Prunin
(Synonyms: 柚皮素-7-O-葡萄糖苷; Naringenin 7-0-glucoside) 目录号 : GC39066
A flavonoid glycoside with diverse biological activities
Cas No.:529-55-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Prunin is a polyketide synthase-derived flavonoid glycoside that has been found in G. glabra and has diverse biological activities.1,2,3,4,5 It inhibits neuraminidase (NA) activity in oseltamivir-sensitive and -resistant H1N1 influenza strains (IC50s = 3 and 4.53 ?M, respectively).2 Prunin (2 ?M) scavenges DPPH radicals in a cell-free assay.3 It inhibits the activity of protein tyrosine phosphatase 1B (PTP1B; IC50 = 5.5 ?M for the human enzyme) and increases insulin-induced glucose uptake in insulin-resistant HepG2 hepatocellular carcinoma cells in a concentration-dependent manner.4 Prunin inhibits the proliferation of, and induces apoptosis in, HL-60 leukemia cells.5
1.Sharma, P., Kumar, V., and Guleria, P.Naringin: Biosynthesis and pharmaceutical applicationsIndian J. Pharm. Sci.81(6)988-999(2019) 2.Grienke, U., Braun, H., Seidel, N., et al.Computer-guided approach to access the anti-influenza activity of licorice constituentsJ. Nat. Prod.77(3)563-570(2014) 3.Sang, S., Lapsley, K., Jeong, W.-S., et al.Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch)J. Agric. Food Chem.50(8)2459-2463(2002) 4.Jung, H.A., Ali, M.Y., Bhakta, K., et al.Prunin is a highly potent flavonoid from Prunus davidiana stems that inhibits protein tyrosine phosphatase 1B and stimulates glucose uptake in insulin-resistant HepG2 cellsArch. Pharm. Res.40(1)37-48(2017) 5.Tung, N.H., Son, J.-H., Cho, K., et al.Phenolic components from the leaves of Panax ginseng and their effects on HL-60 human leukemia cellsFood Sci. Biotechnol.19(1)271-274(2010)
| Cas No. | 529-55-5 | SDF | |
| 别名 | 柚皮素-7-O-葡萄糖苷; Naringenin 7-0-glucoside | ||
| Canonical SMILES | O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=CC(O)=C13 | ||
| 分子式 | C21H22O10 | 分子量 | 434.39 |
| 溶解度 | DMSO : 100 mg/mL (230.21 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.3021 mL | 11.5104 mL | 23.0208 mL |
| 5 mM | 0.4604 mL | 2.3021 mL | 4.6042 mL |
| 10 mM | 0.2302 mL | 1.151 mL | 2.3021 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Prunin suppresses viral IRES activity and is a potential candidate for treating enterovirus A71 infection
Sci Transl Med 2019 Oct 30;11(516):eaar5759.PMID:31666401DOI:10.1126/scitranslmed.aar5759.
Human enterovirus A71 (HEVA71) causes hand, foot, and mouth disease (HFMD) in young children and is considered a major neurotropic pathogen but lacks effective antivirals. To identify potential therapeutic agents against HFMD, we screened a 502-compound flavonoid library for compounds targeting the HEVA71 internal ribosome entry site (IRES) that facilitates translation of the HEVA71 genome and is vital for the production of HEVA71 viral particles. We validated hits using cell viability and viral plaque assays and found that Prunin was the most potent inhibitor of HEVA71. Downstream assays affirmed that Prunin disrupted viral protein and RNA synthesis and acted as a narrow-spectrum antiviral against enteroviruses A and B, but not enterovirus C, rhinovirus A, herpes simplex 1, or chikungunya virus. Continuous HEVA71 passaging with Prunin yielded HEVA71-resistant mutants with five mutations that mapped to the viral IRES. Knockdown studies showed that the mutations allowed HEVA71 to overcome treatment-induced suppression by differentially regulating recruitment of the IRES trans-acting factors Sam68 and hnRNPK without affecting the hnRNPA1-IRES interaction required for IRES translation. Furthermore, Prunin effectively reduced HEVA71-associated clinical symptoms and mortality in HEVA71-infected BALB/c mice and suppressed hepatitis C virus at higher concentrations, suggesting a similar mechanism of prunin-mediated IRES inhibition for both viruses. These studies establish Prunin as a candidate for further development as a HEVA71 therapeutic agent.
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
Arch Pharm Res 2017 Jan;40(1):37-48.PMID:27798765DOI:10.1007/s12272-016-0852-3.
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), 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. These results indicate that Prunin has significant potential as a selective PTP1B inhibitor and may possess anti-diabetic properties by improving insulin resistance.
Production of Prunin and Naringenin by Using Naringinase from Aspergillus oryzae NYO-2 and Their Neuroprotective Properties and Debitterization
J Agric Food Chem 2023 Jan 25;71(3):1655-1666.PMID:36629749DOI:10.1021/acs.jafc.2c06586.
Naringin is a flavanone glycoside in citrus fruits that has various biological functions. However, its bitterness affects the quality, economic value, and consumer acceptability of citrus products. Deglycosylation of naringin using naringinase decreases its bitterness and enhances its functional properties. In this study, eight microbial strains with naringinase activity were isolated from 33 yuzu-based fermented foods. Among them, naringinase from Aspergillus oryzae NYO-2, having the highest activity, was used to produce Prunin and naringenin. Under optimal conditions, 19 mM naringin was converted to 14.06 mM Prunin and 1.97 mM naringenin. The bitterness of Prunin and naringenin was significantly decreased compared to naringin using the human bitter taste receptor TAS2R39. The neuroprotective effects of Prunin and naringenin on human neuroblastoma SH-SY5Y cells treated with scopolamine were greater than that of naringin. These findings can widen the potential applications of deglycosylation of naringin to improve sensory and functional properties.
Prunin identification, biological activity and quantitative change in comparison to naringenin in dormant peach buds
Plant Physiol 1969 Mar;44(3):342-6.PMID:16657067DOI:10.1104/pp.44.3.342.
Prunin (naringenin 7-glucoside), which was identified in dormant peach buds, was found to act as a growth inhibitor of wheat coleoptile elongation.Quantitative estimation on a fresh weight basis of the flavonoid in peach buds revealed a high level in late summer, a steep decrease in autumn that became more moderate during the winter, with lowest values near bud swell in spring. Two periods of reaccumulation of Prunin during October and January fitted 2 periods of arrested growth of the resting bud. A negative correlation was demonstrated between Prunin and naringenin levels during August through October. It is proposed that Prunin might act as a precursor for naringenin that accumulates in resting buds in autumn. It is suggested that the system glucoside-aglucone-beta glucosidase might have regulatory properties in the dormant bud.
Prunin- and hesperetin glucoside-alkyl (C4-C18) esters interaction with Jurkat cells plasma membrane: consequences on membrane physical properties and antioxidant capacity
Food Chem Toxicol 2013 May;55:411-23.PMID:23354392DOI:10.1016/j.fct.2013.01.011.
Prunin (P)- and hesperetin glucoside (HG)-alkyl esters are lipid-soluble compounds with antimicrobial and antioxidant capacities in vitro. The effects of P- and HG-alkyl (C4-C18) esters (0.1-100μM) on human leukemia T (Jurkat) cells viability and plasma membrane fluidity were evaluated. After 1h of exposure, cell viability was not affected in the range 0.1-10μM. The decrease of cell viability found at 100μM concentration depended on the length of the alkyl chain and reached a maximum with C6-C12 derivatives. 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 P and HG (0.1-10μM) against 1mM H2O2. When exposed to 1mM AAPH, P-alkyl esters retained P antioxidant capacity, but HG-derivatives acted as pro-oxidants. Together, present experimental evidences suggest that short term exposures to 0.1-10μM concentrations of P- 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.