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Desmethylxanthohumol is a naturally occuring chalcone compound extracted from hop cones (Humulus lupulus L.), acting as a powerful apoptosis inducing agent. Desmethylxanthohumol has antiplasmodial, antiproliferative, and antioxidant bioactivities.
| Targets |
Multiple cellular targets in apoptosis pathways.
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|---|---|
| ln Vitro |
Desmethylxanthohumol is a potent apoptosis-inducing agent in lymphoid leukemic cell assays; it inhibits proliferation of prostate cancer cells in vitro; it demonstrates antiplasmodial, antiproliferative, and antioxidant bioactivities; it also inhibits recombinant human hepatic CYP1A2 with an IC50 of 100 nM.
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| ln Vivo |
Not fully detailed; based on its in vitro potency, Desmethylxanthohumol is expected to show anti-tumor activity in mouse xenograft models (e.g., prostate or leukemia models) when administered intraperitoneally; further in vivo efficacy studies are required to confirm its therapeutic potential; its bioavailability may be limited due to poor water solubility.
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| Enzyme Assay |
CYP1A2 inhibition is measured in cell-free assays using recombinant human CYP1A2 enzyme and fluorogenic substrates (e.g., methoxyresorufin); after incubation with Desmethylxanthohumol, conversion to fluorescent product (resorufin) is measured; IC50 values are calculated from dose-response curves.
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| Cell Assay |
Apoptosis is assessed in lymphoid leukemic cells (e.g., Jurkat or Molt-4) cultured in RPMI-1640 medium; cells are treated with serial dilutions of Desmethylxanthohumol for 24-48 hours; apoptosis is measured by Annexin V-FITC/PI double staining and flow cytometry; caspase-3/7 activity is measured by fluorogenic substrates; anti-proliferative effects are measured by MTT or CellTiter-Glo assays.
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| Animal Protocol |
Typically, prostate cancer cells (e.g., PC-3 or LNCaP) are injected subcutaneously into immunodeficient mice to establish xenografts; when tumors reach a suitable size, Desmethylxanthohumol is administered via intraperitoneal injection daily or intermittently; tumor volume is measured twice weekly; tumors are excised at endpoint for histology and biomarker analysis.
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| ADME/Pharmacokinetics |
PK properties not fully detailed; the compound is soluble in organic solvents but has limited solubility in water, which may affect oral bioavailability; it is known to inhibit CYP1A2, suggesting potential drug-drug interactions; detailed half-life, plasma clearance, and tissue distribution have not been characterized.
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| Toxicity/Toxicokinetics |
Toxicity profile not fully described; as a natural phytochemical, it is expected to have relatively low acute toxicity; however, no formal toxicity studies in animals have been published; chronic toxicity, genotoxicity, and reproductive toxicity data are lacking.
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| References | |
| Additional Infomation |
Demethylxanthumol belongs to the chalcone class of compounds. Its structure is trans-chalcone, with hydroxyl groups substituted at the 4, 2', 4', and 6' positions, and a 3-methylbut-2-en-1-yl substituted at the 3' position. It is a plant metabolite. It belongs to the chalcone class and is also a 2-acyl-4-isopentenylphloroglucinol class of compounds. Functionally, it is related to trans-chalcone. It is the conjugate acid of demethylxanthumol (1-). Demethylxanthumol has been reported to be found in hops (Humulus lupulus), immortelle (Helichrysum dregeanum), and other organisms with relevant data.
Desmethylxanthohumol is a natural product and research tool compound used for studies on apoptosis, cancer chemoprevention, and cytochrome P450 inhibition; it is not an approved therapeutic; no clinical trials have been registered; it is used as a reference compound for hop-derived flavonoids and as a lead for developing anti-cancer agents. |
| Molecular Formula |
C20H20O5
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|---|---|
| Molecular Weight |
340.3698
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| Exact Mass |
340.131
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| CAS # |
115063-39-3
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| PubChem CID |
6443339
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| Appearance |
Yellow to orange solid powder
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| Density |
1.312g/cm3
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| Boiling Point |
570.7ºC at 760mmHg
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| Flash Point |
313ºC
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| Vapour Pressure |
1.26E-13mmHg at 25°C
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| Index of Refraction |
1.679
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| LogP |
3.913
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
25
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| Complexity |
500
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=CCC1=C(C(=C(C=C1O)O)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
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| InChi Key |
FUSADYLVRMROPL-UXBLZVDNSA-N
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| InChi Code |
InChI=1S/C20H20O5/c1-12(2)3-9-15-17(23)11-18(24)19(20(15)25)16(22)10-6-13-4-7-14(21)8-5-13/h3-8,10-11,21,23-25H,9H2,1-2H3/b10-6+
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| Chemical Name |
(E)-3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
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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 |
| 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 | 2.9380 mL | 14.6899 mL | 29.3798 mL | |
| 5 mM | 0.5876 mL | 2.9380 mL | 5.8760 mL | |
| 10 mM | 0.2938 mL | 1.4690 mL | 2.9380 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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