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HINOKIFLAVONE

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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)
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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.

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

HINOKIFLAVONESupplier

Huzhou ZhanShu Biotechnology Co.,Ltd Gold
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0572-8889530 18167260939
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zsubio@163.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
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4006356688 18621169109
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market03@meryer.com
Capot Chemical Co., Ltd
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+86 (0) 571 85 58 67 18
BioBioPha Co., Ltd.
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0871-65217109 13211707573;
Email
y.liu@mail.biobiopha.com
ShangHai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847 13636370518
Email
shyysw007@163.com
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