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Isovitexin

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-I1010

  • Specification : 98%

  • CAS number : 38953-85-4

  • Formula : C21H20O10

  • Molecular Weight : 432.38

  • PUBCHEM ID : 162350

  • Volume : 20mg

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Catalogue Number

BF-I1010

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

432.38

Appearance

Light Yellow crystalline powder

Botanical Source

Swertia bimaculata

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O

Synonyms

Saponaretin/4H-1-Benzopyran-4-one, 6-β-D-glucopyranosyl-5,7- dihydroxy-2-(4-hydroxyphenyl)-/Isovitexin/6-b-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one/D-Glucitol, 1,5-anhydro-1-C-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-6-yl]-, (1S)-/5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-4H-chromen-4-one/5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-4H-chromen-4-one/(1S)-1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-D-glucitol/5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-4H-chromen-4-on/Homovitexin

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Density

1.7±0.1 g/cm3

Solubility

Methanol

Flash Point

287.1±27.8 °C

Boiling Point

807.0±65.0 °C at 760 mmHg

Melting Point

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#:38953-85-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31208440

Abstract

BACKGROUND:
Manganese superoxide dismutase (MnSOD) upregulating FoxM1 have previously been demonstrated promoting lung cancer stemness. Isovitexin exhibits antitumor activities in various cancers. This study aimed to assess whether isovitexin inhibits hepatic carcinoma stem-like cells (HCSLCs) features via regulating MnSOD and FoxM1 expression.

METHODS:
Second-generation spheres from the hepatic carcinoma cell lines, respectively, were used as HCSLCs. Protein amounts of MnSOD, FoxM1 and stemness-associated markers (CD133, CD44, ALDH1, Bmi1, Nanog and Oct4) were determined by immunoblotting. In vitro carcinogenicity was evaluated by sphere- and colony-formation assays. The effects of isovitexin on HCSLC carcinogenicity and stemness were examined in vitro and in xenograft models. An adenoviral delivery system was employed to manipulate MnSOD and/or FoxM1. Luciferase reporter assay was performed to verify isovitexin downregulated FoxM1 by inhibiting MnSOD-mediated effects of E2F1 and/or Sp1 on activation of FoxM1 promoter.

RESULTS:
FoxM1 upregulation by MnSOD contributed to carcinogenicity and stemness, with increased sphere- and colony-formation capabilities, upregulated stemness-associated markers and CD133+ subpopulation as well as elevated oncogenicity in vivo in HCSLCs compared with hepatic carcinoma cells. Isovitexin substantially decreased sphere and colony formation rates, and stemness-associated markers in cultured HCSLCs by suppressing MnSOD and FoxM1 expression. Importantly, isovitexin significantly inhibited tumor growth of in nude mice bearing HCSLCs and reduced CD133 protein expression of xenograft in nude mice. MnSOD or FoxM1 knockdown enhanced the effects of isovitexin suppression on carcinogenicity and stemness in HCSLC. MnSOD or FoxM1 overexpression attenuated the effects of isovitexin. Additionally, isovitexin and MnSOD knockdown could inhibit FoxM1 reporter activity via a decreased binding of E2F1 and/or Sp1 onto FoxM1 promoter. FoxM1 overexpression reversed the effects of isovitexin combined with MnSOD knockdown, without affecting MnSOD expression. Moreover, MnSOD knockdown plus thiostrepton, a FoxM1 specific inhibitor, cooperated with isovitexin to repress xenograft tumor growth and downregulate MnSOD and FoxM1 in nude mice bearing HCSLCs from MHCC97H cells.

CONCLUSIONS:
Isovitexin inhibits carcinogenicity and stemness in HCSLCs by downregulating FoxM1via inhibition of MnSOD.

KEYWORDS

Cancer stem cells; FoxM1; Hepatic carcinoma; Isovitexin; MnSOD

Title

Isovitexin reduces carcinogenicity and stemness in hepatic carcinoma stem-like cells by modulating MnSOD and FoxM1.

Author

Cao X1,2,3, Liu L4,5, Yuan Q6, Li X6, Cui Y1,2, Ren K7,8, Zou C5,9, Chen A1,2, Xu C1,2, Qiu Y1,2, Quan M1,2, Zhang J6, Cao J10,11, Chen X12.

Publish date

2019 Jun 17

PMID

31138294

Abstract

BACKGROUND:
Flavone C-glycosides are difficult to be deglycosylated using traditional chemical methods due to their solid carbon-carbon bond between sugar moieties and aglycones; however, some bacteria may easily cleave this bond because they generate various specific enzymes.

RESULTS:
A bacterial strain, named W12-1, capable of deglycosylating orientin, vitexin, and isovitexin to their aglycones, was isolated from human intestinal bacteria in this study and identified as Enterococcus faecalis based on morphological examination, physiological and biochemical identification, and 16S rDNA sequencing. The strain was shown to preferentially deglycosylate the flavone C-glycosides on condition that the culture medium was short of carbon nutrition sources such as glucose and starch, and its deglycosylation efficiency was negatively correlated with the content of the latter two substances.

CONCLUSION:
This study provided a new bacterial resource for the cleavage of C-glycosidic bond of flavone C-glycosides and reported the carbon nutrition sources reduction induced deglycosylation for the first time.

KEYWORDS

Deglycosylation; Enterococcus faecalis; Flavone C-glycosides; Reduced carbon nutrition source induction

Title

A newly isolated human intestinal bacterium strain capable of deglycosylating flavone C-glycosides and its functional properties.

Author

Zheng S1, Geng D1, Liu S1, Wang Q1, Liu S1, Wang R2.

Publish date

2019 May 28

PMID

30891865

Abstract

INTRODUCTION:
Plant medicine/herbal extracts are typically complex, encompassing a wide range of flavonoid diversity and biological benefits. Combined with a lack of standards; species authentication profiling is a challenge. A non-targeted screening strategy using two-dimensional (2D) separation and specificity of ultra-high-performance liquid chromatography ion mobility collision-induced dissociation mass spectrometry (UHPLC-IM-CID-MS) has been investigated, to identify the 6-C and 8-C-glycosylflavone isomer orientin/isoorientin and vitexin/isovitexin pairs in Passiflora species. Utilising available standards and “known-unknowns” a reference CCS (collision cross-section) speciation finger print for Passiflora extracts could be generated to illustrate species profiling.

MATERIAL AND METHODS:
SPE was performed to extract flavonoids of interest from powdered and ground Passiflora leaf. Chromatographic separation was achieved via UHPLC and analysis performed using positive/negative ion electrospray coupled with linear T-wave IM-MS (calibrated to perform accurate mass and CCS measurements).

RESULTS:
Comparative phytochemical screening of Passiflora alata, P. edulis, P. incarnata and P. caerulea leaf extracts has generated CCS, CID IM product ion spectra, 2D separation with UHPLC-IM-MS, enabling the unequivocal identification of flavone C-glycosides in complex extracts. A phytochemical reference CCS library was generated comprised of “knowns” and “known-unknowns”. Isomers have been differentiated using a CCS metric enabling novel CCS specific isomeric quantitation of co-eluting isomers.

CONCLUSIONS:
The screening approach illustrated has the potential to play an important role in the profiling of medicinal plants to determine phytochemical make-up and improve consumer safety through generation of highly specific speciation profiles.

© 2019 John Wiley & Sons, Ltd.

KEYWORDS

C-glycosylflavone isomers; CCS; authentication profiling; ion mobility mass spectrometry; known−unknowns

Title

Use of ion mobility mass spectrometry to enhance cumulative analytical specificity and separation to profile 6-C/8-C-glycosylflavone critical isomer pairs and known-unknowns in medicinal plants.

Author

McCullagh M1, Pereira CAM2, Yariwake JH3.

Publish date

2019 Jul;


Description :

Isovitexin is a flavonoid isolated from rice hulls of Oryza sativa, possesses anti-inflammatory and anti-oxidant activities; Isovitexin acts like a JNK1/2 inhibitor and inhibits the activation of NF-κB.