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3'-Hydroxypuerarin

CAS# 117060-54-5

3'-Hydroxypuerarin

Catalog No. BCN2816----Order now to get a substantial discount!

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Quality Control of 3'-Hydroxypuerarin

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Chemical structure

3'-Hydroxypuerarin

3D structure

Chemical Properties of 3'-Hydroxypuerarin

Cas No. 117060-54-5 SDF Download SDF
PubChem ID 5748205 Appearance White powder
Formula C21H20O10 M.Wt 432.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 3'-Hydroxy Puerarin;117076-54-5;Pueraria Glycoside; 3'-Hydroxypuerarin
Solubility Soluble in methanol and pyridine
Chemical Name 3-(3,4-dihydroxyphenyl)-7-hydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
SMILES C1=CC(=C(C=C1C2=COC3=C(C2=O)C=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O)O
Standard InChIKey GARZMRVWLORUSR-VPRICQMDSA-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 3'-Hydroxypuerarin

The roots of Pueraria lobata

Biological Activity of 3'-Hydroxypuerarin

Description3'-Hydroxypuerarin has antioxidant activity, it shows marked ONOO(-), NO·, total ROS scavenging activities, and weak ·O(2)(-) scavenging activity.
TargetsNO | NOS | COX | ROS
In vitro

Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots.[Pubmed: 22644850]

Arch Pharm Res. 2012 May;35(5):823-37.


METHODS AND RESULTS:
In order to evaluate the anti-inflammatory and antioxidant activities of Pueraria lobata roots and its active components, in vitro inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) protein expression, and tert-butylhydroperoxide (t-BHP)-induced reactive oxygen species (ROS) generation in RAW 264.7 cells, as well as in vitro scavenging activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH), peroxynitrite (ONOO(-)), nitric oxide (NO·), superoxide anion (·O(2)(-)) and total ROS, and inhibitory activities against ONOO(-)-mediated tyrosine nitration, were determined. Repeated column chromatography was performed to isolate four known compounds from the anti-inflammatory and antioxidant EtOAc fraction: daidzein; genistein; puerarin; (+)-puerarol B-2-O-glucopyranoside; four known compounds from the anti-inflammatory n-hexane fraction: lupenone; lupeol; puerarol; coumestrol; seven known compounds from the antioxidant n-BuOH fraction: allantoin; 3'-Hydroxypuerarin; daidzein 8-C-apiosyl-(1→6)-glucoside; puerarin; genistin; 3'-methoxypuerarin; daidzin. Among these compounds, lupenone and lupeol reduced NO production, as well as iNOS and COX-2 protein levels in LPS-stimulated RAW 264.7 cells. Furthermore, lupeol showed significant inhibitory activity against intracellular ROS generation by t-BHP. Meanwhile, 3'-Hydroxypuerarin showed marked ONOO(-), NO·, total ROS scavenging activities, and weak ·O(2)(-) scavenging activity, while 3'-methoxypuerarin showed ONOO(-) scavenging activity and weak NO· and O(2)(-) scavenging activities, suggesting that existence of the 3'-hydroxyl group in puerarin plays an important role in the scavenging of ONOO(-), NO·, and total ROS, as well as inhibiting the ONOO(-)-mediated tyrosine nitration mechanism.
CONCLUSIONS:
These results indicate that P. lobata roots and its constituents may be a useful therapeutic and preventive approach to various inflammatory diseases and oxidative stress-related disease.

3'-Hydroxypuerarin Dilution Calculator

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3'-Hydroxypuerarin Molarity Calculator

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Preparing Stock Solutions of 3'-Hydroxypuerarin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3128 mL 11.5639 mL 23.1278 mL 46.2556 mL 57.8195 mL
5 mM 0.4626 mL 2.3128 mL 4.6256 mL 9.2511 mL 11.5639 mL
10 mM 0.2313 mL 1.1564 mL 2.3128 mL 4.6256 mL 5.782 mL
50 mM 0.0463 mL 0.2313 mL 0.4626 mL 0.9251 mL 1.1564 mL
100 mM 0.0231 mL 0.1156 mL 0.2313 mL 0.4626 mL 0.5782 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 3'-Hydroxypuerarin

[Determination of five components in Pueraria labta decoction with reference extraction method].[Pubmed:23234135]

Zhongguo Zhong Yao Za Zhi. 2012 Aug;37(16):2388-91.

OBJECTIVE: To establish the reference extraction method for determining five components contained in Pueraria labta decoction and detecting the applicability and feasibility of the application of reference extracts according to the quality standard of traditional Chinese medicine. METHOD: Zorbax C18 chromatographic column (4.6 mm x 250 mm, 5 microm) was used, with methanol-0.02% phosphoric acid (25:75) as the mobile phase and the detection wavelength was set at 250 nm. Self-prepared reference extracts of P. labta was used for determining the content of 3'-hydroxy puerarin, puerarin, 3'-methoxy puerarin, isoflavoues aglycone-8-C-apiose-(1--> 6) glucoside and daidzin and compare with the experimental results obtained with the single reference substance determination method. RESULT: The reference extraction determination method showed high precision, stability and reproducibility, with coincident determination results with the results obtained with the single reference substance determination method. CONCLUSION: The reference extraction determination method of P. labta can be used for quality control of P. labta herbs. The study preliminarily proves the feasibility of the application of P. labta in traditional Chinese medicine.

Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots.[Pubmed:22644850]

Arch Pharm Res. 2012 May;35(5):823-37.

In order to evaluate the anti-inflammatory and antioxidant activities of Pueraria lobata roots and its active components, in vitro inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) protein expression, and tert-butylhydroperoxide (t-BHP)-induced reactive oxygen species (ROS) generation in RAW 264.7 cells, as well as in vitro scavenging activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH), peroxynitrite (ONOO(-)), nitric oxide (NO.), superoxide anion (.O(2)(-)) and total ROS, and inhibitory activities against ONOO(-)-mediated tyrosine nitration, were determined. Repeated column chromatography was performed to isolate four known compounds from the anti-inflammatory and antioxidant EtOAc fraction: daidzein; genistein; puerarin; (+)-puerarol B-2-O-glucopyranoside; four known compounds from the anti-inflammatory n-hexane fraction: lupenone; lupeol; puerarol; coumestrol; seven known compounds from the antioxidant n-BuOH fraction: allantoin; 3'-hydroxypuerarin; daidzein 8-C-apiosyl-(1-->6)-glucoside; puerarin; genistin; 3'-methoxypuerarin; daidzin. Among these compounds, lupenone and lupeol reduced NO production, as well as iNOS and COX-2 protein levels in LPS-stimulated RAW 264.7 cells. Furthermore, lupeol showed significant inhibitory activity against intracellular ROS generation by t-BHP. Meanwhile, 3'-hydroxypuerarin showed marked ONOO(-), NO., total ROS scavenging activities, and weak .O(2)(-) scavenging activity, while 3'-methoxypuerarin showed ONOO(-) scavenging activity and weak NO. and O(2)(-) scavenging activities, suggesting that existence of the 3'-hydroxyl group in puerarin plays an important role in the scavenging of ONOO(-), NO., and total ROS, as well as inhibiting the ONOO(-)-mediated tyrosine nitration mechanism. These results indicate that P. lobata roots and its constituents may be a useful therapeutic and preventive approach to various inflammatory diseases and oxidative stress-related disease.

Qualitative and quantitative analysis of the major constituents in Chinese medicinal preparation Dan-Lou tablet by ultra high performance liquid chromatography/diode-array detector/quadrupole time-of-flight tandem mass spectrometry.[Pubmed:23518306]

J Pharm Biomed Anal. 2013 Jun;80:50-62.

A rapid ultra high performance liquid chromatography/diode-array detector/quadrupole time-of-flight tandem mass spectrometry (UPLC-DAD-QTOF) method and a ultra high performance liquid chromatography coupled with diode-array detector (UPLC-DAD) method were developed for qualitative and quantitative analyses of the major chemical constituents in Dan-Lou tablet. Sixty-eight compounds including flavonoids, phenolic acids, tanshinones, protostane triterpenoids, lactones, and paeoniflorins were unambiguously or tentatively identified by comparing their retention times and accurate mass measurement in 40min with references or literature data. Among them, 19 compounds: gallic acid, danshensu, 5-hydroxymethyl-2-furaldehyde, 3'-hydroxy puerarin, puerarin, 3'-methoxy puerarin, mirificin, daidzin, paeoniflorin, calycosin-7-O-beta-D-glucoside, naringin, genistin, rosmarinic acid, salvianolic acid B, salvianolic acid A, formononetin, calycosin, cryptotanshinone and tanshinone IIA were further quantified in 30min as marker substances. It was found that the calibration curves for all analytes showed good linearity (R(2)>0.9997) within the test ranges. The overall limits of detection (LODs) and limits of quantification (LOQs) were 0.0073-0.34mug/mL and 0.022-1.04mug/mL, respectively. The relative standard deviations (RSDs) for intra- and inter-day precisions were below 1.90% and 2.85%, respectively. The results of repeatability were less than 2.74%. The sample was stable for at least 48h. The mean recovery rates ranged from 95.5% to 105% with the relative standard deviations (RSDs) less than 2.96%. The results showed that the developed quantitative method was linear, sensitive, and precise for quality control of Dan-Lou tablet.

Description

3'-Hydroxypuerarin is an isoflavone isolated from the roots of Pueraria lobata (Willd.) Ohwi. 3'-Hydroxypuerarin is a antioxidant, which shows marked ONOO(-), NO•, total ROS scavenging activities.

Keywords:

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