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Xanthatin

$576

  • Brand : BIOFRON

  • Catalogue Number : BD-D0476

  • Specification : HPLC≥98%

  • CAS number : 26791-73-1

  • Formula : C15H18O3

  • Molecular Weight : 246.31

  • PUBCHEM ID : 5281511

  • Volume : 10mg

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Catalogue Number

BD-D0476

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

2-8°C

Molecular Weight

246.31

Appearance

White crystalline powder

Botanical Source

Xanthium sibiricum Patr./Prod. by Xanthium pennsylvanicum, Xanthium itakicum, Xanthium spinosum, Xanthium strumarium and Xanthium sibiricum

Structure Type

Sesquiterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CC2C(CC=C1C=CC(=O)C)C(=C)C(=O)O2

Synonyms

/(3aR,7S,8aS)-7-Methyl-3-methylene-6-[(1Z)-3-oxo-1-buten-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one/(3aR,7S,8aS)-7-Methyl-3-methylene-6-[(1Z)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one/[3aR-(3aa,7b,8ab)]-3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one/(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(1Z)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one/8-epi-Xanthatin/Xanthatin/2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1Z)-3-oxo-1-buten-1-yl]-, (3aR,7S,8aS)-

IUPAC Name

(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Density

1.1±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

199.1±28.8 °C

Boiling Point

444.3±45.0 °C at 760 mmHg

Melting Point

114.5-115°

InChl

InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1

InChl Key

RBRPTFMVULVGIC-ZTIIIDENSA-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#:26791-73-1) 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

30797985

Abstract

BACKGROUND:
Colorectal cancer is one of the most common malignancies worldwide and is associated with high mortality rates. We previously reported that Xanthium strumarium L. induces mitotic arrest in proliferating cells, a process mediated by xanthatins.

HYPOTHESIS/AIM:
The aim of this work is to study if xanthatins, isolated from X. strumarium total extract, affect the proliferative capacity of CT26WT colon cancer cells and, in consequence, if tumor growth and proliferation of (lung) metastatic sites can also be arrested in vivo.

STUDY DESIGN:
This study consisted of both in vitro and in vivo experiments involving the CT26WT cell line and a subcutaneous mouse model of colon cancer. In vitro cell cycle progression, in vivo tumoral growth and anti-metastatic activity were analyzed to investigate whether xanthatins of X. strumarium induce mitotic arrest in proliferating colorectal carcinoma.

RESULTS:
Our in vitro results show that X. strumarium, mediated by xanthatins, induces G2/M arrest and impair anaphase entrance. This leads to a significant induction of apoptotic and necrotic in CT26WT cells, demonstrating their significant anti-proliferative activity through interfering with the mitotic apparatus. Furthermore, our in vivoresults reveal that X. strumarium inhibits both tumor growth and metastasis progression.

CONCLUSION:
X. strumarium antitumor activities are mainly mediated by xanthatins through inhibition of tumor growth and metastasis, inducing mitotic arrest and apoptosis in colon carcinoma cells. These findings further confirm the therapeutic potential of X. strumarium in colorectal cancer.

Copyright © 2018. Published by Elsevier GmbH.

KEYWORDS

Anti-metastatic; Anti-mitotic; Anti-proliferative; Colon cancer; Xanthatins; Xanthium strumarium

Title

Xanthium strumarium´s xanthatins induces mitotic arrest and apoptosis in CT26WT colon carcinoma cells.

Author

Piloto-Ferrer J1, Sanchez-Lamar a2, Francisco M3, Gonzalez ML3, Merino N4, Aparicio G4, Perez C5, Rodeiro I6, Lopes MTP7.

Publish date

2019 Apr

PMID

30389633

Abstract

Hepatocellular carcinoma (HCC) has high incidence and mortality in patients with chronic liver diseases worldwide. However, there are limited chemotherapeutic agents for HCC in clinic. Xanthatin, a natural sesquiterpene lactone, has significant antitumor activity against a variety of cancers, but little is known about its effects on HCC and the underlying mechanism. Here, we evaluated the antitumor effects of xanthatin on human hepatoma cells. We found that xanthatin caused morphological changes and reduced cell viability in three HCC cell lines in concentration- and time-dependent manners. Xanthatin at 10 μM significantly arrested cell cycle at the G2/M checkpoint, and at 40 μM significantly arrested cell cycle at the S phase in hepatoma cells. Additionally, xanthatin induced apoptosis associated with activation of caspase-3 in hepatoma cells, but did not apparently induce apoptosis in human normal LO2 hepatocytes. We also demonstrated that the three primary signaling pathways of unfolded protein response (UPR) were activated by xanthatin to different extents. Notably, the PERK/eIF-2α/ATF4 axis was most significantly activated by xanthatin. More importantly, both xanthatin and tunicamycin, an endoplasmic reticulum stress (ERS) inducing compound, increased the levels of CHOP and cleaved-caspase-3 in HepG2 cells, but their effects were significantly abolished by siRNA-mediated knockdown of CHOP. Further experiments validated that xanthatin more potently activated ATF4 by promoting its nuclear translocation in hepatoma cells. Taken together, we discovered that xanthatin induced apoptosis in human hepatoma cells by activating ERS. Our current data revealed a novel mechanism for xanthatin as a promising anti-tumor candidate for HCC therapy.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

Apoptosis; Endoplasmic reticulum stress; Hepatocellular carcinoma; Unfolded protein response; Xanthatin

Title

Xanthatin induces apoptosis by activating endoplasmic reticulum stress in hepatoma cells.

Author

Shi TL1, Zhang L2, Cheng QY3, Yu JS4, Liu J3, Shen YJ3, Feng XJ2, Shen YX5.

Publish date

2019 Jan 15;

PMID

30346082

Abstract

To investigate the suppressive effects of xanthatin on glioma growth in a nude mouse xenograft model and rat orthotopic implantation model using magnetic resonance imaging (MRI) to dynamically monitor the antitumour growth and antiangiogenesis effects of xanthatin. The nude mouse xenograft tumour model and rat orthotopic implantation model were established to observe the antitumour effects of xanthatin in vivo. In the rat orthotopic implanted tumour model, MRI scanning was used to dynamically monitor the antitumour growth effect and evaluate the antiangiogenesis effect of xanthatin. We found that xanthatin at a dose of 0.4 mg/10 g dramatically decreased the growth of xenograft tumours in nude mice. The antiangiogenesis effect of xanthatin C6 glioma was evaluated by dynamic contrast-enhanced (DCE) MRI via comparison of the volume transfer constant (Ktrans ) value, a parameter that reflects vessel permeability. We found that xanthatin at the doses of 8 and 16 mg/kg significantly decreased the Ktrans value, which suggests that xanthatin has antiangiogenesis effects. These data demonstrate the suppressive effects of xanthatin on C6 glioma occur via antiangiogenesis. Meanwhile, this study also provides evidence for the application of quantitative parameters of DCE-MRI for dynamically evaluating the growth and angiogenesis of intracranial tumours and for experimental and clinical research.

© 2018 John Wiley & Sons, Ltd.

KEYWORDS

MRI and DCE-MRI; VEGF; antiangiogenesis; glioma; xanthatin

Title

The antitumour growth and antiangiogenesis effects of xanthatin in murine glioma dynamically evaluated by dynamic contrast-enhanced magnetic resonance imaging.

Author

Bi SX1,2,3, Li XH1, Wei CS2,3, Xiang HH1,2,3, Shen YX2,3, Yu YQ1.

Publish date

2019 Jan


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