Luteolin-7-O-glucuronide CAS NO.29741-10-4

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Quick Details

ProName: Luteolin-7-O-glucuronide
CasNo: 29741-10-4
Molecular Formula: C21H18O12=462.36
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3?working?days?after?confirming?the?...
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: 1 Metric Ton/Day
Purity: ≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 10 Milligram
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: company standard
Storage: Store in dry, dark and ventilated plac...
PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
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D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
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1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
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5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Luteolin-7-O-glucuronide

Cas No.	29741-10-4
PubChem ID	5488307	Appearance	Yellow powder
Formula	C₂₁H₁₈O₁₂	M.Wt	462.36
Type of Compound	Flavonoids	Storage	Desiccate at -20°C
Synonyms	Cyanidenon 7-glucuronide; 3',4',5,7-Tetrahydroxyflavone 7-glucuronide
Solubility	DMSO : 130 mg/mL (281.17 mM; Need ultrasonic)
Chemical Name	(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES	C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O)O
Standard InChIKey	VSUOKLTVXQRUSG-DAZJWRSOSA-N
Standard InChI	InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21?/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 Luteolin-7-O-glucuronide

1 Chrysanthemum sp. 2 Cichorium sp. 3 Cynara sp. 4 Ixeris sp. 5 Lycopus sp. 6 Plantago sp. 7 Salvia sp. 8 Scutellaria sp. 9 Tanacetum sp.

Biological Activity of Luteolin-7-O-glucuronide

Description	Luteolin-7-O-glucuronide has anti-inflammatory activity. Luteolin 7-O-glucuronide shows potent α-glucosidase inhibitory effect with IC50 values of 14.7 uM, it also exhibits moderate α-amylase activity with IC50 values 61.5uM.Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.
Targets	NOS \| COX \| ROS \| NO \| α-glucosidase \| α-amylase \| MMP-1 \| MMP-3 \| MMP-8 \| MMP-9 \| MMP-13
In vitro	Quantification of major compounds from Ixeris dentata, Ixeris dentata Var. albiflora, and Ixeris sonchifolia and their comparative anti-inflammatory activity in lipopolysaccharide-stimulated RAW 264.7 cells.[Pubmed: 25383596] J Med Food. 2015 Jan;18(1):83-94. The aim of the present study was to evaluate the comparative anti-inflammatory activities of Ixeris dentata (ID), Ixeris dentata var. albiflora (IDA), and Ixeris sonchifolia (IS) and to identify the main compounds present in extracts. The anti-inflammatory activity was evaluated through lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 murine macrophages. Five main compounds consisting of chlorogenic acid, caffeic acid, luteolin-7-O-glucoside, Luteolin-7-O-glucuronide, and luteolin were used for simultaneous high-performance liquid chromatography quantification. METHODS AND RESULTS: The total phenolic content present in ID (30 mg/g GAE), IDA (35.33 mg/g GAE), and IS (43.79 mg/g GAE) was correlated to the corresponding LPS-induced NO production inhibitory effect in RAW 264.7 cells as expressed with IC(50) values 26.19, 21.43, and 7.59 μg/mL, respectively. Luteolin-7-O-glucoside was found as the major compound in ID (8.76 mg/g dry weight) and IDA (10.35 mg/g dry weight) and Luteolin-7-O-glucuronide was the major compound in IS (34.66 mg/g dry weight). Luteolin 7-O-glucoside and Luteolin-7-O-glucuronide inhibited LPS-induced NO production with IC(50) values of 30 and 4.5 μM, respectively. Furthermore, luteolin, luteolin-7-O-glucoside, and luteolin- 7-O-glucuronide suppressed the expression of iNOS and COX-2, and t-BHP-induced ROS generation in LPS-stimulated RAW 264.7 cells. CONCLUSIONS: These results clearly showed that the anti-inflammatory potential of ID, IDA, and IS extract are primarily due to their contents of luteolin-7-O-glucoside and Luteolin-7-O-glucuronide, respectively. Correlating In Vitro Target-Oriented Screening and Docking: Inhibition of Matrix Metalloproteinases Activities by Flavonoids.[Pubmed: 28288492 ] Planta Med. 2017 Jul;83(11):901-911. Metalloproteases are a family of zinc-containing endopeptidases involved in a variety of pathological disorders. The use of flavonoid derivatives as potential metalloprotease inhibitors has recently increased.Particular plants growing in Sicily are an excellent yielder of the flavonoids luteolin, apigenin, and their respective glycoside derivatives (7-O-rutinoside, 7-O-glucoside, and 7-O-glucuronide). METHODS AND RESULTS: The inhibitory activity of luteolin, apigenin, and their respective glycoside derivatives on the metalloproteases MMP-1, MMP-3, MMP-13, MMP-8, and MMP-9 was assessed and rationalized correlating in vitro target-oriented screening and in silico docking.The flavones apigenin, luteolin, and their respective glucosides have good ability to interact with metalloproteases and can also be lead compounds for further development. Glycones are more active on MMP-1, -3, -8, and -13 than MMP-9. Collagenases MMP-1, MMP-8, and MMP-13 are inhibited by compounds having rutinoside glycones. Apigenin and luteolin are inactive on MMP-1, -3, and -8, which can be interpreted as a better selectivity for both -9 and -13 peptidases. The more active compounds are apigenin-7-O-rutinoside on MMP-1 and luteolin-7-O-rutinoside on MMP-3. The lowest IC50 values were also found for apigenin-7-O-glucuronide, apigenin-7-O-rutinoside, and Luteolin-7-O-glucuronide. The glycoside moiety might allow for a better anchoring to the active site of MMP-1, -3, -8, -9, and -13. CONCLUSIONS: Overall, the in silico data are substantially in agreement with the in vitro ones (fluorimetric assay).
In vivo	Bioavailability of hydroxycinnamic acids from Crepidiastrum denticulatum using simulated digestion and Caco-2 intestinal cells.[Pubmed: 24841645] J Agric Food Chem. 2014 Jun 11;62(23):5290-5. Hydroxycinnamic acids have antioxidant properties and potentially beneficial effects on human health. This study investigated the digestive stability, bioaccessibility, and permeability of hydroxycinnamic acids from Crepidiastrum denticulatum using simulated digestion and Caco-2 intestinal cells. METHODS AND RESULTS: The major compounds of C. denticulatum were determined to be four hydroxycinnamic acids [caftaric acid, chlorogenic acid, chicoric acid, and 3,5-di-O-caffeoylquinic acid (3,5-DCQA)] and one flavonoid (Luteolin-7-O-glucuronide) by high-performance liquid chromatography and electrospray ionization mass spectrometry. Hydroxycinnamic acids from C. denticulatum were rapidly released in the stomach and duodenum phase, maximizing the possibility of absorption in the intestinal Caco-2 cells. The digestive stability and bioaccessibility of hydroxycinnamic acids from C. denticulatum were markedly low after simulated digestion and remained minimal in the soluble fraction of the ileum phase. Unlike the four hydroxycinnamic acids, Luteolin-7-O-glucuronide was stable in terms of digestive stability and bioaccessibility during simulated digestion. The cell permeabilities (P(app A to B)/P(app B to A)) of caftaric acid (0.054) and chlorogenic acid (0.055) were higher than those of chicoric acid (0.011) and 3,5-DCQA (0.006) in general. That of Luteolin-7-O-glucuronide was not detectable, showing its low absorption in Caco-2 cells. CONCLUSIONS: These results indicate that the rapid release of hydroxycinnamic acids in the stomach and duodenum phase may increase the potential for absorption in Caco-2 cells, and that Luteolin-7-O-glucuronide, which was stable in terms of digestive stability and bioaccessibility, has relatively low absorption compared with hydroxycinnamic acids.

Protocol of Luteolin-7-O-glucuronide

Animal Research

Anti-arthritic activity of the Indian leafy vegetable Cardiospermum halicacabum in Wistar rats and UPLC-QTOF-MS/MS identification of the putative active phenolic components.[Pubmed: 23052184 ]

Inflamm Res. 2013 Jan;62(1):115-26.

The present work was carried out to investigate the free radical scavenging activity of the ethanol extract of C. halicacabum leaves (EECH), to study its antioxidant properties and anti-rheumatic effects in Wistar rats with CFA-induced arthritis, and to profile the phenolic components thereof by LC-MS/MS.
METHODS AND RESULTS:
The free radical scavenging activities of the extract was evaluated by NO and superoxide anion scavenging assays. Arthritis was induced to the albino Wistar rats by CFA. Fifteen days after CFA induction, arthritic rats received EECH orally at the doses of 250 and 500 mg/kg daily for 20 days. Diclofenac sodium was used as reference standard. EECH is subjected to LC-MS/MS analysis for the identification of phenolic compounds. The IC(50) value of the EECH to scavenge the NO and superoxide radicals are 83 and 60 μg/ml respectively. Ultrasonography and histology images of hind limb in EECH treated groups confirmed the complete cartilage regeneration. The LC/MS/MS analysis indicated the presence of anti-inflammatory compounds Luteolin-7-O-glucuronide, apigenin-7-O-glucuronide and chrysoeriol.
CONCLUSIONS:
These findings lend pharmacological support to the reported folkloric use of C. halicacabum in the treatment and management of painful, arthritic inflammatory conditions.

Preparing Stock Solutions of Luteolin-7-O-glucuronide

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1628 mL	10.8141 mL	21.6282 mL	43.2563 mL	54.0704 mL
5 mM	0.4326 mL	2.1628 mL	4.3256 mL	8.6513 mL	10.8141 mL
10 mM	0.2163 mL	1.0814 mL	2.1628 mL	4.3256 mL	5.407 mL
50 mM	0.0433 mL	0.2163 mL	0.4326 mL	0.8651 mL	1.0814 mL
100 mM	0.0216 mL	0.1081 mL	0.2163 mL	0.4326 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 Luteolin-7-O-glucuronide

Quantification of major compounds from Ixeris dentata, Ixeris dentata Var. albiflora, and Ixeris sonchifolia and their comparative anti-inflammatory activity in lipopolysaccharide-stimulated RAW 264.7 cells.[Pubmed:25383596]

J Med Food. 2015 Jan;18(1):83-94.

The aim of the present study was to evaluate the comparative anti-inflammatory activities of Ixeris dentata (ID), Ixeris dentata var. albiflora (IDA), and Ixeris sonchifolia (IS) and to identify the main compounds present in extracts. The anti-inflammatory activity was evaluated through lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 murine macrophages. Five main compounds consisting of chlorogenic acid, caffeic acid, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, and luteolin were used for simultaneous high-performance liquid chromatography quantification. The total phenolic content present in ID (30 mg/g GAE), IDA (35.33 mg/g GAE), and IS (43.79 mg/g GAE) was correlated to the corresponding LPS-induced NO production inhibitory effect in RAW 264.7 cells as expressed with IC(50) values 26.19, 21.43, and 7.59 mug/mL, respectively. Luteolin 7-O-glucoside was found as the major compound in ID (8.76 mg/g dry weight) and IDA (10.35 mg/g dry weight) and luteolin 7-O-glucuronide was the major compound in IS (34.66 mg/g dry weight). Luteolin 7-O-glucoside and luteolin 7-O-glucuronide inhibited LPS-induced NO production with IC(50) values of 30 and 4.5 muM, respectively. Furthermore, luteolin, luteolin 7-O-glucoside, and luteolin 7-O-glucuronide suppressed the expression of iNOS and COX-2, and t-BHP-induced ROS generation in LPS-stimulated RAW 264.7 cells. These results clearly showed that the anti-inflammatory potential of ID, IDA, and IS extract are primarily due to their contents of luteolin 7-O-glucoside and luteolin 7-O-glucuronide, respectively.

Anti-arthritic activity of the Indian leafy vegetable Cardiospermum halicacabum in Wistar rats and UPLC-QTOF-MS/MS identification of the putative active phenolic components.[Pubmed:23052184]

Inflamm Res. 2013 Jan;62(1):115-26.

OBJECTIVES: The present work was carried out to investigate the free radical scavenging activity of the ethanol extract of C. halicacabum leaves (EECH), to study its antioxidant properties and anti-rheumatic effects in Wistar rats with CFA-induced arthritis, and to profile the phenolic components thereof by LC-MS/MS. METHODS: The free radical scavenging activities of the extract was evaluated by NO and superoxide anion scavenging assays. Arthritis was induced to the albino Wistar rats by CFA. Fifteen days after CFA induction, arthritic rats received EECH orally at the doses of 250 and 500 mg/kg daily for 20 days. Diclofenac sodium was used as reference standard. EECH is subjected to LC-MS/MS analysis for the identification of phenolic compounds. RESULTS: The IC(50) value of the EECH to scavenge the NO and superoxide radicals are 83 and 60 mug/ml respectively. Ultrasonography and histology images of hind limb in EECH treated groups confirmed the complete cartilage regeneration. The LC/MS/MS analysis indicated the presence of anti-inflammatory compounds Luteolin-7-O-glucuronide, apigenin-7-O-glucuronide and chrysoeriol. CONCLUSION: These findings lend pharmacological support to the reported folkloric use of C. halicacabum in the treatment and management of painful, arthritic inflammatory conditions.

Bioavailability of hydroxycinnamic acids from Crepidiastrum denticulatum using simulated digestion and Caco-2 intestinal cells.[Pubmed:24841645]

J Agric Food Chem. 2014 Jun 11;62(23):5290-5.

Hydroxycinnamic acids have antioxidant properties and potentially beneficial effects on human health. This study investigated the digestive stability, bioaccessibility, and permeability of hydroxycinnamic acids from Crepidiastrum denticulatum using simulated digestion and Caco-2 intestinal cells. The major compounds of C. denticulatum were determined to be four hydroxycinnamic acids [caftaric acid, chlorogenic acid, chicoric acid, and 3,5-di-O-caffeoylquinic acid (3,5-DCQA)] and one flavonoid (Luteolin-7-O-glucuronide) by high-performance liquid chromatography and electrospray ionization mass spectrometry. Hydroxycinnamic acids from C. denticulatum were rapidly released in the stomach and duodenum phase, maximizing the possibility of absorption in the intestinal Caco-2 cells. The digestive stability and bioaccessibility of hydroxycinnamic acids from C. denticulatum were markedly low after simulated digestion and remained minimal in the soluble fraction of the ileum phase. Unlike the four hydroxycinnamic acids, Luteolin-7-O-glucuronide was stable in terms of digestive stability and bioaccessibility during simulated digestion. The cell permeabilities (P(app A to B)/P(app B to A)) of caftaric acid (0.054) and chlorogenic acid (0.055) were higher than those of chicoric acid (0.011) and 3,5-DCQA (0.006) in general. That of Luteolin-7-O-glucuronide was not detectable, showing its low absorption in Caco-2 cells. These results indicate that the rapid release of hydroxycinnamic acids in the stomach and duodenum phase may increase the potential for absorption in Caco-2 cells, and that Luteolin-7-O-glucuronide, which was stable in terms of digestive stability and bioaccessibility, has relatively low absorption compared with hydroxycinnamic acids.

Description

Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

Keywords:

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