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| 5mg |
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| 10mg |
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| 25mg |
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| ln Vitro |
8-Prenylnaringenin inhibited the growth of HCT-116 cells in a time-dependent manner with IC50 values of 56.67 ± 8.2 μg/ml (24 h), 23.83 ± 2.9 μg/ml (48 h), and 19.91 ± 4.1 μg/ml (72 h) as determined by MTT assay. At similar concentrations, it showed no cytotoxic effect against non-cancerous colon CCD-841 cells. AO/PI staining revealed morphological changes characteristic of apoptosis: cells showed blebbing, greenish-orange color indicating early apoptosis, and reddish-orange color for late apoptosis, with the percentage of apoptotic/necrotic cells increasing time-dependently. Cell cycle analysis by flow cytometry showed that 8-Prenylnaringenin significantly arrested HCT-116 cells at G0/G1 phase in a time-dependent manner (24, 48, 72 h), with decreased cell numbers in S and G2 phases. Annexin V/PI assay showed that after 48 h treatment, 38.5% of cells were in early apoptosis and 14.4% in late apoptosis; after 72 h, 59.1% in early apoptosis and 14.4% in late apoptosis. Caspase activity assay revealed that 8-Prenylnaringenin significantly increased the activities of caspase-3/7, caspase-8, and caspase-9 after 48 and 72 h of treatment compared to control (p<0.05, p<0.01, p<0.0001), indicating activation of both intrinsic and extrinsic apoptotic pathways [1].
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| Cell Assay |
Cell viability was measured by MTT assay. HCT-116 and CCD-841 cells (5000 cells/well in 96-well plates) were treated with serial dilutions of 8-Prenylnaringenin (up to 100 μg/ml) for 24, 48, and 72 h at 37°C in 5% CO2. Then 20 μl MTT was added, incubated for 4 h, formazan dissolved in DMSO, and absorbance read at 570 nm. IC50 values calculated from linear plots. AO/PI double staining: 10^6 cells treated with IC50 of 8-Prenylnaringenin for 24, 48, 72 h, then stained with 10 μg/ml AO and 10 μg/ml PI, observed under fluorescence inverted microscope. Cell cycle analysis: cells treated as above, fixed with 70% ethanol overnight at -20°C, stained with 500 μl PI/RNase staining buffer for 30 min at room temperature, analyzed by BD FACSCanto II flow cytometer (15,000 events/sample), data analyzed with ModFit LT 3.0. Annexin V/PI assay: cells treated as above, suspended in 1x binding buffer (1×10^6 cells/ml), 100 μl transferred to FACS tubes, incubated with 5 μl FITC-Annexin V and 5 μl PI for 20 min at room temperature, then 400 μl 1x binding buffer added, analyzed by FACS Calibur. Caspase activity assay: HCT-116 cells (1×10^4 cells/well in white 96-well plates) treated with IC50 of 8-Prenylnaringenin for 24, 48, 72 h. Then 100 μl of Caspase-Glo 3/7, 8, or 9 reagent (containing substrate, buffer, and MG-132 inhibitor) was added, mixed at 300-500 rpm for 30 sec, incubated in dark at room temperature for 1 h, and luminescence measured using a microplate reader [1].
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| Toxicity/Toxicokinetics |
8-Prenylnaringenin at concentrations up to 100 μg/ml did not show cytotoxic effect against normal colon CCD-841 cells, indicating high selectivity for cancer cells. No other toxicity data reported [1].
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| References |
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| Additional Infomation |
Sophoraflavanone B is a trihydroxyflavonoid, consisting of (S)-naringin with an isopentenyl group linked at the 8-position. It has anti-platelet aggregation activity and is also a plant metabolite. It is a trihydroxyflavonoid, belonging to the 4'-hydroxyflavonoid class, and is also a (2S)-flavan-4-one. Functionally, it is related to (S)-naringin. It is the conjugate acid of Sophoraflavanone B(1-). 8-Isopentenylnaringin has been reported in hops, apple wood, and other organisms with relevant data.
8-Prenylnaringenin is a prenylflavonoid derived from hops and beer, with molecular weight 340.37 g/mol and purity >98%. It has been previously shown to inhibit angiogenesis in endothelial cells and induce apoptosis in MCF-7 breast cancer cells. This study demonstrates its anti-proliferative and pro-apoptotic effects on HCT-116 colon cancer cells via G0/G1 cell cycle arrest and activation of both intrinsic (caspase-9) and extrinsic (caspase-8) apoptotic pathways. The IC50 of 8-PN against HCT-116 after 48 h was 23.83 μg/ml, which is lower than that reported for Caco-2 cells (40-50 μM) [1]. |
| Molecular Formula |
C20H20O5
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|---|---|
| Molecular Weight |
340.38
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| Exact Mass |
340.131
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| CAS # |
53846-50-7
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| PubChem CID |
480764
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
597.6±50.0 °C at 760 mmHg
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| Flash Point |
216.4±23.6 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.642
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| LogP |
5.28
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
25
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| Complexity |
504
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
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| InChi Key |
LPEPZZAVFJPLNZ-SFHVURJKSA-N
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| InChi Code |
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
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| Chemical Name |
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
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| Synonyms |
Sophoraflavanone B YS04 Flavaprenin 8-Prenylnaringenin 8 Prenylnaringenin 8Prenylnaringenin
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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) |
DMSO : ~250 mg/mL (~734.49 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.11 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 20.8 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: ≥ 2.08 mg/mL (6.11 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 20.8 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: ≥ 2.08 mg/mL (6.11 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 | 2.9379 mL | 14.6895 mL | 29.3789 mL | |
| 5 mM | 0.5876 mL | 2.9379 mL | 5.8758 mL | |
| 10 mM | 0.2938 mL | 1.4689 mL | 2.9379 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT03140397 | COMPLETED | Dietary Supplement: Placebo Dietary Supplement: 6-prenylnaringenin Dietary Supplement: 8-prenylnaringenin |
Immune Cells Activity Pharmacokinetics After Oral Intake Safety After Oral Intake |
University of Hohenheim | 2016-01 | Early Phase 1 |
| NCT05524714 | COMPLETED | Dietary Supplement: solubilized Xanthohumol low dose Dietary Supplement: solubilized Xanthohumol high dose Dietary Supplement: native Xanthohumol low dose Dietary Supplement: native Xanthohumol high dose |
Plasmakinetics of Xanthohumol | University of Bonn | 2022-08-01 | Not Applicable |
| NCT02848430 | COMPLETED | Dietary Supplement: Humulus lupulus | Food-Drug Interactions | University of Illinois at Chicago | 2016-08-15 | Not Applicable |
| NCT03735420 | ACTIVE, NOT RECRUITINGWITH RESULTS | Drug: Xanthohumol Drug: Placebo oral capsule |
Healthy | National University of Natural Medicine | 2019-08-12 | Phase 1 |
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