Prunin

CAS# 529-55-5

Prunin

Catalog No. BCN5693----Order now to get a substantial discount!

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Chemical structure

Prunin

3D structure

Chemical Properties of Prunin

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.
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 Prunin

The heartwood of Podocarpus macrophyllus.

Biological Activity of Prunin

DescriptionPrunin 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.
TargetsHMG-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.
METHODS AND RESULTS:
The effects of Prunin- and HG-alkyl (C4-C18) esters (0.1-100μM) on human leukemia T (Jurkat) cells viability and plasma membrane fluidity were evaluated. At this concentration, cell hyperpolarization and shrinkage were also observed. Cell plasma membrane fluidity was not affected, regardless the depths of the membrane level evaluated, but mild changes in plasma membrane hydration were found. Esterification did not affect the antioxidant capacity of Prunin and HG (0.1-10μM) against 1mM H2O2. When exposed to 1mM AAPH, P-alkyl esters retained Prunin antioxidant capacity, but HG-derivatives acted as pro-oxidants.
CONCLUSIONS:
Together, present experimental evidences suggest that short term exposures to 0.1-10μM concentrations of Prunin- and HG-alkyl (C4-C18) esters can be considered safe for cultured human cells, and further studies are required to investigate their long term effects, as well their safety for human consumption.

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.
METHODS AND RESULTS:
The naringinase enzyme was purified and had a molecular weight of 70kDa. The α-l-rhamnosidase activity of this enzyme was optimal at pH 6.0 and stable in the pH range of 5.5-8.0. The purified enzyme also had β-d-glucosidase activity, but the activity was relatively weak compared to the activity of the naringinase from Penicillium decumbens. The enzymatic bioconversion by A. sojae naringinase of naringin to Prunin was efficiently performed with a 91% yield and a negligible amount of naringenin. The bioconversion was achieved by repetitive batch reactions with enzyme recycling. Prunin exhibited a markedly enhanced solubility compared to naringenin and naringin while maintaining the in vitro inhibition of HMG-CoA reductase.
CONCLUSIONS:
The results reported in this paper show that the naringinase produced by A. sojae will be useful in enhancing the potential bioavailability of naringin by efficiently converting it to Prunin as a food component in citrus.

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.
METHODS AND RESULTS:
P and its lauroyl ester were tested against Gram-negative and Gram-positive bacteria, yeasts and moulds.Prunin showed no inhibitory effect against the micro-organisms assayed, but stimulated growth of Pseudomonas aeruginosa and different Bacilllus sp. A bactericidal effect was also determined on L. monocytogenes sensitive and bacteriocin-resistant mutant strains.Prunin did not show any antimicrobial property at all.
CONCLUSIONS:
PL is a potential antimicrobial compound with a high anti-Listeria property.

Protocol of Prunin

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.
METHODS AND RESULTS:
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), α-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 μM, and significant inhibitory activity against α-glucosidase, with an IC50 value of 317 ± 2.12 μM. Moreover, a kinetics study revealed that Prunin inhibited PTP1B (K i = 8.66) and α-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.
CONCLUSIONS:
These results indicate that Prunin has significant potential as a selective PTP1B inhibitor and may possess anti-diabetic properties by improving insulin resistance.

Prunin Dilution Calculator

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Prunin Molarity Calculator

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Preparing Stock Solutions of Prunin

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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References on Prunin

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.

Description

Prunin is a potent inhibitor of human enterovirus A71 (HEVA71). Prunin shows strong inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), with an IC50 of 5.5 µM.

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