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Apigenin-7-glucuronide

CAS# 29741-09-1

Apigenin-7-glucuronide

Catalog No. BCN5326----Order now to get a substantial discount!

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Quality Control of Apigenin-7-glucuronide

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Chemical structure

Apigenin-7-glucuronide

3D structure

Chemical Properties of Apigenin-7-glucuronide

Cas No. 29741-09-1 SDF Download SDF
PubChem ID 5319484 Appearance Yellowish powder
Formula C21H18O11 M.Wt 446.36
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Scutellarin A; 4',5,7-Trihydroxyflavone 7-glucuronide
Solubility DMSO : 65 mg/mL (145.62 mM; Need ultrasonic)
Chemical Name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
SMILES C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
Standard InChIKey JBFOLLJCGUCDQP-ZFORQUDYSA-N
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 Apigenin-7-glucuronide

1 Chrysanthemum sp. 2 Clerodendrum sp. 3 Dendranthema sp. 4 Leucanthemum sp. 5 Mentha sp. 6 Nepeta sp. 7 Origanum sp. 8 Scutellaria sp. 9 Tanacetum sp. 10 Verbena sp.

Biological Activity of Apigenin-7-glucuronide

DescriptionApigenin-7-glucuronide possesses multiple pharmacological activities, including anti-oxidant, anti-complement, anti-inflammatory, and aldose reductase inhibitory activities, it can inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively. Apigenin 7-O-β-D-glucuronide protects mice from LPS-induced endotoxin shock by inhibiting proinflammatory cytokine production, it may be used as a dietary complement for health promotion.
TargetsNO | PGE | TNF-α | NOS | COX | AP-1 | ERK | p38MAPK | MMP-3 | MMP-8 | MMP-9 | MMP-13
In vivo

Apigenin-7-O-β-D-glucuronide inhibits LPS-induced inflammation through the inactivation of AP-1 and MAPK signaling pathways in RAW 264.7 macrophages and protects mice against endotoxin shock.[Pubmed: 26750400 ]

Food Funct. 2016 Feb;7(2):1002-13.

Apigenin-7-O-β-D-glucuronide (Apigenin-7-glucuronide,AG), an active flavonoid derivative isolated from the agricultural residue of Juglans sigillata fruit husks, possesses multiple pharmacological activities, including anti-oxidant, anti-complement, and aldose reductase inhibitory activities. To date, no report has identified the anti-inflammatory mechanisms of AG.
METHODS AND RESULTS:
This study was therefore designed to characterize the molecular mechanisms of AG on lipopolysaccharide (LPS)-induced inflammatory cytokines in RAW 264.7 cells and on endotoxin-induced shock in mice. AG suppressed the release of nitric oxide (NO), prostaglandin E2 (PGE2), and tumour necrosis factor-α (TNF-α) in LPS-stimulated RAW 264.7 macrophages in a dose-dependent manner without affecting cell viability. Additionally, AG suppressed LPS-induced mRNA expression of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and TNF-α. AG treatment decreased the translocation of c-Jun into the nucleus, and decreased activator protein-1 (AP-1)-mediated luciferase activity through the inhibition of both p38 mitogen-activated protein kinase (MAPK) and extracellular signal-regulated kinase (ERK) phosphorylation. Consistent with the in vitro observations, AG protected mice from LPS-induced endotoxin shock by inhibiting proinflammatory cytokine production.
CONCLUSIONS:
Taken together, these results suggest that AG may be used as a source of anti-inflammatory agents as well as a dietary complement for health promotion.

Protocol of Apigenin-7-glucuronide

Structure Identification
Arch Pharm Res. 2008 Jan;31(1):28-33.

Comparative antioxidant activity and HPLC profiles of some selected Korean thistles.[Pubmed: 18277604]

As yet, no comparative analyses have been conducted regarding the comparative antioxidant activities and HPLC profiles of thistles distributed in Korea.
METHODS AND RESULTS:
Thus, this study was performed in order to evaluate the antioxidant potentials of seven Korean thistles: Cirsium lineare, Cirsium chanroenicum, Cirsium setidens, Cirsium japonicum var. ussuriense, Cirsium nipponicum, Cirslum pendulum and Carduus crispus, via peroxynitrite and DPPH free radical assays. Among seven Korean thistles, Carduus crispus exhibited the most significant antioxidant activity in both DPPH assay and peroxynitrite. In order to characterize the compounds contained in Korean thistles, we conducted HPLC analyses on the following ten flavonoids: luteolin-5-glucoside (1), luteolin-7-glucoside (2), apigenin-7-glucoside (3), hispidulin-7-neohesperidoside (4), Apigenin-7-glucuronide (5), cirsimarin (6), pectolinarin (7), luteolin (8), apigenin (9) and acacetin (10).
CONCLUSIONS:
The results of our HPLC analyses indicated the presence of pectolinarin in the whole plants of C. setidens, C. lineare, C. nipponicum, C. pendulum, the aerial and underground parts of C. japonicum var. ussuriense, and the aerial parts of C. chanroenicum. Moreover, we were able to identify hispidulin-7-neohesperidoside and luteolin-7-glucoside in the whole plants of Carduus crispus, acacetin in the aerial parts of C. chanroenicum, cirsimarin in C. lineare.

Apigenin-7-glucuronide Dilution Calculator

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Preparing Stock Solutions of Apigenin-7-glucuronide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2403 mL 11.2017 mL 22.4034 mL 44.8069 mL 56.0086 mL
5 mM 0.4481 mL 2.2403 mL 4.4807 mL 8.9614 mL 11.2017 mL
10 mM 0.224 mL 1.1202 mL 2.2403 mL 4.4807 mL 5.6009 mL
50 mM 0.0448 mL 0.224 mL 0.4481 mL 0.8961 mL 1.1202 mL
100 mM 0.0224 mL 0.112 mL 0.224 mL 0.4481 mL 0.5601 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 Apigenin-7-glucuronide

Comparative antioxidant activity and HPLC profiles of some selected Korean thistles.[Pubmed:18277604]

Arch Pharm Res. 2008 Jan;31(1):28-33.

As yet, no comparative analyses have been conducted regarding the comparative antioxidant activities and HPLC profiles of thistles distributed in Korea. Thus, this study was performed in order to evaluate the antioxidant potentials of seven Korean thistles: Cirsium lineare, Cirsium chanroenicum, Cirsium setidens, Cirsium japonicum var. ussuriense, Cirsium nipponicum, Cirslum pendulum and Carduus crispus, via peroxynitrite and DPPH free radical assays. Among seven Korean thistles, Carduus crispus exhibited the most significant antioxidant activity in both DPPH assay and peroxynitrite. In order to characterize the compounds contained in Korean thistles, we conducted HPLC analyses on the following ten flavonoids: luteolin-5-glucoside (1), luteolin-7-glucoside (2), apigenin-7-glucoside (3), hispidulin-7-neohesperidoside (4), Apigenin-7-glucuronide (5), cirsimarin (6), pectolinarin (7), luteolin (8), apigenin (9) and acacetin (10). The results of our HPLC analyses indicated the presence of pectolinarin in the whole plants of C. setidens, C. lineare, C. nipponicum, C. pendulum, the aerial and underground parts of C. japonicum var. ussuriense, and the aerial parts of C. chanroenicum. Moreover, we were able to identify hispidulin-7-neohesperidoside and luteolin-7-glucoside in the whole plants of Carduus crispus, acacetin in the aerial parts of C. chanroenicum, cirsimarin in C. lineare.

Description

Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.

Keywords:

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