| Size | Price | Stock | Qty |
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| Targets |
Positive allosteric modulator at the α+β- interface of the GABAA receptor (IC50 for potentiation of GABA-induced [3H]EBOB displacement in native forebrain GABAA receptors: 3.7 ± 0.4 μM) [1].
Null modulator at the flumazenil-sensitive α+γ2- (classical benzodiazepine) binding interface of the GABAA receptor [1]. |
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| ln Vitro |
(2S)-6-Prenylnaringenin (6-Prenylnaringenin) demonstrates low micromolar doses of regulatory action. (2S)With an IC50 value of 3.7 μM in native GABAA receptors, -6-prenylnaringenin increases GABA-induced [3H]EBOB binding displacement in a concentration-dependent manner [1].
At 30 μM, 6-Prenylnaringenin displaced 72.9% of GABA-induced [3H]EBOB binding in rat forebrain membranes (P < 0.001) and 92.4% in rat cerebellar membranes (P < 0.001) [1]. In a concentration-dependent manner, it potentiated GABA-induced [3H]EBOB displacement with an IC50 of 3.7 ± 0.4 μM in rat forebrain membranes. At 1 μM, it displaced 35.2 ± 0.5% of [3H]EBOB binding (P < 0.001) [1]. At 30 μM, 6-Prenylnaringenin did not displace [3H]EBOB binding in the absence of GABA, indicating no direct agonist effects [1]. The positive modulation of GABA-induced [3H]EBOB displacement by 6Prenylnaringenin (5 μM) was insensitive to antagonism by flumazenil (2 μM) [1]. At 30 μM, 6-Prenylnaringenin significantly displaced [3H]flunitrazepam binding (47.1 ± 4.1%, P < 0.001) and [3H]Ro 15-4513 binding (59.4 ± 0.48%, P < 0.001) in rat forebrain membranes [1]. It showed a concentration-dependent displacement of [3H]flunitrazepam, with a calculated Ki of 16.5 μM [1]. |
| Enzyme Assay |
The [3H]EBOB binding assay was used to measure GABA-potentiating effects. Rat forebrain/midbrain and cerebellar membranes were incubated with 1 nM [3H]EBOB and various concentrations of 6-Prenylnaringenin (30 nM to 30 μM) in the presence or absence of 2 μM GABA for 2 hours at room temperature with shaking. Non-specific binding was determined with 100 μM picrotoxin. The incubation was terminated by filtration onto glass fiber filters, which were then rinsed and counted for radioactivity [1].
The [3H]flunitrazepam and [3H]Ro 15-4513 binding assays were used to examine binding to the classical benzodiazepine site. Rat forebrain membranes were incubated on ice at 4°C for 1 hour with 1 nM [3H]flunitrazepam or 2 nM [3H]Ro 15-4513 in the absence or presence of 6-Prenylnaringenin. Non-specific binding was determined with 10 μM flumazenil. The incubation was terminated by filtration onto glass fiber filters, which were then washed and counted for radioactivity [1]. |
| Toxicity/Toxicokinetics |
6-Prenylnaringenin (30 mg/kg, i.p.) had no impact on locomotor activity in mice as assessed by open field and rotarod tests in a cited external study (Sekiguchi et al., 2018) [1].
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| References | |
| Additional Infomation |
6-Isopentenylnaringenin is a trihydroxyflavanone with the structure of naringenin at the C-6 position. It is a T-type calcium channel blocker. It belongs to the trihydroxyflavanone class and is a member of the 4'-hydroxyflavanone and (2S)-flavan-4-one compounds. Its function is related to (S)-naringenin. 6-Isopentenylnaringenin has been reported in hops (Humulus lupulus), pea buds (Macaranga denticulata), and other organisms with relevant data.
6-Prenylnaringenin is an isomer of the prenylflavonoid 8-prenylnaringenin and is considered a weak phytoestrogen (< 1/100 of 8PN) [1]. It is also a potent T-type calcium channel blocker [1]. Its precursor in hops is desmethylxanthohumol (DMX), which undergoes spontaneous isomerization into 6-prenylnaringenin during brewing [1]. Despite being found in low concentrations in hops (<0.01%), it has received attention for its promising bioactivities including antifungal, antiosteoporotic, anti-proliferative, and pain-relieving properties [1]. Molecular docking studies at the GABAA receptor α1β2γ2 isoform predicted that 6-Prenylnaringenin binds at both the α1+β2- and α1+γ2- interfaces, with binding energies of -71.13 kcal/mol and -67.11 kcal/mol (MMGBSA ΔG bind), respectively [1]. The article suggests a dual mode of action for 6-Prenylnaringenin on GABAA receptors: as a positive allosteric modulator at the α+β- interface and as a null modulator at the flumazenil-sensitive α+γ2- interface [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 # |
68236-13-5
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| Related CAS # |
(2R/S)-6-PNG;68682-01-9
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| PubChem CID |
155094
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| Appearance |
White to off-white solid powder
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| Density |
1.314±0.06 g/cm3
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| LogP |
4.018
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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=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC=C(C=C3)O)O)C
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| InChi Key |
YHWNASRGLKJRJJ-KRWDZBQOSA-N
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| InChi Code |
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3/t17-/m0/s1
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| Chemical Name |
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
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| Synonyms |
6-PNYS03 6-Prenylnaringenin 6Prenylnaringenin6 Prenylnaringenin
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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 : ~100 mg/mL (~293.80 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.34 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (7.34 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 (7.34 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 |
| NCT03286777 | COMPLETED | Dietary Supplement: Placebo Dietary Supplement: Native 6-prenylnaringenin Dietary Supplement: Micellar 6-prenylnaringenin |
PBMC Activity After Native vs. Micellar 6-PN Oral Intake Pharmacokinetics of Native vs. Micellar 6-PN After Oral Intake Safety of Native vs. Micellar 6-PN After Oral Intake |
University of Hohenheim | 2017-06-22 | Not Applicable |
| 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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