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Isomangiferin

$383

  • Brand : BIOFRON

  • Catalogue Number : BD-P0173

  • Specification : 98.0%(HPLC)

  • CAS number : 24699-16-9

  • PUBCHEM ID : 5318597

  • Volume : 25mg

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Catalogue Number

BD-P0173

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

Powder

Botanical Source

Anemarrhena asphodeloides Bge.

Structure Type

Xanthones

Category

Standards;Natural Pytochemical;API

SMILES

C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O

Synonyms

1,3,6,7-tetrahydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one/D-Glucitol, 1,5-anhydro-1-C-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-4-yl)-, (1S)-/Isomangiferin/isomagniferin/(1S)-1,5-Anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-4-yl)-D-glucitol/9H-Xanthen-9-one, 4-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-

IUPAC Name

1,3,6,7-tetrahydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one

Applications

Isomangiferin, a natural product, is reported to have antiviral activity.

Density

1.8±0.1 g/cm3

Solubility

Methanol

Flash Point

288.2±26.4 °C

Boiling Point

798.8±60.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C19H18O11/c20-4-11-15(26)16(27)17(28)19(30-11)13-9(24)2-8(23)12-14(25)5-1-6(21)7(22)3-10(5)29-18(12)13/h1-3,11,15-17,19-24,26-28H,4H2/t11-,15-,16+,17-,19+/m1/s1

InChl Key

CDYBOKJASDEORM-HBVDJMOISA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:24699-16-9) 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

29628979

Abstract

Purpose: Vascular endothelial growth factor (VEGF) signal transduction mainly depends on its binding to VEGF receptor 2 (VEGFR-2). VEGF downstream signaling proteins mediate several of its effects in cancer progression, including those on tumor growth, metastasis, and blood vessel formation. The activation of VEGFR-2 signaling is a hallmark of and is considered a therapeutic target for breast cancer. Here, we report a study of the regulation of the VEGFR-2 signaling pathway by a small molecule, isomangiferin.
Methods: A human breast cancer xenograft mouse model was used to investigate the efficacy of isomangiferin in vivo. The inhibitory effect of isomangiferin on breast cancer cells and the underlying mechanism were examined in vitro.
Results: Isomangiferin suppressed tumor growth in xenografts. In vitro, isomangiferin treatment inhibited cancer cell proliferation, migration, invasion, and adhesion. The effect of isomangiferin on breast cancer growth was well coordinated with its suppression of angiogenesis. A rat aortic ring assay revealed that isomangiferin significantly inhibited blood vessel formation during VEGF-induced microvessel sprouting. Furthermore, isomangiferin treatment inhibited VEGF-induced proliferation of human umbilical vein endothelial cells and the formation of capillary-like structures. Mechanistically, isomangiferin induced caspase-dependent apoptosis of breast cancer cells. Furthermore, VEGF-induced activation of the VEGFR-2 kinase pathway was down-regulated by isomangiferin.
Conclusion: Our findings demonstrate that isomangiferin exerts anti-breast cancer effects via the functional inhibition of VEGFR-2. Pharmaceutically targeting VEGFR-2 by isomangiferin could be an effective therapeutic strategy for breast cancer.

KEYWORDS

Angiogenesis inhibitors; Apoptosis; Breast neoplasms; Isomangiferin; Vascular endothelial growth factor receptor-2.

Title

Isomangiferin, a Novel Potent Vascular Endothelial Growth Factor Receptor 2 Kinase Inhibitor, Suppresses Breast Cancer Growth, Metastasis and Angiogenesis

Author

Banghua Wang 1 , Jia Shen 2 3 , Zexia Wang 1 , Jianxia Liu 4 , Zhifeng Ning 1 , Meichun Hu 1

Publish date

2018 Mar

PMID

24566268

Abstract

The benzophenone, iriflophenone-3-C-glucoside, was isolated from Cyclopia genistoides using a combination of fluid-fluid extraction, high performance counter-current chromatography (HPCCC) and semi-preparative high performance liquid chromatography (HPLC). The microplate oxygen radical absorbance capacity (ORAC) assay, with fluorescein as probe, was adapted for use in an on-line HPLC configuration. The method was validated using a mixture of authentic standards including iriflophenone-3-C-glucoside, and the xanthones, mangiferin and isomangiferin. Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) was included in the mixture for calculation of Trolox equivalent antioxidant capacity (TEAC) values. Using the on-line HPLC-ORAC assay, as well as 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(+)) on-line assays, the antioxidant activity of iriflophenone-3-C-glucoside and isomangiferin was demonstrated for the first time. Iriflophenone-3-C-glucoside presented no radical scavenging ability against DPPH, but scavenged ABTS(+) and peroxyl radicals (TEACABTS of 1.04 and TEACORAC of 3.61). Isomangiferin showed slightly lower antioxidant capacity than mangiferin against DPPH (TEACDPPH of 0.57 vs. 0.62), but higher capacity against ABTS(+) (TEACABTS of 1.82 vs. 1.67) and peroxyl radical (TEACORAC of 4.14 vs. 3.69) than mangiferin. The on-line HPLC-ORAC assay was shown to be more sensitive for radical scavengers, but at the same time less selective for rapid radical scavengers than the DPPH assay.

KEYWORDS

Angiogenesis inhibitors; Apoptosis; Breast neoplasms; Isomangiferin; Vascular endothelial growth factor receptor-2.

Title

Iriflophenone-3-C-glucoside From Cyclopia Genistoides: Isolation and Quantitative Comparison of Antioxidant Capacity With Mangiferin and Isomangiferin Using On-Line HPLC Antioxidant Assays

Author

Christiaan J Malherbe 1 , Elize Willenburg 2 , Dalene de Beer 2 , Susan L Bonnet 3 , Jan H van der Westhuizen 4 , Elizabeth Joubert 5

Publish date

2014 Mar 1

PMID

27257129

Abstract

A sensitive and specific liquid chromatography with tandem mass spectrometry method was firstly developed for the measurement of isomangiferin in rat plasma. Chloramphenicol was selected as the internal standard. Sample preparation was carried out through a simple one-step protein precipitation procedure with methanol. Negative electrospray ionization was performed using multiple reaction monitoring mode with transitions of m/z 421.1/301.1 for isomangiferin, and 321.1/151.9 for chloramphenicol. The calibration curve was linear over the range of 0.1-600 ng/mL, with a lower limit of quantification at 0.1 ng/mL. The intra- and interday precisions (relative standard deviation) were no more than 8.2% and accuracies (relative error) were within the range of -8.4 to 2.2%. The recovery, matrix effect and stability under different conditions were all proved acceptable. The validated method has been successfully applied to a preclinical pharmacokinetic study of isomangiferin in rats for the first time.

KEYWORDS

somangiferin; Liquid chromatography with tandem mass spectrometry; Pharmacokinetics; Rat plasma.

Title

Development and Validation of a Liquid Chromatography With Tandem Mass Spectrometry Method for the Determination of Isomangiferin in Rat Plasma With Application to a Preclinical Pharmacokinetic Study

Author

Fengjun Sun 1 , Zhirui Liu 1 , Bo Yang 1 , Peiyuan Xia 1

Publish date

2016 Aug