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Hinokiflavone

$432

  • Brand : BIOFRON

  • Catalogue Number : BD-D1300

  • Specification : 98%(HPLC)

  • CAS number : 19202-36-9

  • Formula : C30H18O10

  • Molecular Weight : 538.46

  • PUBCHEM ID : 5281627

  • Volume : 20MG

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Catalogue Number

BD-D1300

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8℃

Molecular Weight

538.46

Appearance

Yellow crystalline powder

Botanical Source

Selaginella tamariscina(P. Beauv.)Spring/Obt. from leaves of Chamaecyparis obtusa. Also from Psilotum triquetrum. Present in the Cupressaceae, Cycadales and many other plants

Structure Type

Bisflavones

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)OC4=CC=C(C=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O

Synonyms

6-[4-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one/hynokiflavone/hinokiflavone/4H-1-Benzopyran-4-one, 6-(4-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-/4',6''-O-Biapigenin/6-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one/6-(4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone/4',6"-O-Biapigenin/4H-1-Benzopyran-4-one, 6-[4-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-

IUPAC Name

6-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Applications

Hinokiflavone is a novel modulator of pre-mRNA splicing activity in vitro and in cellulo. Hinokiflavone blocks splicing of pre-mRNA substrates by inhibiting spliceosome assembly, specifically preventing B complex formation. Hinokiflavone is a SUMO protease inhibitor, inhibiting sentrin-specific protease 1 (SENP1) activity[1].

Density

1.6±0.1 g/cm3

Solubility

DMF; DMSO

Flash Point

284.8±27.8 °C

Boiling Point

841.5±65.0 °C at 760 mmHg

Melting Point

353-355ºC

InChl

InChI=1S/C30H18O10/c31-16-5-1-14(2-6-16)24-12-21(35)28-26(40-24)13-22(36)30(29(28)37)38-18-7-3-15(4-8-18)23-11-20(34)27-19(33)9-17(32)10-25(27)39-23/h1-13,31-33,36-37H

InChl Key

WTDHMFBJQJSTMH-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:19202-36-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

2526343

Abstract

Hinokiflavone (1) was isolated as the cytotoxic principle from the drupes of Rhus succedanea L. A comparison of the cytotoxicity of 1 and other related biflavonoids, including amentoflavone (2), robustaflavone (3), agathisflavone (4), rhusflavone (5), rhusflavanone (6) and its hexaacetate (7), succedaneaflavanone (8) and its hexaacetate (9), cupressuflavone (10), neorhusflavanone (11), volkensiflavone (12) and its hexamethyl ether (13), spicataside (14) and its nonaacetate (15), morelloflavone (16) and its heptaacetate (17) and heptamethyl ether (18), GB-1a (19) and its hexamethyl ether (20) and 7″-O-beta-glucoside (21), and GB-2a (22), indicates that an ether linkage between two units of apigenin as seen in 1 is structurally required for significant cytotoxicity. Compounds 13 and 20 also demonstrated significant cytotoxicity.

Title

Hinokiflavone, a Cytotoxic Principle From Rhus Succedanea and the Cytotoxicity of the Related Biflavonoids

Author

Y M Lin, F C Chen, K H Lee

Publish date

1989 Apr

PMID

32107809

Abstract

Hinokiflavone is a natural product, isolated from Selaginella P. Beauv, Juniperus phoenicea and Rhus succedanea. Even though hinokiflavone was reported to possess cytotoxicity to many cancer cells, and has potential in cancer treatment, the anti-proliferation and anti-metastasis efficacy of hinokiflavone on human breast cancer cells has not a further research. In this study, we investigated the anti-cancer activity of hinokiflavone in human breast cancer cells in vitro and in vivo. Hinokiflavone exhibited a time- and dose-dependent manner apoptosis induction by upregulating expression of Bax and downregulating Bcl-2 in breast cancer cells. Furthermore, hinokiflavone significantly inhibited the migration and invasion of breast cancer cells by impairing the process of epithelial-to-mesenchymal transition. In addition, the tumour growth was distinctly inhibited by treatment of hinokiflavone in a xenograft tumour mouse model of MDA-MB-231 cells. Immunohistochemical analysis of tumour sections showed that MMP-2+ cells and Ki-67+ cells were remarkably decreased in tumour tissues of mice after treatment of hinokiflavone, indicating that hinokiflavone inhibits not only proliferation but also metastasis of breast cancer cells. Our study suggested that hinokiflavone can be a potential drug to breast cancer. SIGNIFICANCE OF THE STUDY: Hinokiflavone significantly inhibited proliferation and induced apoptosis in breast cancer cells. In addition, hinokiflavone remarkably inhibited migration and invasion of breast cancer cells via EMT signalling pathway. It is worth noting that hinokiflavone possesses anti-tumour effect in tumour mouse xenograft model of breast cancer. Overall, our results indicated that hinokiflavone may be a potential anticancer drug for breast cancer treatment.

Title

Hinokiflavone Induces Apoptosis and Inhibits Migration of Breast Cancer Cells via EMT Signalling Pathway

Author

Wenzhen Huang 1 , Chi Liu 2 , Fengen Liu 1 , Zhiyong Liu 1 , Guie Lai 1 , Jian Yi 1

Publish date

2020 Feb 27

PMID

29635122

Abstract

Melanoma, the highest degree of malignancy, is one of the most common skin tumors. However, there is no effective strategy to treat melanoma in current clinical practice. Therefore, it is urgent to find an efficient drug to overcome melanoma. Here, the in vitro anticancer effects of a natural product named hinokiflavone on three melanoma carcinoma cell lines (human melanoma A375 and CHL-1 cells, murine melanoma B16-F10 cells) and mechanisms of action were explored. The results of MTT assay revealed that hinokiflavone inhibited cell proliferation of these cell lines in a dose- and time-dependent manner. Interestingly, hinokiflavone showed low toxicity to normal liver cells. Flow cytometry assay and EdU incorporation assay indicated that hinokiflavone affected A375 and B16 cells survival by inducing apoptosis and blocking cell cycle progression at S phase in a concentration-dependent manner. Moreover, hinokiflavone enhanced the reactive oxygen species (ROS) and decreased the mitochondrial membrane potential obviously. Furthermore, hinokiflavone effectively impaired A375 cells migration and invasion, and down-regulated the expression of matrix metalloproteinase (MMP) MMP2 and MMP9. The above-mentioned results demonstrated that hinokiflavone could be a novel chemotherapeutic agent in melanoma treatment by inhibiting cell proliferation, inducing apoptosis and cell cycle arresting and blocking cell migration and invasion.

KEYWORDS

Apoptosis; Hinokiflavone; Invasion; Melanoma; Migration.

Title

Hinokiflavone Induces Apoptosis in Melanoma Cells Through the ROS-mitochondrial Apoptotic Pathway and Impairs Cell Migration and Invasion

Author

Shuping Yang 1 , Yange Zhang 2 , Yi Luo 1 , Bocheng Xu 1 , Yuqin Yao 3 , Yuanle Deng 3 , Fangfang Yang 1 , Tinghong Ye 1 , Gang Wang 4 , Zhiqiang Cheng 5 , Yu Zheng 6 , Yongmei Xie 7

Publish date

2018 Jul