
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|---|---|
| Molecular Weight |
560.72
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| Exact Mass |
560.334
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| CAS # |
99530-82-2
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| PubChem CID |
14165733
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| Appearance |
White to off-white solid
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| LogP |
2.5
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
40
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| Complexity |
1170
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| Defined Atom Stereocenter Count |
10
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| SMILES |
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@@H]([C@H](C4(C)C)O)O)C)C)C)O)O
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| InChi Key |
LMJMTWXDWFWZHV-OBTWUPKTSA-N
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| InChi Code |
InChI=1S/C32H48O8/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/h10,12-13,19-22,25-26,34-35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
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| Chemical Name |
[(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate
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| Synonyms |
CUCURBITACIN Q1; 99530-82-2; [(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate; CUCURBITACINQ1; CHEMBL447610;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7834 mL | 8.9171 mL | 17.8342 mL | |
| 5 mM | 0.3567 mL | 1.7834 mL | 3.5668 mL | |
| 10 mM | 0.1783 mL | 0.8917 mL | 1.7834 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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