Genkwanin

CAS# 437-64-9

Genkwanin

Catalog No. BCN5488----Order now to get a substantial discount!

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Quality Control of Genkwanin

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Chemical structure

Genkwanin

3D structure

Chemical Properties of Genkwanin

Cas No. 437-64-9 SDF Download SDF
PubChem ID 5281617 Appearance White-yellowish powder
Formula C16H12O5 M.Wt 284.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Apigenin 7-methyl ether; 4',5-Dihydroxy 7-methoxyflavone; 7-Methylapigenin; Puddumetin
Solubility DMSO : 5 mg/mL (17.59 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
SMILES COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O
Standard InChIKey JPMYFOBNRRGFNO-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,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 Genkwanin

1 Baccharis sp. 2 Castanea sp. 3 Cistus sp. 4 Daphne sp. 5 Glycyrrhiza sp. 6 Gnidia sp. 7 Lavandula sp. 8 Leonurus sp. 9 Lycopus sp. 10 Monarda sp. 11 Populus sp. 12 Prunus sp. 13 Rosmarinus sp. 14 Salvia sp. 15 Thymus sp. 16 Vanillosmopsis sp. 17 Wikstroemia sp.

Biological Activity of Genkwanin

DescriptionGenkwanin has antitumor, and anti-inflammatory activities, it enhances host immunity, decreases the inflammatory cytokine levels, and regulates the miR-101/MKP-1/MAPK pathway.Genkwanin may have anti-skin ageing activity, it can up-regulate the transcriptional activation of human type vii collagen gene promoter, stimulating the formation of anchoring fibrils at the basement membrane zone in skin contributed to preventing skin ageing; it also induces a decrease of melanin synthesis by inhibiting tyrosinase activity, it could as skin whitening agent in cosmetic preparations.
TargetsNOS | TNF-α | p38MAPK | JNK | AP-1 | Akt | IL Receptor
In vitro

Genkwanin inhibits proinflammatory mediators mainly through the regulation of miR-101/MKP-1/MAPK pathway in LPS-activated macrophages.[Pubmed: 24800851]

PLoS One. 2014 May 6;9(5):e96741.

Genkwanin is one of the major non-glycosylated flavonoids in many herbs with anti-inflammatory activities. Although its anti-inflammatory activity in vivo has been reported, the potential molecular mechanisms remain obscure.
METHODS AND RESULTS:
In this study, by pharmacological and genetic approaches, we explore the anti-inflammatory effects of Genkwanin in LPS-activated RAW264.7 macrophages. Genkwanin potently decreases the proinflammatory mediators, such as iNOS, TNF-α, IL-1β and IL-6, at the transcriptional and translational levels without cytotoxicity, indicating the excellent anti-inflammatory potency of Genkwanin in vitro. Mechanism study shows that Genkwanin significantly suppresses the p38- and JNK-mediated AP-1 signaling pathway and increases the mitogen-activated protein kinase (MAPK) phosphatase 1 (MKP-1) expression at the posttranscriptional level. We also confirmed that microRNA-101 (miR-101) is a negative regulator of MKP-1 expression. Moreover, regardless of miR-101-deficient cells or miR-101-abundant cells, the suppression effects of Genkwanin on supernatant proinflammatory mediators' levels are far less than that in respective negative control cells, suggesting that Genkwanin exerts anti-inflammatory effect mainly through reducing miR-101 production. However, Genkwanin can't affect the level of phospho-Akt (p-Akt), indicating that the phosphorylation of Akt may be not responsible for the effect of Genkwanin on miR-101 production.
CONCLUSIONS:
We conclude that Genkwanin exerts its anti-inflammatory effect mainly through the regulation of the miR-101/MKP-1/MAPK pathway.

Genkwanin up-regulates the transcriptional activation of human type vii collagen gene promoter.[Reference: WebLink]

Int. J.Cosmetic Sci., 2007, 29(4):332- 3.


METHODS AND RESULTS:
In a recent study, stimulating the formation of anchoring fibrils at the basement membrane zone in skin contributed to preventing skin ageing, such as wrinkle formation. Expression of the type VII collagen gene induces the formation of anchoring fibrils composed mainly of collagen type VII. We therefore transiently transfected a keratinocyte cell line with the plasmids containing type VII collagen gene promoter located upstream of the luciferase gene.
CONCLUSIONS:
We investigated the promoter activity under the presence of flavonoids and we found that Genkwanin up-regulates the transcriptional activation of human type VII collagen gene promoter.

In vivo

Antitumor and immunomodulatory activity of genkwanin on colorectal cancer in the APC(Min/+) mice.[Pubmed: 26388189 ]

Int Immunopharmacol. 2015 Dec;29(2):701-707.

Colorectal cancer is the third most common malignant tumor with high morbidity and mortality.
METHODS AND RESULTS:
To evaluate the antitumor effect of Genkwanin on colorectal cancer enhanced by western high-fat diet, we investigated the activity of Genkwanin on HT-29 and SW-480 human colorectal cancer lines in vitro and on the APC(Min/+) mice in vivo. In a cell culture system, six different inflammatory cytokines obviously stimulated two cancer cells growth in a concentration-dependent manner, while Genkwanin significantly inhibited HT-29 and SW-480 human colorectal cancer cells proliferation and inflammatory cytokine IL-8 secretion. In the APC(Min/+) mice, the body weights, spleen and thymus indexes and immunity cytokine secretions were significantly improved after oral administration 12.5 and 25mg/kg/day of Genkwanin. Besides, the tumor multiplicity changes and inflammatory cytokine levels were markedly reduced in two Genkwanin-treated groups. The dysplastic adenomatous changes were also obviously ameliorated in gut histopathology.
CONCLUSIONS:
Taken together, our results indicated that Genkwanin had a better antitumor activity partly via enhancing host immunity and decreasing the inflammatory cytokine levels. Genkwanin may be an effective chemotherapeutic agent for the treatment of colorectal cancer.

Protocol of Genkwanin

Cell Research

Effect of apigenin-7-glucoside, genkwanin and naringenin on tyrosinase activity and melanin synthesis in B16F10 melanoma cells.[Pubmed: 26656314 ]

Life Sci. 2016 Jan 1;144:80-5.

In this study, we have investigated the effects of apigenin-7-glucoside, Genkwanin and naringenin, on mouse melanoma B16F10 cell proliferation. Influence of these natural products on percentage cell distribution in cycle phases and melanogenesis was also studied.
METHODS AND RESULTS:
Cell viability was determined at various periods using the MTT assay, whereas effects of tested compounds on progression through the cell cycle were analyzed by flow cytometry. In addition, amounts of melanin and tyrosinase were measured spectrophotometrically at 475 nm. Besides, the mechanism involved on the death route induced by the tested molecules was evaluated using the bis-benzimide trihydrochloride coloration method (Hoechst 33258). Apigenin-7-glucoside, Genkwanin and naringenin exhibited significant anti-proliferative activity against B16F10 melanoma cells after 24 and 48 h of incubation. Furthermore, apigenin-7-glucoside, Genkwanin and naringenin provoked an increase of subG0/G1, S and G2/M phase cell proportion with a significant decrease of cell proportion in G0/G1 phases. The results evaluated using Hoechst 33,258, confirm that the percentage of B16F10 cells observed in the sub G0/G1 phase were undergoing apoptosis. Moreover, apigenin-7-glucoside and naringenin revealed an ability to enhance melanogenesis synthesis and tyrosinase activity of B16F10 melanoma cells. Whereas Genkwanin induces a decrease of melanin synthesis by inhibiting tyrosinase activity.
CONCLUSIONS:
Our results promote the introduction of Genkwanin in cosmetic preparations, as skin whitening agent, whereas apigenin-7-glucoside and naringenin should be introduced into cosmetic products as natural tanning agents.

Animal Research

Intestinal absorptive transport of Genkwanin from Flos genkwa using a single-pass intestinal perfusion rat model.[Pubmed: 24707867]

Am J Chin Med. 2014;42(2):349-59.


METHODS AND RESULTS:
To investigate the absorptive transport behavior of Genkwanin and the beneficial effects of monoterpene enhancers with different functional groups, the single-pass intestinal perfusion (SPIP) of rats was used. The results showed that Genkwanin was segmentally-dependent and the best absorptive site was the duodenum. The effective permeability coefficient (P eff ) was 1.97 × 10(-4) cm/s and the absorption rate constant (Ka) was 0.62 × 10(-2) s(-1). Transepithelial transportation descended with increasing concentrations of Genkwanin. This was a 1.4-fold increase in P eff by probenecid, whereas a 1.4-fold or 1.6-fold decrease was observed by verapamil and pantoprazole, respectively. Furthermore, among the absorption enhancers, the enhancement with carbonyl (camphor and menthone) was higher than that with hydroxyl (borneol and menthol).
CONCLUSIONS:
The concentration-independent permeability and enhancement by coperfusion of probenecid indicated that Genkwanin was transported by both passive diffusion and multidrug resistance protein (MDR)-mediated efflux mechanisms.

Genkwanin Dilution Calculator

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Preparing Stock Solutions of Genkwanin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5174 mL 17.5871 mL 35.1741 mL 70.3482 mL 87.9353 mL
5 mM 0.7035 mL 3.5174 mL 7.0348 mL 14.0696 mL 17.5871 mL
10 mM 0.3517 mL 1.7587 mL 3.5174 mL 7.0348 mL 8.7935 mL
50 mM 0.0703 mL 0.3517 mL 0.7035 mL 1.407 mL 1.7587 mL
100 mM 0.0352 mL 0.1759 mL 0.3517 mL 0.7035 mL 0.8794 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 Genkwanin

Effect of apigenin-7-glucoside, genkwanin and naringenin on tyrosinase activity and melanin synthesis in B16F10 melanoma cells.[Pubmed:26656314]

Life Sci. 2016 Jan 1;144:80-5.

AIMS: In this study, we have investigated the effects of apigenin-7-glucoside, Genkwanin and naringenin, on mouse melanoma B16F10 cell proliferation. Influence of these natural products on percentage cell distribution in cycle phases and melanogenesis was also studied. MAIN METHODS: Cell viability was determined at various periods using the MTT assay, whereas effects of tested compounds on progression through the cell cycle were analyzed by flow cytometry. In addition, amounts of melanin and tyrosinase were measured spectrophotometrically at 475 nm. Besides, the mechanism involved on the death route induced by the tested molecules was evaluated using the bis-benzimide trihydrochloride coloration method (Hoechst 33258). KEY FINDINGS: Apigenin-7-glucoside, Genkwanin and naringenin exhibited significant anti-proliferative activity against B16F10 melanoma cells after 24 and 48 h of incubation. Furthermore, apigenin-7-glucoside, Genkwanin and naringenin provoked an increase of subG0/G1, S and G2/M phase cell proportion with a significant decrease of cell proportion in G0/G1 phases. The results evaluated using Hoechst 33,258, confirm that the percentage of B16F10 cells observed in the sub G0/G1 phase were undergoing apoptosis. Moreover, apigenin-7-glucoside and naringenin revealed an ability to enhance melanogenesis synthesis and tyrosinase activity of B16F10 melanoma cells. Whereas Genkwanin induces a decrease of melanin synthesis by inhibiting tyrosinase activity. SIGNIFICANCE: Our results promote the introduction of Genkwanin in cosmetic preparations, as skin whitening agent, whereas apigenin-7-glucoside and naringenin should be introduced into cosmetic products as natural tanning agents.

Genkwanin inhibits proinflammatory mediators mainly through the regulation of miR-101/MKP-1/MAPK pathway in LPS-activated macrophages.[Pubmed:24800851]

PLoS One. 2014 May 6;9(5):e96741.

Genkwanin is one of the major non-glycosylated flavonoids in many herbs with anti-inflammatory activities. Although its anti-inflammatory activity in vivo has been reported, the potential molecular mechanisms remain obscure. In this study, by pharmacological and genetic approaches, we explore the anti-inflammatory effects of Genkwanin in LPS-activated RAW264.7 macrophages. Genkwanin potently decreases the proinflammatory mediators, such as iNOS, TNF-alpha, IL-1beta and IL-6, at the transcriptional and translational levels without cytotoxicity, indicating the excellent anti-inflammatory potency of Genkwanin in vitro. Mechanism study shows that Genkwanin significantly suppresses the p38- and JNK-mediated AP-1 signaling pathway and increases the mitogen-activated protein kinase (MAPK) phosphatase 1 (MKP-1) expression at the posttranscriptional level. We also confirmed that microRNA-101 (miR-101) is a negative regulator of MKP-1 expression. Moreover, regardless of miR-101-deficient cells or miR-101-abundant cells, the suppression effects of Genkwanin on supernatant proinflammatory mediators' levels are far less than that in respective negative control cells, suggesting that Genkwanin exerts anti-inflammatory effect mainly through reducing miR-101 production. However, Genkwanin can't affect the level of phospho-Akt (p-Akt), indicating that the phosphorylation of Akt may be not responsible for the effect of Genkwanin on miR-101 production. We conclude that Genkwanin exerts its anti-inflammatory effect mainly through the regulation of the miR-101/MKP-1/MAPK pathway.

Intestinal absorptive transport of Genkwanin from Flos genkwa using a single-pass intestinal perfusion rat model.[Pubmed:24707867]

Am J Chin Med. 2014;42(2):349-59.

To investigate the absorptive transport behavior of Genkwanin and the beneficial effects of monoterpene enhancers with different functional groups, the single-pass intestinal perfusion (SPIP) of rats was used. The results showed that Genkwanin was segmentally-dependent and the best absorptive site was the duodenum. The effective permeability coefficient (P eff ) was 1.97 x 10(-4) cm/s and the absorption rate constant (Ka) was 0.62 x 10(-2) s(-1). Transepithelial transportation descended with increasing concentrations of Genkwanin. This was a 1.4-fold increase in P eff by probenecid, whereas a 1.4-fold or 1.6-fold decrease was observed by verapamil and pantoprazole, respectively. Furthermore, among the absorption enhancers, the enhancement with carbonyl (camphor and menthone) was higher than that with hydroxyl (borneol and menthol). The concentration-independent permeability and enhancement by coperfusion of probenecid indicated that Genkwanin was transported by both passive diffusion and multidrug resistance protein (MDR)-mediated efflux mechanisms.

Antitumor and immunomodulatory activity of genkwanin on colorectal cancer in the APC(Min/+) mice.[Pubmed:26388189]

Int Immunopharmacol. 2015 Dec;29(2):701-707.

Colorectal cancer is the third most common malignant tumor with high morbidity and mortality. To evaluate the antitumor effect of Genkwanin on colorectal cancer enhanced by western high-fat diet, we investigated the activity of Genkwanin on HT-29 and SW-480 human colorectal cancer lines in vitro and on the APC(Min/+) mice in vivo. In a cell culture system, six different inflammatory cytokines obviously stimulated two cancer cells growth in a concentration-dependent manner, while Genkwanin significantly inhibited HT-29 and SW-480 human colorectal cancer cells proliferation and inflammatory cytokine IL-8 secretion. In the APC(Min/+) mice, the body weights, spleen and thymus indexes and immunity cytokine secretions were significantly improved after oral administration 12.5 and 25mg/kg/day of Genkwanin. Besides, the tumor multiplicity changes and inflammatory cytokine levels were markedly reduced in two Genkwanin-treated groups. The dysplastic adenomatous changes were also obviously ameliorated in gut histopathology. Taken together, our results indicated that Genkwanin had a better antitumor activity partly via enhancing host immunity and decreasing the inflammatory cytokine levels. Genkwanin may be an effective chemotherapeutic agent for the treatment of colorectal cancer.

Description

Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

Keywords:

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