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Picrocrocin, a monoterpene glycoside precursor of safranal, is a natural product found in the spice saffron, which comes from the crocus flower. Picrocrocin is a degradation product of the carotenoid zeaxanthin. Picrocrocin exhibits growth inhibitory effects against SKMEL- 2 human malignant melanoma cells by targeting JAK/ STAT5 signaling pathway, cell cycle arrest and mitochondrial mediated apoptosis.
| Targets |
JAK1/2, STAT5[1]
Bax and Bcl-2 (mitochondrial pathway)[1] |
|---|---|
| ln Vitro |
SK-MEL-2 melanoma cells are inhibited in their ability to proliferate by picrocrocin. Following a 24-hour incubation period, the picrocrocin IC50 against SK-MEL-2 cells was 20 μM. Apoptosis and cell cycle arrest are the causes of picrocrocin's antiproliferative action. Furthermore, in SK-MEL-2 cells, picrocrocin can lower MMP levels and increase ROS levels. In conclusion, picrocrocin suppresses the SK-MEL-2 melanoma cells' JAK/STAT5 signaling pathway [1].
Picrocrocin exhibited concentration-dependent growth inhibitory effects on SK-MEL-2 human malignant melanoma cells with an IC50 of 20 µM at 24 h incubation as determined by MTT assay (0-100 µM, 24 h)[1]. Picrocrocin induced apoptosis in SK-MEL-2 cells as shown by DAPI staining (0, 10, 20, 40 µM, 24 h), with apoptotic cell population increasing from 3.2% (control) to 56.5% at 40 µM dose, quantified by Annexin V/PI flow cytometry[1]. Picrocrocin triggered G2/M cell cycle arrest in SK-MEL-2 cells as determined by flow cytometric analysis after treatment with 0, 10, 20, 40 µM for 24 h, with the percentage of cells in G2 phase increasing dose-dependently[1]. Picrocrocin enhanced reactive oxygen species (ROS) levels in SK-MEL-2 cells up to 205% at 40 µM compared to control, measured by DCFH-DA staining and flow cytometry[1]. Picrocrocin decreased mitochondrial membrane potential (MMP) in SK-MEL-2 cells to 44% at 40 µM compared to control, measured by DiOC6 staining and flow cytometry[1]. Picrocrocin increased the protein expression of pro-apoptotic Bax and decreased anti-apoptotic Bcl-2 in a dose-dependent manner (0, 10, 20, 40 µM, 24 h) as assessed by western blotting[1]. Picrocrocin inhibited the phosphorylation of p-JAK1/2 and p-STAT5 in SK-MEL-2 cells without altering total JAK1/2 and STAT5 protein levels, as shown by western blotting[1]. |
| Cell Assay |
Cell viability assay (MTT): SK-MEL-2 cells were seeded at a density of 1×10^6 cells per well in 96-well plates and incubated for 12 h. The cells were then treated with varying concentrations of picrocrocin (0-100 µM) for 24 h. Subsequently, MTT solution (20 µL) was added to each well, followed by addition of 500 µL DMSO to solubilize formazan crystals. Absorbance was measured using an ELISA plate reader. The IC50 was determined as 20 µM[1].
Apoptosis assay (DAPI staining): SK-MEL-2 cells (1×10^6 per well in 6-well plates) were treated with 0, 10, 20, and 40 µM picrocrocin for 24 h. Cells were then stained with DAPI and examined under a fluorescence microscope to visualize apoptotic cells[1]. Apoptosis assay (Annexin V/PI flow cytometry): SK-MEL-2 cells were seeded in 6-well plates, treated with different doses of picrocrocin (0, 10, 20, 40 µM) for 24 h, harvested, washed with PBS, and then stained with Annexin V/FITC and propidium iodide (PI) for 20 min. The percentage of apoptotic cells was analyzed by flow cytometry[1]. Cell cycle analysis: Approximately 1×10^5 SK-MEL-2 cells per well in 6-well plates were allowed to adhere overnight, then treated with various doses of picrocrocin (0, 10, 20, 40 µM) for 24 h. Cell cycle phase distribution was determined by flow cytometry[1]. ROS assay: SK-MEL-2 cells (2×10^5 per well in 6-well plates) were treated with 0, 10, 20, 40 µM picrocrocin for 24 h at 37°C in 5% CO2. Cells were harvested, washed with PBS, resuspended in 500 µL of 10 µM DCFH-DA, and incubated for 30 min at 37°C in the dark. ROS levels were then measured by flow cytometry[1]. MMP assay: SK-MEL-2 cells prepared as above were resuspended in 500 µL of 1 µmol/L DiOC6 and incubated for 30 min at 37°C in the dark. Mitochondrial membrane potential (MMP) was assessed by flow cytometry[1]. Western blotting: SK-MEL-2 cells treated with picrocrocin were lysed, and protein concentration in each lysate was determined by BCA assay. Protein expression of Bax, Bcl-2, JAK1/2, p-JAK1/2, STAT5, and p-STAT5 was detected by western blotting following previously described protocols[1]. |
| References | |
| Additional Infomation |
Picrocrocin is a β-D-glucoside of β-cyclic citral and a precursor of saffron aldehyde. It is the main source of the bitterness in saffron. Its function is related to β-cyclic citral. Picrocrocin has been reported to be present in saffron (Crocus sativus), saffron (Crocus tommasinianus), and spring saffron (Crocus vernus), and relevant data are available for reference.
Melanoma is one of the lethal types of skin malignancies responsible for significant morbidity and mortality worldwide. Current chemotherapy creates many adverse effects and results are often unsatisfactory. Picrocrocin as a saffron apocarotenoid has shown antiproliferative effects against various cancer cells (e.g., cervical cancer, breast cancer, gastric adenocarcinoma) in previous studies. In this study, picrocrocin induced apoptosis via mitochondrial pathway (altered Bax/Bcl-2 ratio, increased ROS, decreased MMP), triggered G2/M cell cycle arrest, and inhibited JAK/STAT5 signaling in SK-MEL-2 melanoma cells. The authors concluded that picrocrocin may be an important lead molecule for melanoma treatment, and further in vivo evaluation and semi-synthesis of more potent derivatives are required[1]. |
| Molecular Formula |
C16H26O7
|
|---|---|
| Molecular Weight |
330.3734
|
| Exact Mass |
330.168
|
| Elemental Analysis |
C, 58.17; H, 7.93; O, 33.90
|
| CAS # |
138-55-6
|
| PubChem CID |
130796
|
| Appearance |
White to off-white solid powder
|
| Density |
1.31g/cm3
|
| Boiling Point |
520.4ºC at 760mmHg
|
| Melting Point |
196 ºC (ethyl acetate )
|
| Flash Point |
187.1ºC
|
| Vapour Pressure |
5.27E-13mmHg at 25°C
|
| Index of Refraction |
1.561
|
| LogP |
-0.5
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
23
|
| Complexity |
473
|
| Defined Atom Stereocenter Count |
6
|
| SMILES |
O([C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])[C@]1([H])C([H])([H])C(C([H])([H])[H])=C(C([H])=O)C(C([H])([H])[H])(C([H])([H])[H])C1([H])[H]
|
| InChi Key |
WMHJCSAICLADIN-WYWSWGBSSA-N
|
| InChi Code |
InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/m1/s1
|
| Chemical Name |
(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
|
| Synonyms |
Picrocrocin; Picrocrocine; Saffron-bitter;
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| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~302.69 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0269 mL | 15.1345 mL | 30.2691 mL | |
| 5 mM | 0.6054 mL | 3.0269 mL | 6.0538 mL | |
| 10 mM | 0.3027 mL | 1.5135 mL | 3.0269 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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