Prunetin
(Synonyms: 樱黄素) 目录号 : GC46002
An isoflavone with diverse biological activities
Cas No.:552-59-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Prunetin is an isoflavone that has been found in P. yedoensis and has diverse biological activities.1,2,3,4,5 It is an allosteric inhibitor of hamster liver aldehyde dehydrogenase 2 (ALDH2; IC50 = 0.45 μM) and an antagonist of the progesterone receptor when used at concentrations of 25 and 50 μM.2,3 It has estrogenic activity in MVLN cells when used at concentrations ranging from 1 to 50 μM and inhibits proliferation of MCF-7 breast cancer cells when used at 0.01 to 50 μM.4 It decreases LPS-induced increases in nitric oxide (NO) and prostaglandin E2 levels, NOS2/iNOS expression, and NF-κB activation in RAW 264.7 macrophages when used at concentrations of 50 and 100 μM.1 Prunetin (10 mg/kg) prevents LPS-induced increases in serum TNF-α, IL-1β, and IL-6 levels in a mouse model of septic shock. It also inhibits the secretion of matrix metalloproteinase-3 (MMP-3) in isolated rabbit articular chondrocytes and prevents the production of MMP-3 in the knee joint of rats in a model of osteoarthritis following administration of a 50 or 100 μM dose into the knee joint.5
|1. Gabsik, Y., Ham, I., and Choi, H.-Y. Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway. Food Chem. Toxicol. 58, 124-132 (2013).|2. Lowe, E.D., Gao, G.-Y., Johnson, L.N., et al. Structure of daidzin, a naturally occurring anti-alcohol-addiction agent, in complex with human mitochondrial aldehyde dehydrogenase. J. Med. Chem. 51(15), 4482-4487 (2008).|3. Lee, J.-H., Dean, M., Austin, J.R., et al. Irilone from red clover (Trifolium pratense) potentiates progesterone signaling. J. Nat. Prod. 81(9), 1962-1967 (2018).|4. Le Bail, J.-C., Champavier, Y., Chulia, A.-J., et al. Effects of phytoestrogens on aromatase, 3β and 17β-hydroxysteroid dehydrogenase activities and human breast cancer cells. Life Sci. 66(14), 1281-1291 (2000).|5. Nam, D.C., Kim, B.K., Lee, H.J., et al. Effects of prunetin on the proteolytic activity, secretion and gene expression of MMP-3 in vitro and production of MMP-3 in vivo. Korean J. Physiol. Pharmacol. 20(2), 221-228 (2016).
| Cas No. | 552-59-0 | SDF | |
| 别名 | 樱黄素 | ||
| Canonical SMILES | COC1=CC(O)=C2C(OC=C(C3=CC=C(O)C=C3)C2=O)=C1 | ||
| 分子式 | C16H12O5 | 分子量 | 284.3 |
| 溶解度 | DMF: 10 mg/ml,DMSO: 10 mg/ml,DMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml | 储存条件 | Store at -20°C |
| 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 | 3.5174 mL | 17.5871 mL | 35.1741 mL |
| 5 mM | 0.7035 mL | 3.5174 mL | 7.0348 mL |
| 10 mM | 0.3517 mL | 1.7587 mL | 3.5174 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。
The Potential Therapeutic Properties of Prunetin against Human Health Complications: A Review of Medicinal Importance and Pharmacological Activities
Drug Metab Bioanal Lett 2022;15(3):166-177.PMID:36098409DOI:10.2174/2949681015666220912104743.
Background: Flavonoids are polyphenolic compounds found to be present in nature and abundant in flowers and fruits. Flavonoidal class phytochemicals have gained interest in the scientific field because of their important pharmacological activities. Several scientific studies have revealed anti-bacterial, anti-oxidant, anti-fungal, analgesic, anti-viral, anti-inflammatory, anti-tumor, anti-parasitic and anti-allergic activities of flavonoidal class phytochemicals. Prunetin is an O-methylated isoflavone that belongs to the phytochemical phytoestrogen class, found to be present in licorice, red cherry, soybean and legumes. Methods: Biological potential and pharmacological activities of Prunetin have been investigated in the present work through scientific data analysis of numerous scientific research works. Numerous literature databases have been searched in order to collect the scientific information on Prunetin in the present work. Pharmacological activities of Prunetin have been investigated in the present work through literature data analysis of different scientific research works. Scientific data have been collected from Google Scholar, Google, PubMed, Science Direct and Scopus. Analytical data on Prunetin has been collected from literature sources and analyzed in the present work. Results: Scientific data analysis revealed the biological importance of Prunetin in medicine. Prunetin was found to be present in the pea, peach, Oregon cherry, skimmed cheese, cheese, cow kefir and goat kefir. Prunetin is also present in the Prunus avium, Andira surinamensis, Butea superba, Dalbergia sympathetica, Ficus nervosa, Pterospartum tridentatum and Pycnanthus angolensis. Pharmacological data analysis revealed the biological importance of Prunetin on bone disorders, cancers, especially hepatocellular carcinoma, urinary bladder cancer, gastric cancer, ovarian cancer, human airway, gut health and enzymes. Scientific data analysis revealed biological effectiveness of Prunetin for their angiogenic effects, anti-inflammatory, anti-oxidant, antimicrobial, estrogenic and vasorelaxant potential. Analytical data revealed the importance of modern analytical techniques for qualitative and quantitative analysis of Prunetin in the scientific fields. Conclusion: Scientific data analysis in the present investigation revealed the biological importance and pharmacological activities of Prunetin in medicine.
Prunetin inhibits nitric oxide activity and induces apoptosis in urinary bladder cancer cells via CASP3 and TNF-α genes
Mol Biol Rep 2021 Nov;48(11):7251-7259.PMID:34599704DOI:10.1007/s11033-021-06719-w.
Background: Urinary bladder cancer (UBC) is considered one of the most prevalent malignant tumors worldwide. Complementary and integrative approaches for the treatment of bladder cancer, such as the intake of isoflavonoid phytoestrogens, are of increasing interest due to the risk of mortality and long-term morbidity associated with surgical procedures. The biological effects of Prunetin, one of the less-studied phytoestrogens, have not yet been examined in this respect. Therefore, this study aimed to explore the efficacy of Prunetin on UBC cells (RT-4). METHODS AND RESULTS: The cytotoxicity and nitric oxide synthase activities of Prunetin were determined in cell cultures. The expression of apoptosis-related genes was determined with RT-PCR. Cell cycle assays were performed using a flow cytometer and cellular apoptotic rate was measured. The results suggested that Prunetin has cytotoxic effects at 21.11 µg/mL on RT-4 cells. Flow cytometry analysis showed that Prunetin induced apoptosis and arrested th cell cycle in the G0/G1 phase. Prunetin exposure was associated with increases in CASP3 and TNF-α gene expression in RT-4 cells at doses of 21.11 and 42.22 µg/mL, respectively. Strong nitric oxide inhibition was observed at IC50 of 5.18 µg/mL under macrophage mediated inflammatory circumstances. Conclusions: Prunetin possesses anti-cancer properties and may be a candidate compound for the prevention of UBC. This is the first study that evaluated Prunetin for its in vitro antitumor activities, clarified its possible apoptotic molecular mechanism and provided novel insights into its anti-inflammatory nature and effects on the expression of related key genes.
Prunetin Relaxed Isolated Rat Aortic Rings by Blocking Calcium Channels
Molecules 2018 Sep 17;23(9):2372.PMID:30227625DOI:10.3390/molecules23092372.
Prunetin, a component of herbal medicines and various foods, such as pea, peach, cherry, and Prunus yedoensis, is a useful pharmacological compound. We previously reported the potent vasorelaxant effect of the bark of P. yedoensis. Therefore, we investigated the vasorelaxant activities of Prunetin on isolated rat aortic rings and hypotensive activity on spontaneously hypertensive rats (SHR) in this study. In the present study, Prunetin (1⁻30 μg/mL) relaxed isolated rat aortic rings pre-contracted by phenylephrine (PE) in a concentration-dependent manner. Pre-incubation with Prunetin (3 and 10 μg/mL) inhibited vasoconstriction induced by the supply of Ca2+ in rat aortic rings pre-contracted with PE or KCl in a Ca2+-free Krebs⁻Henseleit (KH) buffer. Prunetin (10 μg/mL) pre-treatment also inhibited caffeine-induced contraction of aortic rings in a Ca2+-free KH buffer. To investigate the hypotensive effect of Prunetin, the systolic blood pressure (SBP) of the SHR was measured by using a tail cuff assay. The SBP of SHR was significantly lower in the Prunetin (25 mg/kg)-treated group. These results suggested that Prunetin decreased blood pressure and relaxed blood vessels by blocking receptor-operated calcium channels, voltage-dependent calcium channels, and ryanodine receptor channels.
Prunetin 4'- O-Phosphate, a Novel Compound, in RAW 264.7 Macrophages Exerts Anti-Inflammatory Activity via Suppression of MAP Kinases and the NFκB Pathway
Molecules 2021 Nov 12;26(22):6841.PMID:34833933DOI:10.3390/molecules26226841.
Biorenovation, a microbial enzyme-assisted degradation process of precursor compounds, is an effective approach to unraveling the potential bioactive properties of the derived compounds. In this study, we obtained a new compound, Prunetin 4'-O-phosphate (P4P), through the biorenovation of Prunetin (PRN), and investigated its anti-inflammatory effects in lipopolysaccharide (LPS)-treated RAW 264.7 macrophage cells. The anti-inflammatory effect of P4P was evaluated by measuring the production of prostaglandin-E2 (PGE2), nitric oxide (NO), which is an inflammation-inducing factor, and related cytokines such as tumor necrosis factor-α (TNFα), interleukin-1β (IL1β), and interleukin-6 (IL6). The findings demonstrated that P4P was non-toxic to cells, and its inhibition of the secretion of NO-as well as pro-inflammatory cytokines-was concentration-dependent. A simultaneous reduction in the protein expression level of pro-inflammatory proteins such as cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) was observed. Moreover, the phosphorylation of mitogen-activated protein kinases (MAPKs) such as extracellular signal-regulated kinases (ERKs), c-Jun N-terminal kinase (JNK), p38 MAPK (p38), and nuclear factor kappa B (NFκB) was downregulated. To conclude, we report that biorenovation-based phosphorylation of PRN improved its anti-inflammatory activity. Cell-based in vitro assays further confirmed that P4P could be applied in the development of anti-inflammatory therapeutics.
Prunetin inhibits lipopolysaccharide-induced inflammatory cytokine production and MUC5AC expression by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells
Biomed Pharmacother 2018 Oct;106:1469-1477.PMID:30119221DOI:10.1016/j.biopha.2018.07.093.
Allergic rhinitis (AR) is a chronic upper respiratory disorder characterized by inflammation of the nasal mucosa. Prunetin is an O-methylated isoflavone, which has been found to possess anti-inflammatory activity. The aim of the current study was to evaluate the effect of Prunetin on inflammatory cytokine and mucus production and its underlying mechanism in nasal epithelial cells. Results showed that treatment with Prunetin (10, 30, and 50 μM) inhibited lipopolysaccharide (LPS)-induced expression and secretion of interleukin (IL)-6, IL-8, and mucin 5 AC (MUC5 AC) in RPMI2650 cells, and attenuated the effect of LPS on toll-like receptor 4 (TLR4) and myeloid differentiation primary response 88 (MyD88) expression. TAK-242 (an inhibitor of TLR4) treatment or TLR4 knockdown attenuated LPS-induced expression and secretion of IL-6, IL-8 and MUC5 AC. In conclusion, Prunetin inhibited LPS-induced inflammatory cytokine production and MUC5 AC expression and secretion by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells. These results suggested that Prunetin might be a useful agent in the treatment of AR.