Wighteone | CAS:51225-30-0 | Manufacturer ChemFaces

Wighteone

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Description:

Wighteone is an antifungal isoflavone.Wighteone has in vitro cytocidal activity against KB cells, it has a potent anti-proliferative effect on human leukemia HL-60 cancer cell lines, it can effectively inhibit the proliferation of HER2-positive cancer cell lines, and this is considered to be the result of downregulating HSP90 receptor and downstream signaling.

Targets:

HSP (e.g. HSP90) | Antifection

In vitro:

Biotechnol Lett. 2006 Jan;28(2):99-105.

Genome-wide analysis of the expression profile of Saccharomyces cerevisiae in response to treatment with the plant isoflavone, wighteone, as a potential antifungal agent.[Pubmed: 16369693]

The limitations of currently available antifungal agents and the rapid emergence of drug-resistant strains necessitate more efficient approaches to screening and developing novel antifungal drugs.
METHODS AND RESULTS:
The antifungal activity of the natural products of a series of plants was evaluated and Wighteone, 5, 7, 4'-trihydroxy-6-(gamma,gamma-dimethylallyl)isoflavone showed excellent anti-yeast activity (MIC against Saccharomyces cerevisiae was 4 microg/ml).
METHODS AND RESULTS:
Transcriptome profiling of Wighteone-treated S. cerevisiae indicated that Wighteone is different from commonly used antifungal compounds in its mode of action.

Phytochemistry. 2001 Dec;58(7):1113-20.

Cytotoxic isoflavones from Erythrina indica.[Pubmed: 11730876]

METHODS AND RESULTS:
Bioassay-directed fractionation of the CH(2)Cl(2)-MeOH (1:1) extract of the stem bark of Erythrina indica, has resulted in the isolation of two new isoflavone derivatives named indicanines D and E together with 11 known compounds including: six isoflavones (genistein, Wighteone, alpinumisoflavone, dimethylalpinumisoflavone, 8-prenyl erythrinin C, and erysenegalensein E), one cinnamate (erythrinassinate B), two pentacyclic triterpenes (oleanolic acid and erythrodiol), and two phytosterols (stigmasterol and its 3-O-beta-D-glucopyranoside).
CONCLUSIONS:
The structures of the new compounds were elucidated by means of spectroscopic analysis. The in vitro cytocidal activity against KB cells of some of the isolated compounds is also reported.

Wighteone Description

Source:	The herbs of Glycyrrhiza glabra
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.

Cell Research:

Oncol Lett. 2016 Jun;11(6):3719-3722.

HSP90 expression and its association with wighteone metabolite response in HER2-positive breast cancer cells.[Pubmed: 27313682]

It is well known that heat shock protein 90 (HSP90) overexpression is correlated with poor prognosis and chemo-resistance in human malignant cancers. At the same time, Wighteone, or 6-prenyl-5,7,4'-trihydroxyisoflavone, a major isoflavone component of the ornamental tall tree Erythrina suberosa, has been demonstrated to exhibit a potent anti-proliferative effect on human leukemia HL-60 cancer cell lines.
METHODS AND RESULTS:
In this study, the effects of Wighteone on the proliferation of HER2-positive breast cancer cells were investigated, and the action mechanism was explored. MCF-7 HER2-positive breast cancer cells were treated with various concentrations of Wighteone. The growth inhibitory rate of the cells was calculated by MTT assay, apoptosis was detected by flow cytometry, and the expression level of HSP90 was assessed by western blot analysis. The addition of Wighteone at concentrations ranging from 1-10 g/ml in the medium for 48 h had a marked inhibition on the proliferation of HER2-positive cancer cell lines. The growth inhibitory rates with 0.5, 2 or 8 mM Wighteone were significantly higher compared with the control group. Apoptosis in the Wighteone-treated cells was also significantly higher compared with the control group. The expression level of HSP90 in the Wighteone group was significantly lower than that in the control group.
CONCLUSIONS:
Our findings demonstrated that Wighteone effectively inhibited the proliferation of HER2-positive cancer cell lines, and this is considered to be the result of downregulating HSP90 receptor and downstream signaling.

Structure Identification:

Nippon Nōgeikagaku Kaishi, 1985, 59(10):1039-1044.

Fungal Metabolites of Antifungal Isoflavone Wighteone.[Reference: WebLink]

METHODS AND RESULTS:
An antifungal isoflavone, Wighteone [5,7,4′-trihydroxy-6-(3,3-dimethylallyl)isoflavone, 1] was metabolized in cultures of Aspergillus flavus and Botrytis cinerea. The substrate (1) was transformed by the former fungus into 2″, 3″-dihydro-3″-hydroxy Wighteone (Wighteone hydrate, 4) and by the latter into dihydrofurano-isoflavone (2) as major metabolites.
CONCLUSIONS:
A small quantity of dihydropyrano-isoflavone (3), 2 and 2″,3″-dihydrodihydroxyWighteone (5) were detected in the metabolic culture of A.flavus as minor metabolites of 1. Both 3 and 5 were isolated as Wighteone metabolites in B. cinerea cultures.

Product Name	Wighteone
Price:
CAS No.:	51225-30-0
Catalog No.:	CFN98816
Molecular Formula:	C₂₀H₁₈O₅
Molecular Weight:	338.4 g/mol
Purity:	>=98%
Type of Compound:	Flavonoids
Physical Desc.:	Yellow powder
Source:	The herbs of Glycyrrhiza glabra
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	Anticancer Compound Library Antifungal Compound Library Flavonoids Compound Library HSP (e.g. HSP90) Inhibitor Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.9551 mL	14.7754 mL	29.5508 mL	59.1017 mL	73.8771 mL
5 mM	0.591 mL	2.9551 mL	5.9102 mL	11.8203 mL	14.7754 mL
10 mM	0.2955 mL	1.4775 mL	2.9551 mL	5.9102 mL	7.3877 mL
50 mM	0.0591 mL	0.2955 mL	0.591 mL	1.182 mL	1.4775 mL
100 mM	0.0296 mL	0.1478 mL	0.2955 mL	0.591 mL	0.7388 mL

CFN98816	Wighteone	51225-30-0	338.4	C₂₀H₁₈O₅
CFN98097	Erysubin A	221150-18-1	352.3	C₂₀H₁₆O₆
CFN97096	Erythrinin C	63807-85-2	354.4	C₂₀H₁₈O₆
CFN96168	1''-Hydroxyerythrinin C	913690-46-7	370.4	C₂₀H₁₈O₇
CFN96058	1''-Methoxyerythrinin C	221002-11-5	384.4	C₂₁H₂₀O₇
CFN97117	alpha-Isowighteone	65388-03-6	338.4	C₂₀H₁₈O₅
CFN97918	Furowanin A	911004-72-3	438.5	C₂₅H₂₆O₇
CFN96062	Auriculasin	60297-37-2	420.5	C₂₅H₂₄O₆
CFN93047	Pomiferin	572-03-2	420.46	C₂₅H₂₄O₆
CFN98655	Luteone	41743-56-0	354.4	C₂₀H₁₈O₆