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Luteolin-7-O-glucoside

CAS# 5373-11-5

Luteolin-7-O-glucoside

Catalog No. BCN5388----Order now to get a substantial discount!

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Quality Control of Luteolin-7-O-glucoside

Number of papers citing our products

Chemical structure

Luteolin-7-O-glucoside

3D structure

Chemical Properties of Luteolin-7-O-glucoside

Cas No. 5373-11-5 SDF Download SDF
PubChem ID 5291488 Appearance Yellow powder
Formula C21H20O11 M.Wt 448.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Luteolin 7-glucoside; Luteolin 7-O-β-D-glucoside
Solubility DMSO : ≥ 35 mg/mL (78.06 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
Standard InChIKey PEFNSGRTCBGNAN-UHFFFAOYSA-N
Standard InChI InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2
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 Luteolin-7-O-glucoside

1 Achillea sp. 2 Ailanthus sp. 3 Antennaria sp. 4 Apium sp. 5 Baptisia sp. 6 Capsicum sp. 7 Chaerophyllum sp. 8 Chamaemelum sp. 9 Chrysanthemum sp. 10 Cirsium sp. 11 Crataegus sp. 12 Cynara sp. 13 Daphne sp. 14 Dendranthema sp. 15 Eclipta sp. 16 Fraxinus sp. 17 Humulus sp. 18 Hypericum sp. 19 Lippia sp. 20 Lycopus sp. 21 Manihot sp. 22 Melissa sp. 23 Mentha sp. 24 Myrrhis sp. 25 Olea sp. 26 Ononis sp. 27 Persicaria sp. 28 Pimpinella sp. 29 Reseda sp. 30 Rosmarinus sp. 31 Salix sp. 32 Salvia sp. 33 Stevia sp. 34 Symphoricarpus sp. 35 Tanacetum sp. 36 Teucrium sp. 37 Thymus sp. 38 Verbascum sp. 39 Verbena sp. 40 Veronica sp. 41 Vitex sp. 42 Zanthoxylum sp.

Biological Activity of Luteolin-7-O-glucoside

DescriptionLuteolin-7-O-glucoside has cardioprotective, anti-asthmatic, anticancer, anti-inflammatory, and antioxidative activities, it can suppress leukotriene C(4) production and degranulation by inhibiting the phosphorylation of mitogen activated protein kinases and phospholipase Cγ1 in activated mouse bone marrow-derived mast cells.Luteolin-7-O-glucoside modulated the Nrf2/MAPK/ PTEN/Akt /ERK/AP-1/PI3K-Akt signaling pathways, it suppressed the expression of β-catenin.
TargetsWnt/β-catenin | HO-1 | Nrf2 | p38MAPK | Akt | ERK | NF-kB | AP-1 | PI3K | ROS | JNK | NOS | COX | LOX | PGE
In vitro

Cancer chemopreventive potential of luteolin-7-O-glucoside isolated from Ophiorrhiza mungos Linn.[Pubmed: 21161823 ]

Nutr Cancer. 2011;63(1):130-8.

The anticarcinogenic potential of the phytocompound Luteolin-7-O-glucoside (LUT7G), isolated from the leaves of Ophiorrhiza mungos Linn, was studied against 4 different cancer cell lines (COLO 320 DM, AGS, MCF-7, and A549) and normal VERO cell line.
METHODS AND RESULTS:
The ability of LUT7G to induce apoptosis was determined by its antiradical activity, DNA fragmentation, expression of β-catenin, and chemopreventive efficacy in vivo by administering rats with DMH (20 mg/kg b.w., s.c.) for 4 consecutive wk and supplementing with 3 different doses throughout the experimental period of 16 wk. LUT7G scavenged 80% of DPPH radicals generated in vitro at 1000 μM and suppressed the expression of β-catenin to 40% at 120 μM concentrations. LUT7G induced apoptosis by scavenging ROS and suppressing the expression of β-catenin in COLO 320 DM cells and effectively inhibited ACF development in DMH-induced experimental carcinogenesis.
CONCLUSIONS:
Hence LUT7G can be a potent anticancer drug for colon carcinogenesis.

Protection of Luteolin-7-O-Glucoside Against Doxorubicin-Induced Injury Through PTEN/Akt and ERK Pathway in H9c2 Cells.[Pubmed: 25724325]

Cardiovasc Toxicol. 2016 Apr;16(2):101-10.

Luteolin-7-O-glucoside (LUTG) was isolated from the plants of Dracocephalum tanguticum Maxim. Previous research has showed that LUTG pretreatment had a significant protective effect against doxorubicin (DOX)-induced cardiotoxicity by reducing intracellular calcium overload and leakage of creatine kinase and lactate dehydrogenase. But the underlying mechanisms have not been completely elucidated.
METHODS AND RESULTS:
In the present study, we investigated the effects of LUTG on H9c2 cell morphology, viability, apoptosis, reactive oxygen species generation, and the mitochondrial transmembrane potentials. The expression of p-PTEN, p-Akt, p-ERK, p-mTOR, and p-GSK-3β were detected by Western blotting. Compared with DOX alone treatment group, the morphological injury and apoptosis of the cells in groups treated by DOX plus LUTG were alleviated, cell viability was increased, ROS generation was lowered remarkably, and mitochondrial depolarization was mitigated. In DOX group, the expression of p-PTEN was lower than normal group and the expression of p-Akt and p-ERK was higher than normal group. In the groups treated with LUTG (20 μM), the expression of p-PTEN was upregulated and the expression of p-Akt, p-ERK, p-mTOR, and p-GSK-3β was downregulated.
CONCLUSIONS:
These results indicated that the protective effects of LUTG against DOX-induced cardiotoxicity may be related to anti-apoptosis through PTEN/Akt and ERK pathway.

Protocol of Luteolin-7-O-glucoside

Kinase Assay

Luteolin-7-O-glucoside suppresses leukotriene C(4) production and degranulation by inhibiting the phosphorylation of mitogen activated protein kinases and phospholipase Cγ1 in activated mouse bone marrow-derived mast cells.[Pubmed: 21720009]

Biol Pharm Bull. 2011;34(7):1032-6.


METHODS AND RESULTS:
In this study, Luteolin-7-O-glucoside (L7G), an herbal medicine isolated from Ailanthus altissima, inhibited 5-lipoxygenase (5-LOX)-dependent leukotriene C(4) (LTC(4)) production in bone marrow-derived mast cells (BMMCs) in a concentration-dependent manner with an IC(50) of 3.0 μM. To determine the action mechanism of L7G, we performed immunoblotting for cytosolic phospholipase A(2) (cPLA(2)) and mitogen-activated protein kinases (MAPKs) following c-kit ligand (KL)-induced activation of BMMCs with or without L7G. Inhibition of LTC(4) production by L7G was accompanied by a decrease in cPLA(2) phosphorylation, which occurred via the extracellular signal-regulated protein kinase-1/2 (ERK1/2) and p38 and c-Jun N-terminal kinase (JNK) pathways. In addition, L7G also attenuated mast cell degranulation in a dose-dependent manner (IC(50), 22.8 μM) through inhibition of phospholipase Cγ1 (PLCγ1) phosphorylation.
CONCLUSIONS:
Our results suggest that the anti-asthmatic activity of L7G may be mediated in part via the inhibition of LTC(4) generation and mast cell degranulation.

Cell Research

Luteolin and luteolin-7-O-glucoside inhibit lipopolysaccharide-induced inflammatory responses through modulation of NF-κB/AP-1/PI3K-Akt signaling cascades in RAW 264.7 cells.[Pubmed: 24353826]

Luteolin and luteolin-7-O-glucoside strengthen antioxidative potential through the modulation of Nrf2/MAPK mediated HO-1 signaling cascade in RAW 264.7 cells.[Pubmed: 24361407]

Food Chem Toxicol. 2014 Mar;65:70-5.

It has been understood that glycosidic forms of flavonoids were hydrolyzed by gut bacteria and absorbed as aglycones. However, several reports suggested that glycosides were partly absorbed without hydrolysis and remained biologically active.
METHODS AND RESULTS:
In this study, we evaluated the antioxidative potential of luteolin and Luteolin-7-O-glucoside, glycosidic form of luteolin, against the oxidative damage and compared their antioxidative mechanisms in RAW 264.7 cells. Heme oxygenase-1 (HO-1), one of the phase II enzymes showing an antioxidative activity, was potently induced by luteolin and Luteolin-7-O-glucoside treatment, which was in accordance with the translocated nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) into nucleus. Moreover, luteolin and the Luteolin-7-O-glucoside activated HO-1 expression by p38 and c-Jun NH2-terminal kinase (JNK) regulation. In order to identify the antioxidation potential by HO-1, tert-butyl hydroperoxide (t-BHP)-induced oxidative damage was applied and ameliorated by luteolin and the Luteolin-7-O-glucoside treatment in a dose dependent manner, which was confirmed by HO-1 selective inhibitor and inducer, tin protoporphyrin (SnPP) and cobalt protoporphyrin (CoPP), respectively.
CONCLUSIONS:
Consequently, luteolin and Luteolin-7-O-glucoside potently strengthen the HO-1-mediated antioxidative potential through the modulation of the Nrf2/MAPK signaling pathways.

Nutr Res Pract. 2013 Dec;7(6):423-9.

Luteolin is a flavonoid found in abundance in celery, green pepper, and dandelions. Previous studies have shown that luteolin is an anti-inflammatory and anti-oxidative agent.
METHODS AND RESULTS:
In this study, the anti-inflammatory capacity of luteolin and one of its glycosidic forms, Luteolin-7-O-glucoside, were compared and their molecular mechanisms of action were analyzed. In lipopolysaccharide (LPS)-activated RAW 264.7 cells, luteolin more potently inhibited the production of nitric oxide (NO) and prostaglandin E2 as well as the expression of their corresponding enzymes (inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) than Luteolin-7-O-glucoside. The molecular mechanisms underlying these effects were investigated to determine whether the inflammatory response was related to the transcription factors, nuclear factor (NF)-κB and activator protein (AP)-1, or their upstream signaling molecules, mitogen-activated protein kinases (MAPKs) and phosphoinositide 3-kinase (PI3K). Luteolin attenuated the activation of both transcription factors, NF-κB and AP-1, while Luteolin-7-O-glucoside only impeded NF-κB activation. However, both flavonoids inhibited Akt phosphorylation in a dose-dependent manner.
CONCLUSIONS:
Consequently, luteolin more potently ameliorated LPS-induced inflammation than Luteolin-7-O-glucoside, which might be attributed to the differentially activated NF-κB/AP-1/PI3K-Akt pathway in RAW 264.7 cells.

Luteolin-7-O-glucoside Dilution Calculator

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Preparing Stock Solutions of Luteolin-7-O-glucoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2303 mL 11.1513 mL 22.3025 mL 44.605 mL 55.7563 mL
5 mM 0.4461 mL 2.2303 mL 4.4605 mL 8.921 mL 11.1513 mL
10 mM 0.223 mL 1.1151 mL 2.2303 mL 4.4605 mL 5.5756 mL
50 mM 0.0446 mL 0.223 mL 0.4461 mL 0.8921 mL 1.1151 mL
100 mM 0.0223 mL 0.1115 mL 0.223 mL 0.4461 mL 0.5576 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 Luteolin-7-O-glucoside

Cynaroside is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.

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References on Luteolin-7-O-glucoside

Luteolin and luteolin-7-O-glucoside inhibit lipopolysaccharide-induced inflammatory responses through modulation of NF-kappaB/AP-1/PI3K-Akt signaling cascades in RAW 264.7 cells.[Pubmed:24353826]

Nutr Res Pract. 2013 Dec;7(6):423-9.

Luteolin is a flavonoid found in abundance in celery, green pepper, and dandelions. Previous studies have shown that luteolin is an anti-inflammatory and anti-oxidative agent. In this study, the anti-inflammatory capacity of luteolin and one of its glycosidic forms, Luteolin-7-O-glucoside, were compared and their molecular mechanisms of action were analyzed. In lipopolysaccharide (LPS)-activated RAW 264.7 cells, luteolin more potently inhibited the production of nitric oxide (NO) and prostaglandin E2 as well as the expression of their corresponding enzymes (inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) than Luteolin-7-O-glucoside. The molecular mechanisms underlying these effects were investigated to determine whether the inflammatory response was related to the transcription factors, nuclear factor (NF)-kappaB and activator protein (AP)-1, or their upstream signaling molecules, mitogen-activated protein kinases (MAPKs) and phosphoinositide 3-kinase (PI3K). Luteolin attenuated the activation of both transcription factors, NF-kappaB and AP-1, while Luteolin-7-O-glucoside only impeded NF-kappaB activation. However, both flavonoids inhibited Akt phosphorylation in a dose-dependent manner. Consequently, luteolin more potently ameliorated LPS-induced inflammation than Luteolin-7-O-glucoside, which might be attributed to the differentially activated NF-kappaB/AP-1/PI3K-Akt pathway in RAW 264.7 cells.

Luteolin-7-O-glucoside suppresses leukotriene C(4) production and degranulation by inhibiting the phosphorylation of mitogen activated protein kinases and phospholipase Cgamma1 in activated mouse bone marrow-derived mast cells.[Pubmed:21720009]

Biol Pharm Bull. 2011;34(7):1032-6.

In this study, Luteolin-7-O-glucoside (L7G), an herbal medicine isolated from Ailanthus altissima, inhibited 5-lipoxygenase (5-LOX)-dependent leukotriene C(4) (LTC(4)) production in bone marrow-derived mast cells (BMMCs) in a concentration-dependent manner with an IC(50) of 3.0 microM. To determine the action mechanism of L7G, we performed immunoblotting for cytosolic phospholipase A(2) (cPLA(2)) and mitogen-activated protein kinases (MAPKs) following c-kit ligand (KL)-induced activation of BMMCs with or without L7G. Inhibition of LTC(4) production by L7G was accompanied by a decrease in cPLA(2) phosphorylation, which occurred via the extracellular signal-regulated protein kinase-1/2 (ERK1/2) and p38 and c-Jun N-terminal kinase (JNK) pathways. In addition, L7G also attenuated mast cell degranulation in a dose-dependent manner (IC(50), 22.8 microM) through inhibition of phospholipase Cgamma1 (PLCgamma1) phosphorylation. Our results suggest that the anti-asthmatic activity of L7G may be mediated in part via the inhibition of LTC(4) generation and mast cell degranulation.

Cancer chemopreventive potential of luteolin-7-O-glucoside isolated from Ophiorrhiza mungos Linn.[Pubmed:21161823]

Nutr Cancer. 2011;63(1):130-8.

The anticarcinogenic potential of the phytocompound Luteolin-7-O-glucoside (LUT7G), isolated from the leaves of Ophiorrhiza mungos Linn, was studied against 4 different cancer cell lines (COLO 320 DM, AGS, MCF-7, and A549) and normal VERO cell line. The ability of LUT7G to induce apoptosis was determined by its antiradical activity, DNA fragmentation, expression of beta-catenin, and chemopreventive efficacy in vivo by administering rats with DMH (20 mg/kg b.w., s.c.) for 4 consecutive wk and supplementing with 3 different doses throughout the experimental period of 16 wk. LUT7G scavenged 80% of DPPH radicals generated in vitro at 1000 muM and suppressed the expression of beta-catenin to 40% at 120 muM concentrations. LUT7G induced apoptosis by scavenging ROS and suppressing the expression of beta-catenin in COLO 320 DM cells and effectively inhibited ACF development in DMH-induced experimental carcinogenesis. Hence LUT7G can be a potent anticancer drug for colon carcinogenesis.

Protection of Luteolin-7-O-Glucoside Against Doxorubicin-Induced Injury Through PTEN/Akt and ERK Pathway in H9c2 Cells.[Pubmed:25724325]

Cardiovasc Toxicol. 2016 Apr;16(2):101-10.

Luteolin-7-O-glucoside (LUTG) was isolated from the plants of Dracocephalum tanguticum Maxim. Previous research has showed that LUTG pretreatment had a significant protective effect against doxorubicin (DOX)-induced cardiotoxicity by reducing intracellular calcium overload and leakage of creatine kinase and lactate dehydrogenase. But the underlying mechanisms have not been completely elucidated. In the present study, we investigated the effects of LUTG on H9c2 cell morphology, viability, apoptosis, reactive oxygen species generation, and the mitochondrial transmembrane potentials. The expression of p-PTEN, p-Akt, p-ERK, p-mTOR, and p-GSK-3beta were detected by Western blotting. Compared with DOX alone treatment group, the morphological injury and apoptosis of the cells in groups treated by DOX plus LUTG were alleviated, cell viability was increased, ROS generation was lowered remarkably, and mitochondrial depolarization was mitigated. In DOX group, the expression of p-PTEN was lower than normal group and the expression of p-Akt and p-ERK was higher than normal group. In the groups treated with LUTG (20 muM), the expression of p-PTEN was upregulated and the expression of p-Akt, p-ERK, p-mTOR, and p-GSK-3beta was downregulated. These results indicated that the protective effects of LUTG against DOX-induced cardiotoxicity may be related to anti-apoptosis through PTEN/Akt and ERK pathway.

Luteolin and luteolin-7-O-glucoside strengthen antioxidative potential through the modulation of Nrf2/MAPK mediated HO-1 signaling cascade in RAW 264.7 cells.[Pubmed:24361407]

Food Chem Toxicol. 2014 Mar;65:70-5.

It has been understood that glycosidic forms of flavonoids were hydrolyzed by gut bacteria and absorbed as aglycones. However, several reports suggested that glycosides were partly absorbed without hydrolysis and remained biologically active. In this study, we evaluated the antioxidative potential of luteolin and Luteolin-7-O-glucoside, glycosidic form of luteolin, against the oxidative damage and compared their antioxidative mechanisms in RAW 264.7 cells. Heme oxygenase-1 (HO-1), one of the phase II enzymes showing an antioxidative activity, was potently induced by luteolin and Luteolin-7-O-glucoside treatment, which was in accordance with the translocated nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) into nucleus. Moreover, luteolin and the Luteolin-7-O-glucoside activated HO-1 expression by p38 and c-Jun NH2-terminal kinase (JNK) regulation. In order to identify the antioxidation potential by HO-1, tert-butyl hydroperoxide (t-BHP)-induced oxidative damage was applied and ameliorated by luteolin and the Luteolin-7-O-glucoside treatment in a dose dependent manner, which was confirmed by HO-1 selective inhibitor and inducer, tin protoporphyrin (SnPP) and cobalt protoporphyrin (CoPP), respectively. Consequently, luteolin and Luteolin-7-O-glucoside potently strengthen the HO-1-mediated antioxidative potential through the modulation of the Nrf2/MAPK signaling pathways.

Description

Cynaroside is a flavone, a flavonoid-like chemical compound.

Keywords:

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