Xanthohumol D | CAS:274675-25-1 | Manufacturer ChemFaces

Xanthohumol D

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Description:

Xanthohumol and xanthohumol D are potent inducers of quinone reductase, suggests that they could be used as chemoprevention agents.

Targets:

IFN-γ | NO

In vitro:

Bioorg Med Chem. 2013 Apr 1;21(7):2001-6.

Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.[Pubmed: 23434138]

Xanthohumol (1) and Xanthohumol D (2) were isolated from spent hops. Isoxanthohumol (3) was obtained from xanthohumol by isomerisation in alkaline solution.
METHODS AND RESULTS:
Six metabolites were obtained as a result of transformation of xanthohumol (1) by selected fungal cultures. Their structures were established on the basis of their spectral data. One of them: 2″-(2'''-hydroxyisopropyl)-dihydrofurano-[4″,5″:3',4']-4',2-dihydroxy-6'-methoxy-α,β-dihydrochalcone (6) has not been previously reported in the literature. The antioxidant properties of hops flavonoids and Xanthohumol Derivatives were investigated using the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method. The effects of these compounds on proliferation of MCF-7, PC-3 and HT-29 human cancer cell lines were determined by the SRB assay.
CONCLUSIONS:
With the exception of one metabolite, all tested compounds showed antiproliferative activity against the tested human cancer lines. α,β-Dihydroxanthohumol (4), obtained through the biotransformation of xanthohumol, showed higher antiproliferative activity against MCF-7 human breast carcinoma cell line than cisplatin, a widely used anticancer therapeutic agent, and a comparably high activity against PC-3 human prostate cancer cell line.

Xanthohumol D Description

Source:	The herbs of Humulus lupulus
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Anal Chem. 2005 Oct 1;77(19):6407-14.

Screening method for the discovery of potential cancer chemoprevention agents based on mass spectrometric detection of alkylated Keap1.[Pubmed: 16194107]

Natural products are important sources of drugs such as cancer chemopreventive agents, but most assays for the discovery of compounds in natural product extracts are low throughput and provide little information about lead compounds in these complex mixtures. The induction of enzymes such as quinone reductase, glucuronyl transferases, glutathione S-transferases, and sulfotransferases can protect cells against the toxic and neoplastic effects of carcinogens. An increase in the concentration of Nrf2 in the nucleus of a cell upregulates the antioxidant response element and induces the expression of these chemopreventive enzymes.
METHODS AND RESULTS:
Based on the hypothesis that ubiquitination and proteosome-mediated degradation of Nrf2 in the cytoplasm decreases upon the covalent modification of 1 or more of the 27 cysteine sulfhydryl groups on Keap1 (a protein that sequesters Nrf2 in the cytoplasm) and results in higher Nrf2 levels both in the cytoplasm and in the nucleus, a high-throughput mass spectrometry-based screening assay was designed to detect alkylation of sulfhydryl groups of human Keap1. As an initial high-throughput screening step, matrix-assisted laser desorption time-of-flight mass spectrometry was used to determine whether incubation of Keap1 with a botanical sample produced adducts of Keap1. Test extracts found to form adducts with Keap1 were then incubated with the alternative biological nucleophile glutathione and characterized using LC-UV-MS-MS. After validation of the assay using two model alkylating agents, fractions of an extract of hops (Humulus lupulus L.) from the brewing industry were screened, and several compounds were detected as potential chemopreventive agents.
CONCLUSIONS:
Two of these electrophilic hops constituents were identified as xanthohumol and Xanthohumol D. In a subsequent cell-based assay, xanthohumol and Xanthohumol D were confirmed to be potent inducers of quinone reductase, and reaction with Keap1 was also confirmed. Therefore, this new mass spectrometric screening assay was demonstrated to facilitate the discovery of chemoprevention agents in complex natural product mixtures.

Product Name	Xanthohumol D
Price:
CAS No.:	274675-25-1
Catalog No.:	CFN98328
Molecular Formula:	C₂₁H₂₂O₆
Molecular Weight:	370.4 g/mol
Purity:	>=98%
Type of Compound:	Chalcones
Physical Desc.:	Yellow powder
Source:	The herbs of Humulus lupulus
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Cancer chemoprevention Compound Library Chalcones Compound Library NO Inhibitor Library IFN-γ Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.6998 mL	13.4989 mL	26.9978 mL	53.9957 mL	67.4946 mL
5 mM	0.54 mL	2.6998 mL	5.3996 mL	10.7991 mL	13.4989 mL
10 mM	0.27 mL	1.3499 mL	2.6998 mL	5.3996 mL	6.7495 mL
50 mM	0.054 mL	0.27 mL	0.54 mL	1.0799 mL	1.3499 mL
100 mM	0.027 mL	0.135 mL	0.27 mL	0.54 mL	0.6749 mL

CFN92221	Bavachalcone	28448-85-3	324.4	C₂₀H₂₀O₄
CFN98046	4'-O-Methylbroussochalcone B	20784-60-5	338.4	C₂₁H₂₂O₄
CFN98593	Isobavachalcone	20784-50-3	324.37	C₂₀H₂₀O₄
CFN92015	Desmethylxanthohumol	115063-39-3	340.4	C₂₀H₂₀O₅
CFN91405	Dihydroxanthohumol	102448-00-0	356.4	C₂₁H₂₄O₅
CFN98958	Xanthohumol	569-83-5; 6754-58-1	354.4	C₂₁H₂₂O₅
CFN98328	Xanthohumol D	274675-25-1	370.4	C₂₁H₂₂O₆
CFN92227	Corylifol B	775351-90-1	340.4	C₂₀H₂₀O₅
CFN97241	Morachalcone A	76472-88-3	340.4	C₂₀H₂₀O₅
CFN92006	Kuraridine	34981-25-4	438.5	C₂₆H₃₀O₆