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Kaempferide

O-methylated flavonol CAS# 491-54-3

Kaempferide

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Chemical structure

Kaempferide

3D structure

Chemical Properties of Kaempferide

Cas No. 491-54-3 SDF Download SDF
PubChem ID 5281666 Appearance Yellow powder
Formula C16H12O6 M.Wt 300.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Kaempferol 4'-O-methyl ether
Solubility DMSO : 20 mg/mL (66.61 mM; Need ultrasonic)
Chemical Name 3,5,7-trihydroxy-2-(4-methoxyphenyl)chromen-4-one
SMILES COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
Standard InChIKey SQFSKOYWJBQGKQ-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3
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 Kaempferide

1 Alpinia sp. 2 Arnica sp. 3 Eupatorium sp. 4 Geranium sp. 5 Gossypium sp. 6 Phyllanthus sp. 7 Rhamnus sp. 8 Scutellaria sp. 9 Silybum sp. 10 Tamarix sp.

Biological Activity of Kaempferide

DescriptionKaempferide has a variety of effects including anti-carcinogenic, anti-inflammatory, anti-oxidant, anti-bacterial and anti-viral properties.it can protect DNA from radiation induced lesions resulting from radiation exposures under in vitro and ex vivo conditions.
TargetsCaspase | PARP | BMP-2
In vitro

Comparison of effects of kaempferide and anhydroicaritin on biomineralization of cultured osteoblasts[Pubmed: 22993853]

Yao Xue Xue Bao. 2012 Jul;47(7):890-6.

This study is to compare the effects of Kaempferide and anhydroicaritin on biomineralization of rat osteoblasts (ROB) in vitro.
METHODS AND RESULTS:
Calvarias were dissected aseptically from newborn SD rats, the osteoblasts were obtained by enzyme digestion and were cultured in MEM containing 10% FBS. The medium was changed every three days, and serial subculture was performed when cells covered with 90% of the dish. Kaempferide and anhydroicaritin were separately added with final concentrations of 1 x 10(-4), 1 x 10(-5), 1 x 10(-6) and 1 x 10(-7) mol x L(-1) under the conditions of osteogenic differentiation. The proliferation was measured by MTT, and the optimal concentration was detected by the ALP activity at the 9th day after osteogenic induction culture. The osteogenic indexes of Kaempferide, anhydroicaritin and control group with the optimal concentration were compared. The result showed that the anhydroicaritin at concentration of 1 x 10(-5) mol x L(-1) had significantly promoted the activity of ALP, calcium content and osteocalcin content, increased the number of CFU-F(ALP) and mineralized nodules, enhanced the mRNA level of BMP-2, OSX and Runx-2, which are key genes of osteogenic differentiation, and raised the protein content of collagen-I. However, the Kaempferide group had not significantly represented the ability that promoted osteogenic differentiation of ROB.
CONCLUSIONS:
The difference of osteogenic differentiation on ROB between Kaempferide and anhydroicaritin was caused by the prenyl group on C-8 of icariin.

Antioxidant capacity and radioprotective propertiesof the flavonoids galangin and kaempferide isolated from Alpinia galanga L. (Zingiberaceae) against radiation induced cellular DNA damage[Reference: WebLink]

Int.J.Radiat. Res.,2013, 11(2):81-9.

Alpinia galanga L belonging to the family Zingiberaceae is widely grown in the state of Kerala, India. They are effective antioxidant and free radical scavenger under both in vitro and in vivo condition. The efficacy of the isolated flavonoids in conferring protection from radiation induced damages to genomic DNA was studied.
METHODS AND RESULTS:
The bioflavonoids, galangin and Kaempferide were isolated from the AE fractions Alpinia galanga. The isolated flavanoids - galangin and Kaempferide, and the crude extracts (AE and EE) were assayed for their various free radical scavenging activities like DPPH (1,1-diphenyl-2-picryl-hydrazyl), hydroxyl and superoxide radical scavenging activities. The in vitro DNA damage was monitored by assessing the radiation induced relaxation of supercoiled plasmid DNA (pBR 322). Damage to cellular DNA of human peripheral blood leukocytes induced by y-radiation (4 Gy) was monitored by alkaline single cell gel electrophoresis or comet assay. The extracts and pure compounds scavenged hydroxyl radicals in a concentration dependent manner. The compounds demonstrated a concentration dependent scavenging capacity by neutralizing the superoxide radicals. A considerably lower concentration (400-1000 ppm) of the pure flavonoids showed good antioxidant capacity. The presence of 10 mM Kaempferide helped in reducing the extent of DNA damage following 4 Gy gamma irradiation (P<0.001). Galangin (10 mM) also facilitated in reduction of comet parameters.
CONCLUSIONS:
The extracts of Alpinia galanga or the isolated bioflavonoids -galangin and Kaempferide can protect DNA from radiation induced lesions resulting from radiation exposures under in vitro and ex vivo conditions.

Protocol of Kaempferide

Cell Research

Kaempferide, the most active among the four flavonoids isolated and characterized from Chromolaena odorata, induces apoptosis in cervical cancer cells while being pharmacologically safe[Reference: WebLink]

Inhibition of in vitro growth and arrest in the G0/G1 phase of HCT8 line human colon cancer cells by kaempferide triglycoside from Dianthus caryophyllus.[Pubmed: 20104502]

Phytother Res. 2010 Sep;24(9):1302-8.

The effects of phytoestrogens have been studied in the hypothalamic-pituitary-gonadal axis and in various non-gonadal targets. Epidemiologic and experimental evidence indicates a protective effect of phytoestrogens also in colorectal cancer. The mechanism through which estrogenic molecules control colorectal cancer tumorigenesis could possibly involve estrogen receptor beta, the predominantly expressed estrogen receptor subtype in colon mucosa.
METHODS AND RESULTS:
To validate this hypothesis, we therefore used an engineered human colon cancer cell line induced to overexpress estrogen receptor beta, beside its native cell line, expressing very low levels of ERbeta and not expressing ERalpha; as a phytoestrogenic molecule, we used Kaempferide triglycoside, a glycosylated flavonol from a Dianthus caryophyllus cultivar. The inhibitory properties of this molecule toward vegetal cell growth have been previously demonstrated: however, no data on its activity on animal cell or information about the mechanism of this activity are available. Kaempferide triglycoside proved to inhibit the proliferation of native and estrogen receptor beta overexpressing colon cancer cells through a mechanism not mediated by ligand binding dependent estrogen receptor activation. It affected HCT8 cell cycle progression by increasing the G(0)/G(1) cell fraction and in estrogen receptor beta overexpressing cells increased two antioxidant enzymes. Interestingly, the biological effects of this Kaempferide triglycoside were strengthened by the presence of high levels of estrogen receptor beta.
CONCLUSIONS:
Pleiotropic molecular effects of phytoestrogens may explain their protective activity against colorectal cancer and may represent an interesting area for future investigation with potential clinical applications.

Rsc Adv., 2015, 5(122):100912-22.

Chromolaena odorata, commonly known as Siam weed, is popular as a traditional medicine. We report the isolation and characterization of four compounds from a cytotoxic fraction, F-17, isolated from the dichloromethane (DCM) extract of C. odorata by bioactivity-guided fractionation.
METHODS AND RESULTS:
The organic extracts were screened in five cancer cell lines of various origins for their cytotoxic effect. The DCM extract exhibited maximum cytotoxicity and was purified by silica gel column chromatography to obtain four major compounds. The compounds were characterized by 1H-NMR, 13C-NMR, and HR-MS methods and were found to be acacetin (1), dihydroKaempferide (2), isosakuranetin (3), and Kaempferide (4). MTT assay was used for preliminary evaluation of the cytotoxicity of these compounds. Among the cancer cell lines that were screened, HeLa was the most sensitive to Kaempferide (IC50: 16 μM) followed by acacetin (174 μM), dihydroKaempferide (>200 μM) and isosakuranetin (>200 μM). Kaempferide (4) induced morphological characteristics of apoptosis in HeLa cells and was non-toxic to rapidly dividing normal human fibroblasts up to 100μM. Annexin V staining, characteristic of early stage of apoptosis was further confirmed by FACS analysis. Induction of apoptosis was illustrated by its potential to induce the cleavage of caspases and PARP.
CONCLUSIONS:
FACS analysis demonstrated that Kaempferide (4)-induced cytotoxicity is independent of cell cycle arrest. Acute and chronic toxicity studies conducted in vivo proved that the compound is pharmacologically safe. To the best of our knowledge, this is the first study reporting the anticancer potential and pharmacological safety of Kaempferide (4).

Kaempferide Dilution Calculator

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Kaempferide Molarity Calculator

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Preparing Stock Solutions of Kaempferide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.33 mL 16.65 mL 33.3 mL 66.6001 mL 83.2501 mL
5 mM 0.666 mL 3.33 mL 6.66 mL 13.32 mL 16.65 mL
10 mM 0.333 mL 1.665 mL 3.33 mL 6.66 mL 8.325 mL
50 mM 0.0666 mL 0.333 mL 0.666 mL 1.332 mL 1.665 mL
100 mM 0.0333 mL 0.1665 mL 0.333 mL 0.666 mL 0.8325 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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Background on Kaempferide

The effects of phytoestrogens have been studied in the hypothalamic-pituitary-gonadal axis and various non-gonadal targets. Epidemiologic and experimental evidence indicates a protective effect of phytoestrogens also in colorectal cancer. The mechanism through which estrogenic molecules control colorectal cancer tumorigenesis could possibly involve estrogen receptor β, which is the predominantly expressed estrogen receptor subtype in colon mucosa.

In vitro: Kaempferide triglycoside proved to inhibit the proliferation of native and estrogen receptor β overexpressing colon cancer cells via a mechanism not mediated by ligand binding dependent estrogen receptor activation. It affected HCT8 cell cycle progression through increasing the G0/G1 cell fraction and in estrogen receptor β overexpressing cells increased two antioxidant enzymes [1].

In vivo: The aim of one previous study was to evaluate the effect of kaempferol on tissue lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal cancer in male Wistar rats and to compare its efficacy with irinotecan. This study revealed that kaempferol could be safely used as a chemopreventive agent in colorectal cancer [2].

Clinical trial: Up to now, kaempferide is still in the preclinical development stage.

Reference:
[1] Martineti V, Tognarini I, Azzari C, Carbonell Sala S, Clematis F, Dolci M, Lanzotti V, Tonelli F, Brandi ML, Curir P.  Inhibition of in vitro growth and arrest in the G0/G1 phase of HCT8 line human colon cancer cells by kaempferide triglycoside from Dianthus caryophyllus. Phytother Res. 2010 Sep;24(9):1302-8.
[2] Nirmala P, Ramanathan M.  Effect of kaempferol on lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal carcinoma in rats. Eur J Pharmacol. 2011 Mar 1;654(1):75-9.

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References on Kaempferide

[Comparison of effects of kaempferide and anhydroicaritin on biomineralization of cultured osteoblasts].[Pubmed:22993853]

Yao Xue Xue Bao. 2012 Jul;47(7):890-6.

This study is to compare the effects of Kaempferide and anhydroicaritin on biomineralization of rat osteoblasts (ROB) in vitro. Calvarias were dissected aseptically from newborn SD rats, the osteoblasts were obtained by enzyme digestion and were cultured in MEM containing 10% FBS. The medium was changed every three days, and serial subculture was performed when cells covered with 90% of the dish. Kaempferide and anhydroicaritin were separately added with final concentrations of 1 x 10(-4), 1 x 10(-5), 1 x 10(-6) and 1 x 10(-7) mol x L(-1) under the conditions of osteogenic differentiation. The proliferation was measured by MTT, and the optimal concentration was detected by the ALP activity at the 9th day after osteogenic induction culture. The osteogenic indexes of Kaempferide, anhydroicaritin and control group with the optimal concentration were compared. The result showed that the anhydroicaritin at concentration of 1 x 10(-5) mol x L(-1) had significantly promoted the activity of ALP, calcium content and osteocalcin content, increased the number of CFU-F(ALP) and mineralized nodules, enhanced the mRNA level of BMP-2, OSX and Runx-2, which are key genes of osteogenic differentiation, and raised the protein content of collagen-I. However, the Kaempferide group had not significantly represented the ability that promoted osteogenic differentiation of ROB. The difference of osteogenic differentiation on ROB between Kaempferide and anhydroicaritin was caused by the prenyl group on C-8 of icariin.

Inhibition of in vitro growth and arrest in the G0/G1 phase of HCT8 line human colon cancer cells by kaempferide triglycoside from Dianthus caryophyllus.[Pubmed:20104502]

Phytother Res. 2010 Sep;24(9):1302-8.

The effects of phytoestrogens have been studied in the hypothalamic-pituitary-gonadal axis and in various non-gonadal targets. Epidemiologic and experimental evidence indicates a protective effect of phytoestrogens also in colorectal cancer. The mechanism through which estrogenic molecules control colorectal cancer tumorigenesis could possibly involve estrogen receptor beta, the predominantly expressed estrogen receptor subtype in colon mucosa.To validate this hypothesis, we therefore used an engineered human colon cancer cell line induced to overexpress estrogen receptor beta, beside its native cell line, expressing very low levels of ERbeta and not expressing ERalpha; as a phytoestrogenic molecule, we used Kaempferide triglycoside, a glycosylated flavonol from a Dianthus caryophyllus cultivar. The inhibitory properties of this molecule toward vegetal cell growth have been previously demonstrated: however, no data on its activity on animal cell or information about the mechanism of this activity are available. Kaempferide triglycoside proved to inhibit the proliferation of native and estrogen receptor beta overexpressing colon cancer cells through a mechanism not mediated by ligand binding dependent estrogen receptor activation. It affected HCT8 cell cycle progression by increasing the G(0)/G(1) cell fraction and in estrogen receptor beta overexpressing cells increased two antioxidant enzymes. Interestingly, the biological effects of this Kaempferide triglycoside were strengthened by the presence of high levels of estrogen receptor beta.Pleiotropic molecular effects of phytoestrogens may explain their protective activity against colorectal cancer and may represent an interesting area for future investigation with potential clinical applications.

Description

Kaempferide is an O-methylated flavonol, a type of chemical compound.

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