Introduction：Basic information about HINOKIFLAVONE CAS 19202-36-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
HINOKIFLAVONE Basic information
| Product Name: | HINOKIFLAVONE |
| Synonyms: | HINOKIFLAVONE;2-(4-Hydroxyphenyl)-5,7-dihydroxy-6-[4-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-4H-1-benzopyran-4-one;4''',5,5'',7,7''-Pentahydroxy(4',6''-oxybisflavone);4',5,7-Trihydroxy-6-[4-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]flavone;6-[4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;4',5,5'',7,7''-Pentahydroxy-4''' 6-oxydiflavone;4',6''-BIAPIGENIN;4',6''-O-BIAPIGENIN |
| CAS: | 19202-36-9 |
| MF: | C30H18O10 |
| MW: | 538.46 |
| EINECS: | 242-877-4 |
| Product Categories: | Flavones |
| Mol File: | 19202-36-9.mol |
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HINOKIFLAVONE Chemical Properties
| Melting point | 353-355°C |
| Boiling point | 841.5±65.0 °C(Predicted) |
| density | 1.622 |
| storage temp. | 2-8°C |
| solubility | Acetone: Soluble; Chloroform: Soluble; Dichloromethane: Soluble; DMSO: Soluble; Ethyl Acetate: Soluble |
| form | A solid |
| pka | 5.70±0.40(Predicted) |
| color | Light yellow to yellow |
| InChIKey | WTDHMFBJQJSTMH-UHFFFAOYSA-N |
| SMILES | C1(C2=CC=C(O)C=C2)OC2=CC(O)=C(OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C=4)C=C3)C(O)=C2C(=O)C=1 |
| LogP | 5.528 (est) |
Safety Information
| WGK Germany | WGK 3 |
| Storage Class | 11 - Combustible Solids |
HINOKIFLAVONE Usage And Synthesis
| Chemical Properties | Pale yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Selaginella tamariscina (P.Beauv.) Spring. |
| Uses | Hinokiflavone is a novel modulator of pre-mRNA splicing activity extracted from plants with anti-inflammatory, anti-tumor and antiviral activities. Hinokiflavone is also a potent inhibitor for matrix metalloproteinases (MMPs). Hinokiflavone attenuates the virulence of Methicillin (HY-121544)-resistant staphylococcus aureus by inhibiting caseinolytic protease P (ClpP) with an IC50 value of 34.36 mg/mL. Hinokiflavone induces apoptosis via the reactive oxygen species-mitochondria-mediated apoptotic pathway and inhibits tumor cell migration and invasion. Hinokiflavone is a SUMO protease inhibitor against sentrin-specific protease 1 (SENP1) activity[1][2][3]. |
| Definition | ChEBI: A biflavonoid that is apigenin substituted by a 4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy group at position 6. A diflavonyl ether, it is isolated from Rhus succedanea and has been found to possess significant cytotoxic otential. |
| Biological Activity | Hinokiflavone is a plant biflavone th at exhibit potent anticancer, hepatoprotective, antibacterial, antiviral, and anti-inflammatory activities. Hinokiflavone induces apoptosis and cell cycle arrest, and blocks migration and invasion of melanoma cells. It is a potent inhibitor of dengue 2 virus RNA-dependent RNA polymerase (DV-NS5 RdRp). Hinokiflavone is a modulator of pre-mRNA splicing in cells. It increases SUMOylation of a subset of spliceosome proteins by inhibiting SENP1 protease activity. It induces apoptosis in esophageal squamous cell carcinoma (ESCC) through regulation of PI3K/AKT/mTOR pathway. |
| in vivo | Hinokiflavone (25 or 50 mg/kg, i.p., daily for 24 days) has antitumor activity via suppressing tumor proliferation, metastasis and inducing Apoptosis in CT26 tumor-bearing mice[2].
Hinokiflavone (100 mg/kg, s.c., every 12 h for 96 h) shows a protective effect on pneumonia infection by Improving survival rate in mice[3].
| Animal Model: | CT26 tumor-bearing mice model[2] | | Dosage: | 25 or 50 mg/kg | | Administration: | i.p., daily for 24 days | | Result: | Resulted in retarded tumor progression and reduction of tumor weight without affecting body weight of mice, suppressed tumor proliferation and invasion ability by staining nuclear Ki-67 and MMP9, induced the apoptosis by staining cleaved caspase-3. |
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| References | [1] Pawellek A, et al. Characterisation of the biflavonoid hinokiflavone as a pre-mRNA splicing modulator that inhibits SENP. Elife. 2017 Sep 8;6. pii: e27402. DOI:10.7554/eLife.27402
[2] Zhou J, et al. Antitumor activity in colorectal cancer induced by hinokiflavone. J Gastroenterol Hepatol. 2019 Sep;34(9):1571-1580. DOI:10.1111/jgh.14581
[3] Kong X, et al. Hinokiflavone Attenuates the Virulence of Methicillin-Resistant Staphylococcus aureus by Targeting Caseinolytic Protease P. Antimicrob Agents Chemother. 2022 Aug 16;66(8):e0024022. DOI:10.1128/aac.00240-22 |
HINOKIFLAVONE Preparation Products And Raw materials
