Structure of Xanthohumol
CAS No.: 6754-58-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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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 2,5-dihydroxybenzaldehyde 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.
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Keywords: aflatoxin, A. flavus ; metabolomics ; seed coat ; liquid chromatography mass spectrometry (LC-MS) ; radial growth bioassay ; secondary metabolites
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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Target |
|
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 << |
Tags: Xanthohumol | COX | Acyltransferase | Apoptosis | HSV | CMV | Influenza Virus | Cyclooxygenase | Diacylglycerol acyltransferase | Diglyceride acyltransferase | acyl-CoA:cholesterol acyltransferase | mono- acylglycerol acyltransferase | Herpes simplex virus | Cytomegalovirus | DGAT inhibitor | COX-1 inhibitor | COX-2 inhibitor | 6754-58-1
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