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Norathyriol

$980

  • Brand : BIOFRON

  • Catalogue Number : AV-C10492

  • Specification : 98%

  • CAS number : 3542-72-1

  • Formula : C13H8O6

  • Molecular Weight : 260.2

  • PUBCHEM ID : 5281656

  • Volume : 5mg

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Catalogue Number

AV-C10492

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

260.2

Appearance

Yellow powder

Botanical Source

Structure Type

Xanthones

Category

Standards;Natural Pytochemical;API

SMILES

C1=C(C=C2C(=C1O)C(=O)C3=CC(=C(C=C3O2)O)O)O

Synonyms

Norathyriol/magniferitin/1,3,6,7-Tetrahydroxyxanthen-9-one/1,3,6,7-Tetrahydroxyxantone/1,3,6,7-tetrahydroxyxanthone/2,4,6,7-Tetrahydroxyxanthone/1,3,6,7-Tetrahydroxy-9H-xanthen-9-one/9H-Xanthen-9-one, 1,3,6,7-tetrahydroxy-

IUPAC Name

1,3,6,7-tetrahydroxyxanthen-9-one

Applications

Density

1.8±0.1 g/cm3

Solubility

Flash Point

237.8±23.6 °C

Boiling Point

595.1±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C13H8O6/c14-5-1-9(17)12-11(2-5)19-10-4-8(16)7(15)3-6(10)13(12)18/h1-4,14-17H

InChl Key

ZHTQCPCDXKMMLU-UHFFFAOYSA-N

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#:3542-72-1) 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

24985145

Abstract

AIM/HYPOTHESIS:
Protein tyrosine phosphatase 1B (PTP1B) negatively regulates insulin signalling. PTP1B deficiency improves obesity-induced insulin resistance and consequently improves type 2 diabetes in mice. Here, the small molecule norathyriol reversed obesity- and high-fat-diet-induced insulin resistance by inhibiting PTP1B.

METHODS:
The inhibitory mode of PTP1B was evaluated by using the double-reciprocal substrate in the presence of norathyriol. Primary cultured hepatocytes, myoblasts and white adipocytes were used to investigate the effect of norathyriol on insulin signalling. Glucose homeostasis and insulin sensitivity were characterised by glucose and insulin tolerance tests.

RESULTS:
Norathyriol was identified as a competitive inhibitor of PTP1B, with an IC50 of 9.59 ± 0.39 μmol/l. In cultured hepatocytes and myoblasts, norathyriol treatment blocked the PTP1B-mediated dephosphorylation of the insulin receptor. Intraperitoneal injection of norathyriol inhibited liver and muscle PTP1B activity in mice, thus contributing to the improved glucose homeostasis and insulin sensitivity. However, these beneficial effects were abolished in PTP1B-deficient mice. Notably, oral administration of norathyriol protected mice from diet-induced obesity and insulin resistance through inhibition of hypothalamic PTP1B activity.

CONCLUSIONS/INTERPRETATION:
Our results indicate that the small molecule norathyriol is a potent PTP1B inhibitor with good cell permeability and oral availability.

Title

Norathyriol reverses obesity- and high-fat-diet-induced insulin resistance in mice through inhibition of PTP1B.

Author

Ding H1, Zhang Y, Xu C, Hou D, Li J, Zhang Y, Peng W, Zen K, Zhang CY, Jiang X.

Publish date

2014 Oct

PMID

22084399

Abstract

Ultraviolet (UV) irradiation is the leading factor in the development of skin cancer, prompting great interest in chemopreventive agents for this disease. In this study, we report the discovery of norathyriol, a plant-derived chemopreventive compound identified through an in silico virtual screening of the Chinese Medicine Library. Norathyriol is a metabolite of mangiferin found in mango, Hypericum elegans, and Tripterospermum lanceolatum and is known to have anticancer activity. Mechanistic investigations determined that norathyriol acted as an inhibitor of extracellular signal-regulated kinase (ERK)1/2 activity to attenuate UVB-induced phosphorylation in mitogen-activated protein kinases signaling cascades. We confirmed the direct and specific binding of norathyriol with ERK2 through a cocrystal structural analysis. The xanthone moiety in norathyriol acted as an adenine mimetic to anchor the compound by hydrogen bonds to the hinge region of the protein ATP-binding site on ERK2. Norathyriol inhibited in vitro cell growth in mouse skin epidermal JB6 P+ cells at the level of G(2)-M phase arrest. In mouse skin tumorigenesis assays, norathyriol significantly suppressed solar UV-induced skin carcinogenesis. Further analysis indicated that norathyriol mediates its chemopreventive activity by inhibiting the ERK-dependent activity of transcriptional factors AP-1 and NF-κB during UV-induced skin carcinogenesis. Taken together, our results identify norathyriol as a safe new chemopreventive agent that is highly effective against development of UV-induced skin cancer.

?2011 AACR.

Title

Norathyriol suppresses skin cancers induced by solar ultraviolet radiation by targeting ERK kinases.

Author

Li J1, Malakhova M, Mottamal M, Reddy K, Kurinov I, Carper A, Langfald A, Oi N, Kim MO, Zhu F, Sosa CP, Zhou K, Bode AM, Dong Z.

Publish date

2012 Jan 1