Sakuranetin
(Synonyms: 樱花素) 目录号 : GC34773
A flavonoid with diverse biological activities
Cas No.:2957-21-3
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
Sakuranetin is a flavonoid and phytoalexin that has been found in rice and has diverse biological activities.1,2,3,4 It reduces blast fungus mycelium growth in vitro and decreases the number of fungal lesions and fungal DNA in blast fungus-infected rice leaves when applied at concentrations of 0.1 and 0.2 mM.1 Sakuranetin is active against M. luteus and B. subtilis (MICs = 2 and 0.5 ?g/ml, respectively).2 It is cytotoxic to KB nasopharyngal carcinoma cells (EC50 = 10 ?g/ml). Sakuranetin (20 mg/kg) reduces alveolar enlargement, collagen and elastic fiber deposition, and bronchoalveolar lavage fluid (BALF) levels of TNF-α, IL-1β, and M-CSF in a mouse model of elastase-induced emphysema.3 It also reduces collagen fiber deposition and lung inflammation in a mouse model of LPS-induced acute lung injury.4
1.Hasegawa, M., Mitsuhara, I., Seo, S., et al.Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungusMolecules19(8)11404-11418(2014) 2.Orjala, J., Wright, A.D., Behrends, H., et al.Cytotoxic and antibacterial dihydrochalcones from Piper aduncumJ. Nat. Prod.57(1)18-26(1994) 3.Taguchi, L., Pinheiro, N.M., Olivo, C.R., et al.A flavanone from Baccharis retusa (Asteraceae) prevents elastase-induced emphysema in mice by regulating NF-κB, oxidative stress and metalloproteinasesRespir. Res.16(79)1-15(2015) 4.Bittencourt-Mernak, M.I., Pinheiro, N.M., Santana, F.P., et al.Prophylactic and therapeutic treatment with the flavonone sakuranetin ameliorates LPS-induced acute lung injuryAm. J. Physiol. Lung Cell Mol. Physiol.312(2)L217-L230(2017)
| Cas No. | 2957-21-3 | SDF | |
| 别名 | 樱花素 | ||
| Canonical SMILES | O=C1C2=C(O)C=C(OC)C=C2O[C@H](C3=CC=C(O)C=C3)C1 | ||
| 分子式 | C16H14O5 | 分子量 | 286.28 |
| 溶解度 | DMSO : ≥ 125 mg/mL (436.64 mM) | 储存条件 | Store at 2-8°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 | 3.4931 mL | 17.4654 mL | 34.9308 mL |
| 5 mM | 0.6986 mL | 3.4931 mL | 6.9862 mL |
| 10 mM | 0.3493 mL | 1.7465 mL | 3.4931 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。
A Review on Sources and Pharmacological Aspects of Sakuranetin
Nutrients 2020 Feb 18;12(2):513.PMID:32085443DOI:10.3390/nu12020513.
Sakuranetin belongs to the group of methoxylated flavanones. It is widely distributed in Polyomnia fruticosa and rice, where it acts as a phytoalexin. Other natural sources of this compound are, among others, grass trees, shrubs, flowering plants, cheery, and some herbal drugs, where it has been found in the form of glycosides (mainly sakuranin). Sakuranetin has antiproliferative activity against human cell lines typical for B16BL6 melanoma, esophageal squamous cell carcinoma (ESCC) and colon cancer (Colo 320). Moreover, Sakuranetin shows antiviral activity towards human rhinovirus 3 and influenza B virus and was reported to have antioxidant, antimicrobial, antiinflammatory, antiparasitic, antimutagenic, and antiallergic properties. The aim of this review is to present the current status of knowledge of pro-health properties of Sakuranetin.
Sakuranetin exerts anticonvulsant effect in bicuculline-induced seizures
Fundam Clin Pharmacol 2022 Aug;36(4):663-673.PMID:35156229DOI:10.1111/fcp.12768.
Epilepsy is a chronic neurological disorder characterized by an abnormal, spontaneous, and synchronized neuronal hyperactivity. Therapeutic approaches for controlling epileptic seizures are associated with pharmacoresistance and side effects burden. Previous studies reported that different natural products may have neuroprotector effects. Sakuranetin (SAK) is a flavanone with antiparasitic, anti-inflammatory, antimutagenic, antiallergic, and antioxidant activity. In the present work, the effect of SAK on seizures in a model of status epilepticus induced by bicuculline (BIC) in mice was evaluated. Male Swiss mice received an intracerebroventricular injection (i.c.v.) of SAK (1, 10, or 20 mg/kg-SAK1, SAK10, or SAK20). Firstly, animals were evaluated in the open field (OF; 20 min), afterwards in the elevated plus maze (EPM) test (5 min). Next, 30 min prior the administration of BIC (1 mg/kg), mice received an injection of SAK (1 or 10 mg/kg, i.c.v.) and were observed in the OF (20 min) for seizures assessment. After behavioral procedures, immunohistochemical analysis of c-Fos was performed. Our main results showed that the lowest doses of SAK (1 and 10 mg/kg) increased the total distance traveled in the OF, moreover protected against seizures and death on the BIC-induced seizures model. Furthermore, SAK treatment reduced neuronal activity on the dentate gyrus of the BIC-treated animals. Taken together, our results suggest an anticonvulsant effect of SAK, which could be used for the development of anticonvulsants based on natural products from herbal source.
Sakuranetin and its therapeutic potentials - a comprehensive review
Z Naturforsch C J Biosci 2022 Jul 13;78(1-2):27-48.PMID:35844107DOI:10.1515/znc-2022-0024.
Sakuranetin (SKN), a naturally derived 7-O-methylated flavonoid, was first identified in the bark of the cherry tree (Prunus spp.) as an aglycone of sakuranin and then purified from the bark of Prunus puddum. It was later reported in many other plants including Artemisia campestris, Boesenbergia pandurata, Baccharis spp., Betula spp., Juglans spp., and Rhus spp. In plants, it functions as a phytoalexin synthesized from its precursor naringenin and is the only known phenolic phytoalexin in rice, which is released in response to different abiotic and biotic stresses such as UV-irradiation, jasmonic acid, cupric chloride, L-methionine, and the phytotoxin coronatine. Till date, SKN has been widely reported for its diverse pharmacological benefits including antioxidant, anti-inflammatory, antimycobacterial, antiviral, antifungal, antileishmanial, antitrypanosomal, glucose uptake stimulation, neuroprotective, antimelanogenic, and antitumor properties. Its pharmacokinetics and toxicological properties have been poorly understood, thus warranting further evaluation together with exploring other pharmacological properties such as antidiabetic, neuroprotective, and antinociceptive effects. Besides, in vivo studies or clinical investigations can be done for proving its effects as antioxidant and anti-inflammatory, antimelanogenic, and antitumor agent. This review summarizes all the reported investigations with SKN for its health-beneficial roles and can be used as a guideline for future studies.
Sakuranetin interacting with cell membranes models: Surface chemistry combined with molecular simulation
Colloids Surf B Biointerfaces 2022 Aug;216:112546.PMID:35588685DOI:10.1016/j.colsurfb.2022.112546.
Sakuranetin, a natural compound with activity in lipidic biointerfaces, was isolated from Baccharis retusa and studied with two models of lipid membranes: Langmuir monolayers and Molecular Simulation. For that, the mammalian lipid DPPC was chosen. Sakuranetin condensed the monolayers at high surface pressures, decreased the surface compressional modulus, reduced the molecular order of the acyl chains (diminution of all-trans/gauche conformers ratio), and increased the heterogeneity of the interface, forming aggregates. Molecular simulation data gave information on the bioactive compound's most favorable thermodynamic positions along the lipid monolayer, which was the lipid-air interface. These combined results lead to the conclusion that this lipophilic compound may interact with the lipidic layers, preferentially at the lipid-air interface, to minimize the free energy, and reaches this conformation disturbing the thermodynamic, structural, mechanical, rheological, and morphological properties of the well-packed DPPC monolayer.
Sakuranetin downregulates inducible nitric oxide synthase expression by affecting interleukin-1 receptor and CCAAT/enhancer-binding protein β
J Nat Med 2019 Mar;73(2):353-368.PMID:30467676DOI:10.1007/s11418-018-1267-x.
Pruni Cortex is a herbal drug from the bark of the Japanese flowering cherries, Prunus jamasakura or Prunus verecunda, and is included in the traditional Japanese herbal (Kampo) formula Jumihaidokuto, which is administered orally to patients suffering from inflammatory skin diseases. The flavanones contained in Pruni Cortex (e.g., Sakuranetin and naringenin) have potent anti-inflammatory, anti-allergic, and anti-microbial activities. Although the effects of Pruni Cortex on skin disease have been well studied, reports regarding its pharmacological effects on the liver are limited. In this study, we extracted the bark of Prunus jamasakura and purified it to isolate the pharmacologically active constituents by monitoring nitric oxide (NO) production in rat hepatocytes that were treated with the pro-inflammatory cytokine, interleukin (IL)-1β. Sakuranetin and (-)-naringenin, which were present in an ethyl acetate-soluble fraction of the bark extract, significantly inhibited NO induction and inducible nitric oxide synthase (iNOS) expression. These two flavanones decreased the expression of type 1 IL-1 receptor gene and phosphorylation of Akt, also known as protein kinase B, which is regulated by phosphatidylinositol-4,5-bisphosphate 3-kinase (PI3K). Furthermore, Sakuranetin decreased the phosphorylation of the activator isoforms of CCAAT/enhancer-binding protein β (C/EBPβ), which synergistically activates the transcription of the iNOS gene with nuclear factor κB (NF-κB). Therefore, Sakuranetin inhibited the co-activating activity of C/EBPβ with NF-κB, leading to the suppression of iNOS gene expression in hepatocytes. Taken together, Sakuranetin in Pruni Cortex downregulated the iNOS gene by inhibiting PI3K/Akt signal transduction and the phosphorylation of C/EBPβ. These results imply that Sakuranetin may be primarily responsible for the anti-inflammatory effects of Pruni Cortex in the liver.