Homoplantaginin

Details:

Chemical Properties of Homoplantaginin

Cas No.	17680-84-1
PubChem ID	5318083	Appearance	Yellow powder
Formula	C22H22O11	M.Wt	462.40
Type of Compound	Flavonoids	Storage	Desiccate at -20°C
Synonyms	Dinatin 7-glucoside; Hispiduloside; Homoplantaginin; 6-Methoxyapigenin 7-glucoside; 6-Methylscutellarein 7-glucoside; Salvitin 7-glucoside; Scutellarein 6-methyl ether 7-glucoside; 4',5,7-Trihydroxy 6-methoxyflavone 7-glucoside
Solubility	DMSO : ≥ 100 mg/mL (216.26 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES	COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
Standard InChIKey	GCLAFEGUXXHIFT-IWLDQSELSA-N
Standard InChI	InChI=1S/C22H22O11/c1-30-21-14(32-22-20(29)19(28)17(26)15(8-23)33-22)7-13-16(18(21)27)11(25)6-12(31-13)9-2-4-10(24)5-3-9/h2-7,15,17,19-20,22-24,26-29H,8H2,1H3/t15-,17-,19+,20-,22-/m1/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 Homoplantaginin

The herbs of Saluia plebeia R. Br.

Biological Activity of Homoplantaginin

Description	Homoplantaginin shows anti-inflammatory and antioxidant properties, it also has a protective and therapeutic effect on hepatocyte injury and shows potent inhibitory activities against influenza. Homoplantaginin may be used for the prevention and treatment of endothelial dysfunction associated with insulin resistance, it ameliorates endothelial insulin resistance by inhibiting inflammation and modulating cell signalling via the IKKβ/IRS-1/pAkt/peNOS pathway.
Targets	NF-kB | TNF-α | IL Receptor | IkB | NOS | NO | Akt | SOD | IKK | IRS-1
In vivo	Protective effects of Salvia plebeia compound homoplantaginin on hepatocyte injury.[Pubmed: 19406199] Food Chem Toxicol. 2009 Jul;47(7):1710-5. Salvia plebeia R. Br is a traditional Chinese herb which has been considered as an inflammatory mediator used for treatment of many infectious diseases including hepatitis. Previously, the compound Homoplantaginin was isolated in our group. METHODS AND RESULTS: Hence, we evaluated the protective effects of Homoplantaginin on hepatocyte injury. Homoplantaginin displayed an antioxidant property in a cell-free system and showed IC(50) of reduction level of DPPH radical at 0.35 microg/ml. In human hepatocyte HL-7702 cells exposed to H(2)O(2), the addition of 0.1-100 microg/ml of Homoplantaginin, which did not have a toxic effect on cell viability, significantly reduced lactate dehydrogenase (LDH) leakage, and increased glutathione (GSH), glutathione peroxidase (GSH-Px) and superoxide dismutase (SOD) in supernatant. In vivo assay, we employed the model of Bacillus Calmette-Guérin (BCG)/lipopolysaccharide (LPS)-induced hepatic injury mice to evaluate efficacy of Homoplantaginin. Homoplantaginin (25-100mg/kg) significantly reduced the increase in serum alanine aminotranseferase (ALT) and aspartate aminotransferase (AST), decreased the levels of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 (IL-1). The same treatment also reduced the content of thiobarbituric acid-reactive substances (TBARS), elevated the levels of GSH, GSH-Px and SOD in hepatic homogenate. The histopathological analysis showed that the grade of liver injury was ameliorated with reduction of inflammatory cells and necrosis of liver cells in Homoplantaginin treatment mice. CONCLUSIONS: These results suggest that Homoplantaginin has a protective and therapeutic effect on hepatocyte injury, which might be associated with its antioxidant properties.

Protocol of Homoplantaginin

Kinase Assay

Homoplantaginin modulates insulin sensitivity in endothelial cells by inhibiting inflammation.[Pubmed: 22791168] Biol Pharm Bull. 2012;35(7):1171-7. Recent data have indicated that inflammation plays an important role in the development of insulin resistance. The present study aims at examining the activity of Homoplantaginin, a flavonoid from a traditional Chinese medicine Salvia plebeia R. BR., on palmitic acid (PA)-induced insulin sensitivity and the underlying mechanisms of its anti-infammatory properties in the endothelial cells. METHODS AND RESULTS: Pre-treatment of Homoplantaginin on human umbilical vein endothelial cells (HUVECs) significantly inhibited PA induced tumour necrosis factor-α (TNF-α) and interleukin-6 (IL-6) mRNA expression, and inhibitory κB kinase beta (IKKβ) and nuclear factor-κB (NF-κB) p65 phosphorylation. To the PA-impaired insulin-dependent tyrosine phosphorylation of insulin receptor substrate-1 (IRS-1) and decrease in nitric oxide (NO) production, pretreatment of Homoplantaginin could effectively reverse the effects of PA. Additionally, Homoplantaginin significantly modulated the Ser/Thr phosphorylation of IRS-1, improved phosphorylation of Akt and endothelial nitric oxide synthase (eNOS), and increased NO production in the presence of insulin. CONCLUSIONS: Taken together, our results demonstrated that Homoplantaginin ameliorates endothelial insulin resistance by inhibiting inflammation and modulating cell signalling via the IKKβ/IRS-1/pAkt/peNOS pathway, suggesting it may be used for the prevention and treatment of endothelial dysfunction associated with insulin resistance.

Cell Research

Anti-influenza effect of the major flavonoids from Salvia plebeia R.Br. via inhibition of influenza H1N1 virus neuraminidase.[Pubmed: 28504013] Nat Prod Res. 2017 May 15:1-5. METHODS AND RESULTS: To determine the compounds responsible for its anti-influenza activities, we isolated the three flavonoids, 6-hydroxyluteolin 7-O-β-d-glucoside (1), nepitrin (2), Homoplantaginin (3) from the MeOH extract of Salvia plebeia R.Br. and identified them by comparing the spectroscopic data with that reported in the literature. The contents of the three flavonoids in the whole extract were 108.74 ± 0.95, 46.26 ± 2.19, and 69.35 ± 1.22 mg/g for 6-hydroxyluteolin 7-O-β-d-glucoside, nepitrin, and Homoplantaginin, respectively, which demonstrates that they are the major constituents of this plant. The three flavonoids were evaluated for their inhibitory activities against influenza virus H1N1 A/PR/9/34 neuraminidase and H1N1-induced cytopathic effect (CPE) on Madin-Darby canine kidney (MDCK) cells. Our results demonstrated the following arrangement for their anti-influenza activities: nepitrin (2) > 6-hydroxyluteolin 7-O-β-d-glucoside (1) > Homoplantaginin (3). CONCLUSIONS: The potent inhibitory activities of these flavonoids against influenza suggested their potential to be developed as novel anti-influenza drugs in the future.

Preparing Stock Solutions of Homoplantaginin

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1626 mL	10.8131 mL	21.6263 mL	43.2526 mL	54.0657 mL
5 mM	0.4325 mL	2.1626 mL	4.3253 mL	8.6505 mL	10.8131 mL
10 mM	0.2163 mL	1.0813 mL	2.1626 mL	4.3253 mL	5.4066 mL
50 mM	0.0433 mL	0.2163 mL	0.4325 mL	0.8651 mL	1.0813 mL
100 mM	0.0216 mL	0.1081 mL	0.2163 mL	0.4325 mL	0.5407 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.

 

References on Homoplantaginin

Anti-influenza effect of the major flavonoids from Salvia plebeia R.Br. via inhibition of influenza H1N1 virus neuraminidase.[Pubmed:28504013]

Nat Prod Res. 2018 May;32(10):1224-1228.

To determine the compounds responsible for its anti-influenza activities, we isolated the three flavonoids, 6-hydroxyluteolin 7-O-beta-d-glucoside (1), nepitrin (2), Homoplantaginin (3) from the MeOH extract of Salvia plebeia R.Br. and identified them by comparing the spectroscopic data with that reported in the literature. The contents of the three flavonoids in the whole extract were 108.74 +/- 0.95, 46.26 +/- 2.19, and 69.35 +/- 1.22 mg/g for 6-hydroxyluteolin 7-O-beta-d-glucoside, nepitrin, and Homoplantaginin, respectively, which demonstrates that they are the major constituents of this plant. The three flavonoids were evaluated for their inhibitory activities against influenza virus H1N1 A/PR/9/34 neuraminidase and H1N1-induced cytopathic effect (CPE) on Madin-Darby canine kidney (MDCK) cells. Our results demonstrated the following arrangement for their anti-influenza activities: nepitrin (2) > 6-hydroxyluteolin 7-O-beta-d-glucoside (1) > Homoplantaginin (3). The potent inhibitory activities of these flavonoids against influenza suggested their potential to be developed as novel anti-influenza drugs in the future.

Protective effects of Salvia plebeia compound homoplantaginin on hepatocyte injury.[Pubmed:19406199]

Food Chem Toxicol. 2009 Jul;47(7):1710-5.

Salvia plebeia R. Br is a traditional Chinese herb which has been considered as an inflammatory mediator used for treatment of many infectious diseases including hepatitis. Previously, the compound Homoplantaginin was isolated in our group. Hence, we evaluated the protective effects of Homoplantaginin on hepatocyte injury. Homoplantaginin displayed an antioxidant property in a cell-free system and showed IC(50) of reduction level of DPPH radical at 0.35 microg/ml. In human hepatocyte HL-7702 cells exposed to H(2)O(2), the addition of 0.1-100 microg/ml of Homoplantaginin, which did not have a toxic effect on cell viability, significantly reduced lactate dehydrogenase (LDH) leakage, and increased glutathione (GSH), glutathione peroxidase (GSH-Px) and superoxide dismutase (SOD) in supernatant. In vivo assay, we employed the model of Bacillus Calmette-Guerin (BCG)/lipopolysaccharide (LPS)-induced hepatic injury mice to evaluate efficacy of Homoplantaginin. Homoplantaginin (25-100mg/kg) significantly reduced the increase in serum alanine aminotranseferase (ALT) and aspartate aminotransferase (AST), decreased the levels of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 (IL-1). The same treatment also reduced the content of thiobarbituric acid-reactive substances (TBARS), elevated the levels of GSH, GSH-Px and SOD in hepatic homogenate. The histopathological analysis showed that the grade of liver injury was ameliorated with reduction of inflammatory cells and necrosis of liver cells in Homoplantaginin treatment mice. These results suggest that Homoplantaginin has a protective and therapeutic effect on hepatocyte injury, which might be associated with its antioxidant properties.

Homoplantaginin modulates insulin sensitivity in endothelial cells by inhibiting inflammation.[Pubmed:22791168]

Biol Pharm Bull. 2012;35(7):1171-7.

Recent data have indicated that inflammation plays an important role in the development of insulin resistance. The present study aims at examining the activity of Homoplantaginin, a flavonoid from a traditional Chinese medicine Salvia plebeia R. BR., on palmitic acid (PA)-induced insulin sensitivity and the underlying mechanisms of its anti-infammatory properties in the endothelial cells. Pre-treatment of Homoplantaginin on human umbilical vein endothelial cells (HUVECs) significantly inhibited PA induced tumour necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) mRNA expression, and inhibitory kappaB kinase beta (IKKbeta) and nuclear factor-kappaB (NF-kappaB) p65 phosphorylation. To the PA-impaired insulin-dependent tyrosine phosphorylation of insulin receptor substrate-1 (IRS-1) and decrease in nitric oxide (NO) production, pretreatment of Homoplantaginin could effectively reverse the effects of PA. Additionally, Homoplantaginin significantly modulated the Ser/Thr phosphorylation of IRS-1, improved phosphorylation of Akt and endothelial nitric oxide synthase (eNOS), and increased NO production in the presence of insulin. Taken together, our results demonstrated that Homoplantaginin ameliorates endothelial insulin resistance by inhibiting inflammation and modulating cell signalling via the IKKbeta/IRS-1/pAkt/peNOS pathway, suggesting it may be used for the prevention and treatment of endothelial dysfunction associated with insulin resistance.

Description

Homoplantaginin is a flavonoid from a traditional Chinese medicine Salvia plebeia with antiinflammatory and antioxidant properties. Homoplantaginin could inhibit TNF-α and IL-6 mRNA expression, IKKβ and NF-κB phosphorylation.

Keywords:

Homoplantaginin,17680-84-1,Dinatin 7-glucoside; Hispiduloside; Homoplantaginin; 6-Methoxyapigenin 7-glucoside; 6-Methylscutellarein 7-glucoside; Salvitin 7-glucoside; Scutellarein 6-methyl ether 7-glucoside; 4',5,7-Trihydroxy 6-methoxyflavone 7-glucoside,Natural Products, buy Homoplantaginin , Homoplantaginin supplier , purchase Homoplantaginin , Homoplantaginin cost , Homoplantaginin manufacturer , order Homoplantaginin , high purity Homoplantaginin