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    Natural Products
    Isosakuranetin
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    CAS No. 480-43-3 Price $218 / 20mg
    Catalog No.CFN98743Purity>=98%
    Molecular Weight286.3 Type of CompoundFlavonoids
    FormulaC16H14O5Physical DescriptionPowder
    Download Manual    COA    MSDS    SDFSimilar structuralComparison (Web)  (SDF)
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    Isosakuranetin

    Isosakuranetin
    Product Name Isosakuranetin
    CAS No.: 480-43-3
    Catalog No.: CFN98743
    Molecular Formula: C16H14O5
    Molecular Weight: 286.3 g/mol
    Purity: >=98%
    Type of Compound: Flavonoids
    Physical Desc.: Powder
    Targets: ERK | PI3K | Akt | JNK | PKA | GSK-3 | Calcium Channel | Potassium Channel | Tyrosinase | TRPM3 | TRP1 | TRP2
    Source: The fruits of Citrus aurantium L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $218 / 20mg
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  • Preprints2017, 2017120176
  • Nat Chem Biol.2018, 14(8):760-763
  • Eur J Pharmacol.2021, 899:174010.
  • J Sci Food Agric.2017, 97(5):1656-1662
  • Mol Microbiol.2019, 112(1):317-332
  • Neurotox Res.2020, 38(1):163-174.
  • J Pharmacol Sci.2021, 147(2):184-191.
  • Asian Pac J Cancer Prev.2019, 20(1):65-72
  • Food Analytical Methods2020, 13,1603-1612(2020)
  • Molecules.2020, 25(18):4283.
  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
    Related Libraries
  • Antifungal Compound Library
  • Toxicity Compound Library
  • Phytoalexin Compound Library
  • Anti-melanogenic Compound Library
  • Flavonoids Compound Library
  • Tyrosinase Inhibitor Library
  • Potassium Channel Inhibitor Library
  • PKA Inhibitor Library
  • PI3K Inhibitor Library
  • JNK Inhibitor Library
  • GSK-3 Inhibitor Library
  • ERK Inhibitor Library
  • Calcium Channel Inhibitor Library
  • Akt Inhibitor Library
  • Biological Activity
    Description: Isosakuranetin is a plant exudate with known cytotoxic and fungicide properties, it may act on wheat root segments as an inhibitor of K+ permeation. Isosakuranetin is a TRPM3 blocker, significantly reduces the sensitivity of mice to noxious heat and PregS-induced chemical pain; it induced- inhibition of ERK1/2 and PI3K/AKT signaling pathways activate MITF and subsequent expression of Tyr, TRP1, and TRP2.
    Targets: ERK | PI3K | Akt | JNK | PKA | GSK-3 | Calcium Channel | Potassium Channel | Tyrosinase | TRPM3 | TRP1 | TRP2
    In vitro:
    Phytochemistry, 1997, 46(2):245-8.
    The effect of isosakuranetin (5,7-dihydroxy 4′-methoxy flavanone) on potassium uptake in wheat root segments.[Reference: WebLink]
    Isosakuranetin (ISK; 5,7-dihydroxy 4′-methoxy flavanone) is a plant exudate with known cytotoxic and fungicide properties.
    METHODS AND RESULTS:
    When tested on wheat root segments at a concentration of 70μM it inhibited K+ dependent H+ extrusion and net uptake of K+, while leaving the membrane potential (PD) unaltered. Fusicoccin (FC) + ISK treatment resulted in a slight membrane depolarization, while ISK alone did not alter O2 consumption or alternative oxidase activity. ISK did not increase the pyruvate content in incubated root tissues or inhibit Fe2+ uptake. The observed drop in K+ net uptake depended on a decrease in K+ influx into the cell, leading to the suggestion that ISK may act on wheat root segments as an inhibitor of K+ permeation.
    CONCLUSIONS:
    The lack of proton leakage and membrane disruption by ISK made this compound a weak candidate as a phytoalexin, and suggesting a major role as an allelopathic molecule.
    In vivo:
    Mol Pharmacol. 2013 Nov;84(5):736-50.
    Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo.[Pubmed: 24006495]
    Transient receptor potential melastatin 3 (TRPM3) is a calcium-permeable nonselective cation channel that is expressed in a subset of dorsal root (DRG) and trigeminal ganglia sensory neurons. TRPM3 can be activated by the neurosteroid pregnenolone sulfate (PregS) and heat. TRPM3⁻/⁻ mice display an impaired sensation of noxious heat and thermal hyperalgesia. We have previously shown that TRPM3 is blocked by the citrus fruit flavanones hesperetin, naringenin, and eriodictyol as well as by ononetin, a deoxybenzoin from Ononis spinosa.
    METHODS AND RESULTS:
    To further improve the tolerability, potency, and selectivity of TRPM3 blockers, we conducted a hit optimization procedure by rescreening a focused library that was composed of chemically related compounds. Within newly identified TRPM3 blockers, Isosakuranetin and liquiritigenin displayed favorable properties with respect to their inhibitory potency and a selective mode of action. Isosakuranetin, a flavanone whose glycoside is contained in blood oranges and grapefruits, displayed an IC₅₀ of 50 nM and is to our knowledge the most potent inhibitor of TRPM3 identified so far. Both compounds exhibited a marked specificity for TRPM3 compared with other sensory TRP channels, and blocked PregS-induced intracellular free Ca2⁺ concentration signals and ionic currents in freshly isolated DRG neurons. Furthermore, Isosakuranetin and previously identified hesperetin significantly reduced the sensitivity of mice to noxious heat and PregS-induced chemical pain.
    CONCLUSIONS:
    Because the physiologic functions of TRPM3 channels are still poorly defined, the development and validation of potent and selective blockers is expected to contribute to clarifying the role of TRPM3 in vivo.
    Pharmacology . 2017;100(3-4):201-207.
    Antinociceptive Effects of Isosakuranetin in a Rat Model of Peripheral Neuropathy[Pubmed: 28715803]
    Abstract Chronic pain remains a challenging clinical reality, yet currently available analgesics are insufficient to meet clinical needs. Increasing attention has been paid to bioactive compounds from natural plants, which may be efficacious against pain. This study examined the antinociceptive effects of Isosakuranetin, a plant-derived transient receptor potential melastatin 3 blocker, in a rat model of peripheral neuropathy. Adult male Sprague-Dawley rats were first allowed to go through the chronic constriction injury surgery to develop neuropathic pain. They were then treated with Isosakuranetin (1.5, 3, or 6 mg/kg) intraperitoneally and the effects on mechanical, thermal, and cold hyperalgesia were assessed using the von Frey filament test, Hargreaves' plantar test, and cold plate test, respectively. Isosakuranetin dose-dependently alleviated mechanical, thermal, and cold hyperalgesia and the antinociceptive potency was similar across the assays. In the rotarod test, Isosakuranetin did not significantly affect motor performance within the doses tested, confirming the antinociceptive specificity. In summary, these findings suggest that Isosakuranetin may be useful in treating neuropathic pain and deserves further investigation. Keywords: Chronic constriction injury; Hyperalgesia; Isosakuranetin; Neuropathic pain; Rats; Rotarod test.
    Isosakuranetin Description
    Source: The fruits of Citrus aurantium L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.4928 mL 17.4642 mL 34.9284 mL 69.8568 mL 87.321 mL
    5 mM 0.6986 mL 3.4928 mL 6.9857 mL 13.9714 mL 17.4642 mL
    10 mM 0.3493 mL 1.7464 mL 3.4928 mL 6.9857 mL 8.7321 mL
    50 mM 0.0699 mL 0.3493 mL 0.6986 mL 1.3971 mL 1.7464 mL
    100 mM 0.0349 mL 0.1746 mL 0.3493 mL 0.6986 mL 0.8732 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Cell Research:
    Life Sci. 2015 Dec 15;143:43-9.
    Isosakuranetin, a 4'-O-methylated flavonoid, stimulates melanogenesis in B16BL6 murine melanoma cells.[Pubmed: 26524968 ]
    The beneficial effects of 4'-O-methylated flavonoids on induction of melanogenesis are well established. Here, we report the effect of Isosakuranetin (Iso) on melanogenesis in B16BL6 melanoma cells and an analysis of the signaling pathways involved in this activity.
    METHODS AND RESULTS:
    B16BL6 melanoma cells were treated with several concentrations of Iso and melanin content was measured. Activation and expression of factors involved in melanogenesis were assessed via western blotting. Iso (15 and 30μmol/L) strongly stimulated melanogenesis in a dose-dependent manner. Iso increased tyrosinase activity and up-regulated tyrosinase (Tyr), tyrosinase related protein 1 (TRP1), and tyrosinase related protein 2 (TRP2) in a time-dependent manner. Iso decreased B16 cell proliferation at a concentration above 45μmol/L, and had no effect on cell viability as revealed by MTT and trypan blue assays. Iso up-regulated expression of microphthalmia transcription factor (MITF), with a maximum effect after 12h. H89, a specific inhibitor of PKA, showed that MITF up-regulation is mediated through PKA/CREB activation. Furthermore, Iso decreased phosphorylation of MITF at Ser73 after 24h and 48h of exposure, activating MITF and leading to up-regulation of Tyr, TRP1, and TRP2. Iso inhibited phosphorylation and activation of ERK1/2 after 12h, while no significant effects on p38 and JNK phosphorylation were observed. Iso inhibited AKT phosphorylation and led to activation of GSK3β.
    CONCLUSIONS:
    Iso stimulates melanogenesis in B16 melanoma cells via up-regulation of MITF. Furthermore, Iso-induced inhibition of ERK1/2 and PI3K/AKT signaling pathways activate MITF and subsequent expression of Tyr, TRP1, and TRP2.
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