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Isorhamnetin 3-glucoside-7-rhamnoside

CAS# 17331-71-4

Isorhamnetin 3-glucoside-7-rhamnoside

Catalog No. BCN1528----Order now to get a substantial discount!

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Isorhamnetin 3-glucoside-7-rhamnoside: 5mg $265 In Stock
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Quality Control of Isorhamnetin 3-glucoside-7-rhamnoside

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Chemical structure

Isorhamnetin 3-glucoside-7-rhamnoside

3D structure

Chemical Properties of Isorhamnetin 3-glucoside-7-rhamnoside

Cas No. 17331-71-4 SDF Download SDF
PubChem ID 72188972 Appearance Yellow powder
Formula C28H32O16 M.Wt 624.54
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
SMILES CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O
Standard InChIKey NEJKEXUJCSYMCC-PXBUXKMDSA-N
Standard InChI InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(40-9)41-11-6-13(31)17-15(7-11)42-25(10-3-4-12(30)14(5-10)39-2)26(20(17)34)44-28-24(38)22(36)19(33)16(8-29)43-28/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27-,28-/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.
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 Isorhamnetin 3-glucoside-7-rhamnoside

The herbs of Hippophae rhamnoides Linn.

Biological Activity of Isorhamnetin 3-glucoside-7-rhamnoside

Description1. An anti-oxidative composition containing isorhamnetin-3-glucoside-7-rhamnoside (IGR)isolated from Hippophae rhamnoides L. is provided to ensure antioxidative, antibacterial, and anti-cancer effect; a cosmetic composition for preventing or treating aging contains IGR compound as an active ingredient; a health food composition for antioxiaiton contains IGR as an active ingredient; a pharmaceutical composition for antibacterial and anticancer contains IGR as an active ingredient.
TargetsAntifection

Isorhamnetin 3-glucoside-7-rhamnoside Dilution Calculator

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Isorhamnetin 3-glucoside-7-rhamnoside Molarity Calculator

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Preparing Stock Solutions of Isorhamnetin 3-glucoside-7-rhamnoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6012 mL 8.0059 mL 16.0118 mL 32.0236 mL 40.0295 mL
5 mM 0.3202 mL 1.6012 mL 3.2024 mL 6.4047 mL 8.0059 mL
10 mM 0.1601 mL 0.8006 mL 1.6012 mL 3.2024 mL 4.0029 mL
50 mM 0.032 mL 0.1601 mL 0.3202 mL 0.6405 mL 0.8006 mL
100 mM 0.016 mL 0.0801 mL 0.1601 mL 0.3202 mL 0.4003 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 Isorhamnetin 3-glucoside-7-rhamnoside

Isorhamnetin Inhibits Reactive Oxygen Species-Dependent Hypoxia Inducible Factor (HIF)-1alpha Accumulation.[Pubmed:27803454]

Biol Pharm Bull. 2016;39(11):1830-1838.

Isorhamnetin is a flavonoid metabolite of quercetin and isolated from water dropwort (Oenanthe javanica, Umbelliferae). It has been reported that isorhamnetin exerts beneficial effects including antioxidant, anti-inflammatory, and anti-proliferative activities. The present study investigated whether the antioxidant activity of isorhamnetin is correlated with its anti-cancer effects on colorectal cancer cells. Isorhamnetin significantly repressed cobalt chloride (CoCl2)- or hypoxia-induced hypoxia inducible factor-1alpha (HIF-1alpha) accumulation in HCT116 and HT29 cells. When compared with quercetin, isorhamnetin showed potent inhibition of HIF-1alpha. Moreover, it inhibited CoCl2-induced activity of hypoxia response element reporter gene and HIF-1alpha-dependent transcription of genes such as glucose transporter 1, lactate dehydrogenase A, carbonic anhydrase-IX, and pyruvate dehydrogenase kinase 1. Isorhamnetin also blocked hydrogen peroxide (H2O2)-induced HIF-1alpha accumulation. The antioxidant effects of isorhamnetin were confirmed by observation of CoCl2- or H2O2-induced reactive oxygen species (ROS) production. Consistently, overexpressed HIF-1alpha was decreased by isorhamnetin or N-acetyl-L-cysteine in HEK293 cells. In vitro migration and invasion assay further confirmed the inhibitory effects of isorhamnetin on cancer cells. Collectively, these results demonstrate that isorhamnetin inhibits ROS-mediated HIF-1alpha accumulation, which contributes to its anti-metastatic efficacy.

The Metabolic Profiling of Isorhamnetin-3-O-Neohesperidoside Produced by Human Intestinal Flora Employing UPLC-Q-TOF/MS.[Pubmed:27881493]

J Chromatogr Sci. 2017 Mar 1;55(3):243-250.

Isorhamnetin-3-O-neohesperidoside is the major active substance of Puhuang, a traditional herb medicine widely used in clinical practice to tackle many chronic diseases. However, little is known about the interactions between this ingredient and intestinal flora. In this study, ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry together with automated data analysis software (Metabolynx) was used for analysis of the metabolic profile of isorhamnetin-3-O-neohesperidoside by the isolated human intestinal bacteria. The parent and three metabolites isorhamnetin-3-O-glucoside, isorhamnetin and quercetin were detected and identified based on the characteristics of their deprotonated molecules. These metabolites indicated that isorhamnetin-3-O-neohesperidoside was firstly deglycosylated to isorhamnetin-3-O-glucoside and subsequently to the aglycone isorhamnetin, and the latter was demethylated to quercetin. The majority of bacteria such as Escherichia sp. 23 were capable of converting isorhamnetin-3-O-neohesperidoside to considerable amounts of aglycone isorhamnetin and further to minor amounts of quercetin, while minor amounts of isorhamnetin-3-O-glucoside were detected in minority of bacterial samples such as Enterococcus sp. 30. The metabolic pathway and metabolites of isorhamnetin-3-O-neohesperidoside by the different human intestinal bacteria were firstly investigated. Furthermore, the metabolites of isorhamnetin-3-O-neohesperidoside might influence the effects of traditional herb medicines. Thus, our study is helpful to further unravel how isorhamnetin-3-O-neohesperidoside and Puhuang work in vivo.

Isorhamnetin protects against cardiac hypertrophy through blocking PI3K-AKT pathway.[Pubmed:28176246]

Mol Cell Biochem. 2017 May;429(1-2):167-177.

Isorhamnetin, a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L., is well known for its anti-inflammatory, anti-oxidative, anti-adipogenic, anti-proliferative, and anti-tumor activities. However, the role of isorhamnetin in cardiac hypertrophy has not been reported. The aims of the present study were to find whether isorhamnetin could alleviate cardiac hypertrophy and to define the underlying molecular mechanisms. Here, we investigated the effects of isorhamnetin (100 mg/kg/day) on cardiac hypertrophy induced by aortic banding in mice. Cardiac hypertrophy was evaluated by echocardiographic, hemodynamic, pathological, and molecular analyses. Our data demonstrated that isorhamnetin could inhibit cardiac hypertrophy and fibrosis 8 weeks after aortic banding. The results further revealed that the effect of isorhamnetin on cardiac hypertrophy was mediated by blocking the activation of phosphatidylinositol 3-kinase-AKT signaling pathway. In vitro studies performed in neonatal rat cardiomyocytes confirmed that isorhamnetin could attenuate cardiomyocyte hypertrophy induced by angiotensin II, which was associated with phosphatidylinositol 3-kinase-AKT signaling pathway. In conclusion, these data indicate for the first time that isorhamnetin has protective potential for targeting cardiac hypertrophy by blocking the phosphatidylinositol 3-kinase-AKT signaling pathway. Thus, our study suggests that isorhamnetin may represent a potential therapeutic strategy for the treatment of cardiac hypertrophy and heart failure.

Isorhamnetin and hyperoside derived from water dropwort inhibits inflammasome activation.[Pubmed:28160865]

Phytomedicine. 2017 Jan 15;24:77-86.

BACKGROUND: Water dropwort (Oenanthe javanica), an umbelliferous plant, has been reported as hypolipidemic, antiplatelet, antitumor, or immune-stimulating agents and it has been suggested to cure cardiovascular disease and cancer. PURPOSE: Present study aimed to evaluate the effect of the extracts of water dropwort (EWD) and its pharmacological molecules, hyperoside and isorhamnetin, on inflammatory response, especially inflammasome activation. STUDY DESIGN/METHODS: The anti-inflammasome properties of EWD, isorhamnetin, and hyperoside were elucidated by human and mouse macrophages. RESULTS: EWD attenuated secretion of interleukin (IL)-1beta and formation of Asc pyroptosome resulting from NLRP3, NLRC4, and AIM2 inflammasome activation without interruption of cytokine transcription. Isorhamnetin selectively inhibited NLRP3 and AIM2 inflammasome activation and down-regulated expression of pro-inflammatory cytokines. Hyperoside selectively interrupted NLRC4 and AIM2 inflammasome activation but did not alter cytokine expression. In addition, EWD, isorhamnetin, and hyperoside inhibited caspase-1. CONCLUSION: Isorhamnetin and hyperoside, a key molecule of water dropwort, have been suggested as candidates to attenuate inflammasome inhibition.

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