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8-Prenylkaempferol

CAS# 28610-31-3

8-Prenylkaempferol

Catalog No. BCN3311----Order now to get a substantial discount!

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Quality Control of 8-Prenylkaempferol

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Chemical structure

8-Prenylkaempferol

3D structure

Chemical Properties of 8-Prenylkaempferol

Cas No. 28610-31-3 SDF Download SDF
PubChem ID 5318624 Appearance Yellow powder
Formula C20H18O6 M.Wt 354.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
SMILES CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O)C
Standard InChIKey NADCVNHITZNGJU-UHFFFAOYSA-N
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 8-Prenylkaempferol

The roots of Sophora flavescens

Biological Activity of 8-Prenylkaempferol

Description1. 8-Prenylkaempferol is an effective agent for attenuating pro-inflammatory NO induction. 2. 8-Prenylkaempferol induces differentiation/maturation of MC3T3-E1 osteoblasts by BMP-2/p38/Runx2 pathways , might be a promising agent for inducing osteogenesis. 3. 8-Prenylkaempferol might be an anti-inflammatory agent for suppressing influenza A virus-induced RANTES production acts by blocking PI3K-mediated transcriptional activation of NF-κB and IRF-3 and in part by interfering with IκB degradation which subsequently decreases NF-κB translocation.
Targetsp38MAPK | NF-kB | PI3K | NO | NOS | AP-1 | JNK | MEK | ERK | IkB | IKK

8-Prenylkaempferol Dilution Calculator

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Preparing Stock Solutions of 8-Prenylkaempferol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8217 mL 14.1084 mL 28.2167 mL 56.4334 mL 70.5418 mL
5 mM 0.5643 mL 2.8217 mL 5.6433 mL 11.2867 mL 14.1084 mL
10 mM 0.2822 mL 1.4108 mL 2.8217 mL 5.6433 mL 7.0542 mL
50 mM 0.0564 mL 0.2822 mL 0.5643 mL 1.1287 mL 1.4108 mL
100 mM 0.0282 mL 0.1411 mL 0.2822 mL 0.5643 mL 0.7054 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 8-Prenylkaempferol

8-Prenylkaempferol accelerates osteoblast maturation through bone morphogenetic protein-2/p38 pathway to activate Runx2 transcription.[Pubmed:21163272]

Life Sci. 2011 Feb 14;88(7-8):335-42.

AIMS: In this study, we investigated the effect of 8-Prenylkaempferol (8-PK), a prenyl-flavonoid isolated from Sophora flavescens, on osteoblast differentiation and maturation. MAIN METHODS: MC3T3-E1 cells were exposed to 8-PK and the cytotoxicity was assayed. Osteoblast differentiation and maturation were evaluated by analyzing alkaline phosphatase (ALP) activity and cell mineralization, respectively. RT-PCR and Western blot were executed to determine the effects of 8-PK on osteoblast differentiation-related gene expression and signaling pathway. KEY FINDINGS: 8-PK significantly promoted ALP activity, up-regulated mRNA expressions of osteocalcin, osteopontin, and type I collagen, and induced bone nodules formation. Induction of differentiation by 8-PK was associated with increased bone morphogenetic protein (BMP)-2 expression, and sequentially up-regulated the phosphorylations of Smad1/5/8 and p38, and increased the nuclear translocation of runt-related transcription factor 2 (Runx2). Addition of BMP-2 antagonist noggin blocked 8-PK and recombinant mouse BMP-2-induced ALP activity, reconfirming that BMP-2 production is required in 8-PK-mediated osteoblast differentiation. Noggin also abrogated 8-PK evoked phosphorylations of Smad1/5/8 and p38, suggesting that BMP-2 signaling is required for p38 activation in 8-PK-treated cells. Application of p38 inhibitor SB203580 repressed not only 8-PK-mediated activation of ALP, but also the nuclear translocation of Runx2 and bone nodules formation. SIGNIFICANCE: The present results suggested that BMP-2/p38/Runx2 pathways were involved in 8-PK-induced differentiation/maturation of MC3T3-E1 osteoblasts and firstly demonstrated that 8-PK might be a promising agent for inducing osteogenesis.

8-Prenylkaempferol Suppresses Influenza A Virus-Induced RANTES Production in A549 Cells via Blocking PI3K-Mediated Transcriptional Activation of NF-kappaB and IRF3.[Pubmed:19592477]

Evid Based Complement Alternat Med. 2011;2011:920828.

8-Prenylkaempferol (8-PK) is a prenylflavonoid isolated from Sophora flavescens, a Chinese herb with antiviral and anti-inflammatory properties. In this study, we investigated its effect on regulated activation, normal T cell expressed and secreted (RANTES) secretion by influenza A virus (H1N1)-infected A549 alveolar epithelial cells. Cell inoculation with H1N1 evoked a significant induction in RANTES accumulation accompanied with time-related increase in nuclear translocation of nuclear factor-kappaB (NF-kappaB) and interferon regulatory factor 3 (IRF-3), but showed no effect on c-Jun phosphorylation. 8-PK could significantly inhibit not only RANTES production but also NF-kappaB and IRF-3 nuclear translocation. We had proved that both NF-kappaB and IRF-3 participated in H1N1-induced RANTES production since NF-kappaB inhibitor pyrrolidinedithio carbamate (PDTC) and IRF-3 siRNA attenuated significantly RANTES accumulation. H1N1 inoculation also increased PI3K activity as well as Akt phosphorylation and such responsiveness were attenuated by 8-PK. In the presence of wortmannin, nuclear translocation of NF-kappaB and IRF3 as well as RANTES production by H1N1 infection were all reversed, demonstrating that PI3K-Akt pathway is essential for NF-kappaB- and IRF-3-mediated RANTES production in A549 cells. Furthermore, 8-PK but not wortmannin, prevented effectively H1N1-evoked IkappaB degradation. In conclusion, 8-PK might be an anti-inflammatory agent for suppressing influenza A virus-induced RANTES production acts by blocking PI3K-mediated transcriptional activation of NF-kappaB and IRF-3 and in part by interfering with IkappaB degradation which subsequently decreases NF-kappaB translocation.

8-Prenylkaempferol suppresses inducible nitric oxide synthase expression through interfering with JNK-mediated AP-1 pathway in murine macrophages.[Pubmed:18579129]

Eur J Pharmacol. 2008 Aug 20;590(1-3):430-6.

8-Prenylkaempferol is a prenylflavonoid isolated from the roots of Sophora flavescens, a Chinese herb with anti-inflammatory properties. However whether 8-Prenylkaempferol itself displayed an anti-inflammatory activity remained unclear. In this study, we evaluated the effect of 8-Prenylkaempferol on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. 8-Prenylkaempferol inhibited significantly LPS-induced NO production through suppressing inducible NO synthase (iNOS) expression at both protein and mRNA levels but failed to affect sodium nitroprusside-triggered NO production, iNOS enzyme activity, and cell viability. Further investigation of the mechanisms revealed that 8-Prenylkaempferol inhibited LPS-induced c-Jun phosphorylation (a major component of activator protein-1, AP-1), but did not attenuate IkB-alpha degradation nor NF-kappaB nuclear translocation. Cellular signaling analysis using mitogen-activating protein kinase (MAPK) inhibitors including 2'-amino-3'-methoxyflavone (PD98059, MEK1/2 inhibitor), 4-[5-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]pyridine (SB203580, p38 kinase inhibitor) and anthra[1-9-cd]pyrazol-6(2H)-one (SP600125, c-Jun N-terminal kinase inhibitor) demonstrated that extracellular signal-regulated kinase1/2 (ERK1/2), p38 and JNK all participated in LPS-stimulated iNOS expression and NO production, but 8-Prenylkaempferol interfered selectively with JNK phosphorylation. On the other hand, LPS-induced c-Jun phosphorylation was attenuated in the presence of SP600125. We suggested that interfering with JNK-mediated c-Jun phosphorylation and thus blocking AP-1 activation might contribute to the suppression effects of 8-Prenylkaempferol on iNOS. These findings provided the first molecular basis that 8-Prenylkaempferol is an effective agent for attenuating pro-inflammatory NO induction.

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