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Chrysin 7-O-beta-D-glucopyranuronoside

CAS# 35775-49-6

Chrysin 7-O-beta-D-glucopyranuronoside

Catalog No. BCN3249----Order now to get a substantial discount!

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Chrysin 7-O-beta-D-glucopyranuronoside: 5mg $242 In Stock
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Quality Control of Chrysin 7-O-beta-D-glucopyranuronoside

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Chemical structure

Chrysin 7-O-beta-D-glucopyranuronoside

3D structure

Chemical Properties of Chrysin 7-O-beta-D-glucopyranuronoside

Cas No. 35775-49-6 SDF Download SDF
PubChem ID 14135335 Appearance White-yellowish powder
Formula C21H18O10 M.Wt 430.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 5,7-Dihydroxyflavone 7-glucuronide
Solubility Soluble in methan
Chemical Name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
SMILES C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O
Standard InChIKey IDRSJGHHZXBATQ-ZFORQUDYSA-N
Standard InChI InChI=1S/C21H18O10/c22-11-6-10(29-21-18(26)16(24)17(25)19(31-21)20(27)28)7-14-15(11)12(23)8-13(30-14)9-4-2-1-3-5-9/h1-8,16-19,21-22,24-26H,(H,27,28)/t16-,17-,18+,19-,21+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Chrysin 7-O-beta-D-glucopyranuronoside

1 Scutellaria sp.

Chrysin 7-O-beta-D-glucopyranuronoside Dilution Calculator

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Chrysin 7-O-beta-D-glucopyranuronoside Molarity Calculator

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Preparing Stock Solutions of Chrysin 7-O-beta-D-glucopyranuronoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3234 mL 11.6171 mL 23.2342 mL 46.4684 mL 58.0855 mL
5 mM 0.4647 mL 2.3234 mL 4.6468 mL 9.2937 mL 11.6171 mL
10 mM 0.2323 mL 1.1617 mL 2.3234 mL 4.6468 mL 5.8086 mL
50 mM 0.0465 mL 0.2323 mL 0.4647 mL 0.9294 mL 1.1617 mL
100 mM 0.0232 mL 0.1162 mL 0.2323 mL 0.4647 mL 0.5809 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Chrysin 7-O-beta-D-glucopyranuronoside

Chrysin-induced sperm parameters and fatty acid profile changes improve reproductive performance of roosters.[Pubmed:28822243]

Theriogenology. 2017 Dec;104:72-79.

Having antioxidant and androgenic effects, Chrysin was orally administrated to roosters and reproductive performance including sperm quality and fatty acid composition, testis index, fertility and hatchability rates as well as blood testosterone concentration were assessed. Twenty eight 40-week-old Ross 308 roosters were individually housed, equally divided into four groups and received different levels of capsulated Chrysin including 0 (Ch0), 25 (Ch25), 50 (Ch50) or 75 (Ch75) mg/bird/day for 12 consecutive weeks. Body weighting as well as semen and blood sampling were weekly done from 1(st)-10th weeks. A total of three artificial inseminations were carried out on the last two weeks of trial and collected eggs following second insemination were allotted to evaluate fertility and hatchability rates. Sperm fatty acid composition was determined using samples from 12th week. At the end of experiment (12th week) all roosters sacrificed, testis were carefully removed and testis index was calculated. Except for body weight, testis index, sperm abnormality percentage and ejaculated volume, other traits were significantly affected by Chrysin treatment. Sperm total and forward motility, plasma membrane integrity and functionality, semen concentration as well as fertility and hatchability rates were significantly higher in both Ch50 and Ch75 groups compared to control group. In spite of an increasing trend in most of n-3 and n-6 fatty acids, the n-6/n-3 ratio was significantly decreased in both Ch50 and Ch75 compared to other groups. Malondialdehyde concentration was also significantly decreased in Chrysin treated groups compared to control group. Blood testosterone level was only significantly higher in Ch75 group than that other groups. In conclusion, Chrysin administration particularly at higher levels alleviates post-peak fertility reduction in roosters; however, further research are needed to disclose involved mechanism(s).

Protective effects of mirtazapine and chrysin on experimentally induced testicular damage in rats.[Pubmed:28922723]

Biomed Pharmacother. 2017 Nov;95:1059-1066.

Mirtazapine is an antidepressant with prominent antioxidant effects. Chrysin, a natural flavone, exhibits multiple pharmacological actions. This study was designed to investigate the potential protective effects of chrysin and mirtazapine against nitrofurazone-induced testicular damage in rats. Possible underlying mechanisms such as oxidative stress, inflammation and apoptosis were also investigated. Testicular damage was induced by oral administration of nitrofurazone (50mg/kg/day) for two weeks. Chrysin (25 and 50mg/kg/day, p.o.) and mirtazapine (15 and 30mg/kg/day, p.o.) were applied for three weeks, starting one week before nitrofurazone administration. Prophylactic treatment with chrysin and mirtazapine attenuated the elevation of serum acid phosphatase enzyme activity and halted the decline of sperm count and sperm viability resulted from nitrofurazone administration. Moreover, both agents ameliorated nitrofurazone-induced lipid peroxidation, glutathione depletion, elevation in tumor necrosis factor-alpha level and reduction in c-kit level in rat testes. With respect to apoptosis, immunohistochemical analysis revealed that chrysin and mirtazapine reduced the expression of caspase-3 in testicular tissue which was induced by nitrofurazone. Histopathological findings further supported the protective effects of both drugs against nitrofurazone-induced testicular injury. These findings suggest that the cytoprotective effects of chrysin and mirtazapine on rat testes were associated with suppression of oxidative stress and apoptotic tissue damage. Generally, chrysin prophylactic treatment showed a superior testicular protection than mirtazapine at the tested doses.

Anticancer Properties of Chrysin on Colon Cancer Cells, In vitro and In vivo with Modulation of Caspase-3, -9, Bax and Sall4.[Pubmed:28959334]

Iran J Biotechnol. 2016 Sep;14(3):177-184.

BACKGROUND: The SALL4/Sall4 is constitutively expressed in human and mice. SALL4 mRNA could be used as a marker for the diagnosis of different types of cancers. On the other hand, chrysin has diverse biological properties. OBJECTIVES: In the present study, the effect of the chrysin was investigated on the CT26 colon cancer in vitro and in vivo. Furthermore, the expression levels of the stem cell markers; sall4 and Bax was analyzed, as well. MATERIALS AND METHODS: The cytotoxic effects and the type of cell death induced by chrysin were evaluated using a number of biological assays. The apoptotic pathway was examined by caspase-3and caspase-9 assay. The in vivo antitumor efficacy of chrysin on transplanted CT26 tumor cells in BALB/c mice was investigated. In addition, mRNA expression of sall4, Bax was analyzed with RT-PCR. RESULTS: MTT assay and morphological characteristics showed that chrysin exerted a cytotoxic effect on CT26 cells in a dose dependent manner with IC50= 80 mug.mL(-1). The biological assays have indicated that chrysin administrated cytotoxicity on colon cancer cells through recruitment of the apoptosis. Caspase-3 and caspase-9 colorimetric assays, in addition to Bax expression analysis, have indicated the involvement of intrinsic apoptotic pathway in the cytotoxic effect of the chrysin. The in vivo assay revealed a remarkable reduction of the colon tumor volume in treated mice (8, 10 mg.kg (-1)) as compared to the untreated mice. RT-PCR elucidated that chrysin attenuated tumor volume through down regulation of the sall4 and up-regulation of the Bax. CONCLUSIONS: It was demonstrated that chrysin accomplishes anti-cancer effect on colon cancer cells via induction of the apoptosis and attenuation of the sall4 the expression. These findings introduce chrysin as an efficient apoptosis based therapeutic agent against colon cancer.

Synthesis and evaluation of antitumour activity in vitro and in vivo of chrysin salicylate derivatives.[Pubmed:28871827]

Nat Prod Res. 2018 Sep;32(18):2178-2186.

A series of chrysin salicylate derivatives as potential antitumour agents were synthesised and evaluated their antitumour activities in vitro and in vivo. Most of the compounds exhibited moderate to good activities against MCF-7 cells, HepG2 cells, MGC-803cells and MFC cells. Among them, compound 3f showed the most potent activity against MGC-803 cells and MFC cells with IC50 values of 23.83 +/- 3.68 and 27.34 +/- 5.21 muM, respectively. The flow cytometry assay reconfirmed that compound 3f promoted the occurrence of tumour cells' G1/S block under the inhibiting effect of compound 3f. Compound 3f possessed higher antitumour efficacy in tumour-bearing mice, compared with the positive control 5-Fu and the blank control saline.

Chrysin attenuates progression of ovarian cancer cells by regulating signaling cascades and mitochondrial dysfunction.[Pubmed:28816359]

J Cell Physiol. 2018 Apr;233(4):3129-3140.

Chrysin is mainly found in passion flowers, honey, and propolis acts as a potential therapeutic and preventive agent to inhibit proliferation and invasion of various human cancer cells. Although chrysin has anti-carcinogenic effects in several cancers, little is known about its functional roles in ovarian cancer which shows poor prognosis and chemoresistance to traditional therapeutic agents. In the present study, we investigated functional roles of chrysin in progression of ovarian cancer cells using ES2 and OV90 (clear cell and serous carcinoma, respectively) cell lines. Results of the current study demonstrated that chrysin inhibited ovarian cancer cell proliferation and induced cell death by increasing reactive oxygen species (ROS) production and cytoplasmic Ca(2+) levels as well as inducing loss of mitochondrial membrane potential (MMP). Moreover, chrysin activated mitogen-activated protein kinase (MAPK) and phosphoinositide 3-kinase (PI3K)/AKT pathways in ES2 and OV90 cells in concentration-response experiments. Collectively, our results led us to propose that chrysin-induced apoptotic events are mediated by the activation of PI3K and MAPK pathways in human ovarian cancer cells.

Description

Chrysin-7-O-glucuronide is a flavonoid extracted from Scutellaria baicalensis, with antioxidant activity.

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