Kazinol A

CAS# 99624-28-9

Kazinol A

Catalog No. BCN3388----Order now to get a substantial discount!

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Quality Control of Kazinol A

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Chemical structure

Kazinol A

3D structure

Chemical Properties of Kazinol A

Cas No. 99624-28-9 SDF Download SDF
PubChem ID 442414 Appearance Powder
Formula C25H30O4 M.Wt 394.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 4-[(2S)-7-hydroxy-3,4-dihydro-2H-chromen-2-yl]-3,6-bis(3-methylbut-2-enyl)benzene-1,2-diol
SMILES CC(=CCC1=C(C(=C(C(=C1)C2CCC3=C(O2)C=C(C=C3)O)CC=C(C)C)O)O)C
Standard InChIKey QXHVECWDOBLWPW-QFIPXVFZSA-N
Standard InChI InChI=1S/C25H30O4/c1-15(2)5-7-18-13-21(20(11-6-16(3)4)25(28)24(18)27)22-12-9-17-8-10-19(26)14-23(17)29-22/h5-6,8,10,13-14,22,26-28H,7,9,11-12H2,1-4H3/t22-/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 Kazinol A

The barks of Broussonetia papyrifera.

Biological Activity of Kazinol A

Description1. Kazinol A shows strong inhibition of arachidonic acid (AA)-induced platelet aggregation. 2. Kazinol A possesses potent antioxidant activity against 2,2-diphenyl-l-picrylhydrazyl and 2,2′-azino-bis-ethylbenzthiazoline-6-sulfonic acid (ABTS) radicals.

Kazinol A Dilution Calculator

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Kazinol A Molarity Calculator

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Preparing Stock Solutions of Kazinol A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5349 mL 12.6743 mL 25.3485 mL 50.6971 mL 63.3714 mL
5 mM 0.507 mL 2.5349 mL 5.0697 mL 10.1394 mL 12.6743 mL
10 mM 0.2535 mL 1.2674 mL 2.5349 mL 5.0697 mL 6.3371 mL
50 mM 0.0507 mL 0.2535 mL 0.507 mL 1.0139 mL 1.2674 mL
100 mM 0.0253 mL 0.1267 mL 0.2535 mL 0.507 mL 0.6337 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 Kazinol A

Kazinol C from Broussonetia kazinoki activates AMP-activated protein kinase to induce antitumorigenic effects in HT-29 colon cancer cells.[Pubmed:25394483]

Oncol Rep. 2015 Jan;33(1):223-9.

Kazinol C is a 1,3-diphenylpropane, obtained from Broussonetia kazinoki, that has been employed in folk medicine as an edema suppressant. It exerts beneficial effects in oxidative stress-related diseases, such as cancer. However, the molecular mechanism involved in the anticancer effects remains to be determined. AMP-activated protein kinase (AMPK) has emerged as a possible anticancer target molecule. The present study investigated the effect of kazinol C on AMPK activation as well as subsequent HT-29 colon cancer cell viability, apoptosis and migration. Kazinol C markedly induced AMPK phosphorylation and significantly attenuated HT-29 colon cancer cell growth and viability. Compound C, as a wellknown AMPK inhibitor, blocked the kazinol C-induced cell death, and stable transduction of dominant-negative (DN) AMPK in colon cancer cells also inhibited kazinol C-induced cell apoptosis. In addition, kazinol C inhibited HT-29 cell migration and anchorage-independent growth. AMPK inhibition using stable transduction with DN AMPK significantly abrogated the kazinol C-induced inhibition of cancer cell migration. Thus, AMPK is a critical and novel regulator of kazinol C-mediated cancer cell apoptosis and inhibition of migration, suggesting that AMPK is a prime cancer target.

Kazinol-E is a specific inhibitor of ERK that suppresses the enrichment of a breast cancer stem-like cell population.[Pubmed:26774343]

Biochem Biophys Res Commun. 2016 Feb 5;470(2):294-299.

Growing evidence shows that cancer stem-like cells (CSLCs) contribute to breast cancer recurrence and to its resistance to conventional therapies. The extracellular signal-regulated kinase (ERK) signaling pathway is a major determinant in the control of diverse cellular processes, including the maintenance of CSLCs. In this study, we found that Kazinol-E, an antioxidant flavan from Broussonetia kazinoki, decreased the CSLC population of a breast cancer cell line, MCF7. The CSLC population, characterized by CD44 high/CD24 low expression or by high Aldehyde dehydrogenase 1 activity, was decreased by a concentration of Kazinol-E that did not affect the growth of bulk-cultured MCF7 cells. Kazinol-E did not decrease EGF-induced ERK phosphorylation in CSLCs, but did block the phosphorylation of an ERK substrate, p90RSK2, at Thr359/Ser363. We further demonstrated that EGF-induced ERK activity was blocked by Kazinol-E in a wild-type K-Ras-expressing non-small cell lung cancer cell line H226B. An in vitro kinase assay with purified ERK1 and p90RSK2 as its substrate demonstrated a direct inhibition of ERK activity by Kazinol E. Additionally, a the molecular docking study provided putative binding modes of Kazinol-E into the ATP binding pocket of ERK1 Collectively, these results suggest that Kazinol-E is a direct inhibitor of ERK1, and more studies are warranted to develop this reagent for therapeutic breast CSLC targeting.

Kazinol-P from Broussonetia kazinoki enhances skeletal muscle differentiation via p38MAPK and MyoD.[Pubmed:25482443]

Biochem Biophys Res Commun. 2015 Jan 2;456(1):471-5.

The activation of MyoD family transcription factors is critical for myogenic differentiation, which is fundamental to the regeneration of skeletal muscle after injury. Kazinol-P (KP) from Broussonetia kazinoki (B. kazinoki), a natural compound, has been reported to possess an anti-oxidant function. In a screen of natural compounds for agonists of the MyoD activity, we identified KP and examined its effect on myoblast differentiation. Consistently, KP enhanced the myotube formation, accompanied with upregulation of myogenic markers such as MHC, Myogenin and Troponin-T. KP treatment in C2C12 myoblasts led to strong activation of a key promyogenic kinase p38MAPK in a dose, and time-dependent manner. Furthermore, KP treatment enhanced the MyoD-mediated trans-differentiation of 10T1/2 fibroblasts into myoblasts. Taken together, KP promotes myogenic differentiation through activation of p38MAPK and MyoD transcription activities. Thus KP may be a potential therapeutic candidate to prevent fibrosis and improve muscle regeneration and repair.

Cytotoxic effects of kazinol A derived from Broussonetia papyrifera on human bladder cancer cells, T24 and T24R2.[Pubmed:27765366]

Phytomedicine. 2016 Nov 15;23(12):1462-1468.

BACKGROUND: Broussonetia papyrifera (B. papyrifera), also known as paper mulberry, has been used as a traditional medicine for the treatment of several diseases, including ophthalmic disorders and impotency. However, the biological activity of Kazinol A (1) among flavonols isolated from B. papyrifera has not been identified. PURPOSE: We identified a candidate metabolite for anti-human bladder cancer treatment from B. papyrifera and investigated the possible molecular mechanisms underlying its cytotoxic effects in T24 and cisplatin-resistant T24R2 human bladder cancer cells. METHODS: T24 and T24R2 cells were treated with five flavonols from B. papyrifera and their cytotoxic effects were determined using MTT assay, cell cycle analysis, mitochondrial membrane potential, and propidium iodide staining. Autophagy rate was calculated by counting LC3-GFP dots in the cells. All related protein expressions were analyzed by immunoblotting. RESULTS: Compound 1 showed relatively higher cytotoxicity in the human bladder cancer cells, T24 and T24R2, rather than other tissues-originated cancer cells. Compound 1 significantly attenuated cell growth through G0/1 arrest mediated by a decrease in cyclin D1 and an increase of p21. Apoptosis and autophagy induced by compound 1 treatment was accompanied by a modulation of the AKT-BAD pathway and AMPK-mTOR pathway, respectively. CONCLUSIONS: Our results suggest that compound 1 induces cytotoxic effects in human bladder cancer cells, including the cisplatin-resistant T24R2. Compound 1 may be a candidate for the development of effective anti-cancer drug on human urinary bladder cancer.

Kazinol B from Broussonetia kazinoki improves insulin sensitivity via Akt and AMPK activation in 3T3-L1 adipocytes.[Pubmed:27223849]

Fitoterapia. 2016 Jul;112:90-6.

In this study, we evaluated the insulin-sensitizing effect of flavans purified from Broussonetia kazinoki Siebold (BK) on 3T3-L1 adipocytes. Among the tested compounds, kazinol B enhanced intracellular lipid accumulation, gene expression of proliferator-activated receptorgamma (PPARgamma) and CCAAT/enhancer binding protein-alpha (C/EBPalpha), and consistently induced PPARgamma transcriptional activation. To further investigate the insulin-sensitizing effect of kazinol B, we measured glucose analogue uptake by fully differentiated adipocytes and myotubes. Kazinol B increased 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-d-glucose (2-NBDG) uptake by cells by upregulating the gene expression and translocation of glucose transporter 4 (GLUT-4) into the plasma membrane in adipocytes. Kazinol B stimulated the gene expression and secretion of adiponectin, which is associated with a low risk of types 1 and 2 diabetes mellitus. We also suggested the mechanism of the antidiabetic effect of kazinol B by assaying Akt and AMP-activated protein kinase (AMPK) phosphorylation. In conclusion, kazinol B isolated from BK improved insulin sensitivity by enhancing glucose uptake via the insulin-Akt signaling pathway and AMPK activation. These results suggest that kazinol B might be a therapeutic candidate for diabetes mellitus.

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