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| Targets |
8-Prenylnaringenin has multiple biological targets and is known to have anti-cancer, anti-bacterial, and anti-inflammatory properties. As a phytoestrogen, it can interact with estrogen receptors. It also functions as a platelet aggregation inhibitor. Its diverse activities are attributed to its ability to modulate various signaling pathways, including those involved in apoptosis and cell proliferation.
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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].
In vitro, 8-Prenylnaringenin has demonstrated significant anti-proliferative activity against HCT-116 colon cancer cells. It induces apoptosis through both the intrinsic and extrinsic pathways. It also exhibits cytotoxicity, anti-bacterial, and anti-inflammatory properties, making it a versatile compound for studying multiple disease pathways. |
| ln Vivo |
In vivo, 8-Prenylnaringenin, as a naturally occurring flavonoid, may contribute to the health benefits associated with the consumption of hops and other plants. Its anti-inflammatory and anti-cancer activities suggest potential for therapeutic applications. However, specific in vivo efficacy data in animal models are not extensively detailed in the provided literature.
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| Enzyme Assay |
In vitro cytotoxicity assays for 8-Prenylnaringenin are typically performed using cancer cell lines such as HCT-116 colon cancer cells. Cells are treated with varying concentrations of the compound for a defined period (e.g., 24-72 hours). Cell viability is then measured using an MTT or SRB assay, and the IC₅₀ is calculated. Apoptosis can be assessed by measuring caspase-3/7 activity or by flow cytometry.
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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].
In vitro cell-based assays for 8-Prenylnaringenin often use cancer cell lines to assess its anti-proliferative and pro-apoptotic effects. Cells are cultured in appropriate media and treated with the compound. The effects on cell viability, apoptosis, and cell cycle progression are measured using standard assays such as MTT, Annexin V/PI staining, and propidium iodide staining. |
| Animal Protocol |
In vivo animal studies for 8-Prenylnaringenin would typically involve using mouse xenograft models to test its anti-cancer efficacy. Immunodeficient mice are injected with cancer cells (e.g., HCT-116) to establish tumors. Once tumors reach a certain size, mice are treated with 8-Prenylnaringenin, often via intraperitoneal injection. Tumor growth is measured over time to assess the compound's efficacy.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic properties of 8-Prenylnaringenin, such as half-life and bioavailability, are not extensively detailed in the available literature. As a flavonoid, it is likely to be metabolized in the liver and excreted in urine and bile. It is soluble in DMSO.
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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].
Comprehensive toxicological data for 8-Prenylnaringenin are not available in the provided text. As a naturally occurring compound, it is expected to have a moderate safety profile, but it should be handled with standard laboratory precautions. It is intended for research purposes only. |
| 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]. 8-Prenylnaringenin is a prenylflavonoid isolated from hops. It has anti-proliferative activity against cancer cells and induces apoptosis. It also exhibits anti-inflammatory and anti-bacterial properties. This product is for research use only. |
| 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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