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Scutellarein

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-S3010

  • Specification : 98%

  • CAS number : 529-53-3

  • Formula : C15H10O6

  • Molecular Weight : 286.24

  • PUBCHEM ID : 5281697

  • Volume : 25mg

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Catalogue Number

BF-S3010

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

286.24

Appearance

Red crystalline powder

Botanical Source

Scutellaria baicalensis,Houttuynia cordata,Carthamus tinctorius,Erigeron breviscapus,Clerodendrum indicum

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O)O

Synonyms

4H-1-Benzopyran-4-one, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-/5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one/5,6,7,4'-tetrahydroxyflavone/5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one/4',5,6,7-Tetrahydroxyflavanone/6-Hydroxypelargidenon 1465/Scutellarein

IUPAC Name

5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Density

1.7±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

249.9±25.0 °C

Boiling Point

642.9±55.0 °C at 760 mmHg

Melting Point

330ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:529-53-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30551468

Abstract

OBJECTIVES:
Scutellarein is a flavonoid monomer found in traditional Chinese medicine such as Scutellaria barbata. This study aimed to investigate the cytotoxic effect of scutellarein treatment on multiple myeloma (MM) cells.

METHODS:
circulating B lymphocytes (CBL) isolated from healthy donors’ peripheral blood served as control for MM.1R and IM-9 MM cells. CLB and MM cells were treated with various concentrations of scutellarein before their cell viability and apoptosis being evaluated. Nude mice burdened with MM xenograft tumor were intravenously injected with different concentrations of scutellarein, and their tumor burden change were monitored. Apoptosis of MM cells or CBL after scutellarein treatment was assayed by measuring caspase-3, -8 and -9 activities. FADD or APAF1 gene knockdown in MM cells was achieved by lentiviral transfection. Amount of Cytochrome C in cytosol or mitochondria as well as that of Bax and Bcl-2 protein were evaluated by Western blot. Mitochondria-induced apoptosis was assayed by measuring mitochondrial membrane potential change. Production of general reactive oxygen species and mitochondrial superoxide in MM or CBL was detected after scutellarein treatment, which was reduced by MitoTEMPO or apocynin treatment, respectively.

RESULTS:
Scutellarein treatment showed potent cytotoxicity on MM cells but not on viable CBL, and intravenous injection of scutellarein significantly reduced MM xenograft tumor burden in nude mice. Scutellarein treatment in MM cells activated the mitochondrial-mediated intrinsic apoptosis pathway by increasing the production of mitochondrial superoxide, which was reduced to ROS by NADPH, but this effect was weakened in healthy CBL. Co-treatment with scutellarein synergized with bortezomib in inducing apoptosis in MM cells in vitro and in reducing tumor volume in MM xenografted nude mice.

CONCLUSIONS:
Scutellarein induced mitochondrial-mediated intrinsic apoptosis selectively on malignant cells comparing to healthy cells.

Copyright © 2018 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Mitochondria; Multiple myeloma; NADPH; ROS; Scutellarein; Superoxide

Title

Scutellarein selectively targets multiple myeloma cells by increasing mitochondrial superoxide production and activating intrinsic apoptosis pathway.

Author

Shi L1, Wu Y2, Lv DL2, Feng L2.

Publish date

2019 Jan

PMID

30563286

Abstract

To explore whether and how glucuronidation affects pyrogallol-type phytophenols, scutellarein and scutellarin (scutellarein-7-O-glucuronide) were comparatively investigated using a set of antioxidant analyses, including spectrophotometric analysis, UV-vis spectra analysis, and ultra-performance liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis. In spectrophotometric analyses of the scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+•), and 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radicals (PTIO•) and the reduction of Cu2+ ions, scutellarein showed lower IC50 values than scutellarin. However, in •O₂–scavenging spectrophotometric analysis, scutellarein showed higher IC50 value than scutellarin. The analysis of UV-Vis spectra obtained after the Fe2+-chelating reaction of scutellarin showed a typical UV-Vis peak (λmax = 611 nm), while scutellarein showed no typical peak. In UPLC-ESI-Q-TOF-MS/MS analysis, mixing of scutellarein with DPPH• yielded MS peaks (m/z 678, 632, 615, 450, 420, 381, 329, 300, 288, 227, 196, 182, 161, and 117) corresponding to the scutellarein-DPPH adduct and an MS peak (m/z 570) corresponding to the scutellarein-scutellarein dimer. Scutellarin, however, generated no MS peak. On the basis of these findings, it can be concluded that glucuronidation of pyrogallol-type phytophenol antioxidants has a dual effect. On the one hand, glucuronidation can decrease the antioxidant potentials (except for •O₂- scavenging) and further lower the possibility of radical adduct formation (RAF), while on the other hand, it can enhance the •O₂–scavenging and Fe2+-chelating potentials.

KEYWORDS

antioxidant; glucuronidation; pyrogallol-type phytophenol; scutellarein; scutellarin; structure-activity relationship

Title

Dual Effect of Glucuronidation of a Pyrogallol-Type Phytophenol Antioxidant: A Comparison between Scutellarein and Scutellarin.

Author

Liu Q1,2, Li X3,4, Ouyang X5,6, Chen D7,8.

Publish date

2018 Dec 6

PMID

25394920

Abstract

Fibrosarcoma is an aggressive and highly metastatic cancer of the connective tissue, for which effective therapeutic methods are limited. Recently, there has been a renewed interest in small molecular compounds from natural products in the treatment of cancer. In the present study, we investigated the compound, scutellarein, extracted from the perennial herb Scutellaria lateriflora, and it was found to possess anticancer potential. Cell proliferation assay and cell cycle analysis revealed that the proliferation rate of HT1080 human fibrosarcoma cells was significantly suppressed by treatment with scutellarein through the induction of apoptosis. Moreover, an in vivo experiment using Balb/c nude mice revealed that the volume and weight of the tumors were markedly reduced following treatment with scutellarein. We also analyzed the effects of scutellarein on the markers of metastasis, using the HT1080 cells. The results indicated that scutellarein potently inhibited cell migration, invasion and the expression and activity of matrix metalloproteinase (MMP)-2, -9 and -14. Furthermore, MMP activation and cell survival were suppressed due to the scutellarein-mediated downregulation of nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) activation. In conclusion, our data suggest that scutellarein has the ability to attenuate the development of fibrosarcoma and inhibit cancer cell metastasis.

Title

Scutellarein inhibits cancer cell metastasis in vitro and attenuates the development of fibrosarcoma in vivo.

Author

Shi X1, Chen G1, Liu X1, Qiu Y1, Yang S1, Zhang Y1, Fang X2, Zhang C1, Liu X1.

Publish date

2015 Jan


Description :

Scutellarin, a main active ingredient extracted from Erigeron breviscapus (Vant.) Hand-Mazz., has been wildly used to treat acute cerebral infarction and paralysis induced by cerebrovascular diseases.