KaempferitrinCAS# 482-38-2 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 482-38-2 | SDF | Download SDF |
PubChem ID | 5486199 | Appearance | Yellow powder |
Formula | C27H30O14 | M.Wt | 578.5 |
Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
Synonyms | Kaempferol 3,7-di-O-α-L-rhamnoside; Lespedin; Lespenephryl; 3,4',5,7-Tetrahydroxyflavone 3,7-dirhamnoside | ||
Solubility | DMSO : 125 mg/mL (216.07 mM; Need ultrasonic) | ||
Chemical Name | 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]chromen-4-one | ||
SMILES | CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O | ||
Standard InChIKey | PUPKKEQDLNREIM-QNSQPKOQSA-N | ||
Standard InChI | InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/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. |
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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. |
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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. |
Description | Kaempferitrin exerts immunostimulatory, antidepressant-like , antiosteoporotic , cytotoxic and antitumor effects, the general mechanisms include cell cycle arrest in G1 phase and apoptosis via intrinsic pathway in a caspase dependent pathway. Kaempferitrin is an acute lowering effect on blood glucose in diabetic rats and to stimulate the glucose uptake percentile, as efficiently as insulin in muscle from normal rats. |
Targets | PI3K | PKC | MEK | p38MAPK | GLUT | NO | 5-HT Receptor | Akt |
In vitro | Kaempferitrin induces immunostimulatory effects in vitro.[Pubmed: 23588095]J Ethnopharmacol. 2013 Jun 21;148(1):337-40. Justicia spicigera is a plant used as immunostimulatory in Mexican traditional medicine. Recently, we showed that Justicia spicigera extracts exerted immunostimulatory effects and the major component of this extract was Kaempferitrin (KM). This work shows a correlation between the medical traditional use of Justicia spicigera and Kaempferitrin, its active compound. Kaempferitrin induces apoptosis via intrinsic pathway in HeLa cells and exerts antitumor effects.[Pubmed: 23211658]J Ethnopharmacol. 2013 Jan 30;145(2):476-89. Justicia spicigera is used for the empirical treatment of cervical cancer in Mexico. Recently, we showed that Justicia spicigera extracts exerted cytotoxic and antitumoral effects and the major component of this extract was Kaempferitrin (KM). Insulinomimetic effects of kaempferitrin on glycaemia and on 14C-glucose uptake in rat soleus muscle.[Pubmed: 15501431]Chem Biol Interact. 2004 Oct 15;149(2-3):89-96.Bauhinia forficata is one of the Bauhinia species mostly used as an antidiabetic herbal remedy in Brazil. Kaempferitrin (kaempferol-3,7-O-(alpha)-L-dirhamnoside) is the predominant flavonol glycoside found in the B. forficata leaves. |
In vivo | Antidiabetic activity of Sedum dendroideum: metabolic enzymes as putative targets for the bioactive flavonoid kaempferitrin.[Pubmed: 24817132]IUBMB Life. 2014 May;66(5):361-70.The aim of this study was to evaluate the antidiabetic potential of a leaf extract and flavonoids from Sedum dendroideum (SD). Additionally, our goals were to establish a possible structure/activity relationship between these flavonoids and to assess the most active flavonoid on the glycolytic enzyme 6-phosphofructo-1-kinase (PFK). SD juice (LJ), a flavonoid-rich fraction (BF), and separately five flavonoids were evaluated intraperitoneally for their acute hypoglycemic activity in normal and streptozotocin-induced diabetic mice. |
Kinase Assay | Kaempferitrin activates the insulin signaling pathway and stimulates secretion of adiponectin in 3T3-L1 adipocytes.[Pubmed: 19326566]Insulin signaling: a potential signaling pathway for the stimulatory effect of kaempferitrin on glucose uptake in skeletal muscle.[Pubmed: 23458067]Eur J Pharmacol. 2013 Jul 15;712(1-3):1-7.The aim of the study was to investigate the in vitro effect and the mechanism of action of Kaempferitrin on glucose uptake in an insulin target (soleus muscle). Eur J Pharmacol. 2009 Apr 1;607(1-3):27-34.The purpose of the current study was to examine the signal transduction pathways activated and adipokine secreted by Kaempferitrin stimulation to adipocytes. |
Animal Research | Anti-depressant-like effect of kaempferitrin isolated from Justicia spicigera Schltdl (Acanthaceae) in two behavior models in mice: evidence for the involvement of the serotonergic system.[Pubmed: 25532842]Molecules. 2014 Dec 19;19(12):21442-61.We evaluated the antidepressant-like effect of Kaempferitrin (Km) isolated from the plant Justicia spicigera (Asteraceae), which is used in traditional medicine for relieving emotional disorders, such as "la tristeza" (sadness or dysthymia) and "el humor" (mood changes). |
Kaempferitrin Dilution Calculator
Kaempferitrin Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 1.7286 mL | 8.643 mL | 17.2861 mL | 34.5722 mL | 43.2152 mL |
5 mM | 0.3457 mL | 1.7286 mL | 3.4572 mL | 6.9144 mL | 8.643 mL |
10 mM | 0.1729 mL | 0.8643 mL | 1.7286 mL | 3.4572 mL | 4.3215 mL |
50 mM | 0.0346 mL | 0.1729 mL | 0.3457 mL | 0.6914 mL | 0.8643 mL |
100 mM | 0.0173 mL | 0.0864 mL | 0.1729 mL | 0.3457 mL | 0.4322 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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Insulin signaling: a potential signaling pathway for the stimulatory effect of kaempferitrin on glucose uptake in skeletal muscle.[Pubmed:23458067]
Eur J Pharmacol. 2013 Jul 15;712(1-3):1-7.
The aim of the study was to investigate the in vitro effect and the mechanism of action of Kaempferitrin on glucose uptake in an insulin target (soleus muscle). A stimulatory effect of Kaempferitrin on glucose uptake was observed when rat soleus muscle was incubated with 10, 100 and 1000 etaM of this flavonoid glycoside. The presence of specific insulin signaling inhibitors, such as wortmannin, an inhibitor of phosphoinositide 3-kinase (PI3K), RO318220, an inhibitor of protein kinase C (PKC), PD98059, an inhibitor of mitogen-activated protein kinase (MEK), HNMPA(AM)3, an insulin receptor tyrosine kinase activity inhibitor, colchicine, a microtubule-depolymerizing agent, SB239063, an inhibitor of P38 MAPK and cycloheximide, an inhibitor of protein synthesis showed that Kaempferitrin triggers different metabolic and nuclear pathways in skeletal muscle. Besides the influence on glycogen storage, the metabolic action involves the insulin receptor, PI3K, atypical PKC activity and the translocation of GLUT4. Additionally, the nuclear pathways (via MAPK and MEK) provide evidence of the stimulation of the expression of glucose transporters or other signaling proteins, reinforcing proposals that skeletal muscle represents a primary site at which Kaempferitrin exerts its effect promoting glucose homeostasis. Also, these similarities with the signaling pathways of insulin constitute strong evidence for the insulin-mimetic role of Kaempferitrin in glucose homeostasis.
Kaempferitrin induces apoptosis via intrinsic pathway in HeLa cells and exerts antitumor effects.[Pubmed:23211658]
J Ethnopharmacol. 2013 Jan 30;145(2):476-89.
ETHNOPHARMACOLOGICAL RELEVANCE: Justicia spicigera is used for the empirical treatment of cervical cancer in Mexico. Recently, we showed that Justicia spicigera extracts exerted cytotoxic and antitumoral effects and the major component of this extract was Kaempferitrin (KM). MATERIALS AND METHODS: The cytotoxic and apoptotic effect of KM on human cancer cells and human nontumorigenic cells were evaluated using MTT and TUNEL assays, and Annexin V/Propidium iodide detection by flow cytometry. The effect of KM on cell cycle was analyzed by flow cytometry with propidium iodide. The apoptotic and cell cycle effects were also evaluated by western blot analysis. Also, different doses of KM were injected intraperitoneally daily into athymic mice bearing tumors of HeLa cells during 32 days. The growth and weight of tumors were measured. RESULTS: KM induces high cytotoxic effects in vitro and in vivo against HeLa cells. The general mechanisms by which KM induces cytotoxic effects include: cell cycle arrest in G1 phase and apoptosis via intrinsic pathway in a caspase dependent pathway. Also, KM exerts chemopreventive and antitumor effects. CONCLUSION: KM exerts cytotoxic and antitumor effects against HeLa cells.
Kaempferitrin activates the insulin signaling pathway and stimulates secretion of adiponectin in 3T3-L1 adipocytes.[Pubmed:19326566]
Eur J Pharmacol. 2009 Apr 1;607(1-3):27-34.
The purpose of the current study was to examine the signal transduction pathways activated and adipokine secreted by Kaempferitrin stimulation to adipocytes. Activation of insulin receptor beta and insulin receptor substrate 1 was tested in pull-down assays, and phosphorylation of Protein kinase B (PKB/akt) on ser 473 was measured by Western blot. Participation of phosphatidylinositol-3-kinase (PI3-K) in the pathway was tested by addition of wortmannin. GLUT4 translocation was measured on fractions of cell extracts, as well as by confocal imaging on fluorescent immunostained cells. Secreted and cellular adiponectin were measured by Western blot and ELISA. We showed that Kaempferitrin treatment resulted in an up-regulated level of phosphorylation on insulin receptor beta and insulin receptor substrate 1, and ser473 site in PKB/akt. PI3-K acted up-stream of PKB/akt phosphorylation and GLUT4 translocation, as inhibitor of PI3-K wortmannin abolished both. GLUT4 translocated to membrane and GLUT4 protein level increased upon Kaempferitrin stimulation. Kaempferitrin also stimulated more sustained adiponectin secretion than insulin did. This study provided evidence of the dual effects of Kaempferitrin. It improved insulin resistance by the activation of the classical insulin transduction pathway, and increased adiponectin secretion.
Insulinomimetic effects of kaempferitrin on glycaemia and on 14C-glucose uptake in rat soleus muscle.[Pubmed:15501431]
Chem Biol Interact. 2004 Oct 15;149(2-3):89-96.
Bauhinia forficata is one of the Bauhinia species mostly used as an antidiabetic herbal remedy in Brazil. Kaempferitrin (kaempferol-3,7-O-(alpha)-L-dirhamnoside) is the predominant flavonol glycoside found in the B. forficata leaves. The aim of the present work was to study the long-term effect of Kaempferitrin on glycaemia in diabetic rats, as well as the in vitro effect of this compound on 14C-D-glucose uptake and 14C-leucine incorporation into protein in normal rat soleus muscle. Kaempferitrin was found to have an acute lowering effect on blood glucose in diabetic rats and to stimulate the glucose uptake percentile, as efficiently as insulin in muscle from normal rats. This compound did not have any effect on glucosuria or on protein synthesis in muscle from normal and diabetic animals. However, the protein synthesis in the Kaempferitrin-treated groups was maintained at the same level as the respective controls. Thus, the hypoglycaemic effect and the prompt efficiency of the Kaempferitrin in stimulating [U-14C]-2-deoxi-D-glucose uptake in muscle -constitute the first evidence to indicate that the acute effect of this compound on blood glucose lowering may occur as a consequence of the altered intrinsic activity of the glucose transporter (Vmax or glucose transporters translocation?) not involving directly the synthesis of new carriers.
Antidiabetic activity of Sedum dendroideum: metabolic enzymes as putative targets for the bioactive flavonoid kaempferitrin.[Pubmed:24817132]
IUBMB Life. 2014 May;66(5):361-70.
The aim of this study was to evaluate the antidiabetic potential of a leaf extract and flavonoids from Sedum dendroideum (SD). Additionally, our goals were to establish a possible structure/activity relationship between these flavonoids and to assess the most active flavonoid on the glycolytic enzyme 6-phosphofructo-1-kinase (PFK). SD juice (LJ), a flavonoid-rich fraction (BF), and separately five flavonoids were evaluated intraperitoneally for their acute hypoglycemic activity in normal and streptozotocin-induced diabetic mice. First, the major flavonoids kaempferol 3,7-dirhamnoside or Kaempferitrin (1), kaempferol 3-glucoside-7-rhamnoside (2), and kaempferol 3-neohesperidoside-7-rhamnoside (3) were tested. Then, the monoglycosides kaempferol 7-rhamnoside (5) and kaempferol 3-rhamnoside (6) were assayed to establish their structure/activity relationship. The effect of 1 on PFK was evaluated in skeletal muscle, liver, and adipose tissue from treated mice. LJ (400 mg/kg), BF (40 mg/kg), and flavonoid 1 (4 mg/kg) reduced glycemia in diabetic mice (120 min) by 52, 53, and 61%, respectively. Flavonoids 2, 3, 5, and 6 were inactive or showed little activity, suggesting that the two rhamnosyl moieties in Kaempferitrin are important requirements. Kaempferitrin enhanced the PFK activity chiefly in hepatic tissue, suggesting that it is able to stimulate tissue glucose utilization. This result is confirmed testing Kaempferitrin on C2C12 cell line, where it enhanced glucose consumption, lactate production, and the key regulatory glycolytic enzymes. The hypoglycemic activity of Kaempferitrin depends on the presence of both rhamnosyl residues in the flavonoid structure when intraperitoneally administered. Our findings show for the first time that a flavonoid is capable of stimulating PFK in a model of diabetes and that Kaempferitrin stimulates glucose-metabolizing enzymes. This study contributes to the knowledge of the mechanisms by which this flavonoid exerts its hypoglycemic activity.
Anti-depressant-like effect of kaempferitrin isolated from Justicia spicigera Schltdl (Acanthaceae) in two behavior models in mice: evidence for the involvement of the serotonergic system.[Pubmed:25532842]
Molecules. 2014 Dec 19;19(12):21442-61.
We evaluated the antidepressant-like effect of Kaempferitrin (Km) isolated from the plant Justicia spicigera (Asteraceae), which is used in traditional medicine for relieving emotional disorders, such as "la tristeza" (sadness or dysthymia) and "el humor" (mood changes). The actions of Km were evaluated in a forced swimming test (FST) and a suspension tail test (TST) in mice. We explored the involvement of the serotonergic system and the hypothalamic-hypophysis-adrenal axis (HPA) in the antidepressant-like effect of Km. To evaluate nonspecific effects of Km on general activity, the open field test (OFT) was performed. Km at 5, 10, and 20 mg/kg induced an antidepressant-like effect. Sub-effective dose of Km (1 mg/kg) produced a synergistic effect with imipramine (6.25 mg/kg) and fluoxetine (10 mg/kg) but not with desipramine (3.12 mg/kg). Pretreatment with p-chlorophenylalanine methyl ester (PCPA), a serotonin synthesis inhibitor, N-{2-(4-(2-methoxyphenyl)-1-piperazinyl}-N-(2-pyridinyl)cyclohexecarboxamide (WAY-100635), a selective 5-HT1A receptor antagonist, and 8OH-DPAT, a selective 5-HT1A agonist, but not pindolol (10 mg/kg) blocked the anti- immobility effect induced by Km. Taken together, these results indicate that the antidepressant-like effect of Km is related to the serotonergic system, principally 5-HT1A. This effect was not related to changes in locomotor activity.