6-[4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron

Bezeichnung:6-[4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron

CAS-Nr19202-36-9

Englisch Name:HINOKIFLAVONE

CBNumberCB1686946

SummenformelC30H18O10

Molgewicht538.46

MOL-Datei19202-36-9.mol

Synonyma

6-[4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron

6-[4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron physikalisch-chemischer Eigenschaften

Schmelzpunkt	353-355°C
Siedepunkt	841.5±65.0 °C(Predicted)
Dichte	1.622
storage temp.	2-8°C
Löslichkeit	Acetone: Soluble; Chloroform: Soluble; Dichloromethane: Soluble; DMSO: Soluble; Ethyl Acetate: Soluble
Aggregatzustand	A solid
pka	5.70±0.40(Predicted)
Farbe	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)

Sicherheit

WGK Germany	WGK 3
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

HINOKIFLAVONE Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Pale yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Selaginella tamariscina (P.Beauv.) Spring.
Verwenden
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.
Biologische Aktivität
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.

Einzelnachweise
[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

6-[4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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