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Luteolin-4'-O-glucoside

CAS# 6920-38-3

Luteolin-4'-O-glucoside

2D Structure

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Luteolin-4'-O-glucoside

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Chemical Properties of Luteolin-4'-O-glucoside

Cas No. 6920-38-3 SDF Download SDF
PubChem ID 12304738 Appearance Powder
Formula C21H20O11 M.Wt 448.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Juncein; 3',4',5,7-Tetrahydroxyflavone 4'-glucoside
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,7-dihydroxy-2-[3-hydroxy-4-[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
Standard InChIKey UHNXUSWGOJMEFO-MKJMBMEGSA-N
Standard InChI InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-13-2-1-8(3-10(13)24)14-6-12(26)17-11(25)4-9(23)5-15(17)30-14/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21?/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 Luteolin-4'-O-glucoside

1 Antennaria sp. 2 Callicarpa sp. 3 Cynara sp. 4 Inula sp. 5 Leontopodium sp. 6 Olea sp. 7 Spartium sp.

Biological Activity of Luteolin-4'-O-glucoside

DescriptionLuteolin 4'-O-glucoside as a IL-5 inhibitor, it has anti-complementary,and anti-oxdiant activities.
TargetsIL recepter
In vitro

In vitro anti-complementary activity of flavonoids from olive (Olea europaea L.) leaves.[Pubmed: 8941947]

Pharmazie. 1996 Oct;51(10):765-8.


METHODS AND RESULTS:
From extracts of olive (Olea europaea L., Oleaceae) leaves showing anti-complementary activity, the flavonoids apigenin, apigenin-4'-O-rhamnosylglucoside, apigenin-7-O-glucoside, luteolin, Luteolin-4'-O-glucoside, luteolin-7-O-glucoside, chrysoeriol, chrysoeriol-7-O-glucoside and quercetin-3-O-rhamnoside were isolated.
CONCLUSIONS:
Major isolated constituents strongly inhibited the classical pathway of the complement system.

Isolation of Antioxidant and Antibrowning Substance from Chionanthus retusa Leaves[Reference: WebLink]

Journal of the Korean Society of Food Science & Nutrition, 2004, 33(9).


METHODS AND RESULTS:
This study was performed to examine in vitro antioxidative activities such as DPPH radical scavenging activity, reducing power and tyrosinase inhibitory effect of various solvent fractions from Chionanthus retusa leaves. Ethyl acetate fraction showed potent antioxidative activity and tyrosinase inhibitory effect. The active compound was isolated from the butanol fraction by silica gel column chromatography and MPLC. The isolated compound was Luteolin-4'-O-glucoside determined by , -NMR and 2D NMR. Compared with several antioxidant compounds, Luteolin-4'-O-glucoside exhibited effective DPPH radical scavenging activity and reducing power in a concentration dependent manner. Bioassay with pure Luteolin-4'-O-glucoside showed a dose-independent inhibitory effect on L-DOPA oxidation by mushroom tyrosinase and its values were established as 23.2 .
CONCLUSIONS:
Therefore, we may suggest that Luteolin-4'-O-glucoside can be used as a food additive possessing the potent antioxidative activity and skin-whitening cosmetic material.

Studies on anti-complementary activity of extracts and isolated flavones from Ligustrum vulgare and Phillyrea latifolia leaves (Oleaceae).[Pubmed: 10837985]

J Ethnopharmacol. 2000 Jun;70(3):213-7.


METHODS AND RESULTS:
Polar fractions and flavones isolated from methanolic extracts of the leaves of Ligustrum vulgare and Phillyrea latifolia (Oleaceae), whose popular use as an anti-inflammatory is well-known in Mediterranean historical medicine and ethnobotany, showed significant in vitro complement inhibiting effect on the classical pathway of the complement system.
CONCLUSIONS:
Among the isolated flavonoidic structures, apigenin-7-O-glucoside, apigenin-7-O-rutinoside, Luteolin-4'-O-glucoside, luteolin-7-O-glucoside and ligustroflavone presented remarkable activity.

Protocol of Luteolin-4'-O-glucoside

Kinase Assay

Inhibitory effect of luteolin 4'-O-glucoside from Kummerowia striata and other flavonoids on interleukin-5 bioactivity.[Pubmed: 10418337 ]

Planta Med. 1999 Jun;65(5):457-9.

Interleukin (IL)-5 is a chemotactic factor of eosinophils, and promotes the growth and survival of eosinophils, which plays an important role in the eosinophilia-associated allergic inflammation.
METHODS AND RESULTS:
In this study, luteolin-4'-O-glucopyranoside(Luteolin-4'-O-glucoside ) was identified as the IL-5 inhibitor from Kummerowia striata Thunb. (Leguminosae) by activity-guided fractionation followed by structural analysis compared with reported spectral data. The flavone compound exhibited dose-dependent inhibitory effect on IL-5 bioactivity with 95% inhibition at 30 microM, 79% at 15 microM, 60% at 7.5 microM, 54% at 3.8 microM and 29% at 1.9 microM, where 50% of inhibition (IC50) value was shown at the concentration of 3.7 microM. Furthermore, the inhibitory effect on IL-5 bioactivity by other flavonoid compounds available was estimated.
CONCLUSIONS:
In view of the IC50 values, the inhibitory potency on IL-5 bioactivity was in order of luteolin-4'-O-glucopyranoside > cosmosiin (14.2 microM) approximately equal to apigenin (16.4 microM) approximately equal to luteolin (18.7 microM) > quercimeritrin (27.3 microM) approximately equal to kaempferol (30.0 microM).

Luteolin-4'-O-glucoside Dilution Calculator

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Preparing Stock Solutions of Luteolin-4'-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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References on Luteolin-4'-O-glucoside

Luteolin-4'-O-glucoside and its aglycone, two major flavones of Gnaphalium affine D. Don, resist hyperuricemia and acute gouty arthritis activity in animal models.[Pubmed:29519319]

Phytomedicine. 2018 Mar 1;41:54-61.

BACKGROUND: Gnaphalium affine D. Don is a folk medicine of China believed to be efficacious in the treatment of many ailments, including hyperuricemia and gout. PURPOSE: Based on a previous study, we isolated two flavones, luteolin and luteolin-4'-O-glucoside, from G. affine. Our aim was to assess the potential beneficial effects of treatment and mechanisms of these two flavones on hyperuricemia and acute gouty arthritis. METHODS: The model of potassium oxonate (PO)-induced hyperuricemia and monosodium urate (MSU) crystal-induced inflammation in mice has been established. We evaluated serum uric acid (Sur), xanthine oxidase (XO) activity, protein expression of urate transporter 1 (mURAT1) and glucose transporter 9 (mGLUT9) in renal and kidney protection in a hyperuricemia model. In addition, paw swelling and levels of interleukin-1beta (IL-1beta) and tumor necrosis factor-alpha (TNF-alpha) in serum were assessed in MSU crystal-induced mice. RESULTS: Luteolin and luteolin-4'-O-glucoside showed a potent clinical effect in treating hyperuricemia and gout. We observed that the two flavones possess potent effect in hyperuricemia mice by decreasing the level of mURAT1 and inhibiting XO activity, which contribute to enhancing uric acid (UA) excretion and improving hyperuricemia-induced renal dysfunction. In addition, luteolin and luteolin-4'-O-glucoside also alleviated paw swelling and inflammation induced by MSU crystals. Further investigation implied that luteolin and luteolin-4'-O-glucoside improved the symptoms of inflammation by decreasing the levels of IL-1beta and TNF-alpha. CONCLUSION: The present study suggests that luteolin and luteolin-4'-O-glucoside could be developed as therapeutics for treating hyperuricemia and gouty arthritis.

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