PruninCAS# 529-55-5 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 529-55-5 | SDF | Download SDF |
PubChem ID | 92794 | Appearance | Powder |
Formula | C21H22O10 | M.Wt | 434.4 |
Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
Synonyms | Naringenin-7-O-glucoside;Naringenin 7-O-beta-D-glucoside | ||
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one | ||
SMILES | C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O | ||
Standard InChIKey | DLIKSSGEMUFQOK-SFTVRKLSSA-N | ||
Standard InChI | InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,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. |
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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. |
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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. |
Description | Prunin possesses anti-diabetic, and anti-abacterial properties, it can inhibit protein tyrosine phosphatase 1B (PTP1B) and stimulate glucose uptake in insulin-resistant HepG2 cells; it also can stimulate growth of Pseudomonas aeruginosa and different Bacilllus sp. Prunin exhibits a markedly enhanced solubility compared to naringenin and naringin while maintaining the in vitro inhibition of HMG-CoA reductase. |
Targets | HMG-CoA reductase | Antifection |
In vitro | Prunin- and hesperetin glucoside-alkyl (C4-C18) esters interaction with Jurkat cells plasma membrane: consequences on membrane physical properties and antioxidant capacity.[Pubmed: 23354392 ]Food Chem Toxicol. 2013 May;55:411-23.Prunin (P)- and hesperetin glucoside (HG)-alkyl esters are lipid-soluble compounds with antimicrobial and antioxidant capacities in vitro. Purification and characterisation of Aspergillus sojae naringinase: The production of prunin exhibiting markedly enhanced solubility with in vitro inhibition of HMG-CoA reductase.[Reference: WebLink]Food Chemistry, 2011, 124(1):234-241.Aspergillus sojae isolated from a traditional Korean fermented soybean product exhibited strong naringinase activity. Antimicrobial properties of prunin, a citric flavanone glucoside, and its prunin 6″-O-lauroyl ester.[Pubmed: 20553344]J Appl Microbiol. 2010 Oct;109(4):1450-7. To determine the antimicrobial potential of Prunin (P), a flavanone glucoside resulting from the hydrolysis of naringin present in grapefruit, and of its Prunin 6″-O-lauroyl ester (PL), synthesized by enzymatic catalysis. |
Cell Research | Prunin is a highly potent flavonoid from Prunus davidiana stems that inhibits protein tyrosine phosphatase 1B and stimulates glucose uptake in insulin-resistant HepG2 cells.[Pubmed: 27798765 ]Arch Pharm Res. 2017 Jan;40(1):37-48.Prunin is the main flavonoid in Prunus davidiana stems and improves hyperglycemia and hyperlipidemia in streptozotocin-induced diabetic rats. |
Prunin Dilution Calculator
Prunin Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.302 mL | 11.5101 mL | 23.0203 mL | 46.0405 mL | 57.5506 mL |
5 mM | 0.4604 mL | 2.302 mL | 4.6041 mL | 9.2081 mL | 11.5101 mL |
10 mM | 0.2302 mL | 1.151 mL | 2.302 mL | 4.6041 mL | 5.7551 mL |
50 mM | 0.046 mL | 0.2302 mL | 0.4604 mL | 0.9208 mL | 1.151 mL |
100 mM | 0.023 mL | 0.1151 mL | 0.2302 mL | 0.4604 mL | 0.5755 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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Antimicrobial properties of prunin, a citric flavanone glucoside, and its prunin 6''-O-lauroyl ester.[Pubmed:20553344]
J Appl Microbiol. 2010 Oct;109(4):1450-7.
AIMS: To determine the antimicrobial potential of Prunin (P), a flavanone glucoside resulting from the hydrolysis of naringin present in grapefruit, and of its Prunin 6''-O-lauroyl ester (PL), synthesized by enzymatic catalysis. METHODS AND RESULTS: P and its lauroyl ester were tested against Gram-negative and Gram-positive bacteria, yeasts and moulds. P showed no inhibitory effect against the micro-organisms assayed, but stimulated growth of Pseudomonas aeruginosa and different Bacilllus sp. However, 150 mug ml(-1) of PL inhibited Escherichia coli, Salmonella enterica serovar Enteritidis, Salmonella enterica serovar Typhimurium, many Bacillus sp., Staphylococcus aureus ATCC29213, Enterococcus avium DSMZ17511, and different Listeria monocytogenes strains. In the last case, L. monocytogenes, sensitive or bacteriocin-resistant cells, lost nearly 4-log reductions after 30 min of contact. A bactericidal mode of action was determined using both scanning and transmission electronic microscopies. CONCLUSIONS: PL could be used as a food additive, because at low concentration (150 mug ml(-1)) it exhibited antimicrobial activity against important food-borne pathogens. A bactericidal effect was also determined on L. monocytogenes sensitive and bacteriocin-resistant mutant strains. P did not show any antimicrobial property at all. SIGNIFICANCE AND IMPACT OF THE STUDY: PL is a potential antimicrobial compound with a high anti-Listeria property.
Inhibition of growth and xylogenesis and promotion of vacuolation in prunus callus by the flavanone prunin.[Pubmed:24241596]
Plant Cell Rep. 1988 May;7(3):189-92.
Callus tissue of Prunus avium L. responded to supplied Prunin (naringen in 7-glucoside) showing vaculoation and storage of oligomeric proanthocyanidins. In addition, Prunin caused restricted callus initiation and/or less callus growth. When Prunin was omitted from the medium numerous tracheids and more peroxidases were formed in the callus.
Prunin is a highly potent flavonoid from Prunus davidiana stems that inhibits protein tyrosine phosphatase 1B and stimulates glucose uptake in insulin-resistant HepG2 cells.[Pubmed:27798765]
Arch Pharm Res. 2017 Jan;40(1):37-48.
Prunin is the main flavonoid in Prunus davidiana stems and improves hyperglycemia and hyperlipidemia in streptozotocin-induced diabetic rats. The aim of this study was to investigate the in vitro anti-diabetic potential of Prunin via the inhibition of protein tyrosine phosphatase 1B (PTP1B), alpha-glucosidase, peroxynitrite (ONOO(-))-mediated tyrosine nitration, and stimulation of glucose uptake in insulin-resistant hepatocytes. In addition, a molecular docking simulation was performed to predict specific Prunin binding modes during PTP1B inhibition. Prunin showed strong inhibitory activity against PTP1B, with an IC50 value of 5.5 +/- 0.29 microM, and significant inhibitory activity against alpha-glucosidase, with an IC50 value of 317 +/- 2.12 microM. Moreover, a kinetics study revealed that Prunin inhibited PTP1B (K i = 8.66) and alpha-glucosidase (K i = 189.56) with characteristics typical of competitive and mixed type inhibitors, respectively. Docking simulations showed that Prunin selectively inhibited PTP1B by targeting its active site and exhibited good binding affinity, with a docking score of -9 kcal/mol. Furthermore, Prunin exhibited dose-dependent inhibitory activity against ONOO(-)-mediated tyrosine nitration and stimulated glucose uptake by decreasing PTP1B expression level in insulin-resistant HepG2 cells. These results indicate that Prunin has significant potential as a selective PTP1B inhibitor and may possess anti-diabetic properties by improving insulin resistance.