Xanthatin | CAS:26791-73-1 | Manufacturer ChemFaces

Xanthatin

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Description:

Xanthatin is a novel potent inhibitor of VEGFR2 signaling, has significant antitumor activity against a variety of cancer cells through cell cycle arrest and apoptosis induction, it can inhibit angiogenesis and tumor growth in breast cancer cells. Xanthatin has bactericidal and fungicidal activity, including against Colletotrichum gloesporoides, Trichothecium roseum, Bacillus cereus and Staphylococcus aureus.

Targets:

In vitro:

Lett. Appl. Microbiol., 1994, 18(4): 206-8.

Antimicrobial activity of xanthatin from Xanthium spinosum L.[Reference: WebLink]

METHODS AND RESULTS:
Dichloromethane extracts from Xanthium spinosum L. were fractionated and the fractions tested for their bactericidal and fungicidal activity. From the active fraction, a compound was isolated and identified as Xanthatin (I).
CONCLUSIONS:
Xanthatin was active against Colletotrichum gloesporoides, Trichothecium roseum, Bacillus cereus and Staphylococcus aureus.

Int J Clin Exp Pathol. 2015 Sep 1;8(9):10355-64.

Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells.[Pubmed: 26617743 ]

Anti-angiogenesis targeting vascular endothelial growth factor receptor 2 (VEGFR2) has emerged as an important tool for cancer treatment.
METHODS AND RESULTS:
In this study, we described a novel VEGFR2 inhibitor, Xanthatin, which inhibits tumor angiogenesis and growth. The biochemical profiles of Xanthatin were investigated using kinase assay, migration assay, tube formation, Matrigel plug assay, western blot, immunofluorescence and human tumor xenograft model. Xanthatin significantly inhibited growth, migration and tube formation of human umbilical vascular endothelial cell as well as inhibited vascular endothelial growth factor (VEGF)-stimulated angiogenesis. In addition, it inhibited VEGF-induced phosphorylation of VEGFR2 and its downstream signaling regulator. Moreover, Xanthatin directly inhibit proliferation of breast cancer cells MDA-MB-231. Oral administration of Xanthatin could markedly inhibit human tumor xenograft growth and decreased microvessel densities (MVD) in tumor sections.
CONCLUSIONS:
Taken together, these preclinical evaluations suggest that Xanthatin inhibits angiogenesis and may be a promising anticancer drug candidate.

In vivo:

Phytomedicine. 2013 Jul 15;20(10):865-73.

Characterization of xanthatin: anticancer properties and mechanisms of inhibited murine melanoma in vitro and in vivo.[Pubmed: 23664560]

Anti-cancer investigations on Xanthatin mainly focus on in vitro experiments. We herein reported the anti-tumor effects of Xanthatin both in vitro and in vivo.
METHODS AND RESULTS:
MTS assay results showed that Xanthatin had a remarkable anti-proliferative effect on B16-F10 cells. Moreover, the expression of β-catenin was up-regulated both in vitro and in vivo. Animal studies further revealed that Xanthatin killed the tumor cells around the blood vessels which contributes to reduce microvascular density extremely.
CONCLUSIONS:
All these results indicate that Xanthatin inhibited murine melanoma B16-F10 cell proliferation possibly associated with activation of Wnt/β-catenin pathway and its activity against melanoma tumor might also be relevant to inhibition of angiogenesis.

Xanthatin Description

Source:	The fruits of Xanthium sibiricum
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

PLoS One. 2013 Nov 28;8(11):e81945.

Concerted suppression of STAT3 and GSK3β is involved in growth inhibition of non-small cell lung cancer by Xanthatin.[Pubmed: 24312384]

Xanthatin, a sesquiterpene lactone purified from Xanthium strumarium L., possesses prominent anticancer activity.
METHODS AND RESULTS:
We found that disruption of GSK3β activity was essential for Xanthatin to exert its anticancer properties in non-small cell lung cancer (NSCLC), concurrent with preferable suppression of constitutive activation of STAT3. Interestingly, inactivation of the two signals are two mutually exclusive events in Xanthatin-induced cell death. Moreover, we surprisingly found that exposure of Xanthatin failed to trigger the presumable side effect of canonical Wnt/β-Catenin followed by GSK3β inactivation. We further observed that the downregulation of STAT3 was required for Xanthatin to fine-tune the risk.
CONCLUSIONS:
Thus, the discovery of Xanthatin, which has ability to simultaneously orchestrate two independent signaling cascades, may have important implications for screening promising drugs in cancer therapies.

Cell Research:

Planta Med. 2012 Jun;78(9):890-5.

Xanthatin induces G2/M cell cycle arrest and apoptosis in human gastric carcinoma MKN-45 cells.[Pubmed: 22532019]

Xanthatin, a natural bioactive compound of sesquiterpene lactones, was isolated and purified from air-dried aerial part of Xanthium sibiricum Patrin ex Widder. In the present study, we demonstrated the significant antiproliferative and proapoptotic effects of Xanthatin on human gastric carcinoma MKN-45 cells.
METHODS AND RESULTS:
MTS assay showed that Xanthatin produced obvious cytotoxicity in MKN-45 cells with IC50 values of 18.6, 9.3, and 3.9 μM for 12, 24, and 48 h, respectively. Results of flow cytometry analysis indicated that the antiproliferative activity induced by Xanthatin might be executed via G2/M cell cycle arrest and proapoptosis in MKN-45 cells. Western blot analysis elucidated that: a) Xanthatin downregulated expression of Chk1 and Chk2 and phosphorylation of CDC2, which are known as key G2/M transition regulators; b) Xanthatin increased p53 activation, decreased the bcl-2/bax ratio and the levels of downstream procaspase-9 and procaspase-3, which are key regulators in the intrinsic apoptosis pathway; c) Xanthatin blocked phosphorylation of NF-κB (p65 subunit) and of IκBα, which might contribute to its proapoptotic effects on MKN-45 cells.
CONCLUSIONS:
In conclusion, our results suggest that Xanthatin may have therapeutic potential against human gastric carcinoma.

Structure Identification:

Eur J Med Chem. 2015 Jan 27;90:491-6.

Optimization of xanthatin extraction from Xanthium spinosum L. and its cytotoxic, anti-angiogenesis and antiviral properties.[Pubmed: 25481815]

METHODS AND RESULTS:
The aqueous extraction of the sesquiterpene lactone Xanthatin from Xanthium spinosum L. favours the conversion of xanthinin (1) to Xanthatin (2) via the loss of acetic acid. The cytotoxic (Hep-G2 and L1210 human cell lines) and antiviral activities of isolated Xanthatin are established. This natural compound shows significant cytotoxicity against the Hep-G2 cell line and our experimental results reveal its strong anti-angiogenesis capacity in vitro.
CONCLUSIONS:
The structure of Xanthatin is determined by spectroscopic methods and for the first time confirmed by X-ray diffraction.

Product Name	Xanthatin
Price:
CAS No.:	26791-73-1
Catalog No.:	CFN98315
Molecular Formula:	C₁₅H₁₈O₃
Molecular Weight:	246.3 g/mol
Purity:	>=98%
Type of Compound:	Sesquiterpenoids
Physical Desc.:	Powder
Source:	The fruits of Xanthium sibiricum
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Anticancer Compound Library Inhibitors Compound Library Antibacterial Compound Library Antifungal Compound Library Sesquiterpenoids Compound Library Wnt/β-catenin Inhibitor Library VEGFR Inhibitor Library STAT Inhibitor Library p65 Inhibitor Library NF-kB Inhibitor Library GSK-3 Inhibitor Library Chk Inhibitor Library Bcl-2/Bax Inhibitor Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	4.0601 mL	20.3004 mL	40.6009 mL	81.2018 mL	101.5022 mL
5 mM	0.812 mL	4.0601 mL	8.1202 mL	16.2404 mL	20.3004 mL
10 mM	0.406 mL	2.03 mL	4.0601 mL	8.1202 mL	10.1502 mL
50 mM	0.0812 mL	0.406 mL	0.812 mL	1.624 mL	2.03 mL
100 mM	0.0406 mL	0.203 mL	0.406 mL	0.812 mL	1.015 mL

CFN98315	Xanthatin	26791-73-1	246.3	C₁₅H₁₈O₃
CFN89507	8-Epixanthatin	30890-35-8	246.30	C₁₅H₁₈O₃
CFN89001	6alpha-Hydroxytomentosin	1232676-22-0	264.32	C₁₅H₂₀O₄
CFN99644	Xanthinin	153483-31-9	306.4	C₁₇H₂₂O₅
CFN92601	Britannilactone	33620-72-3	266.3	C₁₅H₂₂O₄
CFN90219	1-O-Acetyl britannilactone	681457-46-5	266.34	C₁₇H₂₄O₅
CFN89518	1,6-O,O-Diacetylbritannilactone	1286694-67-4	350.40	C₁₉H₂₆O₆
CFN92598	1-O-Acetyl-6beta-O-Isobutyrylbritannilactone	1087072-50-1	378.5	C₂₁H₃₀O₆
CFN89470	1-O-Acetyl-6alpha-O-(2-methylbutyryl)britannilactone	1932687-71-2	392.48	C₂₂H₃₂O₆
CFN89501	Dibritannilactone B	1829580-18-8	598.72	C₃₄H₄₆O₉