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Chemical Structure| 6754-58-1 Chemical Structure| 6754-58-1

Structure of Xanthohumol
CAS No.: 6754-58-1

Chemical Structure| 6754-58-1

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Xanthohumol, a prenylated chalcone from hop, is an inhibitor of diacylglycerol acetyltransferase (DGAT), COX-1 and COX-2 and shows chemopreventive effects.

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Product Citations

Product Citations

Commey, Leslie ; Mechref, Yehia ; Burow, Mark ; Mendu, Venugopal ;

Abstract: The peanut seed coat acts as a physical and biochemical barrier against Aspergillus flavus infection; however, the nature of the inhibitory chemicals in the peanut seed coat in general is not known. This study identified and characterized peanut seed coat metabolites that inhibit A. flavus growth and aflatoxin contamination. Selected peanut accessions grown under well-watered and water-deficit conditions were assayed for A. flavus resistance, and seed coats were metabolically profiled using liquid chromatography mass spectrometry. Kyoto Encyclopedia of Genes and Genome phenylpropanoid pathway reference analysis resulted in the identification of several seed coat metabolic compounds, and ten selected metabolites were tested for inhibition of A.flavus growth and aflatoxin contamination. Radial growth bioassay demonstrated that inhibited A. flavus growth (98.7%) and reduced the aflatoxin contamination estimate from 994 to 1 μg/kg. Scanning electron micrographs showed distorted hyphae and conidiophores in cultures of 2,5-dihydroxybenzaldehyde-treated A. flavus, indicating its potential use for field application as well as seed coat metabolic engineering.

Keywords: aflatoxin, A. flavus ; metabolomics ; seed coat ; liquid chromatography mass spectrometry (LC-MS) ; radial growth bioassay ; secondary metabolites

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Product Details of Xanthohumol

CAS No. :6754-58-1
Formula : C21H22O5
M.W : 354.40
SMILES Code : O=C(C1=C(OC)C=C(O)C(C/C=C(C)\C)=C1O)/C=C/C2=CC=C(O)C=C2
MDL No. :MFCD00210576
InChI Key :ORXQGKIUCDPEAJ-YRNVUSSQSA-N
Pubchem ID :639665

Safety of Xanthohumol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Isoform Comparison

Biological Activity

Target
  • COX-1

In Vitro:

Cell Line
Concentration Treated Time Description References
RAW 264.7 cells 0, 0.625, 1.25, 2.5, 5, 10 or 20 μM 1 hour To evaluate the effects of Xn and LPS on cell viability, the results showed that LPS (1 μg/mL) plus Xn up to 10 μM were not toxic to RAW 264.7 cells. PMC5345976
RAW 264.7 cells 1.25, 2.5 or 5 μM 1 hour To evaluate the effects of Xn on LPS-induced inflammatory responses, the results showed that Xn significantly inhibited LPS-induced TNF-α, IL-6, IL-1β and ROS production. PMC5345976
HCC827OR 0 μM, 1.5 μM, 3 μM, 6 μM 24 h Xanthohumol significantly inhibited the proliferation and colony formation ability of HCC827OR and H1975OR cells and induced intrinsic apoptosis. PMC11519634
H1975OR 0 μM, 1.5 μM, 3 μM, 6 μM 24 h Xanthohumol significantly inhibited the proliferation and colony formation ability of HCC827OR and H1975OR cells and induced intrinsic apoptosis. PMC11519634
A549 cells 2.5-10 μM 24 hours XN at non-cytotoxic concentrations significantly inhibited the migration and invasion capacity of A549 cells by reducing the expression of MMP-9 and increasing the expression of TIMP-1, thereby impairing PMA-induced invasive behavior. PMC8231538
HCT116 cells 5 μM 24 hours Xanthohumol significantly inhibited glucose consumption and lactate production in HCT116 cells, and inhibited cell proliferation and colony formation PMC6775317
SW620 cells 5 μM 24 hours Xanthohumol significantly inhibited glucose consumption and lactate production in SW620 cells, and inhibited cell proliferation and colony formation PMC6775317
HT29 cells 5 μM 24 hours Xanthohumol significantly inhibited glucose consumption and lactate production in HT29 cells, and inhibited cell proliferation and colony formation PMC6775317
Vero-E6 cells 5.93 µM 24 hours Xanthohumol inhibited SARS-CoV-2 replication with an IC50 value of 5.93 μM and did not significantly affect cell growth at high concentrations. PMC8624673
Vero-E6 cells 7.51 µM 24 hours Xanthohumol inhibited PEDV replication with an IC50 value of 7.51 μM. PMC8624673
rat glioma C6 cell 5 uM to 60 uM 24 hours to 96 hours XN significantly inhibited the proliferation of C6 glioma cells and eventually induced cell death by triggering mitochondrial stress. PMC8123451
CLB70 (B-cell leukemia) 0.1–30 µM 48 hours All eight of the tested flavonoids exerted concentration-dependent cytotoxicity in the selected canine lymphoma/leukemia cell lines. Three compounds markedly decreased the viability of all cell lines with IC50 in the range of 0.5 to 8 μM. PMC10380916
CLBL-1 (B-cell lymphoma) 0.1–30 µM 48 hours All eight of the tested flavonoids exerted concentration-dependent cytotoxicity in the selected canine lymphoma/leukemia cell lines. Three compounds markedly decreased the viability of all cell lines with IC50 in the range of 0.5 to 8 μM. PMC10380916
GL-1 (B-cell leukemia) 0.1–30 µM 48 hours All eight of the tested flavonoids exerted concentration-dependent cytotoxicity in the selected canine lymphoma/leukemia cell lines. Three compounds markedly decreased the viability of all cell lines with IC50 in the range of 0.5 to 8 μM. PMC10380916

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Nude mice Colorectal cancer xenograft model Intraperitoneal injection 10 mg/kg Every two days until the end of the experiment Xanthohumol significantly inhibited the growth of HT29 and HCT116 xenograft tumors, reducing tumor volume and weight PMC6775317
C57BL/6 mice LPS-induced acute lung injury model Intraperitoneal injection 10 or 50 mg/kg Single dose, 12 hours To evaluate the protective effects of Xn on LPS-induced acute lung injury, the results showed that Xn significantly alleviated lung injury, reduced inflammatory cell infiltration and oxidative stress. PMC5345976
Nude mice HCC827OR and H1975OR xenograft model Intraperitoneal injection Low dose: 10 mg/kg/2 days; High dose: 30 mg/kg/2 days Every 2 days, until tumor volume reached about 1000 mm3 Xanthohumol significantly inhibited the tumor growth of HCC827OR and H1975OR cells in nude mice with no significant toxicity. PMC11519634

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02848430 Food-Drug Interactions Not Applicable Active, not recruiting October 18, 2018 United States, Illinois ... More >> University of Illinois at Chicago Chicago, Illinois, United States, 60612 Less <<
NCT01982734 Pharmacokinetics of New Curcum... More >>in Formulations Safety of New Curcumin Formulations Less << Early Phase 1 Completed - Germany ... More >> University of Hohenheim Stuttgart, Baden-Württemberg, Germany, 70599 Less <<
NCT03561116 Metabolic Syndrome Not Applicable Recruiting October 2018 Portugal ... More >> Medical Faculty of University of Porto Recruiting Porto, Portugal, 4200-319 Contact: Raquel Soares, PhD    (+351)225513624    raqsoa@med.up.pt Less <<
NCT01367431 - Completed - United States, Oregon ... More >> Oregon Health & Science University Portland, Oregon, United States, 97201 Less <<
NCT03735420 Healthy Phase 1 Not yet recruiting August 2021 -
NCT02432651 Oxidative Stress Phase 1 Completed - United States, Oregon ... More >> Oregon State University Corvallis, Oregon, United States, 97331 Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.82mL

0.56mL

0.28mL

14.11mL

2.82mL

1.41mL

28.22mL

5.64mL

2.82mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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